benzyl (3S,4R)-3-azido-4-(benzhydrylideneamino)piperidine-1-carboxylate | 1007596-65-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl (3S,4R)-3-azido-4-(benzhydrylideneamino)piperidine-1-carboxylate
• 英文别名: benzyl (3S,4R)-azido-4-[(diphenylmethylene)amino]piperidine-1-carboxylate；Benzyl (3S,4R)-3-azido-4-[(diphenylmethylene)amino]piperidine-1-carboxylate
• CAS: 1007596-65-7
• 化学式: C₂₆H₂₅N₅O₂
• 分子量: 439.517
• InChiKey: CBGYMBHFXWQGFB-RPWUZVMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  56.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl (3S,4R)-3-azido-4-(benzhydrylideneamino)piperidine-1-carboxylate 在 copper(II) sulfate 水 、 4-甲基苯磺酸吡啶 、 sodium ascorbate 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 38.5h， 生成 benzyl (3S,4R)-3-[(cyanomethyl)-1H-1,2,3-triazol-1-yl]-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidine-1-carboxylate
  参考文献：
  名称：

  WO2008/20222

  摘要：

  公开号：
• 作为产物：
  描述：

  叠氮磷酸二苯酯 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 14.5h， 以50%的产率得到benzyl (3S,4R)-3-azido-4-(benzhydrylideneamino)piperidine-1-carboxylate
  参考文献：
  名称：

  WO2008/20222

  摘要：

  公开号：

文献信息

• PYRROLE DERIVATIVES WITH ANTIBACTERIAL ACTIVITY
  申请人：Basarab Gregory

  公开号：US20100286181A1

  公开（公告）日：2010-11-11

  Compounds of formula (I) and their pharmaceutically acceptable salts are described. Processes for their preparation, pharmaceutical compositions containing them, their use as medicaments and their use in the treatment of bacterial infections are also described.

  本文描述了化学式（I）的化合物及其药用可接受的盐。还描述了制备它们的过程，含有它们的药物组合物，它们作为药物的用途以及它们在治疗细菌感染方面的用途。
• Optimization of Pyrrolamide Topoisomerase II Inhibitors Toward Identification of an Antibacterial Clinical Candidate (AZD5099)
  作者：Gregory S. Basarab、Pamela J. Hill、C. Edwin Garner、Ken Hull、Oluyinka Green、Brian A. Sherer、P. Brian Dangel、John I. Manchester、Shanta Bist、Sheila Hauck、Fei Zhou、Maria Uria-Nickelsen、Ruth Illingworth、Richard Alm、Mike Rooney、Ann E. Eakin

  DOI：10.1021/jm500462x

  日期：2014.7.24

  AZD5099 (compound 63) is an antibacterial agent that entered phase 1 clinical trials targeting infections caused by Gram-positive and fastidious Gram-negative bacteria. It was derived from previously reported pyrrolamide antibacterials and a fragment-based approach targeting the ATP binding site of bacterial type II topoisomerases. The program described herein varied a 3-piperidine substituent and incorporated 4-thiazole substituents that form a seven-membered ring intramolecular hydrogen bond with a 5-position carboxylic acid. Improved antibacterial activity and lower in vivo clearances were achieved. The lower clearances were attributed, in part, to reduced recognition by the multidrug resistant transporter Mrp2. Compound 63 showed notable efficacy in a mouse neutropenic Staphylococcus aureus infection model. Resistance frequency versus the drug was low, and reports of clinical resistance due to alteration of the target are few. Hence, 63 could offer a novel treatment for serious issues of resistance to currently used antibacterials.
• WO2008/20222
  申请人：——

  公开号：——

  公开（公告）日：——