Synthesis and Antiproliferative Activity Evaluation of Aryl(Hetaryl)Cyclopentenone Analogs of Combretastatin A-4

被引：6

作者：

Shirinyan, V. Z. ^{[1
]}

Markosyan, A. I. ^{[2
]}

Baryshnikova, M. A. ^{[3
]}

Yaminova, L. V. ^{[4
]}

L'vov, A. G. ^{[1
]}

Gabrielyan, S. A. ^{[2
]}

机构：

[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, 47 Leninskii Prosp, Moscow 119991, Russia

[2] Natl Acad Sci Armenia, Sci & Technol Ctr Organ & Pharmaceut Chem, 26 Azatutyan Pr,0014, Yerevan 375014, Armenia

[3] Russian Acad Med Sci, NN Blokhin Russian Canc Res Ctr, 23 Kashirskoe Shosse, Moscow 115478, Russia

[4] DI Mendeleev Univ Chem Technol Russia, 9 Miusskaya Pl, Moscow 125047, Russia

来源：

PHARMACEUTICAL CHEMISTRY JOURNAL | 2018年 / 51卷 / 10期

基金：

俄罗斯基础研究基金会;

关键词：

cyclopentenone; antitumor activity; combretastatin A-4; divinylketones; Nazarov reaction; lymphocytic leukemia; SPECTRAL PROPERTIES; ANTITUMOR-ACTIVITY; TUBULIN; AGENTS; BINDING; DIARYLETHENES; CYTOTOXICITY; A4;

D O I：

10.1007/s11094-018-1706-8

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of previously unreported di- and triaryl(hetaryl)cyclopentenone derivatives were prepared using a convenient synthetic method and screened preliminarily for antitumor activity in four human cell lines, i.e., T-cell leukemia (Jurkat), lung adenocarcinoma (A-549), colon cancer (HCT-116), and breast adenocarcinoma (MCF-7). The most cytotoxic of the tested compounds was 2-(3,4,5-trimethoxyphenyl)-3-(4-methoxyphenyl) cyclopent-2-en-1-one. However, it was inactive against lymphocytic leukemia P388 in mice despite its cytotoxicity in in vitro tests.

引用

页码：867 / 872

页数：6

共 32 条

[1] Role of the colchicine ring a and its methoxy groups in the binding to tubulin and microtubule inhibition [J].

Andreu, JM ;

Perez-Ramirez, B ;

Gorbunoff, MJ ;

Ayala, D ;

Timasheff, SN .

BIOCHEMISTRY, 1998, 37 (23) :8356-8368

[2]

[Anonymous], 2012, METHODICAL RECOMME 1, P642

[3]

Atkins JH, 2002, NAT REV DRUG DISCOV, V1, P491, DOI 10.1038/nrd842

[4]

Avendaño C, 2008, MEDICINAL CHEMISTRY OF ANTICANCER DRUGS, P229, DOI 10.1016/B978-0-444-52824-7.00008-1

[5]

Bradbury R. H., 2007, TOPICS MED CHEM, V1

[6]

Brown T, 2006, TOP HETEROCYCLIC CHE, V2, P1, DOI 10.1007/7081_003

[7]

Chaplin DJ, 1996, BRIT J CANCER, V74, pS86

[8] Combretastatins: from natural products to drug discovery [J].

Cirla, A ;

Mann, J .

NATURAL PRODUCT REPORTS, 2003, 20 (06) :558-564

[9] Microtubule-binding agents: a dynamic field of cancer therapeutics [J].

Dumontet, Charles ;

Jordan, Mary Ann .

NATURE REVIEWS DRUG DISCOVERY, 2010, 9 (10) :790-803

[10] Structural requirements for the interaction of combretastatins with tubulin: how important is the trimethoxy unit? [J].

Gaukroger, K ;

Hadfield, JA ;

Lawrence, NJ ;

Nolan, S ;

McGown, AT .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (17) :3033-3037

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