fahimeh abedinifar | University of Tehran (original) (raw)

Papers by fahimeh abedinifar

Research paper thumbnail of Synthesis and biological evaluation of a new series of benzofuran‐1,3,4‐oxadiazole containing 1,2,3‐triazole‐acetamides as potential α‐glucosidase inhibitors

Journal of Biochemical and Molecular Toxicology, Dec 28, 2020

This study demonstrates the use of new compound N5 with potential characteristics for the develop... more This study demonstrates the use of new compound N5 with potential characteristics for the development of drugs combining coagulant and platelet activities.

Research paper thumbnail of Hybridization of the effective pharmacophores for treatment of epilepsy: design, synthesis, in vivo anticonvulsant activity, and in silico studies of phenoxyphenyl-1,3,4-oxadiazole-thio-N-phenylacetamid hybrids

BMC chemistry, Jul 17, 2023

Background Epilepsy is a common neurological disorder. The available drugs for this disease only ... more Background Epilepsy is a common neurological disorder. The available drugs for this disease only control convulsions in nearly 70% of patients, while bearing many side effects. In this study, a new series of phenoxyphenyl-1,3,4-oxadiazolethio-N-phenylacetamid hybrids 8a-m was designed, synthesized, and evaluated as potent anticonvulsant agents. Methods Phenoxyphenyl-1,3,4-oxadiazole-thio-N-phenylacetamid derivatives 8a-m were synthesized with well-known chemical reactions and anticonvulsant activity of them was determined by pentylenetetrazole (PTZ) and maximal electroshock (MES) induced seizures in mice. Phenoxyphenyl-1,3,4-oxadiazole-thio-N-phenylacetamid scaffold has the necessary pharmacophores to be a benzodiazepine (BZD) receptor agonist, thus, the most potent anticonvulsant compounds were assayed in vivo and in silico as BZD receptor agonist. Furthermore, in vivo neurotoxicity evaluation and in silico physicochemical, pharmacokinetic, and toxicity study on the most potent compounds were also performed. Results Obtained results demonstrated that two compounds among the title new compounds have anticonvulsant activity in PTZ test while all of the new compounds are active in the MES test. The best anticonvulsant activities were obtained with nitro derivatives 8k and 8L. In vivo evaluation of flumazenil effect (a BZD receptor antagonist) on anticonvulsant activity of compound 8k confirmed that this compound is a BZD receptor agonist. The most potent compounds 8k and 8L interacted with the important residues of BZD-binding site of GABA A receptor. Furthermore, neurotoxicity of the latter compounds was lower than positive control diazepam. Conclusion According to these results, our designed scaffold can be a valuable lead structure for further structural developments and assessments to obtain a new potent anticonvulsant agent.

Research paper thumbnail of Nitroenediamines (EDAMs), and N-methyl-1-(methylthio)-2-nitroethenamine (NMSM) derivatives: scaffolds for heterocycle molecular diversity (update from 2012 to 2021)

RSC Advances

This review highlights recent heterocyclization of the nitroenediamine derivatives based on catal... more This review highlights recent heterocyclization of the nitroenediamine derivatives based on catalyst and catalyst-free approaches from 2012 onwards.

Research paper thumbnail of New 4,5-diphenylimidazole-acetamide-1,2,3-triazole hybrids as potent α-glucosidase inhibitors: synthesis, in vitro and in silico enzymatic and toxicity evaluations

Monatshefte für Chemie - Chemical Monthly, 2021

Herein, a new series of 4,5-diphenylimidazole-acetamide-1,2,3-triazole hybrids as potent α-glucos... more Herein, a new series of 4,5-diphenylimidazole-acetamide-1,2,3-triazole hybrids as potent α-glucosidase inhibitors was designed and synthesized. All the synthesized compounds exhibited excellent inhibition potencies (IC50 values = 55.6–149.2 μM) against α-glucosidase when compared with the standard inhibitor acarbose (IC50 = 750.0 μM). Among the newly synthesized compounds, 4-methyl, 4-methoxy, and 2,3-dichloro derivatives exhibited the highest anti-α-glucosidase activities and were also non-cytotoxic against human normal dermal fibroblast cells. In silico druglikeness, ADME, and toxicity studies of these compounds were performed and obtained results were compared with acarbose. All the synthesized compounds were also inactive against α-amylase in comparison to acarbose. Kinetic study of the most potent compound, 4-methyl derivative, against α-glucosidase demonstrated that this compound is a competitive inhibitor. Furthermore, in silicoinduced fit docking and molecular dynamic studie...

Research paper thumbnail of Recent Opportunities and Challenges in Selective C-H Functionalization of Methyl Azaarenes: a Highlight from 2010 to 2020 Literatures

Current organic synthesis, 2021

Azaarenes are unique scaffolds frequently found in pharmaceuticals. Herein, we have summarized th... more Azaarenes are unique scaffolds frequently found in pharmaceuticals. Herein, we have summarized the recent synthetic available methods in C-H functionalization of methylazaarenes from 2010 to 2020. Multiple approaches involving halogenation and alkylation via different methods, such as alkenylation, oxidative functionalization, and cyclization of the methylazaarenes will be discussed in this review.

Research paper thumbnail of Design, synthesis, and evaluation of metronidazole-1,2,3-triazole derivatives as potent urease inhibitors

Chemical Papers, 2021

A new series of metronidazole-1,2,3-triazole derivatives 6a–o was synthesized and evaluated as He... more A new series of metronidazole-1,2,3-triazole derivatives 6a–o was synthesized and evaluated as Helicobacter pylori urease inhibitors. All the synthesized compounds were more potent than standard inhibitor thiourea against urease. Among the synthesized compounds, compound 6f (IC50 = 1.975 ± 0.25 µM) with inhibitory activity around 11-fols more than thiourea (IC50 = 22.00 ± 0.14 µM) was the most potent compound. Kinetic study of this compound revealed that compound 6f inhibited urease in an uncompetitive mode. Based on molecular modeling study, compound 6f pointed toward the bi-nickel center and stabilized by H-bond and T-shape π–π hydrophobic interactions with the critical residues His492 and Asp633. Moreover, it anchored to the helix-turn-helix motif in the active site cavity through interaction with His593 and Arg609. Consequently, it proposed that compound 6f through stabilization of active site flap inhibited urease activity.

Research paper thumbnail of Recent strategies in the synthesis of thiophene derivatives: highlights from the 2012–2020 literature

Research paper thumbnail of A review on the latest progress of C‐S cross‐coupling in diaryl sulfide synthesis: Update from 2012 to 2021

Applied Organometallic Chemistry

Research paper thumbnail of The recent development of donepezil structure-based hybrids as potential multifunctional anti-Alzheimer's agents: highlights from 2010 to 2020

RSC Advances

This review highlights recent examples of multi-target-directed ligands (MTDLs) based on donepezi... more This review highlights recent examples of multi-target-directed ligands (MTDLs) based on donepezil structure modification from 2010 onwards.

Research paper thumbnail of Design and synthesis of new benzofuran-1,2,3-triazole hybrid preservatives and the evaluation of their antifungal potential against white and brown-rot fungi

BioResources

A series of novel benzofuran-1,2,3-triazole hybrids were synthesized and investigated as fungicid... more A series of novel benzofuran-1,2,3-triazole hybrids were synthesized and investigated as fungicidal preservatives. The compounds were evaluated for their antifungal potential against white-rot (Trametes versicolor), dry brown-rot (Poria placenta), and wet brown-rot (Coniophora puteana and Gloeophyllum trabeum) fungi, at different concentrations (500 ppm and 1000 ppm). The tests of the final products (8a, 8b, 8c, 8d, 8e, 8f, and 8g) demonstrated that compound N-((1-(4-fluorobenzyl)-1H-1,2,3-triazol-4-yl)methyl)benzofuran-2-carboxamide (8f) at a concentration of 500 ppm was the most active against wet brown-rot C. puteana (23.86% inhibition) and G. trabeum (47.16% inhibition) fungi. However, testing demonstrated that compounds 8a, 8b, 8c, 8d, and 8g at a concentration of 500 ppm did not exhibit acceptable antifungal effects against white-rot T. versicolor and dry brown-rot P. placenta fungi.

Research paper thumbnail of Recent developments in arylation of N-nucleophiles via Chan-Lam reaction: updates from 2012 onwards

Current Organic Synthesis

: ''Chan-Evans-Lam'' (CEL) reaction is the copper-mediated cross-... more : ''Chan-Evans-Lam'' (CEL) reaction is the copper-mediated cross-coupling of N-nucleophiles with boronic acids that was independently reported in 1998 by Chan, Evans, and Lam for the first time. This reaction is accomplished at room temperature with a remarkably wide range of nucleophiles. In the recent decade, it has been particularly attractive as a convenient method for constructing the various C–N bonds in organic synthesis. Therefore, a comprehensive survey through all reported process was crucial. In this review, we summarized research progress about N-Arylation, based on the type of N-nucleophile involved in this reaction and catalysts from 2012 onwards.

Research paper thumbnail of Synthesis and activity evaluation of new benzofuran-1,3,4-oxadiazole hybrids against wood-degrading fungi

BioResources

A series of novel benzofuran-1,3,4-oxadiazole hybrids were synthesized and evaluated as antifunga... more A series of novel benzofuran-1,3,4-oxadiazole hybrids were synthesized and evaluated as antifungal agents. The synthetic pathway was started from salicylaldehyde, which afforded 5-(substituted benzylthio)-1,3,4-oxadiazole derivatives in moderate to good yields. The compounds were investigated for their antifungal potential against white-rot, Trametes versicolor and brown-rot, Poria placenta and Coniophora puteana fungi at different concentrations (500, 1000 ppm). The obtaining results demonstrated that most of the compounds at 500 ppm concentration did not exhibit acceptable antifungal effects but they had better antifungal activity at 1000 ppm concentration. Compounds 5a, 5c, and 5i showed inhibition percentages of 14.6%, 23.0%, and 14.7%, against the growth of P. placenta and C. puteana, respectively. Among the compounds, the 2-(benzofuran-2-yl)-5-((2,6-difluorobenzyl)thio)-1,3,4-oxadiazole (5h) hybrid was the most active one.

Research paper thumbnail of Synthesis and cholinesterase inhibitory activity of new 2-benzofuran carboxamide-benzylpyridinum salts

Research paper thumbnail of Multivariate curve resolution for infrared spectrometric monitoring of the microwave assisted synthesis of bio-based polyols

Current Chemistry Letters, 2012

A new analytical approach was proposed to monitor the reaction between epoxidized soybean oil and... more A new analytical approach was proposed to monitor the reaction between epoxidized soybean oil and diethylene glycol in the presence of ZnCl2 as an epoxide ring opening catalyst for microwave assisted synthesis of polyol. Infrared spectra of the products were used as the input data, being processed by multivariate curve resolution-alternating least squares (MCR-ALS) for quantitative monitoring. The data obtained in different MW powers were analyzed by MCR factor analysis coupled with ALS optimization procedure. Standard deviation of residuals for experimental data and the variance explained at the optimum condition (r2) were 0.135 and 97.24% respectively.

Research paper thumbnail of Synthesis and biological evaluation of a new series of benzofuran‐1,3,4‐oxadiazole containing 1,2,3‐triazole‐acetamides as potential α‐glucosidase inhibitors

Journal of Biochemical and Molecular Toxicology, Dec 28, 2020

This study demonstrates the use of new compound N5 with potential characteristics for the develop... more This study demonstrates the use of new compound N5 with potential characteristics for the development of drugs combining coagulant and platelet activities.

Research paper thumbnail of Hybridization of the effective pharmacophores for treatment of epilepsy: design, synthesis, in vivo anticonvulsant activity, and in silico studies of phenoxyphenyl-1,3,4-oxadiazole-thio-N-phenylacetamid hybrids

BMC chemistry, Jul 17, 2023

Background Epilepsy is a common neurological disorder. The available drugs for this disease only ... more Background Epilepsy is a common neurological disorder. The available drugs for this disease only control convulsions in nearly 70% of patients, while bearing many side effects. In this study, a new series of phenoxyphenyl-1,3,4-oxadiazolethio-N-phenylacetamid hybrids 8a-m was designed, synthesized, and evaluated as potent anticonvulsant agents. Methods Phenoxyphenyl-1,3,4-oxadiazole-thio-N-phenylacetamid derivatives 8a-m were synthesized with well-known chemical reactions and anticonvulsant activity of them was determined by pentylenetetrazole (PTZ) and maximal electroshock (MES) induced seizures in mice. Phenoxyphenyl-1,3,4-oxadiazole-thio-N-phenylacetamid scaffold has the necessary pharmacophores to be a benzodiazepine (BZD) receptor agonist, thus, the most potent anticonvulsant compounds were assayed in vivo and in silico as BZD receptor agonist. Furthermore, in vivo neurotoxicity evaluation and in silico physicochemical, pharmacokinetic, and toxicity study on the most potent compounds were also performed. Results Obtained results demonstrated that two compounds among the title new compounds have anticonvulsant activity in PTZ test while all of the new compounds are active in the MES test. The best anticonvulsant activities were obtained with nitro derivatives 8k and 8L. In vivo evaluation of flumazenil effect (a BZD receptor antagonist) on anticonvulsant activity of compound 8k confirmed that this compound is a BZD receptor agonist. The most potent compounds 8k and 8L interacted with the important residues of BZD-binding site of GABA A receptor. Furthermore, neurotoxicity of the latter compounds was lower than positive control diazepam. Conclusion According to these results, our designed scaffold can be a valuable lead structure for further structural developments and assessments to obtain a new potent anticonvulsant agent.

Research paper thumbnail of Nitroenediamines (EDAMs), and N-methyl-1-(methylthio)-2-nitroethenamine (NMSM) derivatives: scaffolds for heterocycle molecular diversity (update from 2012 to 2021)

RSC Advances

This review highlights recent heterocyclization of the nitroenediamine derivatives based on catal... more This review highlights recent heterocyclization of the nitroenediamine derivatives based on catalyst and catalyst-free approaches from 2012 onwards.

Research paper thumbnail of New 4,5-diphenylimidazole-acetamide-1,2,3-triazole hybrids as potent α-glucosidase inhibitors: synthesis, in vitro and in silico enzymatic and toxicity evaluations

Monatshefte für Chemie - Chemical Monthly, 2021

Herein, a new series of 4,5-diphenylimidazole-acetamide-1,2,3-triazole hybrids as potent α-glucos... more Herein, a new series of 4,5-diphenylimidazole-acetamide-1,2,3-triazole hybrids as potent α-glucosidase inhibitors was designed and synthesized. All the synthesized compounds exhibited excellent inhibition potencies (IC50 values = 55.6–149.2 μM) against α-glucosidase when compared with the standard inhibitor acarbose (IC50 = 750.0 μM). Among the newly synthesized compounds, 4-methyl, 4-methoxy, and 2,3-dichloro derivatives exhibited the highest anti-α-glucosidase activities and were also non-cytotoxic against human normal dermal fibroblast cells. In silico druglikeness, ADME, and toxicity studies of these compounds were performed and obtained results were compared with acarbose. All the synthesized compounds were also inactive against α-amylase in comparison to acarbose. Kinetic study of the most potent compound, 4-methyl derivative, against α-glucosidase demonstrated that this compound is a competitive inhibitor. Furthermore, in silicoinduced fit docking and molecular dynamic studie...

Research paper thumbnail of Recent Opportunities and Challenges in Selective C-H Functionalization of Methyl Azaarenes: a Highlight from 2010 to 2020 Literatures

Current organic synthesis, 2021

Azaarenes are unique scaffolds frequently found in pharmaceuticals. Herein, we have summarized th... more Azaarenes are unique scaffolds frequently found in pharmaceuticals. Herein, we have summarized the recent synthetic available methods in C-H functionalization of methylazaarenes from 2010 to 2020. Multiple approaches involving halogenation and alkylation via different methods, such as alkenylation, oxidative functionalization, and cyclization of the methylazaarenes will be discussed in this review.

Research paper thumbnail of Design, synthesis, and evaluation of metronidazole-1,2,3-triazole derivatives as potent urease inhibitors

Chemical Papers, 2021

A new series of metronidazole-1,2,3-triazole derivatives 6a–o was synthesized and evaluated as He... more A new series of metronidazole-1,2,3-triazole derivatives 6a–o was synthesized and evaluated as Helicobacter pylori urease inhibitors. All the synthesized compounds were more potent than standard inhibitor thiourea against urease. Among the synthesized compounds, compound 6f (IC50 = 1.975 ± 0.25 µM) with inhibitory activity around 11-fols more than thiourea (IC50 = 22.00 ± 0.14 µM) was the most potent compound. Kinetic study of this compound revealed that compound 6f inhibited urease in an uncompetitive mode. Based on molecular modeling study, compound 6f pointed toward the bi-nickel center and stabilized by H-bond and T-shape π–π hydrophobic interactions with the critical residues His492 and Asp633. Moreover, it anchored to the helix-turn-helix motif in the active site cavity through interaction with His593 and Arg609. Consequently, it proposed that compound 6f through stabilization of active site flap inhibited urease activity.

Research paper thumbnail of Recent strategies in the synthesis of thiophene derivatives: highlights from the 2012–2020 literature

Research paper thumbnail of A review on the latest progress of C‐S cross‐coupling in diaryl sulfide synthesis: Update from 2012 to 2021

Applied Organometallic Chemistry

Research paper thumbnail of The recent development of donepezil structure-based hybrids as potential multifunctional anti-Alzheimer's agents: highlights from 2010 to 2020

RSC Advances

This review highlights recent examples of multi-target-directed ligands (MTDLs) based on donepezi... more This review highlights recent examples of multi-target-directed ligands (MTDLs) based on donepezil structure modification from 2010 onwards.

Research paper thumbnail of Design and synthesis of new benzofuran-1,2,3-triazole hybrid preservatives and the evaluation of their antifungal potential against white and brown-rot fungi

BioResources

A series of novel benzofuran-1,2,3-triazole hybrids were synthesized and investigated as fungicid... more A series of novel benzofuran-1,2,3-triazole hybrids were synthesized and investigated as fungicidal preservatives. The compounds were evaluated for their antifungal potential against white-rot (Trametes versicolor), dry brown-rot (Poria placenta), and wet brown-rot (Coniophora puteana and Gloeophyllum trabeum) fungi, at different concentrations (500 ppm and 1000 ppm). The tests of the final products (8a, 8b, 8c, 8d, 8e, 8f, and 8g) demonstrated that compound N-((1-(4-fluorobenzyl)-1H-1,2,3-triazol-4-yl)methyl)benzofuran-2-carboxamide (8f) at a concentration of 500 ppm was the most active against wet brown-rot C. puteana (23.86% inhibition) and G. trabeum (47.16% inhibition) fungi. However, testing demonstrated that compounds 8a, 8b, 8c, 8d, and 8g at a concentration of 500 ppm did not exhibit acceptable antifungal effects against white-rot T. versicolor and dry brown-rot P. placenta fungi.

Research paper thumbnail of Recent developments in arylation of N-nucleophiles via Chan-Lam reaction: updates from 2012 onwards

Current Organic Synthesis

: ''Chan-Evans-Lam'' (CEL) reaction is the copper-mediated cross-... more : ''Chan-Evans-Lam'' (CEL) reaction is the copper-mediated cross-coupling of N-nucleophiles with boronic acids that was independently reported in 1998 by Chan, Evans, and Lam for the first time. This reaction is accomplished at room temperature with a remarkably wide range of nucleophiles. In the recent decade, it has been particularly attractive as a convenient method for constructing the various C–N bonds in organic synthesis. Therefore, a comprehensive survey through all reported process was crucial. In this review, we summarized research progress about N-Arylation, based on the type of N-nucleophile involved in this reaction and catalysts from 2012 onwards.

Research paper thumbnail of Synthesis and activity evaluation of new benzofuran-1,3,4-oxadiazole hybrids against wood-degrading fungi

BioResources

A series of novel benzofuran-1,3,4-oxadiazole hybrids were synthesized and evaluated as antifunga... more A series of novel benzofuran-1,3,4-oxadiazole hybrids were synthesized and evaluated as antifungal agents. The synthetic pathway was started from salicylaldehyde, which afforded 5-(substituted benzylthio)-1,3,4-oxadiazole derivatives in moderate to good yields. The compounds were investigated for their antifungal potential against white-rot, Trametes versicolor and brown-rot, Poria placenta and Coniophora puteana fungi at different concentrations (500, 1000 ppm). The obtaining results demonstrated that most of the compounds at 500 ppm concentration did not exhibit acceptable antifungal effects but they had better antifungal activity at 1000 ppm concentration. Compounds 5a, 5c, and 5i showed inhibition percentages of 14.6%, 23.0%, and 14.7%, against the growth of P. placenta and C. puteana, respectively. Among the compounds, the 2-(benzofuran-2-yl)-5-((2,6-difluorobenzyl)thio)-1,3,4-oxadiazole (5h) hybrid was the most active one.

Research paper thumbnail of Synthesis and cholinesterase inhibitory activity of new 2-benzofuran carboxamide-benzylpyridinum salts

Research paper thumbnail of Multivariate curve resolution for infrared spectrometric monitoring of the microwave assisted synthesis of bio-based polyols

Current Chemistry Letters, 2012

A new analytical approach was proposed to monitor the reaction between epoxidized soybean oil and... more A new analytical approach was proposed to monitor the reaction between epoxidized soybean oil and diethylene glycol in the presence of ZnCl2 as an epoxide ring opening catalyst for microwave assisted synthesis of polyol. Infrared spectra of the products were used as the input data, being processed by multivariate curve resolution-alternating least squares (MCR-ALS) for quantitative monitoring. The data obtained in different MW powers were analyzed by MCR factor analysis coupled with ALS optimization procedure. Standard deviation of residuals for experimental data and the variance explained at the optimum condition (r2) were 0.135 and 97.24% respectively.