REDUCTION STUDIES OF ANTIFUNGAL ECHINOCANDIN LIPOPEPTIDES - ONE-STEP CONVERSION OF ECHINOCANDIN-B TO ECHINOCANDIN-C

被引：17

作者：

BALKOVEC, JM

BLACK, RM

机构：

[1] Department of Synthetic Chemical Research Merck Research Laboratories, Rahway, NJ 07065-0900

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 32期

关键词：

ANTIFUNGAL; 1,3-BETA-GLUCAN SYNTHESIS INHIBITOR; SELECTIVE REDUCTION; SODIUM CYANOBOROHYDRIDE-TFA; SODIUM TRIACETOXYBOROHYDRIDE-TFA;

D O I：

10.1016/S0040-4039(00)61304-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Sodium cyanoborohydride in trifluoroacetic acid selectively reduced the C5-orn and C4-htyr carbinols to methylene groups in echinocandin lipopeptides. The selective reduction of either hydroxyl is also described. The first conversion of echinocandin B to echinocandin C was accomplished.

引用

页码：4529 / 4532

页数：4

共 16 条

[1] N-METHYLATION OF AMIDES, LACTAMS, AND UREAS
AUERBACH, J
ZAMORE, M
WEINREB, SM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (04) : 725 - 726
[2] SYNTHESIS, STABILITY, AND BIOLOGICAL EVALUATION OF WATER-SOLUBLE PRODRUGS OF A NEW ECHINOCANDIN LIPOPEPTIDE - DISCOVERY OF A POTENTIAL CLINICAL AGENT FOR THE TREATMENT OF SYSTEMIC CANDIDIASIS AND PNEUMOCYSTIS-CARINII PNEUMONIA (PCP)
BALKOVEC, JM
BLACK, RM
HAMMOND, ML
HECK, JV
ZAMBIAS, RA
ABRUZZO, G
BARTIZAL, K
KROPP, H
TRAINOR, C
SCHWARTZ, RE
MCFADDEN, DC
NOLLSTADT, KH
PITTARELLI, LA
POWLES, MA
SCHMATZ, DM
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (01) : 194 - 198
[3] METABOLIC PRODUCTS OF MICROORGANISM .143. ECHINOCANDIN B, A NEW POLYPEPTIDE ANTIBIOTIC FROM ASPERGILLUS NIDULANS VAR ECHINULATUS - ISOLATION AND BUILDING UNITS
BENZ, F
KNUSEL, F
NUESCH, J
TREICHLER, HJ
VOSER, W
[J]. HELVETICA CHIMICA ACTA, 1974, 57 (08) : 2459 - 2477
[4] Gordee R S, 1988, Ann N Y Acad Sci, V544, P294, DOI 10.1111/j.1749-6632.1988.tb40415.x
[5] INVITRO AND INVIVO ANTI-CANDIDA ACTIVITY AND TOXICOLOGY OF LY121019
GORDEE, RS
ZECKNER, DJ
ELLIS, LF
THAKKAR, AL
HOWARD, LC
[J]. JOURNAL OF ANTIBIOTICS, 1984, 37 (09) : 1054 - 1065
[6] HAMMOND ML, 1992, CUTANEOUS ANTIFUNGAL
[7] HENSENS OD, 1992, IN PRESS J ANTIBIOT
[8] HORNE DA, 1978, TETRAHEDRON LETT, P1357
[9] KELLERJUSLEN C, 1976, TETRAHEDRON LETT, P4147
[10] REDUCTION OF N-(PHENYLSULFONYL)PYRROLES WITH SODIUM CYANOBOROHYDRIDE IN TRIFLUOROACETIC-ACID
KETCHA, DM
CARPENTER, KP
ZHOU, Q
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (03) : 1318 - 1320

← 1 2 →