Synthesis and biological activity of novel macrocyclic antifungals: Modification of the tyrosine moiety of the lipopeptidolactone FR901469

被引：11

作者：

Barrett, D

Tanaka, A

Harada, K

Watabe, E

Maki, K

Ikeda, F

机构：

[1] Fujisawa Pharmaceut Co Ltd, Med Chem Res Labs, Yodogawa Ku, Osaka 5328514, Japan

[2] Fujisawa Pharmaceut Co Ltd, Med Biol Res Labs, Yodogawa Ku, Osaka 5328514, Japan

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2001年 / 11卷 / 14期

关键词：

D O I：

10.1016/S0960-894X(01)00317-1

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of tyrosine-modified derivatives of the macrocyclic lipopeptidolactone FR901469 have been prepared and evaluated for in vitro and in vivo antifungal activity and for hemolytic activity towards red blood cells. Compound 14 displayed significantly reduced hemolytic potential at 1 mg/mL and a comparable protective effect to FR901469 in a mouse candidiasis model. (C) 2001 Elsevier Science Ltd. All rights reserved.

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页码：1843 / 1849

页数：7

相关论文

共 14 条

[1]

AOKI M, 2000, Patent No. 0005251

[2] PNEUMOCANDIN ANTIFUNGAL LIPOPEPTIDES - THE PHENOLIC HYDROXYL IS REQUIRED FOR 1,3-BETA-GLUCAN SYNTHESIS INHIBITION [J].

BALKOVEC, JM ;

BLACK, RM ;

ABRUZZO, GK ;

BARTIZAL, K ;

DREIKORN, S ;

NOLLSTADT, K .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (10) :2039-2042

[3] Synthesis and biological activity of novel macrocyclic antifungals: Acylated conjugates of the ornithine moiety of the lipopeptidolactone FR901469 [J].

Barrett, D ;

Tanaka, A ;

Harada, K ;

Ohki, H ;

Watabe, E ;

Maki, K ;

Ikeda, F .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (04) :479-482

[4] An expedient synthesis of the amide analog of the potent antifungal lipopeptidolactone FR901469 [J].

Barrett, D ;

Tanaka, A ;

Fujie, A ;

Shigematsu, N ;

Hashimoto, M ;

Hashimoto, S .

TETRAHEDRON LETTERS, 2001, 42 (04) :703-705

[5] Synthesis and structure-activity relationships of novel 3'-HTY-substituted pneumocandins [J].

Black, RM ;

Balkovec, JM ;

Nollstadt, KM ;

Dreikorn, S ;

Bartizal, KF ;

Abruzzo, GK .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (22) :2879-2884

[6]

Debono M, 1988, Ann N Y Acad Sci, V544, P152, DOI 10.1111/j.1749-6632.1988.tb40398.x

[7]

Fujie A, 2000, J ANTIBIOT, V53, P912, DOI 10.7164/antibiotics.53.912

[8] Update on antifungals targeted to the cell wall:: focus on β-1,3-glucan synthase inhibitors [J].

Georgopapadakou, NH .

EXPERT OPINION ON INVESTIGATIONAL DRUGS, 2001, 10 (02) :269-280

[9]

HOWARD LC, 1982, TOXICOLOGIST, V2, P1984

[10] Synthesis and antifungal activities of novel 1,3-β-D-glucan synthase inhibitors.: Part 1 [J].

Masubuchi, K ;

Okada, T ;

Kohchi, M ;

Sakaitani, M ;

Mizuguchi, E ;

Shirai, H ;

Aoki, M ;

Watanabe, T ;

Kondoh, O ;

Yamazaki, T ;

Satoh, Y ;

Kobayashi, K ;

Inoue, T ;

Horii, I ;

Shimma, N .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (03) :395-398