Synthesis and antimicrobial activity of 7-fluoro-3-aminosteroids

被引：26
作者：
Khan, Sharaf Nawaz
Kim, Bong Jin
Kim, Hong-Seok [1 ]
机构：
[1] Kyungpook Natl Univ, Dept Appl Chem, Taegu 702701, South Korea
[2] KRICT, Div Med Sci, Taejon 305600, South Korea
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2007年 / 17卷 / 18期
关键词：
fluorinated steroids; reductive amination; antimicrobial activity; RESISTANT STAPHYLOCOCCUS-AUREUS; PHASE-TRANSFER CATALYSIS; STREPTOCOCCUS-PNEUMONIAE; DIETHYLAMINOSULFUR TRIFLUORIDE; SQUALAMINE; FLUORINATION; ANALOGS; SHARK; FLUORIDE; ACID;
D O I：
10.1016/j.bmcl.2007.07.001
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
A series of 7-fluoro-3-aminosteroids were synthesized and their in vitro antimicrobial activities were evaluated against Gram-positive and Gram-negative bacteria. The nucleophilic fluorination of several 7 beta-hydroxysteroids by diethylaminosulfur trifluoride in n-pentane, followed by reductive amination of the resulting 7-fluoro-3-ketosteroids with spermidine in the presence of NaBH3CN, afforded 7-fluoro-3-aminosteroids in high yield. Compound 25 showed the highest antimicrobial activity against Staphylococcus aureus, Pseudomonas aeruginosa, Streptococcus pyogenes, and Escherichia coli. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5139 / 5142
页数：4
相关论文
共 29 条
  • [1] Antimicrobial resistance among clinical isolates of Streptococcus pneumoniae in the United States during 1999-2000, including a comparison of resistance rates since 1994-1995
    Doern, GV
    Heilmann, KP
    Huynh, HK
    Rhomberg, PR
    Coffman, SL
    Brueggemann, AB
    [J]. ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2001, 45 (06) : 1721 - 1729
  • [2] The Staphylococcus aureus "superbug"
    Foster, TJ
    [J]. JOURNAL OF CLINICAL INVESTIGATION, 2004, 114 (12) : 1693 - 1696
  • [3] Efficient calf thymus DNA condensation upon binding with novel bile acid polyamine Amides
    Geall, AJ
    Al-Hadithi, D
    Blagbrough, IS
    [J]. BIOCONJUGATE CHEMISTRY, 2002, 13 (03) : 481 - 490
  • [4] β-lactams against methicillin-resistant Staphylococcus aureus
    Guignard, B
    Entenza, JM
    Moreillon, P
    [J]. CURRENT OPINION IN PHARMACOLOGY, 2005, 5 (05) : 479 - 489
  • [5] Hao D, 2003, CLIN CANCER RES, V9, P2465
  • [6] Herbst RS, 2003, CLIN CANCER RES, V9, P4108
  • [7] The synthesis and characterization of analogs of the antimicrobial compound squalamine: 6 beta-hydroxy-3-aminosterols synthesized from hyodeoxycholic acid
    Jones, SR
    Kinney, WA
    Zhang, XH
    Jones, LM
    Selinsky, BS
    [J]. STEROIDS, 1996, 61 (10) : 565 - 571
  • [8] Squalamine analogues as potential anti-trypanosomal and anti-leishmanial compounds
    Khabnadideh, S
    Tan, CL
    Croft, SL
    Kendrick, H
    Yardley, V
    Gilbert, IH
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (11) : 1237 - 1239
  • [9] A highly stereoselective reductive amination of 3-ketosteroid with amines:: an improved synthesis of 3α-aminosteroid
    Khan, SN
    Bae, SY
    Kim, HS
    [J]. TETRAHEDRON LETTERS, 2005, 46 (45) : 7675 - 7678
  • [10] Antimicrobial activities of squalamine mimics
    Kikuchi, K
    Bernard, EM
    Sadownik, A
    Regen, SL
    Armstrong, D
    [J]. ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1997, 41 (07) : 1433 - 1438
123