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Molbank, Volume 2021, Issue 3 (September 2021) – 25 articles

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Short Note
4′,4′′′,4′′′′′-Nitrilotris(4-methoxy-[1,1′-biphenyl]-3-carbaldehyde)
Molbank 2021, 2021(3), M1263; https://doi.org/10.3390/M1263 - 31 Jul 2021
Viewed by 124
Abstract
Multipodal salicylaldehydes have attracted much scientific interest as scaffolds for the construction of multinuclear complexes, as well as metal and covalent organic frameworks. Herein, we report a preparation of 4′,4′′′,4′′′′′-nitrilotris(4-methoxy-[1,1′-biphenyl]-3-carbaldehyde), a direct precursor for the tripodal salicylaldehyde with triphenylamine core. The structure of [...] Read more.
Multipodal salicylaldehydes have attracted much scientific interest as scaffolds for the construction of multinuclear complexes, as well as metal and covalent organic frameworks. Herein, we report a preparation of 4′,4′′′,4′′′′′-nitrilotris(4-methoxy-[1,1′-biphenyl]-3-carbaldehyde), a direct precursor for the tripodal salicylaldehyde with triphenylamine core. The structure of the product was confirmed by molecular spectroscopy. The reported approach may be broadened over a variety of multipodal salicylaldehydes. Full article
(This article belongs to the Section Organic Synthesis)
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Short Note
1-Tosyl-6-vinyl-4,5,6,7-tetrahydro-1H-benzo [d] imidazole-2-amine
Molbank 2021, 2021(3), M1262; https://doi.org/10.3390/M1262 - 31 Jul 2021
Viewed by 125
Abstract
The alkene functionalised 2-aminobenzimidazole ring found in terrazoanthine natural products was synthesized in 3 steps from 1,2-epoxy-4-vinylcyclohexane via epoxide ring opening with toluenesulphonamide yielding 2 regioisomeric, separable amino alcohols. One isomer was oxidized to the corresponding ketone and subsequently condensed with cyanamide to [...] Read more.
The alkene functionalised 2-aminobenzimidazole ring found in terrazoanthine natural products was synthesized in 3 steps from 1,2-epoxy-4-vinylcyclohexane via epoxide ring opening with toluenesulphonamide yielding 2 regioisomeric, separable amino alcohols. One isomer was oxidized to the corresponding ketone and subsequently condensed with cyanamide to furnish the title compound, which was characterized by 1H-NMR and 13C-NMR spectroscopy. Full article
(This article belongs to the Section Organic Synthesis)
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Short Note
4,4′-Di-tert-butyl-2,2′-bipyridinium Trifluoromethanesulfonate
Molbank 2021, 2021(3), M1261; https://doi.org/10.3390/M1261 - 28 Jul 2021
Viewed by 204
Abstract
4,4′-di-tert-butyl-2,2′-bipyridinium trifluoromethanesulfonate was synthesized by stirring 4,4′-di-tert-butyl-2,2′-bipyridine with scandium(III) trifluoromethanesulfonate in acetonitrile, followed by precipitation with diethyl ether. The structure of the new compound was characterized by FT-IR, 1H, 13C{1H} and 19F{1H} [...] Read more.
4,4′-di-tert-butyl-2,2′-bipyridinium trifluoromethanesulfonate was synthesized by stirring 4,4′-di-tert-butyl-2,2′-bipyridine with scandium(III) trifluoromethanesulfonate in acetonitrile, followed by precipitation with diethyl ether. The structure of the new compound was characterized by FT-IR, 1H, 13C{1H} and 19F{1H} NMR spectroscopy and CHN elemental analysis. This is a safe and simple method to obtain mono-protonated bipyridinium trifluoromethanesulfonate without the direct use of trifluoromethanesulfonic acid. Full article
(This article belongs to the Section Organic Synthesis)
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Short Note
N-(Benzo[d]thiazol-2-yl)-2-(2-fluoro-[1,1′-biphenyl]-4-yl)propanamide
Molbank 2021, 2021(3), M1260; https://doi.org/10.3390/M1260 - 26 Jul 2021
Viewed by 272
Abstract
N-(Benzo[d]thiazol-2-yl)-2-(2-fluoro-[1,1′-biphenyl]-4-yl)propanamide was prepared by a reaction between benzo[d]thiazol-2-amine and flurbiprofen in high yield. The newly obtained flurbiprofen derivative was fully analyzed and characterized via 1H, 13C, UV, IR, and mass spectral data. Full article
(This article belongs to the Section Structure Determination)
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Short Note
Poly[3-methyl-1,3-oxazolidin-2-iminium[µ3-cyanido-tri-µ2-cyanido-κ9C:N-tricuprate(I)]]
Molbank 2021, 2021(3), M1259; https://doi.org/10.3390/M1259 - 26 Jul 2021
Viewed by 164
Abstract
The unexpected formation of an oxazole ring has occurred during synthesis of a copper(I) cyanide network polymer as part of our ongoing studies of the structural chemistry of these networks. Crystals of the title compound were formed during the synthesis of a previously [...] Read more.
The unexpected formation of an oxazole ring has occurred during synthesis of a copper(I) cyanide network polymer as part of our ongoing studies of the structural chemistry of these networks. Crystals of the title compound were formed during the synthesis of a previously reported CuCN network solid containing protonated N-methylethanolamine and have been characterized by single crystal X-ray structure analysis. The structure shows well-defined oxazole-2-iminium cations sitting in continuous channels along the short a-axis of the crystal in a new three-dimensional copper(I) cyanide polymeric network. Evidently, a reaction has occurred between the cyanide ion and the protonated N-methylethanolamine base. Full article
(This article belongs to the Special Issue Molecules from Side Reactions II)
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Communication
2-Hydroxy-5-(3,5,7-trihydroxy-4-oxo-4H-chromen-2-yl)phenyl (E)-3-(4-hydroxy-3-methoxyphenyl)acrylate: Synthesis, In Silico Analysis and In Vitro Pharmacological Evaluation
Molbank 2021, 2021(3), M1258; https://doi.org/10.3390/M1258 - 23 Jul 2021
Viewed by 252
Abstract
Quercetin and ferulic acid are two phytochemicals extensively represented in the plant kingdom and daily consumed in considerable amounts through diets. Due to a common phenolic structure, these two molecules share several pharmacological properties, e.g., antioxidant and free radical scavenging, anti-cancer, anti-inflammatory, anti-arrhythmic, [...] Read more.
Quercetin and ferulic acid are two phytochemicals extensively represented in the plant kingdom and daily consumed in considerable amounts through diets. Due to a common phenolic structure, these two molecules share several pharmacological properties, e.g., antioxidant and free radical scavenging, anti-cancer, anti-inflammatory, anti-arrhythmic, and vasorelaxant. The aim of the present work was the combination of the two molecules in a single chemical entity, conceivably endowed with more efficacious vasorelaxant activity. Preliminary in silico studies herein described suggested that the new hybrid compound bound spontaneously and with high affinity on the KCa1.1 channel. Thus, the synthesis of the 3′-ferulic ester derivative of quercetin was achieved and its structure confirmed by 1H- and 13C-NMR spectra, HSQC and HMBC experiments, mass spectrometry, and elementary analysis. The effect of the new hybrid compound on vascular KCa1.1 and CaV1.2 channels revealed a partial loss of the stimulatory activity that characterizes the parent compound quercetin. Therefore, further studies are necessary to identify a better strategy to improve the vascular properties of this flavonoid. Full article
(This article belongs to the Special Issue Innovative Approaches to Modify Polyphenols)
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Short Note
N-(2,2-Diphenylethyl)-2-(6-methoxynaphthalen-2-yl)propanamide
Molbank 2021, 2021(3), M1257; https://doi.org/10.3390/M1257 - 23 Jul 2021
Viewed by 278
Abstract
N-(2,2-Diphenylethyl)-2-(6-methoxynaphthalen-2-yl)propanamide was prepared by a reaction between 2,2-diphenylethan-1-amine and naproxen in high yield. The newly obtained naproxen derivative was fully analyzed and characterized via 1H, 13C, UV, IR, and mass spectral data. Full article
(This article belongs to the Section Structure Determination)
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Short Note
9a-Phenyl-2,3,3a,3b,9a,9b-hexahydro-4H-furo[3‘,2’:3,4]cyclobuta- [1,2-b]chromen-4-one: A Flavone-Based [2 + 2]-Photocycloadduct
Molbank 2021, 2021(3), M1256; https://doi.org/10.3390/M1256 - 23 Jul 2021
Viewed by 268
Abstract
The intermolecular [2 + 2]-photocycloaddition of the parent flavone molecule (4) as the triplet energy-accepting species and the electron-rich alkene 2, 3-dihydrofuran (5) was performed by visible-light-mediated triplet-sensitization with an iridium-based organometallic sensitizer. The reaction proceeds with high diastereo- [...] Read more.
The intermolecular [2 + 2]-photocycloaddition of the parent flavone molecule (4) as the triplet energy-accepting species and the electron-rich alkene 2, 3-dihydrofuran (5) was performed by visible-light-mediated triplet-sensitization with an iridium-based organometallic sensitizer. The reaction proceeds with high diastereo- and regioselectivity (>98:2 for the regiochemical orientation and with 95% d.s.). In contrast to numerous other ene/enone combinations that are described in the literature and were also performed by us, the reaction between 4 and 5 almost solely afforded the cis-syn-cis cyclobutane 6, whereas analogous conjugated six- and five-membered cycloalkenones preferentially react to cis-anti-cis cyclobutanes or a mixture of both diastereoisomers (e.g., for the cyclohexanone-derived example 9). Full article
(This article belongs to the Section Organic Synthesis)
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N,N-Bis(hexyl α-d-acetylmannosyl) Acrylamide
Molbank 2021, 2021(3), M1255; https://doi.org/10.3390/M1255 - 22 Jul 2021
Viewed by 194
Abstract
Glycosyl monomers for the assembly of multivalent ligands are typically synthesized using carbohydrates with biological functions and polymerizable functional groups such as acrylamide or styrene introduced into the carbohydrate aglycon, and monomers polymerized using a radical initiator. Herein, we report the acryloylation of [...] Read more.
Glycosyl monomers for the assembly of multivalent ligands are typically synthesized using carbohydrates with biological functions and polymerizable functional groups such as acrylamide or styrene introduced into the carbohydrate aglycon, and monomers polymerized using a radical initiator. Herein, we report the acryloylation of 6-aminohexyl α-d-mannoside and its conversion into the glycosyl monomer bearing an acrylamide group. The general acryloylation procedure afforded the desired N-hexyl α-d-acetylmannosyl acrylamide monomer as well as an unexpected compound with a close Rf value. The compounds were separated and analyzed by nuclear magnetic resonance spectroscopy and mass spectrometry, which revealed the unknown compound to be the bivalent N,N-bis(hexyl α-d-acetylmannosyl) acrylamide monomer, which contains two hexyl mannose units and one acrylamide group. To the best of our knowledge, this side reaction has not previously been disclosed, and may be useful for the construction of multivalent sugar ligands. Full article
(This article belongs to the Special Issue Molecules from Side Reactions II)
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Short Note
Thiophene-3-carbonyl Chloride
Molbank 2021, 2021(3), M1254; https://doi.org/10.3390/M1254 - 22 Jul 2021
Viewed by 224
Abstract
The X-ray structure of the title compound has been determined for the first time. It shows the ring flip disorder common among thiophene-3-carbonyl derivatives and the occurrence of this phenomenon in the structures of such compounds is discussed. Full article
(This article belongs to the Section Structure Determination)
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Short Note
4-Chloro-6-(chloromethyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidine
Molbank 2021, 2021(3), M1253; https://doi.org/10.3390/M1253 - 22 Jul 2021
Viewed by 178
Abstract
A novel 4-chloro-6-(chloromethyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidine was prepared by a rational and short two-step synthesis from commercially available ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate via 6-(chloromethyl)-1-methyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one. The structure of the synthesized compounds was established by elemental analysis, high-resolution mass-spectrometry, 1 [...] Read more.
A novel 4-chloro-6-(chloromethyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidine was prepared by a rational and short two-step synthesis from commercially available ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate via 6-(chloromethyl)-1-methyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one. The structure of the synthesized compounds was established by elemental analysis, high-resolution mass-spectrometry, 1H, 13C-NMR and IR spectroscopy and mass-spectrometry. 4-Chloro-6-(chloromethyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidine is a convenient intermediate for various disubstituted 1-methyl-1H-pyrazolo[3,4-d]pyrimidines, which may be of interest as substances with useful pharmacological properties. Full article
(This article belongs to the Section Organic Synthesis)
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Short Note
1-(4-Formyl-2,6-dimethoxyphenoxy)-4-chlorobut-2-yne
Molbank 2021, 2021(3), M1252; https://doi.org/10.3390/M1252 - 21 Jul 2021
Viewed by 213
Abstract
A reaction of biomass-derived aldehyde synringaldehyde and half an equivalent of 1,4-dichlorobut-2-yne was attempted in order to obtain a bis-aldehyde with an alkyne spacer. The reaction was carried out in a basic media to effect bis O-alkylation, as described in literature for [...] Read more.
A reaction of biomass-derived aldehyde synringaldehyde and half an equivalent of 1,4-dichlorobut-2-yne was attempted in order to obtain a bis-aldehyde with an alkyne spacer. The reaction was carried out in a basic media to effect bis O-alkylation, as described in literature for the preparation of structurally similar compounds. Nevertheless, only mono alkylation was observed. Full article
(This article belongs to the Section Organic Synthesis)
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Communication
Synthesis of Aminopropyltriethoxysilyl-Substituted Imines and Amides
Molbank 2021, 2021(3), M1251; https://doi.org/10.3390/M1251 - 18 Jul 2021
Viewed by 277
Abstract
A series of small molecules containing aminopropyltriethoxysilyl-substituted imines and amides were synthesized so that they could potentially be incorporated into self-assembled monolayers (SAMs) on metal oxide surfaces. Simple one-step imine preparations and two-step amide preparations are reported here. Full article
(This article belongs to the Section Organic Synthesis)
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Communication
Ambient-Temperature Synthesis of (E)-N-(3-(tert-Butyl)-1-methyl-1H-pyrazol-5-yl)-1-(pyridin-2-yl)methanimine
Molbank 2021, 2021(3), M1250; https://doi.org/10.3390/M1250 - 07 Jul 2021
Viewed by 446
Abstract
We report the ambient-temperature synthesis of novel (E)-N-(3-(tert-butyl)-1-methyl-1H-pyrazol-5-yl)-1-(pyridin-2-yl)methanamine 3 in 81% yield by a condensation reaction between 3-(tert-butyl)-1-methyl-1H-pyrazol-5-amine 1 and 2-pyridinecarboxaldehyde 2 in methanol using magnesium sulfate as a drying agent. [...] Read more.
We report the ambient-temperature synthesis of novel (E)-N-(3-(tert-butyl)-1-methyl-1H-pyrazol-5-yl)-1-(pyridin-2-yl)methanamine 3 in 81% yield by a condensation reaction between 3-(tert-butyl)-1-methyl-1H-pyrazol-5-amine 1 and 2-pyridinecarboxaldehyde 2 in methanol using magnesium sulfate as a drying agent. The N-pyrazolyl imine 3 was full characterized by IR, 1D, and 2D NMR spectroscopy, mass spectrometry, and elemental analysis. Full article
(This article belongs to the Special Issue Heterocycle Reactions)
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Communication
Pyridinium Pentachloridooxomolybdate(V), (PyH)2[MoOCl5], Revisited: Single-Crystal X-ray Structure Determination
Molbank 2021, 2021(3), M1249; https://doi.org/10.3390/M1249 - 06 Jul 2021
Viewed by 353
Abstract
(PyH)2[MoOCl5] was obtained in the form of emerald green crystals unintentionally from (PyH)5[MoOCl4(H2O)]3Cl2 in acetonitrile. (PyH)2[MoOCl5] has been used as a starting material in molybdenum(V) coordination [...] Read more.
(PyH)2[MoOCl5] was obtained in the form of emerald green crystals unintentionally from (PyH)5[MoOCl4(H2O)]3Cl2 in acetonitrile. (PyH)2[MoOCl5] has been used as a starting material in molybdenum(V) coordination chemistry for decades, yet its true identity has not been known until now. The X-ray structure analysis has undoubtedly confirmed the existence of this compound. The [MoOCl5]2− ion displays the usual structural characteristics of the mononuclear MoO3+-containing compounds. Full article
(This article belongs to the Section Structure Determination)
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Communication
Synthesis of the Guanidine Derivative: N-{[(7-(4,5-Dihydro-1H-imidazol-2-yl)-2-(p-tolyl)-6,7-dihydro-2H-imidazo[2,1-c][1,2,4]triazol-3(5H)-ylidene)amino](phenylamino)methylene}benzamide
Molbank 2021, 2021(3), M1246; https://doi.org/10.3390/M1246 - 06 Jul 2021
Viewed by 357
Abstract
The guanidine derivative N-{[(7-(4,5-dihydro-1H-imidazol-2-yl)-2-(p-tolyl)-6,7-dihydro-2H-imidazo[2,1-c][1,2,4]triazol-3(5H)-ylidene)amino](phenylamino)methylene}benzamide (3) has been obtained by the reaction of one measure of N-{[7-(4,5-dihydro-1H-imidazol-2-yl)-2-(p-tolyl)-6,7-dihydro-2H-imidazo[2,1-c][1,2,4]triazol-3(5H)-ylidene]carbamothioyl}benzamide (2) [...] Read more.
The guanidine derivative N-{[(7-(4,5-dihydro-1H-imidazol-2-yl)-2-(p-tolyl)-6,7-dihydro-2H-imidazo[2,1-c][1,2,4]triazol-3(5H)-ylidene)amino](phenylamino)methylene}benzamide (3) has been obtained by the reaction of one measure of N-{[7-(4,5-dihydro-1H-imidazol-2-yl)-2-(p-tolyl)-6,7-dihydro-2H-imidazo[2,1-c][1,2,4]triazol-3(5H)-ylidene]carbamothioyl}benzamide (2) with one measure of aniline in the presence of mercury(II) chloride and triethylamine in anhydrous dimethylformamide. The structure of product 3 was confirmed by 1H and 13C-NMR, infrared spectroscopy, and elemental analysis. Full article
(This article belongs to the Section Organic Synthesis)
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Short Note
(2,3-Dihydro-1H-indol-5-ylmethyl)amine
Molbank 2021, 2021(3), M1248; https://doi.org/10.3390/M1248 - 05 Jul 2021
Viewed by 312
Abstract
New (2,3-dihydro-1H-indol-5-ylmethyl)amine was synthesized from 2-((1-acetylindolin-5-yl)methyl)isoindoline-1,3-dione by simultaneous deprotection of phthalimide and acetyl groups. The structure of the newly synthesized compounds was established by elemental analysis, high resolution mass-spectrometry, 1H, 13C NMR and IR spectroscopy and mass-spectrometry. The resulting [...] Read more.
New (2,3-dihydro-1H-indol-5-ylmethyl)amine was synthesized from 2-((1-acetylindolin-5-yl)methyl)isoindoline-1,3-dione by simultaneous deprotection of phthalimide and acetyl groups. The structure of the newly synthesized compounds was established by elemental analysis, high resolution mass-spectrometry, 1H, 13C NMR and IR spectroscopy and mass-spectrometry. The resulting compound is a convenient intermediate for various disubstituted 1-(indolin-5-yl)methanamines, which may be of interest as substances with useful pharmacological properties. Full article
(This article belongs to the Special Issue Heterocycle Reactions)
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Short Note
tert-Butyl Bis(4′-(Hexyloxy)-[1,1′-biphenyl]-4-yl)carbamate
Molbank 2021, 2021(3), M1247; https://doi.org/10.3390/M1247 - 05 Jul 2021
Viewed by 320
Abstract
New donor building blocks, i.e., triarylamino derivatives, are of great interest for the production of organic photovoltaic materials. In this communication, bis(4′-(hexyloxy)-[1,1′-biphenyl]-4-yl)amine was synthesized in a two-step process via hydrolysis of its tert-butyl carbamate derivative. tert-Butyl bis(4′-(hexyloxy)-[1,1′-biphenyl]-4-yl)carbamate was obtained by Suzuki [...] Read more.
New donor building blocks, i.e., triarylamino derivatives, are of great interest for the production of organic photovoltaic materials. In this communication, bis(4′-(hexyloxy)-[1,1′-biphenyl]-4-yl)amine was synthesized in a two-step process via hydrolysis of its tert-butyl carbamate derivative. tert-Butyl bis(4′-(hexyloxy)-[1,1′-biphenyl]-4-yl)carbamate was obtained by Suzuki cross-coupling reaction of tert-butyl bis(4-bromophenyl)carbamate and (4-(hexyloxy)phenyl)boronic acid in the presence of tetrakis(triphenylphosphine)palladium(0). The structure of newly synthesized compounds was established by means of elemental analysis, high resolution mass-spectrometry, 1H, 13C-NMR, IR and UV spectroscopy and mass-spectrometry. Full article
(This article belongs to the Special Issue Metal-Catalyzed Synthesis)
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2-Hydroxy-3-(4-oxy(2,2,6,6-tetramethylpiperidin-1-oxyl)butoxy)benzaldehyde
Molbank 2021, 2021(3), M1245; https://doi.org/10.3390/M1245 - 03 Jul 2021
Viewed by 331
Abstract
Salen-type complexes with transition metals and corresponding polymers attract great scientific interest due to their high electrochemical properties and potential for use as part of next generation organic energy storage devices. Because of their good conductivity but relatively low capacity, energy-intensive additives such [...] Read more.
Salen-type complexes with transition metals and corresponding polymers attract great scientific interest due to their high electrochemical properties and potential for use as part of next generation organic energy storage devices. Because of their good conductivity but relatively low capacity, energy-intensive additives such as quinones or TEMPO fragments can significantly enhance the capacitive characteristics of the electrode materials. Herein, we report a preparation of precursor for a modified Salen-type complex, the substituted 2,3-Dihydroxybenzaldehyde by butoxy linkers with TEMPO fragment using alkylation reaction. The resulting product was characterized by the 1H and 13C, COSY, HMBC, HSQC nuclear magnetic resonance (NMR), ESI–high resolution mass spectrometry (ESI–HRMS), and Fourier-transform infrared spectroscopy (FTIR). The reported approach opens the way for easy modification of Salen-type complexes in order to increase their specific characteristics. Full article
(This article belongs to the Section Organic Synthesis)
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N-{2-[(3-Oxo-1,3-dihydro-2-benzofuran-1-yl)acetyl]phenyl}acetamide
Molbank 2021, 2021(3), M1244; https://doi.org/10.3390/M1244 - 02 Jul 2021
Viewed by 385
Abstract
With the aim of obtaining different derivatives belonging to the isoindolo[2,1-a]quinoline family, we have synthesized a novel N-{2-[(3-oxo-1,3-dihydro-2-benzofuran-1-yl)acetyl]phenyl}acetamide derivative by a Claisen–Smichdt-type condensation reaction in 75% yield. Full article
(This article belongs to the Special Issue Molecules from Side Reactions II)
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Communication
Unexpected Formation of 4-aryl-1-(Propane-2-ylidenehydrazono)-2,3-diazaspiro[5.5]undec-3-ene by the Reaction of Pyridazinethiones Derivatives with Hydrazine
Molbank 2021, 2021(3), M1243; https://doi.org/10.3390/M1243 - 02 Jul 2021
Viewed by 372
Abstract
After making a new series of spiro[cycloalkane]pyridazinones with high Fsp3 character available, the new target was to synthesize derivatives comprising nitrogen-containing heterocycles, such as triazolo or tetrazolo rings. The corresponding thioxo derivatives (1a,b) seemed to be good starting [...] Read more.
After making a new series of spiro[cycloalkane]pyridazinones with high Fsp3 character available, the new target was to synthesize derivatives comprising nitrogen-containing heterocycles, such as triazolo or tetrazolo rings. The corresponding thioxo derivatives (1a,b) seemed to be good starting materials for the synthesis of tetrazolo derivatives. The reaction of the pyridazinethiones (1a,b) with hydrazine surprisingly resulted in Schiff bases (3a,b) deriving from the reaction of hydrazones (2a,b) with acetone. Full article
(This article belongs to the Special Issue Molecules from Side Reactions II)
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2-(2-(Fluorosulfonyloxy)phenyl)benzoxazole
Molbank 2021, 2021(3), M1242; https://doi.org/10.3390/M1242 - 02 Jul 2021
Viewed by 390
Abstract
The fluorosulfate derivatives of benzoxazole attract attention since benzoxazole-based compounds have a wide range of biological activities, and the ability of the –SO2F group to react with various functional groups makes it possible to synthesize various new derivatives. The new 2-(2-(fluorosulfonyloxy)phenyl)benzoxazole [...] Read more.
The fluorosulfate derivatives of benzoxazole attract attention since benzoxazole-based compounds have a wide range of biological activities, and the ability of the –SO2F group to react with various functional groups makes it possible to synthesize various new derivatives. The new 2-(2-(fluorosulfonyloxy)phenyl)benzoxazole (2) has been synthesized by the SuFEx click reaction in a two-chamber reactor. Compound 2 is the first example of a benzoxazole derivative with a fluorosulfate-containing substituent at position two of the benzoxazole heterocycle. The anti-cancer potency of 2 was evaluated in silico using molecular docking. The docking results suggest that title compound 2 is of great interest for further studies as a possible anaplastic lymphoma kinase inhibitor. Full article
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(R,S)-2-{[4-(4-Methylphenyl)-5-phenyl-4H-1,2,4-triazol-3-yl]thio}-1-phenyl-1-ethanol
Molbank 2021, 2021(3), M1241; https://doi.org/10.3390/M1241 - 01 Jul 2021
Viewed by 349
Abstract
4-(4-Methylphenyl)-5-phenyl-4H-1,2,4-triazol-3-thiol (4) was alkylated to 2-{[4-(4-methylphenyl)-5-phenyl-4H-1,2,4-triazol-3-yl]thio}-1-phenylethan-1-one (5) in alkaline conditions using 2-bromo-1-phenylethanone. The alkylated compound (5) was reduced at the carbonyl group to the corresponding racemic secondary alcohol with an asymmetric carbon, ( [...] Read more.
4-(4-Methylphenyl)-5-phenyl-4H-1,2,4-triazol-3-thiol (4) was alkylated to 2-{[4-(4-methylphenyl)-5-phenyl-4H-1,2,4-triazol-3-yl]thio}-1-phenylethan-1-one (5) in alkaline conditions using 2-bromo-1-phenylethanone. The alkylated compound (5) was reduced at the carbonyl group to the corresponding racemic secondary alcohol with an asymmetric carbon, (R,S)-2-{[4-(4-methylphenyl)-5-phenyl-4H-1,2,4-triazol-3-yl]thio}-1-phenyl-1-ethanol (6). Both synthesized compounds, ketone (5) and secondary alcohol (6), are new and have not yet been reported in the literature. All the synthesized compounds were characterized by IR, 1D and 2D 1H-1H, 1H-13C and 1H-15N NMR spectroscopy and by elemental analysis. Full article
(This article belongs to the Section Organic Synthesis)
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(E)-5-Benzyl-7-(3,4-dimethoxybenzylidene)-3-(3,4-dimethoxyphenyl)-2-phenyl-3,3a,4,5,6,7-hexahydro-2H-pyrazolo[4,3c] Pyridine
Molbank 2021, 2021(3), M1240; https://doi.org/10.3390/M1240 - 01 Jul 2021
Viewed by 375
Abstract
A new pyrazolo-pyridine analogue (title compound) was synthesized in two steps. The first stage was synthesis of monoketone curcumin analogue through Claisen–Schmidt reaction. The second stage was synthesis of the title compound through intermolecular cyclization under reflux condition. The structure of the title [...] Read more.
A new pyrazolo-pyridine analogue (title compound) was synthesized in two steps. The first stage was synthesis of monoketone curcumin analogue through Claisen–Schmidt reaction. The second stage was synthesis of the title compound through intermolecular cyclization under reflux condition. The structure of the title compound has been confirmed by spectroscopic analysis including UV, FT-IR, HRMS, 1D NMR (1H-NMR, 13C-NMR, 1D-TOCSY), and 2D NMR (COSY, HSQC, HMBC). Based on the DPPH assay, the compound has moderate antioxidant activity, with an IC50 value of 194.06 ± 7.88 µg/mL (0.337 mM). Full article
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Short Note
2-((4-((E)-1-(Hydroxyimino)ethyl)phenyl)amino)-2-oxoethyl Cinnamate
Molbank 2021, 2021(3), M1239; https://doi.org/10.3390/M1239 - 25 Jun 2021
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Abstract
Cinnamic acid-nitric oxide (NO) donor hybrids have attracted attention, in recent years, as new pharmacological agents to treat multifactorial diseases. In the present study, hybrid oxime 5 was synthesized and its anti-lipid peroxidation and anti-lipoxygenase activities were evaluated. The new compound showed remarkable [...] Read more.
Cinnamic acid-nitric oxide (NO) donor hybrids have attracted attention, in recent years, as new pharmacological agents to treat multifactorial diseases. In the present study, hybrid oxime 5 was synthesized and its anti-lipid peroxidation and anti-lipoxygenase activities were evaluated. The new compound showed remarkable anti-LOX activity, while its antioxidant activity was quite good in comparison to the appropriate reference compounds. The examined derivative seems to be orally active in accordance to Lipinski’s rule of five. Compound 5 can be considered as a leading structure for the design and synthesis of new hybrids. Full article
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Scheme 1

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