Bile acid amides derived from chiral amino alcohols: novel antimicrobials and antifungals

被引：80

作者：

Hazra, BG ^{[1
]}

Pore, VS

Dey, SK

Datta, S

Darokar, MP

Saikia, D

Khanuja, SPS

Thakur, AP

机构：

[1] Natl Chem Lab, Organ Chem Synth Div, Pune 411008, Maharashtra, India

[2] Near Kukrail Picn Spot, Cent Inst Med & Aromat Plants, Lucknow 226015, Uttar Pradesh, India

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2004年 / 14卷 / 03期

关键词：

D O I：

10.1016/j.bmcl.2003.11.018

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Cholic and deoxycholic acid amides 10-17 have been synthesised from(1R,2R)-1-phenyl-2-amino-1,3-propanediol 2,(1S,2S)-1-phenyl-2-amino-1,3-propanediol 4, (1R,2R)-1-para-nitrophenyl-2-amino-1,3-propanediol 3, (1S,2S)-1-para-nitrophenyl-2-amino-1,3-propanediol 5. Amide 12 derived from N-succinimidyl ester 9 of deoxycholic acid and (1R,2R)-1-phenyl-2-amino-1,3-propanediol 2, found to be active against Cryptococcus neoformans and the amide 17 obtained from N-succinimidyl ester 9 of deoxycholic acid and (IS,2S)-1-para-nitrophenyl-2-amino-1,3-propanediol 5, is found to be potent against various gram-positive bacteria. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：773 / 777

页数：5

共 19 条

[11] SQUALAMINE - AN AMINOSTEROL ANTIBIOTIC FROM THE SHARK [J].

MOORE, KS ;

WEHRLI, S ;

RODER, H ;

ROGERS, M ;

FORREST, JN ;

MCCRIMMON, D ;

ZASLOFF, M .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1993, 90 (04) :1354-1358

[12] In vitro activity of the echinocandin antifungal agent LY303,366 in comparison with itraconazole and amphotericin B against Aspergillus spp. [J].

Oakley, KL ;

Moore, CB ;

Denning, DW .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1998, 42 (10) :2726-2730

[13] CATALYTIC HYDROLYSIS OF PARA-NITROPHENYL ESTERS IN THE PRESENCE OF REPRESENTATIVE AMMONIUM AGGREGATES - SPECIFIC ACTIVATION OF A CHOLESTERYL NUCLEOPHILE BOUND TO A DIALKYLAMMONIUM BILAYER-MEMBRANE [J].

OKAHATA, Y ;

ANDO, R ;

KUNITAKE, T .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1979, 52 (12) :3647-3653

[14] RAPID CONSTRUCTION OF A SQUALAMINE MIMIC [J].

SADOWNIK, A ;

DENG, G ;

JANOUT, V ;

REGEN, SL ;

BERNARD, EM ;

KIKUCHI, K ;

ARMSTRONG, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (22) :6138-6139

[15]

Savage PB, 2002, EUR J ORG CHEM, V2002, P759

[16] Cholic acid derivatives: novel antimicrobials [J].

Savage, PB ;

Li, CH .

EXPERT OPINION ON INVESTIGATIONAL DRUGS, 2000, 9 (02) :263-272

[17] HYDROGEN-BONDING IN MICELLE FORMATION [J].

VENKATESAN, P ;

CHENG, Y ;

KAHNE, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (15) :6955-6956

[18]

Willemen HM, 2002, ANGEW CHEM INT EDIT, V41, P4275, DOI 10.1002/1521-3773(20021115)41:22<4275::AID-ANIE4275>3.0.CO

[19]

2-U

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