Uses of Cyclohexan-1,4-dione for the Synthesis of 2-Amino-4,5-dihydrobenzo[<i>b</i>]thiophen-6(7<i>H</i>)-one Derivatives with Anti-proliferative and Pim-1 Kinase Activities
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- Mohareb Rafat Milad
- Department of Chemistry, Faculty of Science, Cairo University
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- Abbas Nermeen Saeed
- Department of Chemistry, Faculty of Science, Helwan University Department of Chemistry, Faculty of Science, Taibah University
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- Ibrahim Rehab Ali
- Institute of Engineering and Technology
Bibliographic Information
- Other Title
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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
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Description
<p>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.</p>
Journal
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- Chemical and Pharmaceutical Bulletin
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Chemical and Pharmaceutical Bulletin 65 (12), 1117-1131, 2017
The Pharmaceutical Society of Japan
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Details 詳細情報について
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- CRID
- 1390282679153930240
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- NII Article ID
- 130006235014
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- NII Book ID
- AA00602100
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- ISSN
- 13475223
- 00092363
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- NDL BIB ID
- 028675181
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- PubMed
- 29199218
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- Text Lang
- en
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- Data Source
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- JaLC
- NDL
- Crossref
- PubMed
- CiNii Articles
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- Abstract License Flag
- Disallowed