Synthesis and cytotoxic activities of some 2-Arylnaphtho[2,3-d]oxazole-4,9-dione derivatives on androgen-dependent (LNCaP) and androgen-independent (PC3) human prostate cancer cell lines

被引：18

作者：

Brandy, Yakini ^{[1
]}

Ononiwu, Innocent ^{[2
]}

Adedeji, Dolapo ^{[2
]}

Williams, Vonetta ^{[1
]}

Mouamba, Claudia ^{[1
]}

Kanaan, Yasmine ^{[4
,6
]}

Copeland, Robert L., Jr. ^{[3
,4
]}

Wright, Dwayne A. ^{[1
]}

Butcher, Ray J. ^{[1
]}

Denmeade, Samuel R. ^{[5
]}

Bakare, Oladapo ^{[1
]}

机构：

[1] Howard Univ, Dept Chem, Washington, DC 20059 USA

[2] Elizabeth City State Univ, Dept Pharm & Hlth Profess, Elizabeth City, NC 27909 USA

[3] Howard Univ, Coll Med, Dept Pharmacol, Washington, DC 20059 USA

[4] Howard Univ, Coll Med, Ctr Canc, Washington, DC 20059 USA

[5] Johns Hopkins Univ, Sch Med, Sidney Kimmel Comprehens Canc Ctr Johns Hopkins, Baltimore, MD 21231 USA

[6] Howard Univ, Coll Med, Dept Microbiol, Washington, DC 20059 USA

来源：

INVESTIGATIONAL NEW DRUGS | 2012年 / 30卷 / 04期

基金：

美国国家科学基金会;

关键词：

2-arylnaphtho[2,3-d]oxazole-4,9-dione; Oxazolo-1,4-naphthoquinone; Prostate cancer; Naphthoquinone; Anticancer activities; BIOLOGICAL EVALUATION; HETEROCYCLIC QUINONES; 2,3-DICHLORO-5,8-DIMETHOXY-1,4-NAPHTHOQUINONE; INHIBITORS; DISRUPTS; TUBULIN;

D O I：

10.1007/s10637-011-9635-3

中图分类号：

R73 [肿瘤学];

学科分类号：

100214 ;

摘要：

The synthesis of five 2-arylnaphtho[2,3-d]oxazole-4,9-dione derivatives was accomplished by refluxing 2-amino-3-bromo-1,4-naphthoquinone with appropriate benzoyl chloride analogs at elevated temperatures. In vitro anticancer evaluation of these compounds was performed on androgen-dependent, LNCaP, and androgen-independent, PC3, human prostate cancer cell lines. In general, these compounds displayed slightly stronger cytotoxicity on the androgen-dependent LNCaP than on the androgen-independent PC3 prostate cancer cell lines. The meta-substituted 2-(3-Chloro-phenyl)-naphtho[2,3-d]oxazole-4,9-dione (10) appear to display the best cytotoxicity on both cell lines with an IC50 of 0.03 mu M on LNCaP and 0.08 mu M on PC3 after 5 days of exposure.

引用

页码：1709 / 1714

页数：6

共 18 条

[1] The natural naphthoquinone plumbagin exhibits antiproliferative activity and disrupts the microtubule network through tubulin binding
Acharya, Bipul R.
Bhattacharyya, Bhabatarak
Chakrabarti, Gopal
[J]. BIOCHEMISTRY, 2008, 47 (30) : 7838 - 7845
[2] Vitamin K3 Disrupts the Microtubule Networks by Binding to Tubulin: A Novel Mechanism of Its Antiproliferative Activity
Acharya, Bipul R.
Choudhury, Diptiman
Das, Amlan
Chakrabarti, Gopal
[J]. BIOCHEMISTRY, 2009, 48 (29) : 6963 - 6974
[3] Antitumour quinones
Asche, C
[J]. MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2005, 5 (05) : 449 - 467
[4] Synthesis and MEK1 inhibitory activities of imido-substituted 2-chloro-1,4-naphthoquinones
Bakare, O
Ashendel, CL
Peng, HR
Zalkow, LH
Burgess, EM
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (14) : 3165 - 3170
[5] Microwave-Assisted Synthesis of Imido-Substituted 2-Chloro-1,4-naphthoquinone Derivatives and their Cytotoxic Activities on Three Human Prostate Cancer Cell Lines
Berhe, Solomon
Kanaan, Yasmine
Copeland, Robert L., Jr.
Wright, Dwayne A.
Zalkow, Leon H.
Bakare, Oladapo
[J]. LETTERS IN DRUG DESIGN & DISCOVERY, 2008, 5 (08) : 485 - 488
[6] Design, synthesis, and biological evaluation of novel naphthoquinone derivatives with CDC25 phosphatase inhibitory activity
Brun, MP
Braud, E
Angotti, D
Mondésert, O
Quaranta, M
Montes, M
Miteva, M
Gresh, N
Ducommun, B
Garbay, C
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (16) : 4871 - 4879
[7] Synthesis, metabolism and in vitro cytotoxicity studies on novel lavendamycin antitumor agents
Cai, Wen
Hassani, Mary
Karki, Rajesh
Walter, Ervin D.
Koelsch, Katherine H.
Seradj, Hassan
Lineswala, Jayana P.
Mirzaei, Hamid
York, Jeremy S.
Olang, Fatemeh
Sedighi, Minoo
Lucas, Jennifer S.
Eads, Thomas J.
Rose, Anthony S.
Charkhzarrin, Sahba
Hermann, Nicholas G.
Beall, Howard D.
Behforouz, Mohammad
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (05) : 1899 - 1909
[8] Copeland RL, 2007, ANTICANCER RES, V27, P1537
[9] Synthesis of 7-oxo-7H-naphtho[1,2,3-de]quinoline derivatives as potential anticancer agents active on multidrug resistant cell lines
Dzieduszycka, M
Bontemps-Gracz, MM
Stefanska, B
Martelli, S
Piwkowska, A
Arciemiuk, M
Borowski, E
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (09) : 2880 - 2886
[10] Nitrogen-containing Heterocyclic quinones: A class of potential selective antitumor agents
Garuti, Laura
Roberti, Marinella
Pizzirani, Daniela
[J]. MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2007, 7 (05) : 481 - 489

← 1 2 →