Synthesis of optically pure (S)-2-amino-5-arylpent-4-ynoic acids by Sonogashira reactions and their potential use as highly selective potent inhibitors of aldose reductase

被引：14

作者：

Parpart, Silvio ^{[1
]}

Petrosyan, Andranik ^{[1
,2
,3
]}

Shah, Syed Jawad Ali ^{[5
]}

Adewale, Raji Akeem ^{[5
]}

Ehlers, Peter ^{[1
]}

Grigoryan, Tatevik ^{[1
,4
]}

Mkrtchyan, Anna F. ^{[3
,4
]}

Mardiyan, Zorayr Z. ^{[3
]}

Karapetyan, Ani J. ^{[3
]}

Tsaturyan, Avetis H. ^{[3
]}

Saghyan, Ashot S. ^{[3
,4
]}

Iqbal, Jamshed ^{[5
]}

Langer, Peter ^{[1
,2
]}

机构：

[1] Univ Rostock, Inst Chem, D-18059 Rostock, Germany

[2] Univ Rostock, Leibniz Inst Katalyse eV, D-18059 Rostock, Germany

[3] SPC Armbiotechnol SNPO NAS RA, Yerevan 0056, Armenia

[4] Yerevan State Univ, Fac Pharmacol & Chem, Yerevan 0025, Armenia

[5] COMSATS Inst Informat Technol, Ctr Adv Drug Res, Abbottabad 22060, Pakistan

来源：

RSC ADVANCES | 2015年 / 5卷 / 130期

关键词：

ALPHA-AMINO-ACIDS; ALDEHYDE REDUCTASE; NICKEL(II) COMPLEXES; NI(II) COMPLEXES; CHIRAL NI(II)-COMPLEX; ASYMMETRIC-SYNTHESIS; ADDITION-REACTIONS; TERNARY COMPLEX; RATIONAL DESIGN; POLYOL PATHWAY;

D O I：

10.1039/c5ra22407a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new and convenient synthesis of optically pure (S)-2-amino-5-[aryl]pent-4-ynoic acids (alkynylated amino acids) is reported. (S)-2-Aminopent-4-ynoic acid-Ni-(S)-BPB was prepared and then functionalized via Sonogashira cross-coupling reactions to give (S)-2-amino-5-[aryl] pent-4-ynoic acidNi-( S)-BPB. The reaction conditions for the cross-coupling reaction were optimized and twelve derivatives were synthesized. Afterwards the Ni-complexes were cleaved to obtain the free (S)-2-amino5-[ aryl] pent-4-ynoic acids with excellent optical purity. The prepared (S)-2-amino-5-[aryl] pent-4-ynoic acids were tested for biological activity and selectively showed high inhibitory activity against aldose reductase (ALR2) over ALR1. Molecular docking studies have also been carried out to identify the putative binding mode of the compounds in these enzymes.

引用

页码：107400 / 107412

页数：13

共 45 条

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