An expeditious synthesis and anticancer activity of novel 4-(3′-indolyl)oxazoles

被引：82

作者：

Kumar, Dalip ^{[1
]}

Kumar, N. Maruthi ^{[1
]}

Sundaree, Swapna ^{[1
]}

Johnson, Emmanuel O. ^{[2
,3
]}

Shah, Kavita ^{[2
,3
]}

机构：

[1] Birla Inst Technol & Sci, Chem Grp, Pilani 333031, Rajasthan, India

[2] Purdue Univ, Dept Chem, W Lafayette, IN 47907 USA

[3] Purdue Univ, Purdue Canc Ctr, W Lafayette, IN 47907 USA

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2010年 / 45卷 / 03期

关键词：

2,4-Disubstituted oxazoles; 4-(3 '-Indolyl)oxazoles; Anticancer activity; Amides; alpha-Tosyloxy ketones; ORGANIC-SYNTHESIS; OXAZOLES; <HYDROXY(TOSYLOXY)IODO>BENZENE; 5-(3-INDOLYL)OXAZOLES; FERMENTATION; THIAZOLES;

D O I：

10.1016/j.ejmech.2009.12.024

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of 4-(3'-indolyl)oxazole congeners have been synthesized and studied for their cytotoxicity against six cancer cell lines. Reaction of 3-acetyl-1'-benzenesulfonylindole with [hydroxy(tosyloxy)iodo]benzene afforded pure 3-tosyloxyacetyl-1'-benzenesuifonylindole. Microwave-accelerated neat reaction of 3-tosyloxyacetyl-1-benzenesulfonylindole with amides resulted in the exclusive formation of 4-(1'-benzenesulfonylindol-3'-yl)-2-substituted oxazoles (4) in very good yield. Treatment of 4 with aqueous sodium hydroxide under refluxing conditions afforded pure 4-(3'-indolyl)-2-substituted oxazoles (5) in excellent yield. The 4-(T-indolyl)oxazoles; 5d and 11 were found to be most cytotoxic and selective against various cancer cell lines. Compounds 5g, 5j and 51 showed moderate anticancer activity. (C) 2010 Elsevier Masson SAS. All rights reserved.

引用

页码：1244 / 1249

页数：6

共 22 条

[1] A versatile synthesis of 2,4-substituted oxazoles [J].

Chudasama, Vijay ;

Wilden, Jonathan D. .

CHEMICAL COMMUNICATIONS, 2008, (32) :3768-3770

[2] FUNCTIONALIZED OXAZOLES FROM RHODIUM-CATALYZED REACTION OF DIMETHYL DIAZOMALONATE WITH NITRILES [J].

CONNELL, R ;

SCAVO, F ;

HELQUIST, P ;

AKERMARK, B .

TETRAHEDRON LETTERS, 1986, 27 (46) :5559-5562

[3] Aminophenyl oxazoles and thiazoles [J].

Friedman, BS ;

Sparks, M ;

Adams, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1937, 59 :2262-2264

[4] An approach to substituted 4-hydroxypyran-2-ones: The total synthesis of phenoxan [J].

Garey, D ;

Ramirez, ML ;

Gonzales, S ;

Wertsching, A ;

Tith, S ;

Keefe, K ;

Pena, MR .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (14) :4853-4856

[5] Camalexin [J].

Glawischnig, Erich .

PHYTOCHEMISTRY, 2007, 68 (04) :401-406

[6] STUDIES ON MACROCYCLIC LACTONE ANTIBIOTICS .7. STRUCTURE OF A PHYTOTOXIN RHIZOXIN PRODUCED BY RHIZOPUS-CHINENSIS [J].

IWASAKI, S ;

KOBAYASHI, H ;

FURUKAWA, J ;

NAMIKOSHI, M ;

OKUDA, S ;

SATO, Z ;

MATSUDA, I ;

NODA, T .

JOURNAL OF ANTIBIOTICS, 1984, 37 (04) :354-362

[7] ONE-STEP ALPHA-TOSYLOXYLATION OF KETONES WITH [HYDROXY(TOSYLOXY)IODO]BENZENE [J].

KOSER, GF ;

RELENYI, AG ;

KALOS, AN ;

REBROVIC, L ;

WETTACH, RH .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (12) :2487-2489

[8]

Koser GF, 2001, ALDRICHIM ACTA, V34, P89

[9] A facile synthesis of naturally occurring 5-(3-indolyl)oxazoles [J].

Kumar, Dalip ;

Sundaree, Swapna ;

Patel, Gautam ;

Rao, V. S. .

TETRAHEDRON LETTERS, 2008, 49 (05) :867-869

[10] An efficient synthesis and biological study of novel indolyl-1,3,4-oxadiazoles as potent anticancer agents [J].

Kumar, Dalip ;

Sundaree, Swapna ;

Johnson, Emmanuel O. ;

Shah, Kavita .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (15) :4492-4494

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