N-(2-methoxybenzyl)-2-(2,4-dichlorophenoxy)propanamide | 426238-22-4

• 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: N-(2-methoxybenzyl)-2-(2,4-dichlorophenoxy)propanamide
• 英文别名: 2-(2,4-dichlorophenoxy)-N-(2-methoxybenzyl)propanamide；2-(2,4-dichlorophenoxy)-N-[(2-methoxyphenyl)methyl]propanamide
• CAS: 426238-22-4
• 化学式: C₁₇H₁₇Cl₂NO₃
• 分子量: 354.233
• InChiKey: AVFDDZAMLYYXDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  邻甲氧基苄胺 、 2,4-滴丙酸 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以77%的产率得到N-(2-methoxybenzyl)-2-(2,4-dichlorophenoxy)propanamide
  参考文献：
  名称：

  Synthesis and structure–activity relationships of novel phenoxyacetamide inhibitors of the Pseudomonas aeruginosa type III secretion system (T3SS)

  摘要：

  The increasing prevalence of drug-resistant bacterial infections is driving the discovery and development not only of new antibiotics, but also of inhibitors of virulence factors that are crucial for in vivo pathogenicity. One such virulence factor is the type III secretion system (T3SS), which plays a critical role in the establishment and dissemination of Pseudomonas aeruginosa infections. We have recently described the discovery and characterization of a series of inhibitors of P. aeruginosa T3SS based on a phenoxyacetamide scaffold. To better characterize the factors involved in potent T3SS inhibition, we have conducted a systematic exploration of this structure, revealing several highly responsive structure-activity relationships indicative of interaction with a specific target. Most of the structural features contributing to potency were additive, and combination of those features produced optimized inhibitors with IC50 values <1 mu M. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.01.011

文献信息

• [EN] INHIBITORS OF BACTERIAL TYPE III SECRETION SYSTEM<br/>[FR] INHIBITEURS DU SYSTÈME DE SÉCRÉTION DE TYPE III BACTÉRIEN
  申请人：MICROBIOTIX INC

  公开号：WO2010118046A1

  公开（公告）日：2010-10-14

  Organic compounds showing the ability to inhibit effector toxin secretion or translocation mediated by bacterial type III secretion systems are disclosed. The disclosed type III secretion system inhibitor compounds are useful for combating infections by Gram-negative bacteria such as Salmonella spp., Shigella flexneri, Pseudomonas spp., Yersinia spp., enteropathogenic and enteroinvasive Escherichia coli, and Chlamydia spp. having such type III secretion systems.

  本发明公开了有机化合物，它们能够抑制由细菌III型分泌系统介导的效应毒素分泌或转位。公开的III型分泌系统抑制剂化合物可用于对抗由革兰氏阴性菌引起的感染，例如沙门氏菌属、弯曲杆菌、假单胞菌属、耶尔森氏菌属、肠致病性和肠侵袭性大肠杆菌以及具有此类III型分泌系统的沙眼衣原体属。
• Inhibitors Of Bacterial Type III Secretion System
  申请人：Moir Donald T.

  公开号：US20120114633A1

  公开（公告）日：2012-05-10

  Organic compounds showing the ability to inhibit effector toxin secretion or translocation mediated by bacterial type III secretion systems are disclosed. The disclosed type III secretion system inhibitor compounds are useful for combating infections by Gram-negative bacteria such as Salmonella spp., Shigella flexneri, Pseudomonas spp., Yersinia spp., enteropathogenic and enteroinvasive Escherichia coli , and Chlamydia spp. having such type III secretion systems.

  本发明揭示了有机化合物，具有抑制细菌III型分泌系统介导的效应毒素分泌或转位的能力。所述的III型分泌系统抑制剂化合物可用于对抗由革兰氏阴性菌引起的感染，如沙门氏菌属，弯曲杆菌属，假单胞菌属，耶尔森菌属，肠致病性和肠侵袭性大肠杆菌以及具有此类III型分泌系统的沙眼衣原体属。
• INHIBITORS OF BACTERIAL TYPE III SECRETION SYSTEM
  申请人：Microbiotix, Inc.

  公开号：EP2416661A1

  公开（公告）日：2012-02-15
• US8906945B2
  申请人：——

  公开号：US8906945B2

  公开（公告）日：2014-12-09
• Synthesis and structure–activity relationships of novel phenoxyacetamide inhibitors of the Pseudomonas aeruginosa type III secretion system (T3SS)
  作者：John D. Williams、Matthew C. Torhan、Venugopal R. Neelagiri、Carson Brown、Nicholas O. Bowlin、Ming Di、Courtney T. McCarthy、Daniel Aiello、Norton P. Peet、Terry L. Bowlin、Donald T. Moir

  DOI：10.1016/j.bmc.2015.01.011

  日期：2015.3

  The increasing prevalence of drug-resistant bacterial infections is driving the discovery and development not only of new antibiotics, but also of inhibitors of virulence factors that are crucial for in vivo pathogenicity. One such virulence factor is the type III secretion system (T3SS), which plays a critical role in the establishment and dissemination of Pseudomonas aeruginosa infections. We have recently described the discovery and characterization of a series of inhibitors of P. aeruginosa T3SS based on a phenoxyacetamide scaffold. To better characterize the factors involved in potent T3SS inhibition, we have conducted a systematic exploration of this structure, revealing several highly responsive structure-activity relationships indicative of interaction with a specific target. Most of the structural features contributing to potency were additive, and combination of those features produced optimized inhibitors with IC50 values <1 mu M. (C) 2015 Elsevier Ltd. All rights reserved.