Solid phase synthesis of 1,3,4-oxadiazin-5 (6R)-one and 1,3,4-oxadiazol-2-one scaffolds from acyl hydrazides

被引：5

作者：

Sarma, Bani Kanta ^{[1
]}

Liu, Xiaodan ^{[2
,3
]}

Wu, Hao ^{[2
,3
]}

Gao, Yu ^{[2
,3
]}

Kodadek, Thomas ^{[2
,3
]}

机构：

[1] Shiv Nadar Univ, Sch Nat Sci, Dept Chem, Dadri 201314, Uttar Pradesh, India

[2] Scripps Res Inst, Dept Chem, Jupiter, FL 33458 USA

[3] Scripps Res Inst, Dept Canc Biol, Jupiter, FL 33458 USA

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2015年 / 13卷 / 01期

关键词：

ONE-COMPOUND LIBRARIES; COMBINATORIAL LIBRARIES; INHIBITORS; DERIVATIVES; CHEMISTRY; PEPTOIDS; SYSTEM; POTENT;

D O I：

10.1039/c4ob01883d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Solid phase synthesis of 1,3,4-oxadiazin-5(6R)-one and 1,3,4-oxadiazol-2-one scaffolds from resin-bound acyl hydrazides is described. We demonstrate here that the reactions of resin-bound aryl or hetero-aromatic acyl hydrazides with 2-substituted-2-bromo-acetic acids and 4-nitrophenyl chloroformate and subsequent treatment with DIEA lead to intramolecular cyclization reactions to produce six-membered 1,3,4-oxadiazin-5(6R)-ones and five-membered 1,3,4-oxadiazol-2-ones, respectively. We also show that acyl hydrazide-derived 1,3,4-oxadiazol-2-ones may be useful serine hydrolase inhibitors.

引用

页码：59 / 63

页数：5

共 33 条

[1] Incorporation of Heterocycles into the Backbone of Peptoids to Generate Diverse Peptoid-Inspired One Bead One Compound Libraries [J].

Aditya, Animesh ;

Kodadek, Thomas .

ACS COMBINATORIAL SCIENCE, 2012, 14 (03) :164-169

[2]

Aquino C, 2012, NAT CHEM, V4, P99, DOI [10.1038/NCHEM.1200, 10.1038/nchem.1200]

[3] Use of an inhibitor to identify members of the hormone-sensitive lipase family [J].

Ben Ali, Yassine ;

Chahinian, Henri ;

Petry, Stefan ;

Muller, Guenter ;

Lebrun, Regine ;

Verger, Robert ;

Carriere, Frederic ;

Mandrich, Luigi ;

Rossi, Mose ;

Manco, Giuseppe ;

Sarda, Louis ;

Abousalham, Abdelkarim .

BIOCHEMISTRY, 2006, 45 (47) :14183-14191

[4] The molecular mechanism of human hormone-sensitive lipase inhibition by substituted 3-phenyl-5-alkoxy-1,3,4-oxadiazol-2-ones [J].

Ben Ali, Yassine ;

Verger, Robert ;

Carriere, Frederic ;

Petry, Stefan ;

Muller, Guenter ;

Abousalhama, Abdelkarim .

BIOCHIMIE, 2012, 94 (01) :137-145

[5] Functionalisation of aldehydes via aerobic hydroacylation of azodicarboxylates 'on' water [J].

Chudasama, Vijay ;

Ahern, Jenna M. ;

Dhokia, Dipti V. ;

Fitzmaurice, Richard J. ;

Caddick, Stephen .

CHEMICAL COMMUNICATIONS, 2011, 47 (11) :3269-3271

[6] Activity-based protein profiling: From enzyme chemistry [J].

Cravatt, Benjamin F. ;

Wright, Aaron T. ;

Kozarich, John W. .

ANNUAL REVIEW OF BIOCHEMISTRY, 2008, 77 :383-414

[7] SYNTHESIS AND MITICIDAL AND INSECTICIDAL ACTIVITIES OF 4-(2-FLUOROETHYL)-5,6-DIHYDRO-4H-1,3,4-OXADIAZINES [J].

DEKEYSER, MA ;

MCDONALD, PT ;

ANGLE, GW ;

DOWNER, RGH .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1993, 41 (08) :1329-1331

[8] QUANTITATIVE STRUCTURE-ACTIVITY-RELATIONSHIPS IN ACARICIDAL 4H-1,3,4-OXADIAZIN-5(6H)-ONES [J].

DEKEYSER, MA ;

BORTH, DM ;

MOORE, RC ;

MISHRA, A .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1991, 39 (02) :374-379

[9] DESIGN AND SYNTHESIS OF 5,6-DIHYDRO-4H-1,3,4-OXADIAZINES AS POTENTIAL OCTOPAMINERGIC INSECTICIDES [J].

DEKEYSER, MA ;

HARRISON, WA ;

MCDONALD, PT ;

DOWNER, RGH .

PESTICIDE SCIENCE, 1993, 38 (04) :309-314

[10] IMPROVED SYNTHESIS AND SPECTRAL CHARACTERIZATION OF D5281, AN OXADIAZINE MITICIDE/INSECTICIDE [J].

DEKEYSER, MA ;

MITCHELL, DS ;

DOWNER, RGH .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1994, 42 (08) :1783-1785

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