Synthesis and evaluation of phenoxyoxazaphospholidine, phenoxyoxazaphosphinane, and benzodioxaphosphininamine sulfides and related compounds as potential anti-malarial agents

被引：6

作者：

Mara, Christine ^{[1
]}

Dempsey, Enda ^{[2
]}

Bell, Angus ^{[2
]}

Barlow, James W. ^{[1
]}

机构：

[1] Royal Coll Surgeons Ireland, Dept Pharmaceut & Med Chem, Dublin 2, Ireland

[2] Trinity Coll Dublin, Moyne Inst Prevent Med, Sch Genet & Microbiol, Dept Microbiol, Dublin 2, Ireland

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2013年 / 23卷 / 12期

关键词：

Phenoxyoxazaphospholidines; Phenoxyoxazaphosphinanes; Benzodioxaphosphininamines; Anti-malarial; Tubulin; DRUG DISCOVERY;

D O I：

10.1016/j.bmcl.2013.04.026

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of phenoxyoxazaphospholidine, phenoxyoxazaphosphinane and benzodioxaphosphininamine sulfides and related cyclic organophosphorus compounds based on the lead anti-tubulin herbicides amiprophos methyl and butamifos were synthesised and evaluated for anti-malarial activity. Of these compounds, while none of the phenoxyoxazaphospholidines, phenoxyoxazaphosphinanes or benzodioxaphosphininamine sulphides were more potent than APM, phosphorothioamidate 30, a dual compound also bearing an aminoquinoline motif, showed promising activity against Plasmodium falciparum (IC50 0.038 mu M) and warrants further study. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：3580 / 3583

页数：4

共 24 条

[11] Kinetics and mechanism of the aminolysis of aryl phenyl chlorothiophosphates with anilines [J].

Hoque, Md. Ehtesham Ul ;

Dey, Shuchismita ;

Guha, Arun Kanti ;

Kim, Chan Kyung ;

Lee, Bon-Su ;

Lee, Hai Whang .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (15) :5493-5499

[12] Synthesis of novel chiral 2-oxo- and 2-thio-1,3,2-oxazaphospholidines via asymmetric cyclization of L-methionol with (thio)phosphoryl dichlorides [J].

Liu, L ;

Chen, R ;

Huang, Y .

HETEROATOM CHEMISTRY, 2005, 16 (01) :33-38

[13] Synthesis and evaluation of phosphoramidate and phosphorothioamidate analogues of amiprophos methyl as potential antimalarial agents [J].

Mara, Christine ;

Dempsey, Enda ;

Bell, Angus ;

Barlow, James W. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (20) :6180-6183

[14] Global malaria mortality between 1980 and 2010: a systematic analysis [J].

Murray, Christopher J. L. ;

Rosenfeld, Lisa C. ;

Lim, Stephen S. ;

Andrews, Kathryn G. ;

Foreman, Kyle J. ;

Haring, Diana ;

Fullman, Nancy ;

Naghavi, Mohsen ;

Lozano, Rafael ;

Lopez, Alan D. .

LANCET, 2012, 379 (9814) :413-431

[15] Application of multicomponent reactions to antimalarial drug discovery.: Part 2:: New antiplasmodial and antitrypanosomal 4-aminoquinoline γ- and δ-lactams via a 'catch and release' protocol [J].

Musonda, Chitalu C. ;

Gut, Jiri ;

Rosenthal, Philip J. ;

Yardley, Vanessa ;

De Souza, Renata C. Carvalho ;

Chibale, Kelly .

BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (16) :5605-5615

[16]

Reddy C.B., 2011, J CHEM PHARM RES, V3, P84

[17]

Rigterink R. H., [No title captured], Patent No. 3268536

[18]

Sato N., 1996, Jpn. Kokai Tokkyo Koho, Patent No. [JP 08026919 A 19960130, 08026919]

[19]

Shipov A. E., 1993, J ORG CHEM, V63, P1196

[20] Synthesis and physiological activity of new organophosphorus pesticides of 1,3,2-oxazaphosphorinane series [J].

Shipov, AE ;

Genkina, GK ;

Artyushin, OI ;

Mndzhoyan, ZO ;

Gushchin, BE ;

Chumakova, EI ;

Roslavtseva, SA ;

Eremina, OY ;

Bakanova, EI ;

Kagan, YS ;

Ershova, EA ;

Mastryukova, TA ;

Kabachnik, MI .

RUSSIAN CHEMICAL BULLETIN, 1995, 44 (11) :2147-2156

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