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Uses of Cyclohexan-1,4-dione for the Synthesis of 2-Amino-4,5-dihydrobenzo[b]thiophen-6(7H)-one Derivatives with Anti-proliferative and Pim-1 Kinase Activities.

Authors
  • Mohareb, Rafat Milad1
  • Abbas, Nermeen Saeed2, 3
  • Ibrahim, Rehab Ali4
  • 1 Department of Chemistry, Faculty of Science, Cairo University.
  • 2 Department of Chemistry, Faculty of Science, Helwan University.
  • 3 Department of Chemistry, Faculty of Science, Taibah University.
  • 4 Institute of Engineering and Technology.
Type
Published Article
Journal
Chemical and Pharmaceutical Bulletin
Publisher
Pharmaceutical Society of Japan
Publication Date
Jan 01, 2017
Volume
65
Issue
12
Pages
1117–1131
Identifiers
DOI: 10.1248/cpb.c17-00582
PMID: 29199218
Source
Medline
Keywords
Language
English
License
Unknown

Abstract

The reaction of cyclohexan-1,4-dione with elemental sulfur and any of the 2-cyano-N-arylacetamide derivatives 2a-c gave the 2-amino-4,5-dihydrobenzo[b]thiophen-6(7H)-one derivatives 3a-c to be used in some heterocyclization reactions. The multicomponent reactions of any of compounds 3a-c with aromatic aldehydes 6a-c and either of malononitrile or ethylcyanoacetate gave the 5,9-dihydro-4H-thieno[2,3-f]chromene derivatives 9a-r, respectively. The anti-proliferative evaluation of the newly synthesized compounds against the six cancer cell lines A549, HT-29, MKN-45, U87MG, SMMC-7721 and H460 showed that the nine compounds 3c, 5c, 9e, 9h, 9i, 9j, 9l, 9q, 11e and 13e with highest cytotoxcity. Toxicity of these compounds against shrimp larvae revealed that compounds 3c, 9j, 9q, and 13e showed no toxicity against the tested organisms. The c-Met kinase inhibition of the most potent compounds showed that compounds 9j, 9q, 10e, 12e and 13e have the highest activities. Compounds 9j, 9l, 9q and 11e showed high activity towards tyrosine kinases. Moreover, compounds 9j, 9q and 13e showed the highest inhibitor activity towards Pim-1 kinase.

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