5-[(E)-2-(4-isopropyl-1,3-thiazol-2-yl)-1-ethenyl]-3-pyridineamine | 422280-07-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-[(E)-2-(4-isopropyl-1,3-thiazol-2-yl)-1-ethenyl]-3-pyridineamine
• 英文别名: 5-[(E)-2-(4-propan-2-yl-1,3-thiazol-2-yl)ethenyl]pyridin-3-amine
• CAS: 422280-07-7
• 化学式: C₁₃H₁₅N₃S
• 分子量: 245.348
• InChiKey: DQAOTDGMJXSCDD-ONEGZZNKSA-N

物化性质

• 沸点：
  469.8±55.0 °C(predicted)
• 密度：
  1.221±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  80
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  高邻苯二甲酸酐 、 5-[(E)-2-(4-isopropyl-1,3-thiazol-2-yl)-1-ethenyl]-3-pyridineamine 以 甲苯 为溶剂， 生成 2-({5-[(E)-2-(4-Isopropyl-thiazol-2-yl)-vinyl]-pyridin-3-ylcarbamoyl}-methyl)-benzoic acid
  参考文献：
  名称：

  MexAB-OprM-Specific efflux pump inhibitors in Pseudomonas aeruginosa. Part 1: Discovery and early strategies for lead optimization

  摘要：

  The identification of a series of compounds that specifically inhibit efflux by the MexAB-OprM pump system in Pseudomonas aeruginosa is described. Synthesis and in vitro structure-activity relationships (SARs) are outlined. Early leads lacked activity in animal models, and efforts to improve solubility and reduce serum protein binding by the introduction of polar groups are discussed. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.07.024
• 作为产物：
  描述：

  3,5-吡啶二甲酸 在 lithium aluminium tetrahydride 、 TEA 、 二苯基磷酸 、 sodium methylate 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 5-[(E)-2-(4-isopropyl-1,3-thiazol-2-yl)-1-ethenyl]-3-pyridineamine
  参考文献：
  名称：

  MexAB-OprM-Specific efflux pump inhibitors in Pseudomonas aeruginosa. Part 1: Discovery and early strategies for lead optimization

  摘要：

  The identification of a series of compounds that specifically inhibit efflux by the MexAB-OprM pump system in Pseudomonas aeruginosa is described. Synthesis and in vitro structure-activity relationships (SARs) are outlined. Early leads lacked activity in animal models, and efforts to improve solubility and reduce serum protein binding by the introduction of polar groups are discussed. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.07.024

文献信息

• Drug efflux pump inhibitor
  申请人：DAIICHI PHARMACEUTICAL CO., LTD.

  公开号：EP1652839A2

  公开（公告）日：2006-05-03

  A medicament for preventive and/or therapeutic treatment of a microbial infection having an activity of eliminating resistance of a microorganism with acquired resistance to an antimicrobial agent, which comprises as an active ingredient a compound represented by the following general formula (I), a physiologically acceptable salt thereof, or a hydrate thereof: wherein R1 and R2 independently represent hydrogen atom, a halogen atom, carboxyl group and the like; J1 represents a 5- or 6-membered heteroaromatic ring; W1 represents -CH=CH-, -C≡C-, -CH2CH2- and the like; A1 represents phenylene group, pyridinediyl group, furandiyl group and the like; G1 represents oxygen atom, carbonyl group, ethynyl group and the like; p represents an integer of from 0 to 3; G2 represents phenylene group, furandiyl group, tetrahydrofurandiyl group and the like; G3 represents -CH2- or single bond; m and n represent an integer of 0 or 1; and Q1 represents an acidic group.

  一种用于预防和/或治疗微生物感染的药物，具有消除对抗菌剂产生抗药性的微生物的抗药性的活性，其活性成分包括下式（I）所代表的化合物、其生理上可接受的盐或其水合物： 其中 R1 和 R2 分别代表氢原子、卤素原子、羧基等；J1 代表 5 或 6 元杂芳环；W1 代表 -CH=CH-、-C≡C-、-CH2CH2- 等；A1 代表亚苯基、吡啶二基、呋喃二基等；G1 代表氧原子、羰基、乙炔基等；p 代表 0 至 3 的整数；G2 代表亚苯基、呋喃二基、四氢呋喃二基等；G3 代表 -CH2- 或单键；m 和 n 代表 0 或 1 的整数；以及 Q1 代表酸性基团。
• DRUG DISCHARGE PUMP INHIBITORS
  申请人：Trine Pharmaceuticals, Inc.

  公开号：EP1227084B1

  公开（公告）日：2005-12-14
• MexAB-OprM-Specific efflux pump inhibitors in Pseudomonas aeruginosa. Part 1: Discovery and early strategies for lead optimization
  作者：Kiyoshi Nakayama、Yohei Ishida、Masami Ohtsuka、Haruko Kawato、Ken-ichi Yoshida、Yoshihiro Yokomizo、Shigeru Hosono、Toshiharu Ohta、Kazuki Hoshino、Hiroko Ishida、Kumi Yoshida、Thomas E. Renau、Roger Léger、Jason Z. Zhang、Ving J. Lee、William J. Watkins

  DOI：10.1016/j.bmcl.2003.07.024

  日期：2003.12

  The identification of a series of compounds that specifically inhibit efflux by the MexAB-OprM pump system in Pseudomonas aeruginosa is described. Synthesis and in vitro structure-activity relationships (SARs) are outlined. Early leads lacked activity in animal models, and efforts to improve solubility and reduce serum protein binding by the introduction of polar groups are discussed. (C) 2003 Elsevier Ltd. All rights reserved.