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Current Organic Synthesis


ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

Research Article

Synthesis, Molecular Docking, in vitro Antiproliferative and Antioxidant Activity of Novel Pyrrolidinyl-Carbazole Derivatives

Author(s): Padmaja Pannala*, Pedavenkatagari Narayana Reddy , Basireddy V. Subba Reddy , Sunil Misra , Koude Dhevendar and Surender Singh Jadav

Volume 14 , Issue 8 , 2017

Page: [1172 - 1179] Pages: 8

DOI: 10.2174/1570179414666170606120934

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Aim and Objective: Carbazoles and pyrrolidines derivatives exhibit a broad spectrum of biological and pharmacological properties, which exist in numerous drugs. Due to the high significance of these two classes of moieties in drug discovery, the synthesis of the compounds containing both of these two moieties are highly desirable.

Method: A metal- and catalyst-free three-component decarboxylative coupling reaction of proline, aldehyde and 4-hydroxycarbazole has been developed. The synthesized compounds were examined for their antiproliferative and antioxidant activities. Molecular docking studies were performed on all synthesized compounds against tubulin structure using Schrodinger’s Glide software.

Results: This atom economic approach provides an access to pyrrolidinyl-carbazole derivatives in good yields. The antiproliferative activity of newly synthesized compounds was investigated on both normal cell line (CHO) and cancer cancer cell lines (MCF7, MDA-MB-231 and A549). The results indicated that, these compounds showed selective cytotoxicity against both normal and cancer cells. In addition, most of the compounds showed very good antioxidant activity. Molecular docking studies demonstrated that all the lead compounds selectively occupy the colchicine binding site of the tubulin polymer.

Conclusion: In conclusion, we have developed a simple, metal- and catalyst-free three-component protocol to access synthetically as well as biologically important pyrrolidinyl-carbazole derivatives via decarboxylative coupling reaction involving proline, aldehydes and 4-hydroxycarbazole. The synthesized compounds were examined for their antiproliferative and antioxidant activities. The trend in the observed antiproliferative activity was further rationalized by molecular docking studies.

Keywords: Proline, pyrrolidines, 4-hydroxycarbazole, decarboxylative coupling reaction, antiproliferative activity, antioxidant acivity, molecular docking.

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