Publication:
Synthesis and structure-activity relationship of mono-indole-, bis-indole-, and tris-indole-based sulfonamides as potential anticancer agents

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Issued Date

2013

Resource Type

Article

File Type

application/pdf

ISSN

13811991

DOI

10.1007/s11030-013-9457-7

Other identifier(s)

2-s2.0-84880829458

Rights Holder(s)

มหาวิทยาลัยศรีนครินทรวิโรฒ

Bibliographic Citation

Molecular Diversity. Vol 17, No.3 (2013), p.595-604

Suggested Citation

Pingaew R., Prachayasittikul S., Ruchirawat S., Prachayasittikul V. Synthesis and structure-activity relationship of mono-indole-, bis-indole-, and tris-indole-based sulfonamides as potential anticancer agents. Molecular Diversity. Vol 17, No.3 (2013), p.595-604. doi:10.1007/s11030-013-9457-7 Retrieved from: https://hdl.handle.net/20.500.14740/6601

Title

Synthesis and structure-activity relationship of mono-indole-, bis-indole-, and tris-indole-based sulfonamides as potential anticancer agents

Author(s)

Pingaew R.
 Prachayasittikul S.
 Ruchirawat S.
 Prachayasittikul V.

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.

Subject(s)

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

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URI

https://hdl.handle.net/20.500.14740/6601

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Scopus: Year 1983-2021

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