A FACILE METHOD TO APPEND PEPTIDAL SIDE-CHAINS ONTO STEROIDAL TEMPLATES

被引:2
作者
HORWELL, DC [1 ]
LENNON, IC [1 ]
ROBERTS, E [1 ]
机构
[1] ADDENBROOKES HOSP,PARKE DAVIS NEUROSCI RES CTR,CAMBRIDGE CB2 2QB,ENGLAND
关键词
D O I
10.1016/S0040-4020(01)86716-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Side-chains corresponding to phenylalanine, tyrosine and tryptophan are introduced onto a steroid template in a highly efficient manner via a condensation of the appropriate lithium acetylide with a steroidal ketone. The subsequent acetylene functionality can be selectively reduced in the presence of a modified benzyl ether and steroid ring unsaturation.
引用
收藏
页码:4225 / 4234
页数:10
相关论文
共 9 条
[1]  
COREY EJ, 1972, TETRAHEDRON LETT, P3769
[2]   THE 1ST DESIGN AND SYNTHESIS OF A STEROIDAL PEPTIDOMIMETIC - THE POTENTIAL VALUE OF PEPTIDOMIMETICS IN ELUCIDATING THE BIOACTIVE CONFORMATION OF PEPTIDE LIGANDS [J].
HIRSCHMANN, R ;
SPRENGELER, PA ;
KAWASAKI, T ;
LEAHY, JW ;
SHAKESPEARE, WC ;
SMITH, AB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (24) :9699-9701
[3]   NONPEPTIDAL PEPTIDOMIMETICS WITH A BETA-D-GLUCOSE SCAFFOLDING - A PARTIAL SOMATOSTATIN AGONIST BEARING A CLOSE STRUCTURAL RELATIONSHIP TO A POTENT, SELECTIVE SUBSTANCE-P ANTAGONIST [J].
HIRSCHMANN, R ;
NICOLAOU, KC ;
PIETRANICO, S ;
SALVINO, J ;
LEAHY, EM ;
SPRENGELER, PA ;
FURST, G ;
SMITH, AB ;
STRADER, CD ;
CASCIERI, MA ;
CANDELORE, MR ;
DONALDSON, C ;
VALE, W ;
MAECHLER, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (23) :9217-9218
[4]   DE-NOVO DESIGN AND SYNTHESIS OF SOMATOSTATIN NONPEPTIDE PEPTIDOMIMETICS UTILIZING BETA-D-GLUCOSE AS A NOVEL SCAFFOLDING [J].
HIRSCHMANN, R ;
NICOLAOU, KC ;
PIETRANICO, S ;
LEAHY, EM ;
SALVINO, J ;
ARISON, B ;
CICHY, MA ;
SPOORS, PG ;
SHAKESPEARE, WC ;
SPRENGELER, PA ;
HAMLEY, P ;
SMITH, AB ;
REISINE, T ;
RAYNOR, K ;
MAECHLER, L ;
DONALDSON, C ;
VALE, W ;
FREIDINGER, RM ;
CASCIERI, MR ;
STRADER, CD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (26) :12550-12568
[5]   FURTHER SYNTHETIC STUDIES ON RIFAMYCIN-S [J].
NAGAOKA, H ;
KISHI, Y .
TETRAHEDRON, 1981, 37 (23) :3873-3888
[6]   CONCEPTS AND PROGRESS IN THE DEVELOPMENT OF PEPTIDE MIMETICS [J].
OLSON, GL ;
BOLIN, DR ;
BONNER, MP ;
BOS, M ;
COOK, CM ;
FRY, DC ;
GRAVES, BJ ;
HATADA, M ;
HILL, DE ;
KAHN, M ;
MADISON, VS ;
RUSIECKI, VK ;
SARABU, R ;
SEPINWALL, J ;
VINCENT, GP ;
VOSS, ME .
JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (21) :3039-3049
[7]  
OLSON GL, 1989, P BIOTECHNOL US C MA, pS384
[8]  
PERRINE DM, 1986, HETEROCYCLES, V24, P365
[9]   NONPEPTIDE BETA-TURN MIMETICS OF ENKEPHALIN [J].
SU, T ;
NAKANISHI, H ;
XUE, L ;
CHEN, B ;
TULADHAR, S ;
JOHNSON, ME ;
KAHN, M .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (05) :835-840