Electrophilic Aromatic Selenylation: New OPRT Inhibitors

被引：62

作者：

Abdo, Mohannad ^{[1
]}

Zhang, Yong ^{[2
]}

Schramm, Vern L. ^{[2
]}

Knapp, Spencer ^{[1
]}

机构：

[1] Rutgers State Univ, Dept Chem & Chem Biol, Piscataway, NJ 08854 USA

[2] Albert Einstein Coll Med, Bronx, NY 10461 USA

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 13期

关键词：

ORGANOSELENIUM COMPOUNDS; DERIVATIVES; ELIMINATION; SELENOXIDES; NUCLEOSIDES; 5-POSITION; DISELENIDE; DISULFIDE; CHEMISTRY; CHLORIDE;

D O I：

10.1021/ol1010032

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Ethoxyethaneseleninic acid reacts with electron-rich aromatic substrates to deliver, by way of the selenoxides, the (2-ethoxyethyl)seleno ethers, which can in turn be transformed into a diverse set of aryl-selenylated products. Among these, a family of 5-uridinyl derivatives shows submicromolar inhibition of human and malarial orotate phosphoribosyltransferase.

引用

页码：2982 / 2985

页数：4

共 30 条

[1] Seleninate in place of phosphate: Irreversible inhibition of protein tyrosine phosphatases [J].

Abdo, Mohannad ;

Liu, Sijiu ;

Zhou, Bo ;

Walls, Chad D. ;

Wu, Li ;

Knapp, Spencer ;

Zhang, Zhong-Yin .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (40) :13196-13197

[2] Biomimetic seleninates and selenonates [J].

Abdo, Mohannad ;

Knapp, Spencer .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (29) :9234-+

[3] α-selenoconotoxins, a new class of potent α7 neuronal nicotinic receptor antagonists [J].

Armishaw, Christopher J. ;

Daly, Norelle L. ;

Nevin, Simon T. ;

Adams, David J. ;

Craik, David J. ;

Alewood, Paul F. .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2006, 281 (20) :14136-14143

[4]

Back T.G., 2000, ORGANOSELENIUM CHEM

[5] THE METATHESIS OF N-SILYLAMINES AND BENZENESELENENYL CHLORIDE - AN EFFICIENT SELENENAMIDE SYNTHESIS [J].

BACK, TG ;

KERR, RG .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1986, 64 (02) :308-310

[6] Structure-activity relationships of C6-uridine derivatives targeting Plasmodia orotidine monophosphate decarboxylase [J].

Bello, Angelica M. ;

Poduch, Ewa ;

Liu, Yan ;

Wei, Lianhu ;

Crandall, Ian ;

Wang, Xiaoyang ;

Dyanand, Christopher ;

Kain, Kevin C. ;

Pai, Emil F. ;

Kotra, Lakshmi P. .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (03) :439-448

[7] SYNTHESIS OF 5-SELENIUM-SUBSTITUTED URACIL DERIVATIVES - INHIBITION OF THYMIDYLATE SYNTHETASE BY 5-HYDROSELENO-2'-DEOXYURIDYLATE [J].

CHOI, S ;

KALMAN, TI ;

BARDOS, TJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1979, 22 (06) :618-621

[8] REACTION OF TRYPTOPHAN DERIVATIVES WITH PHENYLSULFENYL CHLORIDE AND PHENYLSELENENYL BROMIDE [J].

CRICH, D ;

DAVIES, JW .

TETRAHEDRON LETTERS, 1989, 30 (32) :4307-4308

[9] Synthesis and characterization of a novel iNOS/Akt inhibitor Se,Se′-1,4-phenylenebis(1,2-ethanediyl)bisisoselenourea (PBISe)-against colon cancer [J].

Desai, Dhimant ;

Madhunapantula, SubbaRao V. ;

Gowdahalli, Krishnegowda ;

Sharma, Arati ;

Chandagaludoreswamy, Raghavendragowda ;

El-Bayoumy, Karam ;

Robertson, Gavin P. ;

Amin, Shantu .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (06) :2038-2043

[10] DIRECT SELENATION OF ELECTRON-RICH AROMATIC-COMPOUNDS WITH (PHENYLSELENO)DIMETHYLSULFONIUM TETRAFLUOROBORATE [J].

GASSMAN, PG ;

MIURA, A ;

MIURA, T .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (06) :951-954

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