Synthesis, Bacteriostatic and Anticancer Activity of Novel Phenanthridines Structurally Similar to Benzo[c] phenanthridine Alkaloids

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61389030%3A_____%2F18%3A00495765" target="_blank" >RIV/61389030:_____/18:00495765 - isvavai.cz</a>

Alternative codes found

RIV/61989592:15110/18:73591195 RIV/61989592:15310/18:73591195

Result on the web

<a href="http://dx.doi.org/10.3390/molecules23092155" target="_blank" >http://dx.doi.org/10.3390/molecules23092155</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.3390/molecules23092155" target="_blank" >10.3390/molecules23092155</a>

Result language

angličtina

Original language name

Synthesis, Bacteriostatic and Anticancer Activity of Novel Phenanthridines Structurally Similar to Benzo[c] phenanthridine Alkaloids

Original language description

In this study, we report the synthesis, antibacterial and anticancer evaluation of 38 novel phenanthridines that were designed as analogs of the benzo[c] phenanthridine alkaloids. The prepared phenanthridines differ from the benzo[c] phenanthridines in the absence of a benzene A-ring. All novel compounds were prepared from 6-bromo-2-hydroxy-3-methoxybenzaldehyde in several synthetic steps through reduction of Schiff bases and accomplished by radical cyclization. Twelve derivatives showed high antibacterial activity against Bacillus subtilis, Micrococcus luteus and/or Mycobacterium vaccae at single digit micromolar concentrations. Some compounds also displayed cytotoxicity against the K-562 and MCF-7 cancer cell lines at as low as single digit micromolar concentrations and were more potent than chelerythrine and sanguinarine. The active compounds caused cell-cycle arrest in cancer cells, increased levels of p53 protein and caused apoptosis-specific fragmentation of PARP-1. Biological activity was connected especially with the presence of the N-methyl quaternary nitrogen and 7-benzyloxy substitution (compounds 7i, 7j, 7k, and 7l) of phenanthridine.

Czech name

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Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

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OECD FORD branch

10401 - Organic chemistry

Project

Result was created during the realization of more than one project. More information in the Projects tab.

Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2018

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Molecules

ISSN

1420-3049

e-ISSN

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Volume of the periodical

23

Issue of the periodical within the volume

9

Country of publishing house

CH - SWITZERLAND

Number of pages

24

Pages from-to

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UT code for WoS article

000447365100068

EID of the result in the Scopus database

2-s2.0-85052659857