Synthesis and biological evaluation of new piplartine analogues as potent aldose reductase inhibitors (ARIs)

被引：61

作者：

Rao, Vidadala Ramasubba ^{[1
]}

Muthenna, Puppala ^{[2
]}

Shankaraiah, Gundeti ^{[1
]}

Akileshwari, Chandrasekhar ^{[2
]}

Babu, Kothapalli Han ^{[1
]}

Suresh, Ganji ^{[1
]}

Babu, Katragadda Suresh ^{[1
]}

Kumar, Rotte Sateesh Chandra ^{[1
]}

Prasad, Kothakonda Rajendra ^{[1
]}

Yadav, Potharaju Ashok ^{[1
]}

Petrash, J. Mark ^{[3
]}

Reddy, Geereddy Bhanuprakash ^{[2
]}

Rao, Janaswamy Madhusudana ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Nat Prod Lab, Div Nat Prod Chem, CSIR, Hyderabad 500607, Andhra Pradesh, India

[2] Natl Inst Nutr, Div Biochem, Hyderabad 500007, Andhra Pradesh, India

[3] Univ Colorado, Dept Ophthalmol, Aurora, CO USA

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2012年 / 57卷

关键词：

Piper chaba; Piplartine; Chemical modification; Aldose reductase inhibition; Michael addition; Baylis-Hillman reaction; CONJUGATE ADDITION; INDOLES; NITROALKENES; DERIVATIVES; CONSTITUENTS; CATALYSIS;

D O I：

10.1016/j.ejmech.2012.09.014

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

As a continuation of our efforts directed towards the development of anti-diabetic agents from natural sources, piplartine was isolated from Piper chaba, and was found to inhibit recombinant human ALR2 with an IC50 of 160 mu M. To improve the efficacy, a series of analogues have been synthesized by modification of the styryl/aromatic and heterocyclic ring functionalities of this natural product lead. All the derivatives were tested for their ALR2 inhibitory activity, and results indicated that adducts 3c, 3e and 2j prepared by the Michael addition of piplartine with indole derivatives displayed potent ARI activity, while the other compounds displayed varying degrees of inhibition. The active compounds were also capable of preventing sorbitol accumulation in human red blood cells. (C) 2012 Elsevier Masson SAS. All rights reserved.

引用

页码：344 / 361

页数：18

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