Molbank

Open AccessCommunication

Synthesis and Ring-Chain Tautomerism of 1-(4-Ethoxyphenyl)-5-formyl-1H-1,2,3-triazole-4-carboxylic Acid: The First Representative of a 5-Formyl-1H-1,2,3-triazole-4-carboxylic Acids Series

by

Nazariy T. Pokhodylo

and

Mykola D. Obushak

Molbank 2022, 2022(3), M1397; https://doi.org/10.3390/M1397 - 28 Jun 2022

Abstract

Synthesis of the first representative of a 5-formyl-1H-1,2,3-triazole-4-carboxylic acids series – 1-(4-ethoxyphenyl)-5-formyl-1H-1,2,3-triazole-4-carboxylic acid was performed. The 1-azido-4-ethoxybenzene was chosen as a starting reagent in a two-step synthesis, which reacted with the ethyl 4,4-diethoxy-3-oxobutanoate under base catalysis to form ethyl [...] Read more.

Synthesis of the first representative of a 5-formyl-1H-1,2,3-triazole-4-carboxylic acids series – 1-(4-ethoxyphenyl)-5-formyl-1H-1,2,3-triazole-4-carboxylic acid was performed. The 1-azido-4-ethoxybenzene was chosen as a starting reagent in a two-step synthesis, which reacted with the ethyl 4,4-diethoxy-3-oxobutanoate under base catalysis to form ethyl 5-(diethoxymethyl)-1-(4-ethoxyphenyl)-1H-1,2,3-triazole-4-carboxylate with protected formyl and acid groups. By the subsequent saponification of the ester group and removing of acetal protection, the target 1-(4-ethoxyphenyl)-5-formyl-1H-1,2,3-triazole-4-carboxylic acid was obtained. It has been found that the free acid form predominated in the solution under its cyclic 6-hydroxy-1,6-dihydro-4H-furo[3,4-d][1,2,3]triazol-4-one tautomer. According to ¹H NMR, cyclic hemiacetal is about 20%. Full article

(This article belongs to the Section Organic Synthesis)

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Graphical abstract

Open AccessShort Note

1,1′-{[3,5-Bis(dodecyloxycarbonyl)-4-(naphthalen-2-yl)-1,4-dihydropyridine-2,6-diyl]bis(methylene)}bis{4-[(E)-2-(naphthalen-2-yl)vinyl]pyridin-1-ium}dibromide

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Molbank 2022, 2022(3), M1396; https://doi.org/10.3390/M1396 - 27 Jun 2022

Abstract

Synthesis of a double-charged cationic amphiphilic 1,4-dihydropyridine derivative with dodecyl ester groups at positions 3 and 5 of the 1,4-DHP ring was performed starting from Hantzsch type cyclization of dodecyl acetoacetate, 2-naphthaldehyde and ammonium acetate. Bromination of this compound followed by nucleophilic substitution [...] Read more.

Synthesis of a double-charged cationic amphiphilic 1,4-dihydropyridine derivative with dodecyl ester groups at positions 3 and 5 of the 1,4-DHP ring was performed starting from Hantzsch type cyclization of dodecyl acetoacetate, 2-naphthaldehyde and ammonium acetate. Bromination of this compound followed by nucleophilic substitution of bromine with (E)-4-(2-(naphthalen-2-yl)vinyl)pyridine gave the desired cationic amphiphilic 1,1′-{[3,5-bis(dodecyloxycarbonyl)-4-(naphthalen-2-yl)-1,4-dihydropyridine-2,6-diyl]bis(methylene)}bis{4-[(E)-2-(naphthalen-2-yl)vinyl]pyridin-1-ium}dibromide. The obtained target compound was fully characterized by IR, UV, ¹H-NMR, ¹³C-NMR, HRMS and microanalysis. The characterization of the cationic 1,4-DHP nanoparticles in an aqueous solution was performed by DLS measurements. The obtained results showed that the compound formed nanoparticles with an average diameter of around 300 nm, a PDI value of around 490 and a zeta-potential of around 20 mV for freshly prepared samples. However, after one week of storage at room temperature, an aggregation of nanoparticles was detected. Full article

(This article belongs to the Section Organic Synthesis)

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Scheme 1

Open AccessShort Note

N,N-Diethyl-3-methylbenzamide

by

María Albert-Soriano

and

Isidro M. Pastor

Molbank 2022, 2022(3), M1395; https://doi.org/10.3390/M1395 - 25 Jun 2022

Abstract

The development of new techniques for the preparation of organic compounds is important, with catalytic processes being key to this innovation. The development of copper-based metal-organic frameworks to promote oxidative couplings has allowed the synthesis of amides in a very effective manner. This [...] Read more.

The development of new techniques for the preparation of organic compounds is important, with catalytic processes being key to this innovation. The development of copper-based metal-organic frameworks to promote oxidative couplings has allowed the synthesis of amides in a very effective manner. This methodology has been successfully applied to the unique preparation of the bioactive compound N,N-diethyl-3-methylbenzamide, with excellent performance (>99% conversion and 95% yield of pure isolated product) on a preparative scale. The described procedure can be classified as an excellent synthesis (EcoScale) considering environmental and economic factors based on different “green metrics” (atom economy, reaction mass efficiency, materials recovery factor, stoichiometric factor, E-factor). Full article

(This article belongs to the Section Organic Synthesis)

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Figure 1

Open AccessShort Note

3-(2-Diisopropylaminoethyl)-5-(4-methoxybenzylidene)thiazolidine-2,4-dione

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Molbank 2022, 2022(3), M1394; https://doi.org/10.3390/M1394 - 24 Jun 2022

Abstract

Thiazolidine-2,4-dione core is widely used in the medicinal chemistry of different types of potential drug-like small molecules. In the present work, the synthesis of a novel non-condensed thiazolidine-2,4-dione-bearing derivative is reported by the two-step cost-effective approach including alkylation and Knoevenagel condensation. The structure [...] Read more.

Thiazolidine-2,4-dione core is widely used in the medicinal chemistry of different types of potential drug-like small molecules. In the present work, the synthesis of a novel non-condensed thiazolidine-2,4-dione-bearing derivative is reported by the two-step cost-effective approach including alkylation and Knoevenagel condensation. The structure of the synthesized 3-(2-diisopropylaminoethyl)-5-(4-methoxybenzylidene)thiazolidine-2,4-dione was determined and characterized using ¹H, ¹³C NMR, LC-MS spectra and the X-ray diffraction method. Full article

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Graphical abstract

Open AccessCommunication

One-Pot Synthesis of Push–Pull Butadienes from 1,3-Diethyl-2-thiobarbituric Acid and Propargylic Alcohols

by

Javier Francos

and

Victorio Cadierno

Molbank 2022, 2022(3), M1393; https://doi.org/10.3390/M1393 - 23 Jun 2022

Abstract

A new synthetic procedure for obtaining two previously reported donor-acceptor butadiene dyes, namely 5-(3,3-bis(4-methoxyphenyl)allylidene)-1,3-diethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione and 5-(3,3-bis(4-(dimethylamino)phenyl)allylidene)-1,3-diethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione, based on the InCl₃-catalyzed coupling 1,3-diethyl-2-thiobarbituric acid with 1,1-bis(4-methoxyphenyl)prop-2-yn-1-ol and 1,1-bis(4-(dimethylamino)phenyl)prop-2-yn-1-ol, respectively, is presented. The reactions, which [...] Read more.

A new synthetic procedure for obtaining two previously reported donor-acceptor butadiene dyes, namely 5-(3,3-bis(4-methoxyphenyl)allylidene)-1,3-diethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione and 5-(3,3-bis(4-(dimethylamino)phenyl)allylidene)-1,3-diethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione, based on the InCl₃-catalyzed coupling 1,3-diethyl-2-thiobarbituric acid with 1,1-bis(4-methoxyphenyl)prop-2-yn-1-ol and 1,1-bis(4-(dimethylamino)phenyl)prop-2-yn-1-ol, respectively, is presented. The reactions, which cleanly proceed in water under MW irradiation, involve the initial generation of the corresponding enals by Meyer-Schuster rearrangement of the alkynols and their subsequent Knoevenagel condensation with the 2-thiobarbituric acid derivative. By following the same approach, the novel butadiene 5-(3,3-bi([1,1′-biphenyl]-4-yl)allylidene)-1,3-diethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione, which was characterized by ¹H and ¹³C{¹H} NMR, IR, UV-Vis, elemental analysis and HRMS, was synthesized in 79% yield. Full article

(This article belongs to the Section Organic Synthesis)

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Figure 1

Open AccessCommunication

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

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

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

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

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

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

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

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

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

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

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

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

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

Open AccessCommunication

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

by

Angélica Salinas-Torres

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

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

Open AccessShort Note

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

by

Timofey N. Chmovzh

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Timofey A. Kudryashev

and

Oleg A. Rakitin

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

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

Open AccessCommunication

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

by

Ekaterina S. Spesivaya

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Ida A. Lupanova

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Dzhamilya N. Konshina

and

Valery V. Konshin

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

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

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

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

Open AccessShort Note

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

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

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

Open AccessShort Note

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

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

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

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

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Ilona Jonuškienė

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Kristina Kantminienė

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Zigmuntas Jonas Beresnevičius

and

Ingrida Tumosienė

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

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

Open AccessShort Note

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

by

Ioannis Fotopoulos

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George-Christos Papaioannou

and

Dimitra Hadjipavlou-Litina

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

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

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