Design, synthesis and cytotoxic activities of scopoletin-isoxazole and scopoletin-pyrazole hybrids.

Authors :: Shi W
Hu J
Bao N
Li D
Chen L
Sun J
Source :: Bioorganic & medicinal chemistry letters [Bioorg Med Chem Lett] 2017 Jan 15; Vol. 27 (2), pp. 147-151. Date of Electronic Publication: 2016 Dec 01.
Publication Year :: 2017
Abstract: 12 novel scopoletin-isoxazole and scopoletin-pyrazole hybrids were designed, synthesized and their chemical structures were confirmed by HR-MS, IR, <superscript>1</superscript> H NMR and <superscript>13</superscript> C NMR spectra. The anticancer activities of the newly synthesized compounds were evaluated in vitro against three human cancer cell lines including HCT-116, Hun7 and SW620 by MTT assay. The screening results showed that six compounds (9a, 9c, 9d, 12a, 18b and 18d) exhibited potent cytotoxic activities with IC <subscript>50</subscript> values below 20μM. Besides, we have further evaluated the growth inhibitory activities of six compounds against the human normal tissue cell lines HFL-1. Especially, compound 9d displayed significant anti-proliferative activity with IC <subscript>50</subscript> values ranging from 8.76μM to 9.83μM and weak cytotoxicity with IC <subscript>50</subscript> value of 90.9μM on normal cells HFL-1, which suggested that isoxazole-based hybrids of scopoletin were an effective chemical modification to improve the anticancer activity of scopoletin.<br /> (Copyright © 2016 Elsevier Ltd. All rights reserved.)

Subjects :: Antineoplastic Agents chemical synthesis
Antineoplastic Agents toxicity
Cell Line, Tumor
Humans
Indoles pharmacology
Isoxazoles chemical synthesis
Isoxazoles toxicity
Pyrazoles chemical synthesis
Pyrazoles toxicity
Pyrroles pharmacology
Scopoletin chemical synthesis
Scopoletin toxicity
Sunitinib
Antineoplastic Agents pharmacology
Isoxazoles pharmacology
Pyrazoles pharmacology
Scopoletin analogs & derivatives
Scopoletin pharmacology

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