tert-butyl 2-{[(6-chloropyridin-3-yl)carbonyl]amino}-5-cyanobenzoate | 668969-23-1

• 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: tert-butyl 2-{[(6-chloropyridin-3-yl)carbonyl]amino}-5-cyanobenzoate
• 英文别名: Tert-butyl 2-[(6-chloropyridine-3-carbonyl)amino]-5-cyanobenzoate；tert-butyl 2-[(6-chloropyridine-3-carbonyl)amino]-5-cyanobenzoate
• CAS: 668969-23-1
• 化学式: C₁₈H₁₆ClN₃O₃
• 分子量: 357.796
• InChiKey: VKRDOUUDDSVOKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  92.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-{[(6-chloropyridin-3-yl)carbonyl]amino}-5-cyanobenzoate 在 三氟乙酸 作用下， 以 1,4-二氧六环 为溶剂， 生成 5-Cyano-2-[(6-methylsulfanylpyridine-3-carbonyl)amino]benzoic acid
  参考文献：
  名称：

  Preparation of novel anthranilic acids as antibacterial agents: Extensive evaluation of structural and physical properties on antibacterial activity and human serum albumin affinity

  摘要：

  In the past few years a significant effort has been devoted by Pharmacia toward the discovery of novel antibiotics. We have recently described the identification of an anthranilic acid lead 1 and the optimization resulting in the advanced lead 2. In this report, we describe the preparation of several selected analogs to probe the dependency of this template for antibacterial activity and the affinity these compounds have for human serum albumin (HSA). These analogs illustrate that decreased affinity for HSA can be achieved while retaining relevant antibacterial activity. The most important factor for reduced HSA affinity is decrease in log P rather than a structural change. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.03.036
• 作为产物：
  描述：

  t-butyl 2-amino-5-cyanobenzoate 、 6-氯烟酸 在 吡啶 、 草酰氯 作用下， 以 二氯甲烷 为溶剂， 以55%的产率得到tert-butyl 2-{[(6-chloropyridin-3-yl)carbonyl]amino}-5-cyanobenzoate
  参考文献：
  名称：

  Preparation of novel anthranilic acids as antibacterial agents: Extensive evaluation of structural and physical properties on antibacterial activity and human serum albumin affinity

  摘要：

  In the past few years a significant effort has been devoted by Pharmacia toward the discovery of novel antibiotics. We have recently described the identification of an anthranilic acid lead 1 and the optimization resulting in the advanced lead 2. In this report, we describe the preparation of several selected analogs to probe the dependency of this template for antibacterial activity and the affinity these compounds have for human serum albumin (HSA). These analogs illustrate that decreased affinity for HSA can be achieved while retaining relevant antibacterial activity. The most important factor for reduced HSA affinity is decrease in log P rather than a structural change. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.03.036

文献信息

• [EN] ANTIBACTERIAL BENZOIC ACID DERIVATIVES<br/>[FR] DERIVES D'ACIDES BENZOIQUES ANTIBACTERIENS
  申请人：UPJOHN CO

  公开号：WO2004018428A1

  公开（公告）日：2004-03-04

  The invention provides antimicrobial agents and methods of using the agents for sterilization, sanitation, antisepsis, disinfection, and treatment of infections in mammals.

  这项发明提供了抗菌剂和使用这些剂进行哺乳动物的消毒、卫生、防腐、消毒和治疗感染的方法。
• Antibacterial benzoic acid derivatives
  申请人：——

  公开号：US20040110802A1

  公开（公告）日：2004-06-10

  The invention provides antimicrobial agents and methods of using the agents for sterilization, sanitation, antisepsis, disinfection, and treatment of infections in mammals.

  这项发明提供了抗微生物药剂及其使用方法，用于哺乳动物的消毒、卫生、防腐、消毒和治疗感染。
• Preparation of novel anthranilic acids as antibacterial agents: Extensive evaluation of structural and physical properties on antibacterial activity and human serum albumin affinity
  作者：Atli Thorarensen、Jianke Li、Brian D. Wakefield、Donna L. Romero、Keith R. Marotti、Michael T. Sweeney、Gary E. Zurenko、Ronald W. Sarver

  DOI：10.1016/j.bmcl.2007.03.036

  日期：2007.6

  In the past few years a significant effort has been devoted by Pharmacia toward the discovery of novel antibiotics. We have recently described the identification of an anthranilic acid lead 1 and the optimization resulting in the advanced lead 2. In this report, we describe the preparation of several selected analogs to probe the dependency of this template for antibacterial activity and the affinity these compounds have for human serum albumin (HSA). These analogs illustrate that decreased affinity for HSA can be achieved while retaining relevant antibacterial activity. The most important factor for reduced HSA affinity is decrease in log P rather than a structural change. (C) 2007 Elsevier Ltd. All rights reserved.