Design, synthesis and biological evaluation of dihydronaphthalene and benzosuberene analogs of the combretastatins as inhibitors of tubulin polymerization in cancer chemotherapy

Bioorganic & Medicinal Chemistry
Madhavi SriramKevin G Pinney

Abstract

A novel series of dihydronaphthalene and benzosuberene analogs bearing structural similarity to the combretastatins in terms of 1,2-diarylethene, trimethoxyphenyl, and biaryl functionality has been synthesized. The compounds have been evaluated in regard to their ability to inhibit tubulin assembly and for their cytotoxicity against selected human cancer cell lines. From this series of compounds, benzosuberene analogs 2 and 4 inhibited tubulin assembly at concentrations comparable to that of combretastatin A-4 (CA4) and combretastatin A-1 (CA1). Furthermore, analog 4 demonstrated remarkable cytotoxicity against the three human cancer cell lines evaluated (for example GI(50)=0.0000032 microM against DU-145 prostate carcinoma).

References

Jun 7, 2002·Acta Crystallographica. Section C, Crystal Structure Communications·Mallinath B HadimaniKevin G Pinney
Apr 2, 2004·Nature Reviews. Cancer·Mary Ann Jordan, Leslie Wilson
Jun 16, 2004·Cancer·Dietmar W SiemannMichael R Horsman
Jun 2, 2005·Nature Reviews. Cancer·Gillian M TozerBruce C Baguley
Nov 22, 2007·Expert Opinion on Therapeutic Targets·Chryso Kanthou, Gillian M Tozer

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Citations

Jul 3, 2013·Bioorganic & Medicinal Chemistry Letters·Ganesh S JedheGangadhar J Sanjayan
Jan 29, 2013·European Journal of Medicinal Chemistry·Evelia RasolofonjatovoMouad Alami
May 28, 2013·European Journal of Medicinal Chemistry·Zong-Ying LiuDavid W Boykin
Jul 3, 2013·Cellular & Molecular Biology Letters·Renata MikstackaJakub Różański
Sep 23, 2014·European Journal of Medicinal Chemistry·Ramandeep KaurJitender Bariwal
Jan 19, 2016·Bioorganic & Medicinal Chemistry·Christine A HerdmanKevin G Pinney
Jan 17, 2015·The Journal of Organic Chemistry·Samantha VothJ Adam McCubbin
Oct 11, 2017·Expert Opinion on Therapeutic Patents·Haider BehbehaniThoraya A Farghaly
May 1, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Li LiuRalph P Mason
Jun 26, 2021·European Journal of Medicinal Chemistry·Shannon PecnardOlivier Provot
Jan 15, 2015·Journal of Medicinal Chemistry·Ubaldina GalliGian Cesare Tron
Oct 23, 2018·ACS Medicinal Chemistry Letters·Wenlong LiJinyi Xu
Feb 18, 2020·European Journal of Medicinal Chemistry·Abdallah HamzeOlivier Provot

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