Literature DB >> 25815147

Synthesis and Structure-Activity Relationship Study of 1-Phenyl-1-(quinazolin-4-yl)ethanols as Anticancer Agents.

Kenta Kuroiwa1, Hirosuke Ishii2, Kenji Matsuno2, Akira Asai2, Yumiko Suzuki1.   

Abstract

A quinazoline derivative PVHD121 (1a) was shown to have strong antiproliferative activity against various tumor-derived cell lines, including A549 (lung), NCI-H460 (lung), HCT116 (colon), MCF7 (breast), PC3 (prostate), and HeLa (cervical) cells with IC50 values from 0.1 to 0.3 μM. A structure-activity relationship (SAR) study at the 2- and 4-position of the quinazoline core lead to the discovery of more potent anticancer agents (14, 16, 17, 19, 24, and 31). The results of an in vitro tubulin polymerization assay and fluorescent-based colchicine site competition assay with purified tubulin indicated that 1a inhibits tubulin polymerization by binding to the colchicine site.

Entities:  

Keywords:  Quinazoline; anticancer; colchicine binding site; structure−activity relationship study; tubulin inhibitor

Year:  2015        PMID： 25815147      PMCID： PMC4360158          DOI： 10.1021/ml5004684

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  16 in total

1.  A combinatorial scaffold approach toward kinase-directed heterocycle libraries.

Authors:  Sheng Ding; Nathanael S Gray; Xu Wu; Qiang Ding; Peter G Schultz
Journal:  J Am Chem Soc       Date:  2002-02-27       Impact factor: 15.419

2.  Structure-activity relationships of ustiloxin analogues.

Authors:  Madeleine M Joullié; Simon Berritt; Ernest Hamel
Journal:  Tetrahedron Lett       Date:  2011-04       Impact factor: 2.415

3.  Synthesis and biological evaluation of 2-(3',4',5'-trimethoxybenzoyl)-3-amino 5-aryl thiophenes as a new class of tubulin inhibitors.

Authors:  Romeo Romagnoli; Pier Giovanni Baraldi; Vincent Remusat; Maria Dora Carrion; Carlota Lopez Cara; Delia Preti; Francesca Fruttarolo; Maria Giovanna Pavani; Mojgan Aghazadeh Tabrizi; Manlio Tolomeo; Stefania Grimaudo; Jan Balzarini; Mary Ann Jordan; Ernest Hamel
Journal:  J Med Chem       Date:  2006-10-19       Impact factor: 7.446

Review 4.  Understanding microtubule dynamics for improved cancer therapy.

Authors:  S Honore; E Pasquier; D Braguer
Journal:  Cell Mol Life Sci       Date:  2005-12       Impact factor: 9.261

5.  Discovery of N-(4-methoxyphenyl)-N,2-dimethylquinazolin-4-amine, a potent apoptosis inducer and efficacious anticancer agent with high blood brain barrier penetration.

Authors:  Nilantha Sirisoma; Azra Pervin; Hong Zhang; Songchun Jiang; J Adam Willardsen; Mark B Anderson; Gary Mather; Christopher M Pleiman; Shailaja Kasibhatla; Ben Tseng; John Drewe; Sui Xiong Cai
Journal:  J Med Chem       Date:  2009-04-23       Impact factor: 7.446

6.  Discovery of quinazolines as histamine H4 receptor inverse agonists using a scaffold hopping approach.

Authors:  Rogier A Smits; Iwan J P de Esch; Obbe P Zuiderveld; Joachim Broeker; Kamonchanok Sansuk; Elena Guaita; Gabriella Coruzzi; Maristella Adami; Eric Haaksma; Rob Leurs
Journal:  J Med Chem       Date:  2008-12-25       Impact factor: 7.446

7.  Promotion of fluorescence upon binding of colchicine to tubulin.

Authors:  B Bhattacharyya; J Wolff
Journal:  Proc Natl Acad Sci U S A       Date:  1974-07       Impact factor: 11.205

8.  Novel benzylidene-9(10H)-anthracenones as highly active antimicrotubule agents. Synthesis, antiproliferative activity, and inhibition of tubulin polymerization.

Authors:  Helge Prinz; Yukihito Ishii; Takeo Hirano; Thomas Stoiber; Juan A Camacho Gomez; Peter Schmidt; Heiko Düssmann; Angelika M Burger; Jochen H M Prehn; Eckhard G Günther; Eberhard Unger; Kazuo Umezawa
Journal:  J Med Chem       Date:  2003-07-17       Impact factor: 7.446

9.  A history of cancer chemotherapy.

Authors:  Vincent T DeVita; Edward Chu
Journal:  Cancer Res       Date:  2008-11-01       Impact factor: 12.701

Review 10.  Microtubule-associated proteins as targets in cancer chemotherapy.

Authors:  Kumar M R Bhat; Vijayasaradhi Setaluri
Journal:  Clin Cancer Res       Date:  2007-05-15       Impact factor: 12.531
View more
  2 in total

1.  Discovery of a Potent Anticancer Agent PVHD303 with in Vivo Activity.

Authors:  Yumiko Suzuki; Ayana Otake; Satoshi Ueno; Kensuke Hayashi; Hirosuke Ishii; Nao Miyoshi; Kenta Kuroiwa; Masashi Tachikawa; Yuki Fujimaki; Kotaro Nishiyama; Kei Manabe; Ryuta Yamazaki; Akira Asai
Journal:  ACS Med Chem Lett       Date:  2020-05-08       Impact factor: 4.345

Review 2.  An insight into the therapeutic potential of quinazoline derivatives as anticancer agents.

Authors:  Irshad Ahmad
Journal:  Medchemcomm       Date:  2017-04-07       Impact factor: 3.597
  2 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.