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Title: | Synthesis and structure-activity relationship of mono-indole-, bis-indole-, and tris-indole-based sulfonamides as potential anticancer agents |
Authors: | Pingaew R. Prachayasittikul S. Ruchirawat S. Prachayasittikul V. |
Keywords: | antineoplastic agent sulfonamide sulfonyl bis indole derivative sulfonyl mono indole derivative sulfonyl tris indole derivative unclassified drug antineoplastic activity antiproliferative activity article controlled study drug screening drug synthesis human human cell IC 50 priority journal structure activity relation Antineoplastic Agents Arylsulfonates Carcinoma, Hepatocellular Cell Line, Tumor Cell Proliferation Cholangiocarcinoma Drug Screening Assays, Antitumor Hep G2 Cells Humans Indoles Liver Neoplasms Lung Neoplasms Neoplasms Precursor Cell Lymphoblastic Leukemia-Lymphoma Structure-Activity Relationship Sulfonamides |
Issue Date: | 2013 |
Abstract: | A series of arylsulfonyl mono-indoles (10-15), bis-indoles (16-27), and tris-indoles (28-32) have been synthesized and evaluated for their cytotoxicity toward four human cancer cell lines including HuCCA-1 (cholangiocarcinoma), HepG2 (hepatocellular carcinoma), A-549 (lung carcinoma), and MOLT-3 (lymphoblastic leukemia). Most of the synthesized indoles displayed cytotoxicity against the MOLT-3 cell line except for analogs 16, 17, and 32. Significantly, the NN -sulfonylphenolic bis-indole series (18-27) and the NN -chlorobenzenesulfonyl tris-indole (30) showed higher antiproliferative activity against HepG2 cell than the reference drug, etoposide. Promisingly, the NN -chlorobenzenesulfonyl bis-indole (20) and tris-indole (30) provided 3-fold and 2-fold stronger activity, respectively, against HepG2 cell than etoposide. Moreover, the phenolic bis-indole (20) was also shown to be the most potent cytotoxic agent against HuCCA-1 and A-549 cell lines with IC50 values of 7.75 and 8.74 μ M, respectively. The tris-indole analogs 28, 29, and 31 also exhibited selectivity against MOLT-3 cell. The findings disclosed that NN -arylsulfonyl bis-indoles-bearing phenolic groups are potentially interesting lead pharmacophores of anticancer agents that should be further investigated in more detail. © 2013 Springer Science+Business Media Dordrecht. |
URI: | https://ir.swu.ac.th/jspui/handle/123456789/14024 https://www.scopus.com/inward/record.uri?eid=2-s2.0-84880829458&doi=10.1007%2fs11030-013-9457-7&partnerID=40&md5=f954dc5a8a04272b455f3e4346568f8a |
ISSN: | 13811991 |
Appears in Collections: | Scopus 1983-2021 |
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