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  3. Synthesis and biological evaluation of novel biaryl type α-noscapine congeners

Synthesis and biological evaluation of novel biaryl type α-noscapine congeners

  • Bioorg Med Chem Lett. 2014 Dec 15;24(24):5752-5757. doi: 10.1016/j.bmcl.2014.10.046.
Naresh K Manchukonda 1,  Pradeep K Naik 2,  Balasubramanian Sridhar 3,  Srinivas Kantevari 4
Affiliations

Affiliations

  • 1 Organic Chemistry Division-II (CPC Division), CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, Telangana, India.
  • 2 Department of Biotechnology, Guru Ghasidas Vishwavidyalaya, A Central University, Koni, Bilaspur 495 009, Chhattisgarh, India. Electronic address: pknaik1973@gmail.com.
  • 3 Laboratory of X-ray Crystallography, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, Telangana, India.
  • 4 Organic Chemistry Division-II (CPC Division), CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, Telangana, India; Academy of Scientific and Innovative Research, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, Telangana, India. Electronic address: kantevari@yahoo.com.
PMID: 25453814 DOI: 10.1016/j.bmcl.2014.10.046
Abstract

Natural α-noscapine, a known antitussive drug, is also now known to possess weak Anticancer efficacy with relatively safe toxicity profile. In this study, we report synthesis and evaluation of novel biaryl type α-noscapine congeners designed by adding aryl unit to the tetrahydroisoquinoline part of natural α-noscapine core. Palladium catalyzed Suzuki cross coupling of 9-bromo α-noscapine with aryl boronic acids was employed using mild and inexpensive reagents to attain desired noscapinoids 5a-g in excellent yields. Screening anti-proliferative activity for new noscapinoids 5b-g, on human Cancer cell lines resulted three compounds 5b, 5d and 5f as potent analogues, active against human breast epithelial (MCF-7), human cervix Cancer (HeLa) and human lung adenocarcinoma epithelial (A549) cell lines.

Keywords

Alkaloid; Isoquinoline; Noscapine; Suzuki reaction; Tubulin.

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