(1S,2R,3R,4S,6R)-4,6-diazido-3-[[7-(trifluoromethyl)quinolin-4-yl]sulfanylmethoxy]cyclohexane-1,2-diol | 609342-87-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (1S,2R,3R,4S,6R)-4,6-diazido-3-[[7-(trifluoromethyl)quinolin-4-yl]sulfanylmethoxy]cyclohexane-1,2-diol
• CAS: 609342-87-2
• 化学式: C₁₇H₁₆F₃N₇O₃S
• 分子量: 455.42
• InChiKey: ROSSWNMPHQENCO-XVLPMQGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  117
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (1S,2R,3R,4S,6R)-4,6-diazido-3-[[7-(trifluoromethyl)quinolin-4-yl]sulfanylmethoxy]cyclohexane-1,2-diol 在 4-二甲氨基吡啶 、 sodium hydride 、 二异丁基氢化铝 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 34.0h， 生成 (4aR,5R,6S,8R,8aS)-6,8-Diazido-5-(7-trifluoromethyl-quinolin-4-ylsulfanylmethoxy)-octahydro-benzo[1,4]dioxin-2-ol
  参考文献：
  名称：

  The synthesis and 16S A-site rRNA recognition of carbohydrate-free aminoglycosides

  摘要：

  The first carbohydrate-free aminoglycoside analogs bearing the 2-deoxystreptamine moiety were synthesized from asymmetrically protected 2-deoxystrepamine and subsequently demonstrated to have significant binding to the 16S A-site rRNA target and moderate functional activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.08.027
• 作为产物：
  描述：

  在 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 10.0h， 生成 (1S,2R,3R,4S,6R)-4,6-diazido-3-[[7-(trifluoromethyl)quinolin-4-yl]sulfanylmethoxy]cyclohexane-1,2-diol
  参考文献：
  名称：

  基于质谱RNA结合测定法设计和合成巴龙霉素相关的杂环取代的氨基糖苷模拟物。

  摘要：

  DOI：

  10.1002/anie.200351354

文献信息

• Antimicrobial 2-deoxystreptamine compounds
  申请人：ISIS Pharmaceuticals, Inc.

  公开号：US06759523B2

  公开（公告）日：2004-07-06

  The present invention is directed to analogs of aminoglycoside compounds of the class having a glycosylated 2-deoxystreptamine (2-DOS) ring as well as their preparation and use as prophylactic or therapeutics against microbial infection. Compounds of the invention comprises at least one aryl, heteroaryl, substituted aryl or substituted heteroaryl group in place of a glycosyl group attached to the 2-deoxystreptamine ring.

  本发明涉及氨基糖苷类化合物的类似物，其具有糖基化的2-去氧链霉素（2-DOS）环，以及它们的制备和用作预防或治疗微生物感染的用途。本发明的化合物包括至少一个芳基、杂环芳基、取代芳基或取代杂环芳基取代2-去氧链霉素环上的糖基。
• Probing the ribosomal RNA A-site with functionally diverse analogues of paromomycin—synthesis of ring I mimetics
  作者：Stephen Hanessian、Susanta Adhikari、Janek Szychowski、Kandasmy Pachamuthu、Xiaojing Wang、Michael T. Migawa、Richard H. Griffey、Eric E. Swayze

  DOI：10.1016/j.tet.2006.10.079

  日期：2007.1

  Methods were developed to selectively cleave the 2-amino-2-deoxy-alpha-D-glucopyranosyl ring in paromomycin. The preferentially N- and O-protected products were alkylated on the liberated C4 hydroxyl group of the deoxystreptalnine subunit. Further manipulation furnished a series of aromatic, heteroaromatic, and aliphatic appendages as spatial mimics offing 1. Modest inhibitory activity was found against Staphylococcus aureus with two analogues (27 and 63), although cell-free functional transcription/translation assays were similar to paromomycin for analogue 27. (c) 2006 Elsevier Ltd. All rights reserved.