Indole-3-carbinol and 1,3,4-Oxadiazole Hybrids: Synthesis and Study of Anti-Proliferative and Anti-Microbial Activity
Nikhila Gokhale A , Naveen Panathur A , Udayakumar Dalimba A C and Manjunatha Kumsi B
+ Author Affiliations
- Author Affiliations
A Organic Chemistry Laboratory, Department of Chemistry, National Institute of Technology Karnataka, Surathkal, Srinivasanagar, Mangalore-575025, Karnataka, India.
B Department of Chemistry, Nagarjuna College of Engineering and Technology, Devanahalli, Bangalore-562110, Karnataka, India.
C Corresponding author. Email: udayaravi80@gmail.com; udayakumar@nitk.ac.in
Australian Journal of Chemistry 68(10) 1603-1613 https://doi.org/10.1071/CH15116
Submitted: 9 March 2015 Accepted: 1 May 2015 Published: 5 June 2015
Abstract
In the present study, molecular hybrids of indole-3-carbinol and 1,3,4-oxadiazole-2-thiols have been designed and synthesized. The thiol analogues consisted of diversely substituted benzyl and alkyl groups with different electronic properties. The structures of all the newly synthesized scaffolds and target compounds were ascertained using 1H NMR, 13C NMR, mass spectrometry, and elemental analyses. All the final compounds were screened in vitro for their anti-proliferative and anti-microbial activity. Three compounds showed excellent anti-proliferative activity with more than 70 % cell growth inhibition against three cancer cell lines, HepG2 (human liver hepatocellular carcinoma), HeLa (human cervix carcinoma), and MCF-7 (human breast carcinoma). In the anti-microbial studies, compounds with electron-withdrawing fluoro or nitro substituent displayed appreciable activity similar to that of standard drugs. Also, the final compounds are non-toxic to non-cancerous Vero cell line.
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