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Molbank, Volume 2021, Issue 1 (March 2021) – 22 articles

Cover Story (view full-size image): Here, we describe the synthesis and characterization of N-(6-chloro-3-nitropyridin-2-yl)5-(1-methyl-1H-pyrazol-4-yl)isoquinolin-3-amine. This compound was designed as an irreversible inhibitor of the monopolar spindle 1 kinase (MPS1 or TTK), a promising anticancer target. MPS1 harbors a poorly conserved cysteine in the middle hinge region, which we aimed to address with a reactive warhead relying on nucleophilic aromatic substitution (SNAr) chemistry. While the title compound did not show the expected MPS1 inhibition, mid-nanomolar potency on the kinase p70S6Kβ (S6K2) was observed, offering a new starting point to target this under-investigated enzyme. View this paper.
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Short Note
5-(4-Fluorophenyl)-3-(naphthalen-1-yl)-1-phenyl-1H-pyrazole
Molbank 2021, 2021(1), M1197; https://0-doi-org.brum.beds.ac.uk/10.3390/M1197 - 10 Mar 2021
Viewed by 851
Abstract
A new fluorinated pyrazole, 5-(4-fluorophenyl)-3-(naphthalen-1-yl)-1-phenyl-1H-pyrazole was successfully synthesized via a two-step reaction. Firstly, the synthesis of pyrazoline was performed via one-pot three-component reaction under microwave irradiation. Secondly, the synthesis of pyrazole was performed via oxidative aromatization of pyrazoline under conventional heating. [...] Read more.
A new fluorinated pyrazole, 5-(4-fluorophenyl)-3-(naphthalen-1-yl)-1-phenyl-1H-pyrazole was successfully synthesized via a two-step reaction. Firstly, the synthesis of pyrazoline was performed via one-pot three-component reaction under microwave irradiation. Secondly, the synthesis of pyrazole was performed via oxidative aromatization of pyrazoline under conventional heating. The structure of the synthesized compound was confirmed by spectroscopic analysis, including FT-IR, HR-MS, 1D and 2D NMR analysis. Then, molecular docking study showed that the binding affinity of the synthesized compound to human estrogen alpha receptor (ERα) was close to 4-OHT as a native ligand. Full article
(This article belongs to the Section Organic Synthesis)
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Short Note
3-(tert-Butyl)-N-(4-methoxybenzyl)-1-methyl-1H-pyrazol-5-amine
Molbank 2021, 2021(1), M1196; https://0-doi-org.brum.beds.ac.uk/10.3390/M1196 - 10 Mar 2021
Cited by 2 | Viewed by 604
Abstract
We reported an efficient one-pot two-step synthesis of 3-(tert-butyl)-N-(4-methoxybenzyl)-1-methyl-1H-pyrazol-5-amine 3 in good yield by a solvent-free condensation/reduction reaction sequence starting from 3-(tert-butyl)-1-methyl-1H-pyrazol-5-amine 1 and p-methoxybenzaldehyde 2. The one-pot reductive amination proceeded [...] Read more.
We reported an efficient one-pot two-step synthesis of 3-(tert-butyl)-N-(4-methoxybenzyl)-1-methyl-1H-pyrazol-5-amine 3 in good yield by a solvent-free condensation/reduction reaction sequence starting from 3-(tert-butyl)-1-methyl-1H-pyrazol-5-amine 1 and p-methoxybenzaldehyde 2. The one-pot reductive amination proceeded by the formation in situ of the N-(5-pyrazolyl)imine 4 as key synthetic intermediate of other valuable pyrazole derivatives. This methodology is distinguished by its operational easiness, short reaction time, isolation and purification of the aldimine intermediate is not required. The structure of the synthesized N-heterocyclic amine 3 was fully characterized by FTIR-ATR, 1D and 2D NMR experiments, EIMS, and elemental analysis. Full article
(This article belongs to the Special Issue Heterocycle Reactions)
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Short Note
(E)-4-(3-(3-(4-Methoxyphenyl)acryloyl)phenoxy)butyl 2-Hydroxybenzoate
Molbank 2021, 2021(1), M1195; https://0-doi-org.brum.beds.ac.uk/10.3390/M1195 - 09 Mar 2021
Viewed by 760
Abstract
A new hybrid compound of chalcone-salicylate (title compound) has been successfully synthesized using a linker mode approach under reflux condition. The structure of the title compound has been established by spectroscopic analysis including UV-Vis, FT-IR, HRMS, 1D, and 2D NMR. Then, computational approach [...] Read more.
A new hybrid compound of chalcone-salicylate (title compound) has been successfully synthesized using a linker mode approach under reflux condition. The structure of the title compound has been established by spectroscopic analysis including UV-Vis, FT-IR, HRMS, 1D, and 2D NMR. Then, computational approach was also applied in this study through molecular docking and MD simulation to explore its potency against breast cancer. The results of the molecular docking study showed that the title compound exhibited more negative value of binding free energy (−8.15 kcal/mol) than tamoxifen (−7.00 kcal/mol). In addition, no striking change in the positioning of the interacting residues was recorded before and after the MD simulations. Based on the studies, it can be predicted that the title compound has a cytotoxic activity potency against breast cancer through ERα inhibition and it presumably can be developed as anticancer agent candidate. Full article
(This article belongs to the Section Organic Synthesis)
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Communication
Synthesis of 1,5-Disubstituted Tetrazoles in Aqueous Micelles at Room Temperature
Molbank 2021, 2021(1), M1194; https://0-doi-org.brum.beds.ac.uk/10.3390/M1194 - 09 Mar 2021
Viewed by 481
Abstract
The ongoing study is a Ugi-azide four-component reaction for the synthesis of 1,5-disubstituted tetrazole(1,5-DST), which involves an aldehyde, different amines, isocyanides, and as azide’s source the Trimethylsilylazide (TMSN3), in water as solvent using as catalyst the tetradecyltrimethylammonium bromide (TTAB) with a [...] Read more.
The ongoing study is a Ugi-azide four-component reaction for the synthesis of 1,5-disubstituted tetrazole(1,5-DST), which involves an aldehyde, different amines, isocyanides, and as azide’s source the Trimethylsilylazide (TMSN3), in water as solvent using as catalyst the tetradecyltrimethylammonium bromide (TTAB) with a load of (10% mole), which provides a hydrophobic micellar reaction site. This approach is a step toward a green chemistry reaction of 1,5 disubstituted tetrazole. A serie of 1, 5- disubstituted tetrazole was synthesized by engaging a large substrate scope, leading to yields between 43% and 56%, which are compared afterwards with those obtained with methanol as solvent. The results were confirmed by HRMS, IR, and 1D NMR experiments. Full article
(This article belongs to the Special Issue Heterocycle Reactions)
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Short Note
(Z)-5-(3′,4′-Bis(benzyloxy)benzylidene)furan-2(5H)-one
Molbank 2021, 2021(1), M1193; https://0-doi-org.brum.beds.ac.uk/10.3390/M1193 - 28 Feb 2021
Cited by 1 | Viewed by 702
Abstract
Over the years secondary metabolites have been considered as lead molecules both in their natural form and as templates for medicinal chemistry. Some secondary metabolites such as polyphenols and flavan-3-ols exert beneficial effects after a modification by the microbiota. Synthetic precursors of some [...] Read more.
Over the years secondary metabolites have been considered as lead molecules both in their natural form and as templates for medicinal chemistry. Some secondary metabolites such as polyphenols and flavan-3-ols exert beneficial effects after a modification by the microbiota. Synthetic precursors of some of these modified compounds, in turn, carried a γ-alkylidenebutenolide moiety which characterizes a large class of bioactive natural products endowed with a wide range of biological activities. For these reasons stereoselective preparation of γ-alkylidenebutenolide continues to be an important issue for organic chemists. Our objective is to synthetize the novel compound (Z)-5-(3′,4′-bis(benzyloxy)benzylidene)furan-2(5H)-one in a stereocontrolled-one-pot reaction. The product was obtained in good yield. Furthermore, the theoretical investigation of the transition states suggests a new procedure to achieve Z-isomer of β-unsubstituted γ-alkylidenebutenolide. Full article
(This article belongs to the Special Issue Innovative Approaches to Modify Polyphenols)
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Short Note
Ethyl 1-Butyl-2-(2-hydroxy-4-methoxyphenyl)-1H-benzo[d]imidazole-5-carboxylate
Molbank 2021, 2021(1), M1192; https://0-doi-org.brum.beds.ac.uk/10.3390/M1192 - 24 Feb 2021
Viewed by 514
Abstract
Ethyl 4-(butylamino)-3-nitrobenzoate upon “one-pot” nitro-reductive cyclization using sodium dithionite and substituted aldehyde in dimethyl sulphoxide affords ethyl 1-butyl-2-(2-hydroxy-4-methoxyphenyl)-1H-benzo[d]imidazole-5-carboxylate in an 87% yield. The structural characterization was determined by Fourier-transfer infrared spectroscopy (FT-IR), Proton nuclear magnetic resonance (1H-NMR), [...] Read more.
Ethyl 4-(butylamino)-3-nitrobenzoate upon “one-pot” nitro-reductive cyclization using sodium dithionite and substituted aldehyde in dimethyl sulphoxide affords ethyl 1-butyl-2-(2-hydroxy-4-methoxyphenyl)-1H-benzo[d]imidazole-5-carboxylate in an 87% yield. The structural characterization was determined by Fourier-transfer infrared spectroscopy (FT-IR), Proton nuclear magnetic resonance (1H-NMR), Carbon-13 nuclear magnetic resonance (13C-NMR), mass spectrometry, Ultraviolet-visible(UV-Vis), photoluminescence (PL), thin-film solid emission spectra, cyclic voltammetry (CV) and thermogravimetric (TGA) analysis. Molecular electrostatic potential (MEP) was studied to determine the reactive sites of the molecule. Full article
(This article belongs to the Special Issue Heterocycle Reactions)
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Short Note
2-Amino-5-chloro-1H-pyrrole-3,4-dicarbonitrile
Molbank 2021, 2021(1), M1191; https://0-doi-org.brum.beds.ac.uk/10.3390/M1191 - 13 Feb 2021
Viewed by 946
Abstract
The reaction of tetracyanoethylene (TCNE) with HCl (g) in the presence of Sn (1 equiv) and AcOH resulted in 2-amino-5-chloro-1H-pyrrole-3,4-dicarbonitrile in a 74% yield. The compound was fully characterized. Full article
(This article belongs to the Special Issue Heterocycle Reactions)
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Short Note
4,5,6-Trichloropyrimidine-2-carboxamide
Molbank 2021, 2021(1), M1190; https://0-doi-org.brum.beds.ac.uk/10.3390/M1190 - 09 Feb 2021
Viewed by 690
Abstract
Reaction of 4,5,6-trichloropyrimidine-2-carbonitrile (1) with concentrated sulfuric acid at ca. 20 °C gave 4,5,6-trichloropyrimidine-2-carboxamide (5) in 91% yield. The new compound was fully characterized by IR, MALDI-TOF, NMR and elemental analysis. Full article
(This article belongs to the Section Organic Synthesis)
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Communication
Microwave-Assisted Synthesis of Schiff Bases of Isoniazid and Evaluation of Their Anti-Proliferative and Antibacterial Activities
Molbank 2021, 2021(1), M1189; https://0-doi-org.brum.beds.ac.uk/10.3390/M1189 - 04 Feb 2021
Viewed by 698
Abstract
Three new Schiff bases of isoniazid were synthesized using microwave-assisted synthesis and conventional condensation with aromatic aldehydes. Synthesized compounds were characterized using elemental analysis, IR, NMR, and Mass spectroscopy. Synthesized compounds were evaluated for antiproliferative activity against MCF-7 cell line. The IC50 [...] Read more.
Three new Schiff bases of isoniazid were synthesized using microwave-assisted synthesis and conventional condensation with aromatic aldehydes. Synthesized compounds were characterized using elemental analysis, IR, NMR, and Mass spectroscopy. Synthesized compounds were evaluated for antiproliferative activity against MCF-7 cell line. The IC50 values were from 125 to 276 µM. The compounds were also evaluated for antibacterial activity against Staphylococcus aureus and Escherichia coli. Results showed that the synthesized compounds produce significant antibacterial activity in vitro. Inhibition of compounds ranged from 13 to 18 mm. Full article
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Scheme 1

Communication
Oxygenated Analogues of Santacruzamate A
Molbank 2021, 2021(1), M1188; https://0-doi-org.brum.beds.ac.uk/10.3390/M1188 - 03 Feb 2021
Viewed by 626
Abstract
A new approach for the synthesis of Santacruzamate A analogues is demonstrated. The method allows functionalization at position 3 of the gamma-aminobutyric fragment and carbon chain variation. Full article
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Short Note
N-(2-(1H-Indol-3-yl)ethyl)-2-(6-methoxynaphthalen-2-yl)propanamide
Molbank 2021, 2021(1), M1187; https://0-doi-org.brum.beds.ac.uk/10.3390/M1187 - 31 Jan 2021
Viewed by 638
Abstract
The title compound was obtained in high yield in the reaction between tryptamine and naproxen. The newly synthesized naproxen derivative was fully analyzed and characterized via 1H, 13C-NMR, UV, IR, and mass spectral data. Full article
(This article belongs to the Section Structure Determination)
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Communication
Tetramethyl 1,1′-(2-[{4,5-bis(Methoxycarbonyl)-1H-1,2,3-triazol-1-yl}methyl]-2-[(4-methylphenyl)sulfonamido]propane-1,3-diyl)bis(1H-1,2,3-triazole-4,5-dicarboxylate)
Molbank 2021, 2021(1), M1186; https://0-doi-org.brum.beds.ac.uk/10.3390/M1186 - 31 Jan 2021
Viewed by 644
Abstract
A new compound tetramethyl 1,1′-(2-[{4,5-bis(methoxycarbonyl)-1H-1,2,3-triazol-1-yl}methyl]-2-[(4-methylphenyl)sulfonamido]propane-1,3-diyl)bis(1H-1,2,3-triazole-4,5-dicarboxylate) (3) was prepared in two steps starting from 2-((4-methylphenyl)sulfonamido)-2-((tosyloxy)methyl)propane-1,3-diylbis(4-methylbenzenesulfonate) (1), with an overall yield of 74%. The key step being the copper-free Huisgen cycloaddition between N [...] Read more.
A new compound tetramethyl 1,1′-(2-[{4,5-bis(methoxycarbonyl)-1H-1,2,3-triazol-1-yl}methyl]-2-[(4-methylphenyl)sulfonamido]propane-1,3-diyl)bis(1H-1,2,3-triazole-4,5-dicarboxylate) (3) was prepared in two steps starting from 2-((4-methylphenyl)sulfonamido)-2-((tosyloxy)methyl)propane-1,3-diylbis(4-methylbenzenesulfonate) (1), with an overall yield of 74%. The key step being the copper-free Huisgen cycloaddition between N-(1,3-diazido-2-(azidomethyl)propan-2-yl)-4-methylbenzenesulfonamide (2) and commercially available dimethyl acetylenedicarboxylate. The chemical structure of compound 3 was determined by IR, 1D and 2D NMR experiments, and elemental analysis. Full article
(This article belongs to the Special Issue Heterocycle Reactions)
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Editorial
Acknowledgment to Reviewers of Molbank in 2020
Molbank 2021, 2021(1), M1185; https://0-doi-org.brum.beds.ac.uk/10.3390/M1185 - 25 Jan 2021
Viewed by 638
Abstract
Peer review is the driving force of journal development, and reviewers are gatekeepers who ensure that Molbank maintains its standards for the high quality of its published papers [...] Full article
Short Note
(E)-3-(4-Chlorophenyl)-1-(2-fluoro-4-methoxyphenyl)-2-propen-1-one
Molbank 2021, 2021(1), M1184; https://0-doi-org.brum.beds.ac.uk/10.3390/M1184 - 25 Jan 2021
Viewed by 767
Abstract
Natural products known as chalcones show promise as chemotherapeutic agents for the neglected tropical disease known as leishmaniasis. Our objective is to synthesize new targets of opportunity that may lead to better treatments of this debilitating disease. Claisen-Schmidt condensation of 4-chlorobenzaldehyde with 2′-fluoro-4′-methoxyacetophenone [...] Read more.
Natural products known as chalcones show promise as chemotherapeutic agents for the neglected tropical disease known as leishmaniasis. Our objective is to synthesize new targets of opportunity that may lead to better treatments of this debilitating disease. Claisen-Schmidt condensation of 4-chlorobenzaldehyde with 2′-fluoro-4′-methoxyacetophenone using aqueous sodium hydroxide in ethanol yielded the novel compound (E)-3-(4-chlorophenyl)-1-(2-fluoro-4-methoxyphenyl)-2-propen-1-one. The product was obtained in good yield and purity after recrystallization from ethyl acetate/hexane. With the known antiparasitic properties of halogenated chalcones, this novel compound is suitable for antileishmanial activity study. Full article
(This article belongs to the Section Organic Synthesis)
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Short Note
4′-(5-N-Propylthiophen-2-yl)-2,2′:6′,2″-terpyridine
Molbank 2021, 2021(1), M1183; https://0-doi-org.brum.beds.ac.uk/10.3390/M1183 - 21 Jan 2021
Viewed by 696
Abstract
A new thiophene-substituted terpyridine derivative has been prepared through the reaction between 5-n-propylthiophene-2-carboxaldehyde and 2-acetylpyridine. This terpyridine derivative bears an alkyl chain linked via a thiophene heterocycle. Full article
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Short Note
Cis-Bis(2,2′-Azopyridinido)dicarbonylruthenium(II)
Molbank 2021, 2021(1), M1182; https://0-doi-org.brum.beds.ac.uk/10.3390/M1182 - 18 Jan 2021
Viewed by 577
Abstract
An [Ru(apy)2Cl2] precursor (apy = 2,2′-azopyridine) in 2-methoxyethanol was heated under a pressurized CO atmosphere to afford a diradical complex, [Ru(apy·)2(CO)2], containing one-electron-reduced azo anion radical ligands. The electronic states of the complex [...] Read more.
An [Ru(apy)2Cl2] precursor (apy = 2,2′-azopyridine) in 2-methoxyethanol was heated under a pressurized CO atmosphere to afford a diradical complex, [Ru(apy·)2(CO)2], containing one-electron-reduced azo anion radical ligands. The electronic states of the complex were characterized by spectroscopic techniques and computational studies. Magnetic measurements revealed the existence of antiferromagnetic interactions in the diradical complex. Full article
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Short Note
N-(6-Chloro-3-nitropyridin-2-yl)-5-(1-methyl-1H-pyrazol-4-yl)isoquinolin-3-amine
Molbank 2021, 2021(1), M1181; https://0-doi-org.brum.beds.ac.uk/10.3390/M1181 - 18 Jan 2021
Viewed by 964
Abstract
Here we describe the synthesis of N-(6-chloro-3-nitropyridin-2-yl)5-(1-methyl-1H-pyrazol-4-yl)isoquinolin-3-amine via a three-step procedure including a Buchwald–Hartwig arylamination with benzophenone imine and a highly regioselective nucleophilic aromatic substitution. The title compound was analyzed by nuclear magnetic resonance spectroscopy (1H, 13C, [...] Read more.
Here we describe the synthesis of N-(6-chloro-3-nitropyridin-2-yl)5-(1-methyl-1H-pyrazol-4-yl)isoquinolin-3-amine via a three-step procedure including a Buchwald–Hartwig arylamination with benzophenone imine and a highly regioselective nucleophilic aromatic substitution. The title compound was analyzed by nuclear magnetic resonance spectroscopy (1H, 13C, HSQC, HMBC, COSY, DEPT90 and NOESY), high resolution mass spectrometry (ESI-TOF-HRMS) and infrared spectroscopy (ATR-IR) and its structure was confirmed by single crystal X-ray diffraction. The inhibitory potency of the title compound was evaluated for selected kinases harboring a rare cysteine in the hinge region (MPS1, MAPKAPK2 and p70S6Kβ/S6K2). Full article
(This article belongs to the Special Issue Heterocycle Reactions)
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Communication
Unexpected Metal-Free Dehydrogenation of a β-Ketoester to a Phenol Using a Recyclable Oxoammonium Salt
Molbank 2021, 2021(1), M1180; https://0-doi-org.brum.beds.ac.uk/10.3390/M1180 - 13 Jan 2021
Cited by 1 | Viewed by 879
Abstract
The conversion of ethyl 2-oxocyclohexanecarboxylate to ethyl salicylate using an oxoammonium salt is reported. The dehydrogenation reaction is operationally simple and compares favorably with previous literature examples for the same transformation and expands the scope of oxoammonium salts as reagents for oxidative functionalization [...] Read more.
The conversion of ethyl 2-oxocyclohexanecarboxylate to ethyl salicylate using an oxoammonium salt is reported. The dehydrogenation reaction is operationally simple and compares favorably with previous literature examples for the same transformation and expands the scope of oxoammonium salts as reagents for oxidative functionalization processes. Full article
(This article belongs to the Special Issue Molecules from Side Reactions II)
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Communication
Synthesis and Structural Characterization of (E)-4-[(2-Hydroxy-3-methoxybenzylidene)amino]butanoic Acid and Its Novel Cu(II) Complex
Molbank 2021, 2021(1), M1179; https://0-doi-org.brum.beds.ac.uk/10.3390/M1179 - 06 Jan 2021
Viewed by 919
Abstract
A novel Cu(II) complex based on the Schiff base obtained by the condensation of ortho-vanillin with gamma-aminobutyric acid was synthesized. The compounds are physico-chemically characterized by elemental analysis, HR-ESI-MS, FT-IR, and UV-Vis. The complex and the Schiff base ligand are further [...] Read more.
A novel Cu(II) complex based on the Schiff base obtained by the condensation of ortho-vanillin with gamma-aminobutyric acid was synthesized. The compounds are physico-chemically characterized by elemental analysis, HR-ESI-MS, FT-IR, and UV-Vis. The complex and the Schiff base ligand are further structurally identified by single crystal X-ray diffraction and 1H and 13C-NMR, respectively. The results suggest that the Schiff base are synthesized in excellent yield under mild reaction conditions in the presence of glacial acetic acid and the crystal structure of its Cu(II) complex reflects an one-dimensional polymeric compound. The molecular structure of the complex consists of a Cu(II) ion bound to two singly deprotonated Schiff base bridging ligands that form a CuN2O4 chelation environment, and a coordination sphere with a disordered octahedral geometry. Full article
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Short Note
(S)-1-(Ethoxycarbonyl)ethyl(2R,5S)-2,5-dimethyl-1,3-dioxolan-4-one-2-carboxylate
Molbank 2021, 2021(1), M1178; https://0-doi-org.brum.beds.ac.uk/10.3390/M1178 - 02 Jan 2021
Viewed by 650
Abstract
The title compound was obtained in low yield in the condensation of ethyl pyruvate and lactic acid. Its structure is determined by NMR methods and x-ray diffraction and the mechanism for formation of this 1:2 adduct from the initial 1:1 adduct is considered. [...] Read more.
The title compound was obtained in low yield in the condensation of ethyl pyruvate and lactic acid. Its structure is determined by NMR methods and x-ray diffraction and the mechanism for formation of this 1:2 adduct from the initial 1:1 adduct is considered. Full article
(This article belongs to the Special Issue Heterocycle Reactions)
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Short Note
N-(2-(1H-Indol-3-yl)ethyl)-2-(2-fluoro-[1,1′-biphenyl]-4-yl)propanamide
Molbank 2021, 2021(1), M1177; https://0-doi-org.brum.beds.ac.uk/10.3390/M1177 - 31 Dec 2020
Viewed by 993
Abstract
N-(2-(1H-Indol-3-yl)ethyl)-2-(2-fluoro-[1,1′-biphenyl]-4-yl)propanamide was prepared by a reaction between tryptamine and flurbiprofen, applying N,N’-Dicyclohexylcarbodiimide, as a coupling agent. The obtained new amide has a fragment similar to Brequinar, a compound used in SARS-CoV-2 treatment trials. The newly synthesized [...] Read more.
N-(2-(1H-Indol-3-yl)ethyl)-2-(2-fluoro-[1,1′-biphenyl]-4-yl)propanamide was prepared by a reaction between tryptamine and flurbiprofen, applying N,N’-Dicyclohexylcarbodiimide, as a coupling agent. The obtained new amide has a fragment similar to Brequinar, a compound used in SARS-CoV-2 treatment trials. The newly synthesized compound was fully analyzed and characterized via 1H, 13C-NMR, UV, IR, and mass spectral data. Full article
(This article belongs to the Section Structure Determination)
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Short Note
Methyl (2E)-3-[3-Benzyl-2-(3-methoxy-3-oxoprop-1-yn-1-yl)-2-(1-naphthyl)imidazolidin-1-yl]acrylate
Molbank 2021, 2021(1), M1176; https://0-doi-org.brum.beds.ac.uk/10.3390/M1176 - 30 Dec 2020
Viewed by 671
Abstract
Compounds with propargylamine moiety are useful synthetic precursors of several important classes of nitrogen-containing heterocycles. The title compound, methyl (2E)-3-[3-benzyl-2-(3-methoxy-3-oxoprop-1-yn-1-yl)-2-(1-naphthyl)imidazolidine-1-yl]acrylate, has been prepared by domino-reaction, employing easily available 1-benzyl-2-(1-naphthyl)-4,5-dihydro-1H-imidazole and methyl propiolate in a high 92% yield. The structure [...] Read more.
Compounds with propargylamine moiety are useful synthetic precursors of several important classes of nitrogen-containing heterocycles. The title compound, methyl (2E)-3-[3-benzyl-2-(3-methoxy-3-oxoprop-1-yn-1-yl)-2-(1-naphthyl)imidazolidine-1-yl]acrylate, has been prepared by domino-reaction, employing easily available 1-benzyl-2-(1-naphthyl)-4,5-dihydro-1H-imidazole and methyl propiolate in a high 92% yield. The structure of title compound was determined using 1H-NMR, 13C-NMR, UV, FT-IR and HRMS (High-Resolution Mass Spectrometry). Full article
(This article belongs to the Special Issue Heterocycle Reactions)
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Scheme 1

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