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Synthesis and cytotoxicity of novel imidazo[4,5-d]azepine compounds derived from marine natural product ceratamine A.
- Source :
-
Bioorganic & medicinal chemistry letters [Bioorg Med Chem Lett] 2018 Mar 01; Vol. 28 (5), pp. 866-868. Date of Electronic Publication: 2018 Feb 09. - Publication Year :
- 2018
-
Abstract
- A series of novel imidazo[4,5-d]azepine compounds derived from marine natural product ceratamine A were designed and synthesized in 7 steps. Most compounds exhibited comparable cytotoxicity against five human cancer cell lines (HCT-116, HepG2, BGC-823, A549 and A2780) to natural product ceratamine A. Compound 1k, bearing methoxy group at C-14, C-15 and C-16, showed the best in vitro cytotoxicity, which was better than ceratamine A. The structure and activity relationships study showed that the benzyloxymethyl group on N-3 played an important role on the cytotoxicity.<br /> (Copyright © 2018 Elsevier Ltd. All rights reserved.)
- Subjects :
- Antineoplastic Agents chemical synthesis
Antineoplastic Agents chemistry
Azepines chemical synthesis
Azepines pharmacology
Biological Products chemical synthesis
Biological Products chemistry
Cell Line, Tumor
Cell Proliferation drug effects
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
Humans
Imidazoles chemical synthesis
Imidazoles pharmacology
Molecular Structure
Structure-Activity Relationship
Antineoplastic Agents pharmacology
Azepines chemistry
Biological Products pharmacology
Imidazoles chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 1464-3405
- Volume :
- 28
- Issue :
- 5
- Database :
- MEDLINE
- Journal :
- Bioorganic & medicinal chemistry letters
- Publication Type :
- Academic Journal
- Accession number :
- 29433924
- Full Text :
- https://doi.org/10.1016/j.bmcl.2018.02.004