2. Academic Validation
  3. Synthesis and anticancer activity of γ-(triazolyl ethylidene)butenolides and polyfunctional pyrrolinones

Synthesis and anticancer activity of γ-(triazolyl ethylidene)butenolides and polyfunctional pyrrolinones

  • Eur J Med Chem. 2014 Jul 23:82:106-19. doi: 10.1016/j.ejmech.2014.05.042.
N Devender 1,  K K G Ramakrishna 1,  Hamidullah 2,  Sanjeev K Shukla 3,  Rituraj Konwar 4,  Rama P Tripathi 5
Affiliations

Affiliations

  • 1 Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow 226031, India.
  • 2 Endocrinology Division, CSIR-Central Drug Research Institute, Lucknow 226031, India.
  • 3 Sophisticated Analytical Instrumental Facility, CSIR-Central Drug Research Institute, Lucknow 226031, India; Academy of Scientific and Innovative Research, New Delhi 110001, India.
  • 4 Endocrinology Division, CSIR-Central Drug Research Institute, Lucknow 226031, India; Academy of Scientific and Innovative Research, New Delhi 110001, India.
  • 5 Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow 226031, India; Academy of Scientific and Innovative Research, New Delhi 110001, India. Electronic address: rp_tripathi@cdri.res.in.
PMID: 24880230 DOI: 10.1016/j.ejmech.2014.05.042
Abstract

A series of novel γ-(triazolyl ethylidene)butenolides (4-23) were prepared from commercially available l-ascorbic acid in good yields. These butenolides on reaction with ethanolic ammonia/amines led to formation of respective 5-hydroxy pyrrolinones (24-33). The two of these pyrrolinones on dehydration with p-toluenesulfonic acid, were transformed into γ-(triazolyl ethylidene)pyrrolinones (34, 35). Among all the newly synthesized hybrid molecules tested for Anticancer activity in vitro, compounds 24, 25, 26, 27, 28, 30 and 32 showed significant activity against MCF-7, MDA-MB-231, PC-3 or U-937 cells. In particular compound 25 (IC50 = 11.3 μM) exhibited most potent activity against breast Cancer cells and preliminary studies revealed that potency of this compound is due to ROS generation, subsequent activation of p38, leading to Apoptosis and inhibition of Cancer cells.

Keywords

1,2,3-Triazole; 5-Hydroxy pyrrolinone; Anticancer activity; γ-Ethylidenebutenolide; γ-Ethylidenepyrrolinone.

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