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Design, synthesis and antiproliferative activity of decarbonyl luotonin analogues.
- Source :
-
European journal of medicinal chemistry [Eur J Med Chem] 2017 Sep 29; Vol. 138, pp. 932-941. Date of Electronic Publication: 2017 Jul 18. - Publication Year :
- 2017
-
Abstract
- A small library of benzimidazole-fused pyrrolo[3,4-b]quinoline has been synthesized from readily available benzimidazole 2-carbaldehyde and various substituted arylamines in good to excellent yields utilizing an intramolecular Povarov reaction catalyzed by boron trifluoride diethyl etharate as the key final step. The compounds thus synthesized can be considered as decarbonyl analogues of the anticancer alkaloid luotonin A and were evaluated in a DNA relaxation assay for their ability to inhibit human topoisomerase I. Interestingly, two of the compounds showed a remarkable activity that is comparable to that of the standard drug camptothecin. The compounds were also evaluated for their cytotoxic effect in four highly aggressive human cancer cell lines, namely KB, MDA-MB231 (breast), LNCap (prostate), and HT1080 (fibrosarcoma). Some of the compounds obtained showed promising cytotoxicities for these four cell lines.<br /> (Copyright © 2017 Elsevier Masson SAS. All rights reserved.)
- Subjects :
- Antineoplastic Agents chemical synthesis
Antineoplastic Agents chemistry
Cell Proliferation drug effects
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
Humans
Molecular Structure
Pyrroles chemical synthesis
Pyrroles chemistry
Quinones chemical synthesis
Quinones chemistry
Structure-Activity Relationship
Tumor Cells, Cultured
Antineoplastic Agents pharmacology
Drug Design
Pyrroles pharmacology
Quinones pharmacology
Subjects
Details
- Language :
- English
- ISSN :
- 1768-3254
- Volume :
- 138
- Database :
- MEDLINE
- Journal :
- European journal of medicinal chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 28753517
- Full Text :
- https://doi.org/10.1016/j.ejmech.2017.07.027