Literature DB >> 25913198

Stereoselective synthesis of 11-phenylundeca-5Z,9Z-dienoic acid and investigation of its human topoisomerase I and IIα inhibitory activity.

Vladimir A D'yakonov1, Lilya U Dzhemileva2, Aleksey A Makarov3, Alfiya R Mulukova3, Dmitry S Baev4, Elza K Khusnutdinova5, Tatiana G Tolstikova6, Usein M Dzhemilev3.   

Abstract

(5Z,9Z)-11-Phenylundeca-5,9-dienoic acid was stereoselectively synthesized, based on original cross-cyclomagnesiation of 2-(hepta-5,6-dien-1-yloxy)tetrahydro-2H-pyran and buta-2,3-dien-1-ylbenzene with EtMgBr in the presence of Cp2TiCl2 catalyst giving 2,5-dialkylidenemagnesacyclopentane in 86% yield. The acid hydrolysis of the product and the Jones oxidation of the resulting 2-{[(5Z,9Z)-11-phenylundeca-5,9-dien-1-yl]oxy}tetrahydro-2Н-pyran afforded (5Z,9Z)-11-phenylundeca-5,9-dienoic acid in an overall yield of 75%. A high inhibitory activity of the synthesized acid with respect to human topoisomerase I (hTop1) and II (hTop2α) was determined.
Copyright © 2015 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  5Z,9Z-Dienoic acids; DNA-binding; Molecular docking; Topoisomerase I; Topoisomerase IIα

Mesh：

Substances：

Year:  2015        PMID： 25913198     DOI： 10.1016/j.bmcl.2015.04.011

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  6 in total

1.  Novel Very Long-Chain α-Methoxylated Δ5,9 Fatty Acids from the Sponge Asteropus niger Are Effective Inhibitors of Topoisomerases IB.

Authors:  Néstor M Carballeira; Nashbly Montano; Luis A Amador; Abimael D Rodríguez; Mikhail Y Golovko; Svetlana A Golovko; Rosa M Reguera; Raquel Álvarez-Velilla; Rafael Balaña-Fouce
Journal:  Lipids       Date:  2015-12-22       Impact factor: 1.880

2.  Total Synthesis and Structural Elucidation of Two Unusual Non-Methylene-Interrupted Fatty Acids in Ovaries of the Limpet Cellana toreuma.

Authors:  Kazuaki Shimada; Ayako Sugawara; Toshinobu Korenaga; Hideki Kawashima
Journal:  Lipids       Date:  2017-09-27       Impact factor: 1.880

3.  First Total Synthesis of ω-Phenyl Δ6 Fatty Acids and their Leishmanicidal and Anticancer Properties.

Authors:  Nestor M Carballeira; Christian Morales-Guzman; Ester Alvarez-Benedicto; Zally Torres-Martinez; Yamixa Delgado; Kai H Griebenow; Arthur D Tinoco; Rosa M Reguera; Yolanda Perez-Pertejo; Ruben Carbajo-Andres; Rafael Balana-Fouce
Journal:  Curr Top Med Chem       Date:  2018       Impact factor: 3.295

4.  Synthesis and Anticancer Activity of Hybrid Molecules Based on Lithocholic and (5Z,9Z)-Tetradeca-5,9-dienedioic Acids Linked via Mono(di,tri,tetra)ethylene Glycol and α,ω-Diaminoalkane Units.

Authors:  Vladimir A D'yakonov; Regina A Tuktarova; Lilya U Dzhemileva; Svetlana R Ishmukhametova; Usein M Dzhemilev
Journal:  Pharmaceuticals (Basel)       Date:  2021-01-23

5.  Novel bivalent securinine mimetics as topoisomerase I inhibitors.

Authors:  Wen Hou; Hui Lin; Zhen-Ya Wang; Martin G Banwell; Ting Zeng; Ping-Hua Sun; Jing Lin; Wei-Min Chen
Journal:  Medchemcomm       Date:  2017-01-03       Impact factor: 3.597

6.  Synthesis of New Cu Complex Based on Natural 5Z,9Z-Eicosadienoic Acid: Effective Topoisomerase I Inhibitor and Cytotoxin against the Cisplatin-Resistant Cell Line.

Authors:  Lilya U Dzhemileva; Vladimir A D'yakonov; Leisan K Dil'mukhametova; Usein M Dzhemilev
Journal:  ACS Omega       Date:  2019-10-11
  6 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.