Indole-3-carbinol and 1,3,4-Oxadiazole Hybrids: Synthesis and Study of Anti-Proliferative and Anti-Microbial Activity

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.

Discovering Podophyllotoxin Derivatives as Potential Anti‐Tubulin Agents: Design, Synthesis and Biological Evaluation

“…According to the results of previous structure–activity relationship (SAR) studies on podophyllotoxin 1, the introduction of bulky groups at the four stereogenic carbons in ring C could enhance anti‐tumor activity . In addition, compounds that contain the 1,3,4‐oxadiazole and 1,3,4‐thiadiazole nucleus exhibited increased pharmaceutical activities, including anti‐microbial, anti‐inflammatory, anti‐cancer and anti‐viral effects. In the field of medicinal chemistry, bioisosterism is extensively used to elicit changes in a lead structure to obtain beneficial goals, such as enhancement of the chemical stability or biological activities .…”