2. Academic Validation
  3. Iodine-catalyzed Csp3-H functionalization of methylhetarenes: One-pot synthesis and cytotoxic evaluation of heteroarenyl-benzimidazoles and benzothiazole

Iodine-catalyzed Csp3-H functionalization of methylhetarenes: One-pot synthesis and cytotoxic evaluation of heteroarenyl-benzimidazoles and benzothiazole

  • Bioorg Med Chem Lett. 2017 Sep 1;27(17):4039-4043. doi: 10.1016/j.bmcl.2017.07.051.
Mirza Feroz Baig 1,  Siddiq Pasha Shaik 1,  V Lakshma Nayak 2,  Abdullah Alarifi 3,  Ahmed Kamal 4
Affiliations

Affiliations

  • 1 Medicinal Chemistry and Biotechnology Division, CSIR-Indian Institute of Chemical Technology (IICT), Hyderabad 500007, India; Academy of Scientific and Innovative Research, New Delhi 110 025, India.
  • 2 Medicinal Chemistry and Biotechnology Division, CSIR-Indian Institute of Chemical Technology (IICT), Hyderabad 500007, India.
  • 3 Chemistry Department, College of Science, King Saud University, Riyadh 11451, Saudi Arabia.
  • 4 Medicinal Chemistry and Biotechnology Division, CSIR-Indian Institute of Chemical Technology (IICT), Hyderabad 500007, India; Academy of Scientific and Innovative Research, New Delhi 110 025, India; Chemistry Department, College of Science, King Saud University, Riyadh 11451, Saudi Arabia. Electronic address: ahmedkamal@iict.res.in.
PMID: 28789894 DOI: 10.1016/j.bmcl.2017.07.051
Abstract

An efficient one-pot synthetic procedure has been developed for the preparation of heteroarenyl-benzimidazoles via oxidative Csp3-H functionalization with o-phenylenediamine using I2-DMSO in open air from easily available starting Materials. Based on a logical plan a spectrum of multi fundamental reactions like iodination, Kornblum oxidation and amination were brought into one-pot. By using this simple method a library of heteroarenyl-benzimidazoles derivatives (3a-t and 5a-g) and heteroarenyl-benzothiazole (3u) have been synthesized in good to excellent yield and screened for their cytotoxicity against a group of four human Cancer cell lines. Among them 3h, 3q and 5b showed significant cytotoxic activities with an IC50 of 1.69, 1.62 and 2.81µM respectively against lung Cancer (A549) cell line.

Keywords

C(sp3)-H functionalization; Cytotoxicity; Heteroarenyl-benzimidazoles; Molecular iodine; Oxidation.

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