Solid phase synthesis of heterocyclic compounds from linear peptides: Cyclic ureas and thioureas

被引：65

作者：

Nefzi, A ^{[1
]}

Ostresh, JM ^{[1
]}

Meyer, JP ^{[1
]}

Houghten, RA ^{[1
]}

机构：

[1] TORREY PINES INST MOL STUDIES, SAN DIEGO, CA 92121 USA

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 06期

关键词：

D O I：

10.1016/S0040-4039(96)02516-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The solid phase synthesis of cyclic ureas and thioureas is described. The reduction of acylated dipeptides followed by treatment with carbonyldiimidazole or thiocarbonyldiimidazole affords the corresponding cyclic urea or thiourea in good yield and high purity. This is an example of a broader approach to the solid phase synthesis of individual heterocyclic compounds and combinatorial libraries using peptides as starting materials. (C) 1997, Elsevier Science Ltd.

引用

页码：931 / 934

页数：4

共 11 条

[1] Cuervo J.H., 1995, PEPTIDES 1994, P465
[2] The synthesis of peptidomimetic combinatorial libraries through successive amide alkylations
Dorner, B
Husar, GM
Ostresh, JM
Houghten, RA
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 1996, 4 (05) : 709 - 715
[3] GENERATION AND USE OF SYNTHETIC PEPTIDE COMBINATORIAL LIBRARIES FOR BASIC RESEARCH AND DRUG DISCOVERY
HOUGHTEN, RA
PINILLA, C
BLONDELLE, SE
APPEL, JR
DOOLEY, CT
CUERVO, JH
[J]. NATURE, 1991, 354 (6348) : 84 - 86
[4] HOUGHTEN RA, 1986, INT J PEPT PROT RES, V27, P673
[5] Synthesis of a cyclic urea as a nonnatural biopolymer scaffold
Kim, JM
Wilson, TE
Norman, TC
Schultz, PG
[J]. TETRAHEDRON LETTERS, 1996, 37 (30) : 5309 - 5312
[6] RATIONAL DESIGN OF POTENT, BIOAVAILABLE, NONPEPTIDE CYCLIC UREAS AS HIV PROTEASE INHIBITORS
LAM, PYS
JADHAV, PK
EYERMANN, CJ
HODGE, CN
RU, Y
BACHELER, LT
MEEK, JL
OTTO, MJ
RAYNER, MM
WONG, YN
CHANG, CH
WEBER, PC
JACKSON, DA
SHARPE, TR
ERICKSONVIITANEN, S
[J]. SCIENCE, 1994, 263 (5145) : 380 - 384
[7] LIBRARIES FROM LIBRARIES - CHEMICAL TRANSFORMATION OF COMBINATORIAL LIBRARIES TO EXTEND THE RANGE AND REPERTOIRE OF CHEMICAL DIVERSITY
OSTRESH, JM
HUSAR, GM
BLONDELLE, SE
DORNER, B
WEBER, PA
HOUGHTEN, RA
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1994, 91 (23) : 11138 - 11142
[8] OSTRESH JM, 1996, IN PRESS METHODS ENZ, V267
[9] OSTRESH JM, 1995, PEPTIDES 1994, P416
[10] VERSATILITY OF POSITIONAL SCANNING SYNTHETIC COMBINATORIAL LIBRARIES FOR THE IDENTIFICATION OF INDIVIDUAL COMPOUNDS
PINILLA, C
APPEL, JR
BLONDELLE, SE
DOOLEY, CT
EICHLER, J
OSTRESH, JM
HOUGHTEN, RA
[J]. DRUG DEVELOPMENT RESEARCH, 1994, 33 (02) : 133 - 145

← 1 2 →