Saty Petrosyan - Academia.edu (original) (raw)

Papers by Saty Petrosyan

Research paper thumbnail of CCDC 285985: Experimental Crystal Structure Determination

An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

Research paper thumbnail of BSA Binding and Aggregate Formation of a Synthetic Amino Acid with Potential for Promoting Fibroblast Proliferation: An In Silico, CD Spectroscopic, DLS, and Cellular Study

Biomolecules, May 14, 2024

This article is an open access article distributed under the terms and conditions of the Creative... more This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY

Research paper thumbnail of Asymmetric Synthesis of Enantiomerically Enriched a-Amino Acids Containing 2-Furyl- and 2-Thienyl-1,2,4-triazoles in the Side-Chain

Zeitschrift für Naturforschung B, Apr 1, 2014

An efficient method for the asymmetric synthesis of α-amino acids, containing furyl-and thiopheny... more An efficient method for the asymmetric synthesis of α-amino acids, containing furyl-and thiophenyl-substituted triazoles in their side-chain, is reported. The strategy relies on Michael addition of 3,4,5-substituted 1,2,4-triazoles to the C=C bond of chiral Ni II complexes containing the Schiff base formed from dehydroamino acids (dehydroalanine and (E + Z)-dehydroaminobutyric acid) and from chiral auxiliaries, i. e. (S)-2-N-(N-benzylprolyl)aminobenzophenone and (S)-2-N-(N-2-chlorobenzylprolyl) aminobenzophenone. The reactions proceeded with good to very good diastereoselectivity. Hydrolysis of the diastereomeric mixtures of metal complexes afforded the enantiomerically pure α-amino acids with high enantiomeric excess (ee > 98 %).

Research paper thumbnail of Asymmetric synthesis of potential biologically active new heterocyclic analogs of (S)-α-alanine containing 3,4-substituted 5-thioxo-1,2,4- triazoles in the side-chain radical

Trends in green chemistry, Aug 9, 2017

Statement of the Problem: Non-proteinogenic α-amino acids are constituents of many physiologicall... more Statement of the Problem: Non-proteinogenic α-amino acids are constituents of many physiologically active peptides, antibiotics and other pharmaceutical preparations. Especially α-amino acids and peptides, containing a N-heterocyclic substituent in the side chain, are of considerable importance in medicinal chemistry because they combine the pharmacophoric groups of amino acids and N-heterocycles. These compounds also belong furyl-, thiophenyl-and triazole-containing structures that are important constituents of many biologically and pharmacologically active drugs such as anti-hyperglycemic, analgesic, anti-inflammatory, antibacterial, anticancer, antifungal, antitumoral, antiviral and psychotropic. Aim: The goal of our research work is elaboration of efficient high-selectivity method for asymmetric synthesis of enantiomerically enriched substituted α-alanine containing triazole rings in side chain radical. Materials & Methods: Efficient high-selectivity method for asymmetric synthesis of new heterocyclic substituted derivatives of α-alanine, through the nucleophilic addition of the substituted triazoles to the C=C bond of dehydroalanine moiety in Nill complexes of Shiff 's base with chiral auxiliaries (S)-2-N-(N'-benzylprolyl)aminobenzophenone and (S)-2-N-(N'-chlorbenzylprolyl) aminobenzophenone was elaborated. Results: The results show, that the stereoselectivity of the reaction of nucleophilic addition in case of the complex containing Cl-atom at the 2nd position of Ph-group of N-benzyl proline moiety is increased (up to 96%). Heterocyclic substituted derivatives of (S)-αalanine were isolated with high optical purity (ee>99%) after decomposition of the mixture of the diastereomeric complexes and ion-exchange purification of the target amino acids. Conclusion: The advantage of these complexes is the regenerability of the initial chiral auxiliary reagents in quantitative chemical yield and complete retention of the original chirality (optical activity) after completion of the synthesis and isolation of the desired products. This allows multiple reuses of the chiral auxiliaries.

Research paper thumbnail of Asymmetric Synthesis of Derivatives of Alanine via Michael Addition Reaction and their Biological Study

Synlett

Ni(II) complex of the Schiff base of the chiral auxiliary (S)-2-N-(N′-benzylprolyl)aminobenzophen... more Ni(II) complex of the Schiff base of the chiral auxiliary (S)-2-N-(N′-benzylprolyl)aminobenzophenone (BPB) and dehydroalanine as the initial complex in the addition reaction was investigated. The obtained four new derivatives of α-alanine were investigated as inhibitors of aldose reductase. Only one of them: (S)-2-amino-3-[(4-methylbenzyl)amino]propanoic acid showed activity. It becomes a reason for studying the patterns of biological activity of the structure of α-amino acids. The results of docking analysis indicated that (S)-2-amino-3-[(4-methylbenzyl)amino]propanoic acid demonstrated the ability to form bonds with different functional groups of the enzyme which let us assume that some amino acids of nonfunctional groups, such as Trp20 of ALR2, can play a key role in inhibitor–enzyme interactions.

Research paper thumbnail of Isolation, Identification and Quantitative Determination of Nifedipine from Biological Material

Proceedings of the YSU B: Chemical and Biological Sciences

The optimal conditions of the method, applicable during forensic chemical examinations, were elab... more The optimal conditions of the method, applicable during forensic chemical examinations, were elaborated. Particularly, the investigation of the conditions for the isolation of Nifedipine from liver and skeletal muscle tissues, the identification of the isolated Nifedipine by TLC method and checking the accuracy of the method using HPLC was carried out. As a result, a new alternative express method for the isolation and further identification of Nifedipine from different biomaterials was elaborated. The method is quite fast, accurate and much cheaper.

Research paper thumbnail of Thiophenyl-substituted triazolyl-thione l-alanine: asymmetric synthesis, aggregation and biological properties

Amino Acids, 2014

In this work, we report the asymmetric synthesis and characterization of an artificial amino acid... more In this work, we report the asymmetric synthesis and characterization of an artificial amino acid based on triazolyl-thione L-alanine, which was modified with a thiophenyl-substituted moiety, as well as in vitro studies of its nucleic acid-binding ability. We found, by dynamic light scattering studies, that the synthetic amino acid was able to form supramolecular aggregates having a hydrodynamic diameter higher than 200 nm. Furthermore, we demonstrated, by UV and CD experiments, that the heteroaromatic amino acid, whose enzymatic stability was demonstrated by HPLC analysis also after 24 h of incubation in human serum, was able to bind a RNA complex, which is a feature of biomedical interest in view of innovative antiviral strategies based on modulation of RNA-RNA molecular recognition.

Research paper thumbnail of Asymmetric synthesis of β-heterocycle substituted l-α-amino acids

Tetrahedron: Asymmetry, 2004

A new efficient method of asymmetric synthesis of b-heterocycle substituted L L-a-amino acids thr... more A new efficient method of asymmetric synthesis of b-heterocycle substituted L L-a-amino acids through the addition of 3-amino-1,2,4-thiodiazole and 5-mercapto-1,2,4-triazoles, containing various substituents at the 3 and 4 positions, to the C@C bond of dehydroalanine in the Ni(II) complex of its Schiff base with (S)-2-N-(N 0-benzylprolyl)aminobenzophenone has been elaborated upon. Under thermodynamic control, the stereoselectivity of the nucleophilic addition exceeded 94%. After acidic decomposition of the reaction mixtures, the corresponding b-heterocycle substituted a-amino acids with high enantiomeric purity (ee >98.5%) were isolated.

Research paper thumbnail of New chiral NiII complexes of Schiff’s bases of glycine and alanine for efficient asymmetric synthesis of α-amino acids

Tetrahedron: Asymmetry, 2006

New modified chiral auxiliaries (S)-N-(2-benzoylphenyl)-1-(2-chlorobenzyl) pyrrolidine-2-carboxam... more New modified chiral auxiliaries (S)-N-(2-benzoylphenyl)-1-(2-chlorobenzyl) pyrrolidine-2-carboxamide (2-CBPB) and (S)-N-(2-benzoylphenyl)-1-(3, 4-dimethylbenzyl) pyrrolidine-2-carboxamide (3, 4-DMBPB) and their NiII complexes of Schiff's base with glycine and ...

Research paper thumbnail of A New Approach to the Efficient Method for the Asymmetric Synthesis of (S)-O-, M-, P-Fluorophenylalanines and Their 2-Methyl-substituted Analogs

Synthetic Communications, 2011

Abstract The reactions of asymmetric C-alkylation of glycine and alanine in NiII complexes of the... more Abstract The reactions of asymmetric C-alkylation of glycine and alanine in NiII complexes of their Schiff's bases with modified chiral auxiliaries (S)-2-N-[(N′-2-chlorobenzylprolyl) amino] benzophenone and (S)-2-N-[N′-(3, 4-dimethylbenzylprolyl) amino] ...

Research paper thumbnail of Novel modified chiral NiII complexes with the Schiff bases of (E)-and (Z)-2-aminobut-2-enoic acids: Synthesis and study

Russian Chemical Bulletin, 2006

Ni II complexes with the Schiff bases of (E) and (Z) 2 aminobut 2 enoic acids were obtained with ... more Ni II complexes with the Schiff bases of (E) and (Z) 2 aminobut 2 enoic acids were obtained with (S) N (2 benzoylphenyl) 1 (2 chlorobenzyl)pyrrolidine 2 carboxamide and (S) N (2 benzoylphenyl) 1 (3,4 dimethylbenzyl)pyrrolidine 2 carboxamide as new chiral auxiliaries. Asymmetric addition of nucleophiles to the C=C bond of these complexes was studied.

Research paper thumbnail of CCDC 285985: Experimental Crystal Structure Determination

An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

Research paper thumbnail of BSA Binding and Aggregate Formation of a Synthetic Amino Acid with Potential for Promoting Fibroblast Proliferation: An In Silico, CD Spectroscopic, DLS, and Cellular Study

Biomolecules, May 14, 2024

This article is an open access article distributed under the terms and conditions of the Creative... more This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY

Research paper thumbnail of Asymmetric Synthesis of Enantiomerically Enriched a-Amino Acids Containing 2-Furyl- and 2-Thienyl-1,2,4-triazoles in the Side-Chain

Zeitschrift für Naturforschung B, Apr 1, 2014

An efficient method for the asymmetric synthesis of α-amino acids, containing furyl-and thiopheny... more An efficient method for the asymmetric synthesis of α-amino acids, containing furyl-and thiophenyl-substituted triazoles in their side-chain, is reported. The strategy relies on Michael addition of 3,4,5-substituted 1,2,4-triazoles to the C=C bond of chiral Ni II complexes containing the Schiff base formed from dehydroamino acids (dehydroalanine and (E + Z)-dehydroaminobutyric acid) and from chiral auxiliaries, i. e. (S)-2-N-(N-benzylprolyl)aminobenzophenone and (S)-2-N-(N-2-chlorobenzylprolyl) aminobenzophenone. The reactions proceeded with good to very good diastereoselectivity. Hydrolysis of the diastereomeric mixtures of metal complexes afforded the enantiomerically pure α-amino acids with high enantiomeric excess (ee > 98 %).

Research paper thumbnail of Asymmetric synthesis of potential biologically active new heterocyclic analogs of (S)-α-alanine containing 3,4-substituted 5-thioxo-1,2,4- triazoles in the side-chain radical

Trends in green chemistry, Aug 9, 2017

Statement of the Problem: Non-proteinogenic α-amino acids are constituents of many physiologicall... more Statement of the Problem: Non-proteinogenic α-amino acids are constituents of many physiologically active peptides, antibiotics and other pharmaceutical preparations. Especially α-amino acids and peptides, containing a N-heterocyclic substituent in the side chain, are of considerable importance in medicinal chemistry because they combine the pharmacophoric groups of amino acids and N-heterocycles. These compounds also belong furyl-, thiophenyl-and triazole-containing structures that are important constituents of many biologically and pharmacologically active drugs such as anti-hyperglycemic, analgesic, anti-inflammatory, antibacterial, anticancer, antifungal, antitumoral, antiviral and psychotropic. Aim: The goal of our research work is elaboration of efficient high-selectivity method for asymmetric synthesis of enantiomerically enriched substituted α-alanine containing triazole rings in side chain radical. Materials & Methods: Efficient high-selectivity method for asymmetric synthesis of new heterocyclic substituted derivatives of α-alanine, through the nucleophilic addition of the substituted triazoles to the C=C bond of dehydroalanine moiety in Nill complexes of Shiff 's base with chiral auxiliaries (S)-2-N-(N'-benzylprolyl)aminobenzophenone and (S)-2-N-(N'-chlorbenzylprolyl) aminobenzophenone was elaborated. Results: The results show, that the stereoselectivity of the reaction of nucleophilic addition in case of the complex containing Cl-atom at the 2nd position of Ph-group of N-benzyl proline moiety is increased (up to 96%). Heterocyclic substituted derivatives of (S)-αalanine were isolated with high optical purity (ee>99%) after decomposition of the mixture of the diastereomeric complexes and ion-exchange purification of the target amino acids. Conclusion: The advantage of these complexes is the regenerability of the initial chiral auxiliary reagents in quantitative chemical yield and complete retention of the original chirality (optical activity) after completion of the synthesis and isolation of the desired products. This allows multiple reuses of the chiral auxiliaries.

Research paper thumbnail of Asymmetric Synthesis of Derivatives of Alanine via Michael Addition Reaction and their Biological Study

Synlett

Ni(II) complex of the Schiff base of the chiral auxiliary (S)-2-N-(N′-benzylprolyl)aminobenzophen... more Ni(II) complex of the Schiff base of the chiral auxiliary (S)-2-N-(N′-benzylprolyl)aminobenzophenone (BPB) and dehydroalanine as the initial complex in the addition reaction was investigated. The obtained four new derivatives of α-alanine were investigated as inhibitors of aldose reductase. Only one of them: (S)-2-amino-3-[(4-methylbenzyl)amino]propanoic acid showed activity. It becomes a reason for studying the patterns of biological activity of the structure of α-amino acids. The results of docking analysis indicated that (S)-2-amino-3-[(4-methylbenzyl)amino]propanoic acid demonstrated the ability to form bonds with different functional groups of the enzyme which let us assume that some amino acids of nonfunctional groups, such as Trp20 of ALR2, can play a key role in inhibitor–enzyme interactions.

Research paper thumbnail of Isolation, Identification and Quantitative Determination of Nifedipine from Biological Material

Proceedings of the YSU B: Chemical and Biological Sciences

The optimal conditions of the method, applicable during forensic chemical examinations, were elab... more The optimal conditions of the method, applicable during forensic chemical examinations, were elaborated. Particularly, the investigation of the conditions for the isolation of Nifedipine from liver and skeletal muscle tissues, the identification of the isolated Nifedipine by TLC method and checking the accuracy of the method using HPLC was carried out. As a result, a new alternative express method for the isolation and further identification of Nifedipine from different biomaterials was elaborated. The method is quite fast, accurate and much cheaper.

Research paper thumbnail of Thiophenyl-substituted triazolyl-thione l-alanine: asymmetric synthesis, aggregation and biological properties

Amino Acids, 2014

In this work, we report the asymmetric synthesis and characterization of an artificial amino acid... more In this work, we report the asymmetric synthesis and characterization of an artificial amino acid based on triazolyl-thione L-alanine, which was modified with a thiophenyl-substituted moiety, as well as in vitro studies of its nucleic acid-binding ability. We found, by dynamic light scattering studies, that the synthetic amino acid was able to form supramolecular aggregates having a hydrodynamic diameter higher than 200 nm. Furthermore, we demonstrated, by UV and CD experiments, that the heteroaromatic amino acid, whose enzymatic stability was demonstrated by HPLC analysis also after 24 h of incubation in human serum, was able to bind a RNA complex, which is a feature of biomedical interest in view of innovative antiviral strategies based on modulation of RNA-RNA molecular recognition.

Research paper thumbnail of Asymmetric synthesis of β-heterocycle substituted l-α-amino acids

Tetrahedron: Asymmetry, 2004

A new efficient method of asymmetric synthesis of b-heterocycle substituted L L-a-amino acids thr... more A new efficient method of asymmetric synthesis of b-heterocycle substituted L L-a-amino acids through the addition of 3-amino-1,2,4-thiodiazole and 5-mercapto-1,2,4-triazoles, containing various substituents at the 3 and 4 positions, to the C@C bond of dehydroalanine in the Ni(II) complex of its Schiff base with (S)-2-N-(N 0-benzylprolyl)aminobenzophenone has been elaborated upon. Under thermodynamic control, the stereoselectivity of the nucleophilic addition exceeded 94%. After acidic decomposition of the reaction mixtures, the corresponding b-heterocycle substituted a-amino acids with high enantiomeric purity (ee >98.5%) were isolated.

Research paper thumbnail of New chiral NiII complexes of Schiff’s bases of glycine and alanine for efficient asymmetric synthesis of α-amino acids

Tetrahedron: Asymmetry, 2006

New modified chiral auxiliaries (S)-N-(2-benzoylphenyl)-1-(2-chlorobenzyl) pyrrolidine-2-carboxam... more New modified chiral auxiliaries (S)-N-(2-benzoylphenyl)-1-(2-chlorobenzyl) pyrrolidine-2-carboxamide (2-CBPB) and (S)-N-(2-benzoylphenyl)-1-(3, 4-dimethylbenzyl) pyrrolidine-2-carboxamide (3, 4-DMBPB) and their NiII complexes of Schiff's base with glycine and ...

Research paper thumbnail of A New Approach to the Efficient Method for the Asymmetric Synthesis of (S)-O-, M-, P-Fluorophenylalanines and Their 2-Methyl-substituted Analogs

Synthetic Communications, 2011

Abstract The reactions of asymmetric C-alkylation of glycine and alanine in NiII complexes of the... more Abstract The reactions of asymmetric C-alkylation of glycine and alanine in NiII complexes of their Schiff's bases with modified chiral auxiliaries (S)-2-N-[(N′-2-chlorobenzylprolyl) amino] benzophenone and (S)-2-N-[N′-(3, 4-dimethylbenzylprolyl) amino] ...

Research paper thumbnail of Novel modified chiral NiII complexes with the Schiff bases of (E)-and (Z)-2-aminobut-2-enoic acids: Synthesis and study

Russian Chemical Bulletin, 2006

Ni II complexes with the Schiff bases of (E) and (Z) 2 aminobut 2 enoic acids were obtained with ... more Ni II complexes with the Schiff bases of (E) and (Z) 2 aminobut 2 enoic acids were obtained with (S) N (2 benzoylphenyl) 1 (2 chlorobenzyl)pyrrolidine 2 carboxamide and (S) N (2 benzoylphenyl) 1 (3,4 dimethylbenzyl)pyrrolidine 2 carboxamide as new chiral auxiliaries. Asymmetric addition of nucleophiles to the C=C bond of these complexes was studied.