Molbank

5 pages, 2334 KiB

Open AccessCommunication

Styryl Hemicyanine Dye (E)-3-Methyl-2-(4-thiomorpholinostyryl)benzo[d]thiazol-3-ium Iodide for Nucleic Acids and Cell Nucleoli Visualization

by Aleksey A. Vasilev, Marina Miteva, Nikolay Ishkitiev, Maria Dragneva, Lora Topalova and Meglena I. Kandinska

Molbank 2022, 2022(2), M1392; https://doi.org/10.3390/M1392 - 20 Jun 2022

Cited by 2 | Viewed by 2132

Abstract

(E)-3-Methyl-2-(4-thiomorpholinostyryl)benzo[d]thiazol-3-ium iodide 1 was prepared by a convenient and reliable reaction procedure. The slight molar excess of the starting benzaldehyde and the mixture of ethanol: ethyl acetate in the ratio 3:1 as a solvent afforded a pure reaction product. The photophysical [...] Read more.

(E)-3-Methyl-2-(4-thiomorpholinostyryl)benzo[d]thiazol-3-ium iodide 1 was prepared by a convenient and reliable reaction procedure. The slight molar excess of the starting benzaldehyde and the mixture of ethanol: ethyl acetate in the ratio 3:1 as a solvent afforded a pure reaction product. The photophysical properties of the dye in a TE buffer in the absence and presence of double-stranded DNA (dsDNA) were elucidated. The low intrinsic fluorescence of 1 in TE buffer is followed by an increase in the fluorescence after dsDNA binding. The dye is nontoxic for stem cells from apical papilla and the most concentrated fluorescence is detected in the cell nucleoli. Full article

(This article belongs to the Collection Heterocycle Reactions)

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Graphical abstract

7 pages, 979 KiB

Open AccessShort Note

Fosbergenone: 3-[2-(1,2,5,5-Tetramethyl-7-oxo-1,2,3,4,4a,5,6,7-octahydronaphthalen-1-yl)ethyl]-2,5-dihydrofuran-2-one

by Joy Ebenezer Rajakulendran, Emmanuel T. Oluwabusola, Rainer Ebel and Marcel Jaspars

Molbank 2022, 2022(2), M1391; https://doi.org/10.3390/M1391 - 19 Jun 2022

Cited by 1 | Viewed by 1758 | Correction

Abstract

A new ent-halimane diterpenoid, fosbergenone (1) was isolated from the foliar bud exudate of Gardenia fosbergii. The structure of 1 was elucidated based on spectroscopic data including IR, 1D and 2D NMR, as well as high-resolution mass spectrometry. Full article

(This article belongs to the Section Natural Products)

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Graphical abstract

6 pages, 1743 KiB

Open AccessShort Note

Bis(3-butylamino-4-nitro)piperazine

by M. John Plater, David P. B. Bulloch and William T. A. Harrison

Molbank 2022, 2022(2), M1390; https://doi.org/10.3390/M1390 - 18 Jun 2022

Cited by 1 | Viewed by 1637

Abstract

2,4-Difluoronitrobenzene is treated sequentially with butylamine and then piperazine to prepare a building block for forming a crystalline lattice by non-covalent interactions. A single crystal X-ray structure determination was performed. Full article

(This article belongs to the Section Structure Determination)

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Graphical abstract

3 pages, 342 KiB

Open AccessShort Note

N-[3-(Chloromethyl)-1,2-benzisoxazol-5-yl]acetamide

by Evgeniy N. Khodot and Oleg A. Rakitin

Molbank 2022, 2022(2), M1389; https://doi.org/10.3390/M1389 - 17 Jun 2022

Viewed by 1232

Abstract

Functionally substituted 1,2-benzisoxazoles are very important and promising heterocycles with various pharmacological activities. Benzoxazoles containing reactive 3-chloromethyl and 5-amino groups are practically unexplored derivatives in this series. In this communication, the simple method for the synthesis of N-[3-(chloromethyl)-1,2-benzisoxazol-5-yl]acetamide which is an interesting [...] Read more.

Functionally substituted 1,2-benzisoxazoles are very important and promising heterocycles with various pharmacological activities. Benzoxazoles containing reactive 3-chloromethyl and 5-amino groups are practically unexplored derivatives in this series. In this communication, the simple method for the synthesis of N-[3-(chloromethyl)-1,2-benzisoxazol-5-yl]acetamide which is an interesting precursor for the preparation of a series of 3,5-disubstituted benzoxazoles was described. The structure of the synthesized compound was established by elemental analysis, high-resolution mass spectrometry, ¹H, ¹³C NMR and IR spectroscopy, and mass spectrometry. Full article

(This article belongs to the Section Organic Synthesis)

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Scheme 1

4 pages, 516 KiB

Open AccessShort Note

2,6-Bis[bis(1,1-dimethylethyl)phosphinito-κP]phenyl-κC]-trans-chlorohydro(phenylphosphine)iridium(III)

by Neil T. Mucha and Rory Waterman

Molbank 2022, 2022(2), M1388; https://doi.org/10.3390/M1388 - 17 Jun 2022

Viewed by 1214

Abstract

The molecular structure of an iridium complex featuring a phenylphosphine ligand is described. The reaction of (POCOP)IrHCl (1, POCOP = 2,6-(^tBu₂PO)₂C₆H₃^–) with phenylphosphine gives (POCOP)IrHCl(PH₂Ph) (2) [...] Read more.

The molecular structure of an iridium complex featuring a phenylphosphine ligand is described. The reaction of (POCOP)IrHCl (1, POCOP = 2,6-(^tBu₂PO)₂C₆H₃^–) with phenylphosphine gives (POCOP)IrHCl(PH₂Ph) (2) under mild conditions. The structural features are consistent with a classic pseudo-octahedral iridium compound with three neutral phosphine donors. Compound 1 is unreactive at elevated temperatures and is unreactive toward excess phenylphosphine under the sampled conditions. Full article

(This article belongs to the Section Structure Determination)

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Graphical abstract

10 pages, 1073 KiB

Open AccessCommunication

Synthesis, Spectroscopic Analysis, and In Vitro Anticancer Evaluation of 2-(Phenylsulfonyl)-2H-1,2,3-triazole

by Angélica Salinas-Torres, Jaime Portilla, Hugo Rojas, Diana Becerra and Juan-Carlos Castillo

Molbank 2022, 2022(2), M1387; https://doi.org/10.3390/M1387 - 16 Jun 2022

Cited by 3 | Viewed by 1948

Abstract

The 1,2,3-Triazole derivatives containing the sulfonyl group have proved their biological importance in medicinal chemistry and drug design. In this sense, we describe the regioselective synthesis of 2-(phenylsulfonyl)-2H-1,2,3-triazole 3 in good yield through a classical sulfonamidation reaction of 1H-1,2,3-triazole [...] Read more.

The 1,2,3-Triazole derivatives containing the sulfonyl group have proved their biological importance in medicinal chemistry and drug design. In this sense, we describe the regioselective synthesis of 2-(phenylsulfonyl)-2H-1,2,3-triazole 3 in good yield through a classical sulfonamidation reaction of 1H-1,2,3-triazole 1 with benzenesulfonyl chloride 2 in dichloromethane using a slight excess of triethylamine at 20 °C for 3 h. This procedure is distinguished by its short reaction time, high yield, excellent regioselectivity, clean reaction profile, and operational simplicity. The sulfonamide 3 was characterized by high-resolution mass spectrometry, FT–IR, UV–Vis, 1D and 2D NMR spectroscopy, and elemental analysis. The sulfonamide 3 exhibited moderate activity against UO-31 renal, SNB-75 central nervous system, HCT-116 colon, and BT-549 breast cancer cell lines, with growth inhibition percentages (GI%) ranging from 10.83% to 17.64%. Full article

(This article belongs to the Section Organic Synthesis)

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Graphical abstract

4 pages, 364 KiB

Open AccessShort Note

3,4-Diaminopyridine-2,5-dicarbonitrile

by Timofey N. Chmovzh and Oleg A. Rakitin

Molbank 2022, 2022(2), M1386; https://doi.org/10.3390/M1386 - 16 Jun 2022

Viewed by 1322

Abstract

Pyridines fused with heterocyclic rings are of great interest as both photovoltaic materials and biologically active compounds. The most convenient precursors for these compounds are pyridine-2,3-diamines. In this communication, 3,4-diaminopyridine-2,5-dicarbonitrile was synthesized by the reaction of 2,5-dibromo-3,4-diaminopyridine with copper cyanide; the best yield [...] Read more.

Pyridines fused with heterocyclic rings are of great interest as both photovoltaic materials and biologically active compounds. The most convenient precursors for these compounds are pyridine-2,3-diamines. In this communication, 3,4-diaminopyridine-2,5-dicarbonitrile was synthesized by the reaction of 2,5-dibromo-3,4-diaminopyridine with copper cyanide; the best yield of the target compound was achieved by heating the reaction mixture in N,N-dimethylformamide at 120 °C for 6 h. The structure of the newly synthesized compound was established by means of elemental analysis, high resolution mass-spectrometry, ¹H, ¹³C NMR, IR, UV spectroscopy and mass-spectrometry. Full article

(This article belongs to the Section Organic Synthesis)

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Graphical abstract

4 pages, 399 KiB

Open AccessShort Note

(E)-7-(4-(Diphenylamino)styryl)benzo[c][1,2,5]thiadiazole-4-carbonitrile

by Timofey N. Chmovzh, Timofey A. Kudryashev and Oleg A. Rakitin

Molbank 2022, 2022(2), M1385; https://doi.org/10.3390/M1385 - 15 Jun 2022

Cited by 1 | Viewed by 1326

Abstract

Donor-acceptor-donor (D-A-A) structures with 2,1,3-benzothiadiazole as an internal acceptor and the 4(7)-cyanogroup as anchor acceptor have been investigated for various photovoltaic applications such as dye-sensitized solar cells (DSSCs) and organic light emitting diodes (OLEDs). They are usually obtained by cyanation of 4(7)-bromo-2,1,3-benzothiadiazoles. In [...] Read more.

Donor-acceptor-donor (D-A-A) structures with 2,1,3-benzothiadiazole as an internal acceptor and the 4(7)-cyanogroup as anchor acceptor have been investigated for various photovoltaic applications such as dye-sensitized solar cells (DSSCs) and organic light emitting diodes (OLEDs). They are usually obtained by cyanation of 4(7)-bromo-2,1,3-benzothiadiazoles. In this communication, the reaction of (E)-4-(2-(7-bromobenzo[c][1,2,5]thiadiazol-4-yl)vinyl)-N,N-diphenylaniline with cyanating agents was studied and it was shown that the best yield of (E)-7-(4-(diphenylamino)styryl)benzo[c][1,2,5]thiadiazole-4-carbonitrile was achieved by heating with zinc cyanide in NMP at 120 °C in the presence of tetrakis(triphenylphosphine)palladium (0). The structure of newly synthesized compound was established by means of an elemental analysis, high resolution mass-spectrometry, ¹H, ¹³C-NMR, IR, UV spectroscopy and mass-spectrometry. Full article

(This article belongs to the Special Issue Heteroatom Rich Organic Heterocycles)

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Scheme 1

5 pages, 619 KiB

Open AccessCommunication

A Direct Method for the Efficient Synthesis of Hydroxyalkyl-Containing Azoxybenzenes

by Ekaterina S. Spesivaya, Ida A. Lupanova, Dzhamilya N. Konshina and Valery V. Konshin

Molbank 2022, 2022(2), M1384; https://doi.org/10.3390/M1384 - 14 Jun 2022

Viewed by 1489

Abstract

Reaction of nitrobenzyl alcohol with glucose (200 mol%) in the presence of NaOH in water-ethanol medium gave 1,2-bis(4-(hydroxymethyl)phenyl)diazene oxide, 1,2-bis(2-(hydroxymethyl)phenyl)diazene oxide and 1,2-bis(4-(1-hydroxyethyl)phenyl)diazene oxide in 76%, 76% and 72% yields, respectively. Full article

(This article belongs to the Section Organic Synthesis)

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Scheme 1

7 pages, 569 KiB

Open AccessShort Note

2-(4-Chlorophenyl)-4-(3,4-dimethoxy-phenyl)-6-methoxy-3-methylquinoline

by Duván A. Rodríguez Enciso, Carlos E. Puerto Galvis and Vladimir V. Kouznetsov

Molbank 2022, 2022(2), M1383; https://doi.org/10.3390/M1383 - 13 Jun 2022

Cited by 2 | Viewed by 1715

Abstract

A 2,4-diarylquinoline derivative, 2-(4-chlorophenyl)-4-(3,4-dimethoxyphenyl)-6-methoxy-3-methylquinoline, was synthesized in a conventional two-step procedure from p-anisidine, p-chlorobenzaldehyde and methyl isoeugenol as available starting reagents through a sequence of BF₃·OEt₂-catalyzed Povarov cycloaddition reaction/oxidative dehydrogenation aromatization processes under microwave irradiation conditions in [...] Read more.

A 2,4-diarylquinoline derivative, 2-(4-chlorophenyl)-4-(3,4-dimethoxyphenyl)-6-methoxy-3-methylquinoline, was synthesized in a conventional two-step procedure from p-anisidine, p-chlorobenzaldehyde and methyl isoeugenol as available starting reagents through a sequence of BF₃·OEt₂-catalyzed Povarov cycloaddition reaction/oxidative dehydrogenation aromatization processes under microwave irradiation conditions in the presence of a green oxidative I₂-DMSO system. The structure of the compound was fully characterized by FT-IR, ¹H and ¹³C-NMR, ESI-MS, and elemental analysis. Its physicochemical parameters (Lipinski’s descriptors) were also calculated using the Molinspiration Cheminformatics software. The diarylquinoline molecule obtained is an interesting model with increased lipophilicity and thus permeability, an important descriptor for quinoline-based drug design. Such types of derivatives are known for their anticancer, antitubercular, antifungal, and antiviral activities. Full article

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Graphical abstract

11 pages, 3115 KiB

Open AccessShort Note

2,3,5-Tri-O-benzyl-d-xylofuranose

by Baptiste Taffoureau, Isabelle Gillaizeau, Pascal Retailleau and Cyril Nicolas

Molbank 2022, 2022(2), M1382; https://doi.org/10.3390/M1382 - 07 Jun 2022

Cited by 1 | Viewed by 2104

Abstract

The synthesis and crystallization of 2,3,5-tri-O-benzyl-d-xylofuranose permitted us to isolate the alpha anomer with a small contamination of the beta form (ca 10%), whose first crystallographic structure obtained in the P2₁2₁2₁ [...] Read more.

The synthesis and crystallization of 2,3,5-tri-O-benzyl-d-xylofuranose permitted us to isolate the alpha anomer with a small contamination of the beta form (ca 10%), whose first crystallographic structure obtained in the P2₁2₁2₁ space group was determined at 100 K up to a resolution of sin θ_max/λ = 0.71 Å⁻¹ and refined to an R1 value of 0.0171 with a Hirshfeld atom refinement (HAR) approach. Full article

(This article belongs to the Section Structure Determination)

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Graphical abstract

6 pages, 1883 KiB

Open AccessShort Note

Bis(μ-iodo)-tetrakis(O-methyl N-phenylthiocarbamate)-tetraiodo-dibismuth

by Wafa Arar, Abderrahim Khatyr, Michael Knorr, Carsten Strohmann and Annika Schmidt

Molbank 2022, 2022(2), M1381; https://doi.org/10.3390/M1381 - 06 Jun 2022

Cited by 3 | Viewed by 1614

Abstract

In order to investigate the coordination chemistry of O-alkyl N-aryl thiocarbamate ligands, BiI₃ was reacted with two equivalents of MeOC(=S)N(H)Ph in MeCN solution to afford the dinuclear title compound complexes [{I₂Bi(μ₂-I)₂BiI₂}{κ¹ [...] Read more.

In order to investigate the coordination chemistry of O-alkyl N-aryl thiocarbamate ligands, BiI₃ was reacted with two equivalents of MeOC(=S)N(H)Ph in MeCN solution to afford the dinuclear title compound complexes [{I₂Bi(μ₂-I)₂BiI₂}{κ¹-MeOC(=S)N(H)Ph}₄] 1. Compound 1 was characterized by IR, UV and NMR spectroscopy, the formation of a dinuclear framework is ascertained by a single-crystal X-ray diffraction study performed at 100 K. Full article

(This article belongs to the Section Structure Determination)

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Figure 1

5 pages, 509 KiB

Open AccessShort Note

2-((4-Phenyl-5-(2-(p-tolylamino)ethyl)-4H-1,2,4-triazol-3-yl)thio)-N′-(1-phenylethylidene)acetohydrazide

by Aida Šermukšnytė, Ilona Jonuškienė, Kristina Kantminienė, Zigmuntas Jonas Beresnevičius and Ingrida Tumosienė

Molbank 2022, 2022(2), M1380; https://doi.org/10.3390/M1380 - 05 Jun 2022

Cited by 3 | Viewed by 1379

Abstract

A synthesis of 2-((4-phenyl-5-(2-(p-tolylamino)ethyl)-4H-1,2,4-triazol-3-yl)thio)-N’-(1-phenylethylidene)acetohydrazide from 2-[(3-{2-[(4-methylphenyl)amino]ethyl}-4-phenyl-4,5-dihydro-1H-1,2,4-triazol-5-yl)sulfanyl]acetohydrazide and acetophenone is reported. The title compound has been tested to possess 1.5-fold higher antioxidant ability than the control, butylated hydroxytoluene, as determined by a Ferric reducing antioxidant power assay. Full article

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Graphical abstract

5 pages, 623 KiB

Open AccessCommunication

Modification of 1-Hexene Vinylidene Dimer into Primary and Tertiary Alkanethiols

by Pavel V. Kovyazin, Almira Kh. Bikmeeva, Eldar R. Palatov and Lyudmila V. Parfenova

Molbank 2022, 2022(2), M1379; https://doi.org/10.3390/M1379 - 04 Jun 2022

Viewed by 1559

Abstract

Aliphatic thiols are in high demand in materials chemistry. Herein, a synthesis of thio-derivatives of 1-hexene vinylidene dimer is described. The approach, based on a hydroalumination reaction with further replacement of the organoaluminum function with sulfur using thiourea or dimethyl disulfide, provides anti-Markovnikov [...] Read more.

Aliphatic thiols are in high demand in materials chemistry. Herein, a synthesis of thio-derivatives of 1-hexene vinylidene dimer is described. The approach, based on a hydroalumination reaction with further replacement of the organoaluminum function with sulfur using thiourea or dimethyl disulfide, provides anti-Markovnikov products, 2-butyloctane-1-thiol or 5-(methylsulfanylmethyl)undecane, in moderate yields. The reaction of a vinylidene dimer with phosphorus pentasulfide in the presence of catalytic amounts of (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO) selectively gives the Markovnikov product, 5-methylundecane-5-thiol, with a yield of up to 77%. Full article

(This article belongs to the Section Organic Synthesis)

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Scheme 1

6 pages, 1002 KiB

Open AccessShort Note

Ethyl (E)-(3-(4-((4-bromobenzyl)oxy)phenyl)acryloyl)glycinate

by Ioannis Fotopoulos, George-Christos Papaioannou and Dimitra Hadjipavlou-Litina

Molbank 2022, 2022(2), M1378; https://doi.org/10.3390/M1378 - 04 Jun 2022

Viewed by 1943

Abstract

In an attempt to develop new potent anti-inflammatory agents, a cinnamic -amino acid hybrid molecule was synthesized and in silico drug-likeness, in vitro COX-2 inhibition, and pharmacokinetic properties were studied. The results showed high cyclooxygenase inhibitory activity (IC₅₀ = 6 µM) and [...] Read more.

In an attempt to develop new potent anti-inflammatory agents, a cinnamic -amino acid hybrid molecule was synthesized and in silico drug-likeness, in vitro COX-2 inhibition, and pharmacokinetic properties were studied. The results showed high cyclooxygenase inhibitory activity (IC₅₀ = 6 µM) and favorable pharmacokinetic properties, being orally bioavailable according to Lipinski’s rule of five, making this compound a possible lead to design and develop potent COX inhibitors. The new compound, in comparison with its cinnamic acid precursor (E)-(3-(4-((4-bromobenzyl)oxy)phenyl)acrylic acid, showed improved biological activities. Compound ethyl (E)-(3-(4-((4-bromobenzyl)oxy)phenyl)acryloyl)glycinate can be used as a lead for the synthesis of more effective hybrids. Full article

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Scheme 1

4 pages, 871 KiB

Open AccessShort Note

6,10-Dichloro-1-oxa-4,8-dithia-7,9-diazaspiro[4.5]deca-6,9-diene

by Andreas S. Kalogirou and Panayiotis A. Koutentis

Molbank 2022, 2022(2), M1377; https://doi.org/10.3390/M1377 - 03 Jun 2022

Viewed by 1370

Abstract

Reaction of 3,4,4,5-tetrachloro-4H-1,2,6-thiadiazine with 2-mercaptoethan-1-ol (1 equiv.) gave 6,10-dichloro-1-oxa-4,8-dithia-7,9-diazaspiro[4.5]deca-6,9-diene in 12% yield. The compound was fully characterized. Full article

(This article belongs to the Section Organic Synthesis)

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Figure 1

6 pages, 1095 KiB

Open AccessShort Note

N-(2-Benzoyl-4,5-dimethoxyphenethyl)-2-phenylacetamide

by Petja Marinova, Stoyanka Nikolova, Anna Dołęga and Anife Ahmedova

Molbank 2022, 2022(2), M1376; https://doi.org/10.3390/M1376 - 01 Jun 2022

Cited by 1 | Viewed by 1378

Abstract

The crystal structure of N-(2-benzoyl-4,5-dimethoxyphenethyl)-2-phenylacetamide indicates that the compound crystallizes in the monoclinic C2/c space group with eight molecules in the unit cell. The heteroatoms from the amide group form a chain of intermolecular N-H ··· O hydrogen bonds propagating [...] Read more.

The crystal structure of N-(2-benzoyl-4,5-dimethoxyphenethyl)-2-phenylacetamide indicates that the compound crystallizes in the monoclinic C2/c space group with eight molecules in the unit cell. The heteroatoms from the amide group form a chain of intermolecular N-H ··· O hydrogen bonds propagating along the b axis. The carbonyl group from the benzoyl substituent participates in short contacts with two H-atoms from the ethyl or phenyl groups. Full article

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Graphical abstract

4 pages, 814 KiB

Open AccessShort Note

(E)-3-[4-(1H-Imidazol-1-yl)phenyl]-1-(3-chloro-4-fluorophenyl)prop-2-en-1-one

by Reina Takaki and Bradley O. Ashburn

Molbank 2022, 2022(2), M1375; https://doi.org/10.3390/M1375 - 01 Jun 2022

Viewed by 3041

Abstract

Imidazole-containing chalcones have been shown to be effective against Aspergillus fumigatus, the pathogenic agent for pulmonary aspergillosis. Claisen-Schmidt condensation of 4-(1H-imidazol-1-yl)benzaldehyde with 3′-chloro-4′-fluoroacetophenone using aqueous sodium hydroxide in methanol yielded the novel compound (E)-3-[4-(1H-imidazol-1-yl)phenyl]-1-(3-chloro-4-fluorophenyl)prop-2-en-1-one in good [...] Read more.

Imidazole-containing chalcones have been shown to be effective against Aspergillus fumigatus, the pathogenic agent for pulmonary aspergillosis. Claisen-Schmidt condensation of 4-(1H-imidazol-1-yl)benzaldehyde with 3′-chloro-4′-fluoroacetophenone using aqueous sodium hydroxide in methanol yielded the novel compound (E)-3-[4-(1H-imidazol-1-yl)phenyl]-1-(3-chloro-4-fluorophenyl)prop-2-en-1-one in good purity after purification by silica gel column chromatography. This novel compound is suitable for testing the antifungal properties of the combined pharmacophores against Aspergillus and other pathogenic fungi. Full article

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Graphical abstract

5 pages, 1149 KiB

Open AccessCommunication

Synthesis and Structure Determination of 1-(4-Methoxyphenyl)-5-methyl-N’-(2-oxoindolin-3-ylidene)-1H-1,2,3-triazole-4-carbohydrazide

by Benson M. Kariuki, Bakr F. Abdel-Wahab, Abdelbasset A. Farahat and Gamal A. El-Hiti

Molbank 2022, 2022(2), M1374; https://doi.org/10.3390/M1374 - 31 May 2022

Cited by 5 | Viewed by 1829

Abstract

A reaction of equimolar equivalents of 1-(4-methoxyphenyl)-5-methyl-1H-1,2,3-triazole-4-carbohydrazide (1) and indoline-2,3-dione (2) in boiling ethanol for 4 h under acidic conditions gave 1-(4-methoxyphenyl)-5-methyl-N’-(2-oxoindolin-3-ylidene)-1H-1,2,3-triazole-4-carbohydrazide (3) in 88% yield. The structure of 3 was ascertained by NMR spectroscopy and single-crystal X-ray diffraction. Full article

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Figure 1

4 pages, 304 KiB

Open AccessCommunication

A Convenient Synthesis towards 2-Bromo-2-(methoxy(phenyl)methyl)malononitrile and 2-Iodo-2-(methoxy(phenyl)methyl)malononitrile

by Jialuo Chen, Lili Duan, Kunming Liu and Jin-Biao Liu

Molbank 2022, 2022(2), M1373; https://doi.org/10.3390/M1373 - 30 May 2022

Viewed by 1640

Abstract

This short note elaborates a concise protocol for the synthesis of two novel vicinal haloethers bearing a malonontrile group, 2-bromo-2-(methoxy(phenyl)methyl)malononitrile (1) and 2-iodo-2-(methoxy(phenyl)methyl)malononitrile (2). The structures of the synthesized compounds were confirmed by 1H, 13C-NMR spectroscopy. The final products indicate that methanol not [...] Read more.

This short note elaborates a concise protocol for the synthesis of two novel vicinal haloethers bearing a malonontrile group, 2-bromo-2-(methoxy(phenyl)methyl)malononitrile (1) and 2-iodo-2-(methoxy(phenyl)methyl)malononitrile (2). The structures of the synthesized compounds were confirmed by 1H, 13C-NMR spectroscopy. The final products indicate that methanol not only acts as solvent but also participates in and dominates the reaction result. Full article

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Scheme 1

5 pages, 1738 KiB

Open AccessCommunication

Synthesis and Structure Determination of 2-Cyano-3-(1-phenyl-3-(thiophen-2-yl)-1H-pyrazol-4-yl)acrylamide

by Benson M. Kariuki, Bakr F. Abdel-Wahab, Hanan A. Mohamed and Gamal A. El-Hiti

Molbank 2022, 2022(2), M1372; https://doi.org/10.3390/M1372 - 30 May 2022

Cited by 2 | Viewed by 1457

Abstract

2-Cyano-3-(1-phenyl-3-(thiophen-2-yl)-1H-pyrazol-4-yl)acrylamide (3) was synthesized in 90% yield from condensation of equimolar equivalents of 1-phenyl-3-(thiophen-2-yl)-1H-pyrazole-4-carbaldehyde (1) and 2-cyanoacetamide (2) in boiling ethanol under basic condition for 45 min. The structure of 3 was determined using NMR spectroscopy and single crystal X-ray diffraction. Full article

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Graphical abstract

3 pages, 392 KiB

Open AccessShort Note

5,5′-Thiobis(4-chloro-3H-1,2-dithiole-3-thione)

by Vladimir A. Ogurtsov and Oleg A. Rakitin

Molbank 2022, 2022(2), M1371; https://doi.org/10.3390/M1371 - 27 May 2022

Cited by 1 | Viewed by 1238

Abstract

3H-1,2-Dithiole-3-thiones are important compounds with many types of significant pharmacological activity. Although many derivatives of this class have been described in the literature, their thioethers have not previously been obtained. In this communication, it is shown that the reaction of 4,5-dichloro-3 [...] Read more.

3H-1,2-Dithiole-3-thiones are important compounds with many types of significant pharmacological activity. Although many derivatives of this class have been described in the literature, their thioethers have not previously been obtained. In this communication, it is shown that the reaction of 4,5-dichloro-3H-1,2-dithiole-3-thione with potassium isocyanate unexpectedly gave 5,5′-thiobis(4-chloro-3H-1,2-dithiole-3-thione). The structure of the synthesized compound was established by elemental analysis, high-resolution mass spectrometry, ¹³C NMR and IR spectroscopy, and mass spectrometry. Full article

(This article belongs to the Special Issue Heteroatom Rich Organic Heterocycles)

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Scheme 1

5 pages, 571 KiB

Open AccessShort Note

3′-[4-({[3β,28-Bis(acetyloxy)lup-20(29)-en-30-yl]oxy}carbonyl)-1H-1,2,3-triazol-1-yl]-3′-deoxythymidine

by Ewa Bębenek, Monika Kadela-Tomanek, Elwira Chrobak and Małgorzata Latocha

Molbank 2022, 2022(2), M1370; https://doi.org/10.3390/M1370 - 26 May 2022

Cited by 1 | Viewed by 1496

Abstract

The reaction of the azidothymidine (AZT) with the 30-propynoylated derivative of 3,28-O,O′-diacetylbetulin gave a 1,4-disubstituted 1,2,3-triazole. The chemical structure of new derivative was characterized by ¹H NMR, ¹³C NMR and HR-MS. The triterpene-AZT conjugate was tested against [...] Read more.

The reaction of the azidothymidine (AZT) with the 30-propynoylated derivative of 3,28-O,O′-diacetylbetulin gave a 1,4-disubstituted 1,2,3-triazole. The chemical structure of new derivative was characterized by ¹H NMR, ¹³C NMR and HR-MS. The triterpene-AZT conjugate was tested against a human cancer cell lines such as glioblastoma (SNB-19), amelanotic melanoma (C-32), ovarian adenocarcinoma (SKOV-3) and breast cancer (T47D, and MCF-7). 3′-[4-({[3β,28-Bis(acetyloxy)lup-20(29)-en-30-yl]oxy}carbonyl)-1H-1,2,3-triazol-1-yl]-3′-deoxythymidine shown significant activity against MCF-7 cells, with an IC₅₀ value of 4.37 µM. Full article

(This article belongs to the Section Organic Synthesis)

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5 pages, 1689 KiB

Open AccessShort Note

Diethyl 2,5-Dihydroxy-3,6-diiodoterephthalate

by R. Alan Aitken, Niti Schindler and Alexandra M. Z. Slawin

Molbank 2022, 2022(2), M1369; https://doi.org/10.3390/M1369 - 23 May 2022

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Abstract

The title compound has been characterised for the first time by the full range of spectroscopic methods, and its X-ray structure shows hydrogen bonded stacks with iodine atoms aligned. Full article

(This article belongs to the Section Structure Determination)

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4 pages, 411 KiB

Open AccessShort Note

(E)-4-(2-(7-Bromo-[1,2,5]thiadiazolo[3,4-c]pyridin-4-yl)vinyl)-N,N-diphenylaniline

by Timofey N. Chmovzh and Oleg A. Rakitin

Molbank 2022, 2022(2), M1368; https://doi.org/10.3390/M1368 - 19 May 2022

Cited by 1 | Viewed by 1460

Abstract

(Diphenylamino)phenylethenyl group-containing chromophores are widely employed to design effective materials with useful electronic properties. In this communication, (E)-4-(2-(7-Bromo-[1,2,5]thiadiazolo[3,4-c]pyridin-4-yl)vinyl)-N,N-diphenylaniline was regioselectively obtained by the Heck reaction of 4,7-dibromo-[1,2,5]thiadiazolo[3,4-c]pyridine with N,N-diphenyl-4-vinylaniline. The [...] Read more.

(Diphenylamino)phenylethenyl group-containing chromophores are widely employed to design effective materials with useful electronic properties. In this communication, (E)-4-(2-(7-Bromo-[1,2,5]thiadiazolo[3,4-c]pyridin-4-yl)vinyl)-N,N-diphenylaniline was regioselectively obtained by the Heck reaction of 4,7-dibromo-[1,2,5]thiadiazolo[3,4-c]pyridine with N,N-diphenyl-4-vinylaniline. The structure of the newly synthesized compound was established by means of elemental analysis, high resolution mass-spectrometry, ¹H, ¹³C, NOESY NMR, IR and UV spectroscopy and mass-spectrometry. Full article

(This article belongs to the Special Issue Heteroatom Rich Organic Heterocycles)

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11 pages, 2026 KiB

Open AccessCommunication

Solution Equilibria Formation of Manganese(II) Complexes with Ethylenediamine, 1,3-Propanediamine and 1,4-ButanediaMine in Methanol

by José J. N. Segoviano-Garfias, Gabriela A. Zanor and Fidel Ávila-Ramos

Molbank 2022, 2022(2), M1367; https://doi.org/10.3390/M1367 - 18 May 2022

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Abstract

Manganese is an abundant element that plays critical roles and is at the reaction center of several enzymes. In order to promote an understanding of the behavior of manganese(II) ion with several aliphatic ligands, in this work, the stability and spectral behavior of [...] Read more.

Manganese is an abundant element that plays critical roles and is at the reaction center of several enzymes. In order to promote an understanding of the behavior of manganese(II) ion with several aliphatic ligands, in this work, the stability and spectral behavior of the complexes with manganese(II) and ethylenediamine, 1,3-propanediamine or 1,4-butanediamine were explored. A spectrophotometric study of its speciation in methanol was performed at 293 K. The formation constants obtained for these systems were: manganese(II)-ethylenediamine log β₁₁₀ = 3.98 and log β₁₂₀ = 7.51; for the manganese(II)-1,3-propanediamine log β₁₁₀ = 5.08 and log β₁₂₀ = 8.66; and for manganese(II)-1,4-butanediamine log β₁₁₀ = 4.36 and log β₁₂₀ = 8.46. These results were obtained by fitting the experimental spectrophotometric data using the HypSpec software. The complexes reported in this study show a spectral pattern that could be related to a chelate effect in which the molar absorbance is not directly related to the increase in the carbon chain of the ligands. Full article

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4 pages, 615 KiB

Open AccessShort Note

Tetraethylammonium tribromo(triphenylphosphine)nickelate(II)

by François Baril-Robert, Nicolas Bélanger-Desmarais and Christian Reber

Molbank 2022, 2022(2), M1366; https://doi.org/10.3390/M1366 - 18 May 2022

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Abstract

The crystal structure and vibrational spectra of the tetraethylammonium salt of tribromotriphylphosphinonickel(II) is reported. Br-Ni-Br angles vary between 108° and 121°, deviating from perfect tetrahedral angles. Full article

(This article belongs to the Section Structure Determination)

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6 pages, 974 KiB

Open AccessShort Note

2,4-Diamino-5-(nitromethyl)-5H-chromeno[2,3-b]pyridine-3-carbonitrile

by Yuliya E. Ryzhkova, Fedor V. Ryzhkov, Oleg I. Maslov and Michail N. Elinson

Molbank 2022, 2022(2), M1365; https://doi.org/10.3390/M1365 - 18 May 2022

Cited by 2 | Viewed by 1664

Abstract

Dimethyl sulfoxide (DMSO) is a cheap polar aprotic solvent used in organic synthesis and in pharmacology because of its low cost, high stability, and non-toxicity. Multicomponent reactions (MCRs) are highly convergent processes and have good atom, step, and pot economies. In this communication, [...] Read more.

Dimethyl sulfoxide (DMSO) is a cheap polar aprotic solvent used in organic synthesis and in pharmacology because of its low cost, high stability, and non-toxicity. Multicomponent reactions (MCRs) are highly convergent processes and have good atom, step, and pot economies. In this communication, the multicomponent transformation of salicylaldehyde, malononitrile dimer, and nitromethane in DMSO at room temperature was investigated to give 2,4-diamino-5-(nitromethyl)-5H-chromeno[2,3-b]pyridine-3-carbonitrile in good yield. The structure of the earlier unknown compound was confirmed by means of elemental analysis, mass-, nuclear magnetic resonance, and infrared spectroscopy. Full article

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15 pages, 3362 KiB

Open AccessCommunication

Microwave Assisted Synthesis, Crystal Structure and Hirshfeld Surface Analysis of Some 2-Formimidate-3-carbonitrile Derivatives Bearing 4H-Pyran and Dihydropyridine Moieties

by Sizwe J. Zamisa and Bernard Omondi

Molbank 2022, 2022(2), M1364; https://doi.org/10.3390/M1364 - 16 May 2022

Cited by 1 | Viewed by 1922

Abstract

Two 4H-pyran- and four dihydropyridine-based 2-formimidate-3-carbonitrile derivatives were synthesized via the conventional solvothermal and microwave radiation methods. The use of the latter technique led to the formation of the desired products in the order of minutes as compared to the former. The formation [...] Read more.

Two 4H-pyran- and four dihydropyridine-based 2-formimidate-3-carbonitrile derivatives were synthesized via the conventional solvothermal and microwave radiation methods. The use of the latter technique led to the formation of the desired products in the order of minutes as compared to the former. The formation of the 2-formimidate-3-carbonitrile derivatives was confirmed using spectroscopic techniques whilst the molecular geometry and intermolecular interactions were investigated using single-crystal X-ray diffraction. The formimidate functional group was found to adopt an E configuration in all compounds and this coincides with those of closely related compounds on the Cambridge Structural Database (CSD). Classical but weak intermolecular C—H…O, C—H…N and C—H…π hydrogen bonds were observed in the crystal lattice. According to the Hirshfeld surface analysis, the C—H…π hydrogen bonds contributed the most towards the Hirshfeld surface (14.3–23.9%) than the other two hydrogen bonding types (9.6–12.7%). Full article

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8 pages, 844 KiB

Open AccessCommunication

Probing Adamantane Arylhydroxamic Acids against Trypanosoma brucei and Trypanosoma cruzi

by Angeliki Sofia Foscolos, Andrew Tsotinis, Martin C. Taylor, John M. Kelly and Ioannis P. Papanastasiou

Molbank 2022, 2022(2), M1363; https://doi.org/10.3390/M1363 - 15 May 2022

Viewed by 1686

Abstract

In this work, we present the synthesis and the anti-trypanosomal activity of the 2-(4-(adamant-1-yl)phenyl)-N-hydroxyarylamides, 1a,b and the 2-(4-(adamant-1-yl)phenoxy)-N-hydroxyacetamide, 1c. The 4-(adamant-1-yl)phenyl- and 4-(adamant-1-yl)phenoxy- moieties, which are endowed with promising drug-like properties, are functionalized at the side [...] Read more.

In this work, we present the synthesis and the anti-trypanosomal activity of the 2-(4-(adamant-1-yl)phenyl)-N-hydroxyarylamides, 1a,b and the 2-(4-(adamant-1-yl)phenoxy)-N-hydroxyacetamide, 1c. The 4-(adamant-1-yl)phenyl- and 4-(adamant-1-yl)phenoxy- moieties, which are endowed with promising drug-like properties, are functionalized at the side chain termini as hydroxamic acids. The phenoxy acetohydroxamic derivative, 1c, shows the most interesting profile in terms of activity and toxicity against trypanosomes and merits further investigation. Full article

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Molbank, Volume 2022, Issue 2 (June 2022) – 38 articles

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