N-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-1-benzofuran-2-carboxamide trifluoroacetate | 1093254-66-0

• 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-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-1-benzofuran-2-carboxamide trifluoroacetate
• 英文别名: N-[[4-chloro-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]methyl]-1-benzofuran-2-carboxamide;2,2,2-trifluoroacetic acid
• CAS: 1093254-66-0
• 化学式: C₂HF₃O₂*C₂₃H₁₃Cl₂FN₂O₃
• 分子量: 569.296
• InChiKey: RGALHEJFMPSNBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.11
• 重原子数：
  38
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  3-氯-5-羟基苯甲腈 在 copper(I) oxide 、 N-溴代丁二酰亚胺(NBS) 、 亚硝酸特丁酯 、 sodium dithionite 、 偶氮二异丁腈 、 氨 、 水 、 sodium hydride 、 N,N-二异丙基乙胺 、 三氟乙酸 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 copper dichloride 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 、 mineral oil 为溶剂， 反应 11.0h， 生成 N-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-1-benzofuran-2-carboxamide trifluoroacetate
  参考文献：
  名称：

  Rational Design of Potent Non-Nucleoside Inhibitors of HIV-1 Reverse Transcriptase

  摘要：

  A new series of non-nucleoside reverse transcriptase inhibitors based on an imidazole-amide biarylether scaffold has been identified and shown to possess potent antiviral activity against HIV-1, including the NNRTI-resistant Y188L mutated virus. X-ray crystallography of inhibitors bound to reverse transcriptase, including a structure of the Y188L RT protein, was used extensively to help identify and optimize the key hydrogen-bonding motif. This led directly to the design of compound 43 that exhibits remarkable antiviral activity (EC50 < 1 nM) against a wide range of NNRTI-resistant viruses and a favorable pharmacokinetic profile across multiple species.

  DOI：

  10.1021/jm301294g

文献信息

• CHEMICAL COMPOUNDS
  申请人：Chong PEK Yoke

  公开号：US20100216746A1

  公开（公告）日：2010-08-26

  The present invention relates to compounds that are a non-nucleoside reverse transcriptase inhibitors, and to processes for the preparation and use of the same. Specifically, the present invention includes methods of using such compounds in the treatment of human immunodeficiency virus infection.

  本发明涉及一种非核苷类逆转录酶抑制剂，以及制备和使用该类化合物的方法。具体而言，本发明包括使用这些化合物治疗人类免疫缺陷病毒感染的方法。
• US8304419B2
  申请人：——

  公开号：US8304419B2

  公开（公告）日：2012-11-06
• Rational Design of Potent Non-Nucleoside Inhibitors of HIV-1 Reverse Transcriptase
  作者：Pek Chong、Paul Sebahar、Michael Youngman、Dulce Garrido、Huichang Zhang、Eugene L. Stewart、Robert T. Nolte、Liping Wang、Robert G. Ferris、Mark Edelstein、Kurt Weaver、Amanda Mathis、Andrew Peat

  DOI：10.1021/jm301294g

  日期：2012.12.13

  A new series of non-nucleoside reverse transcriptase inhibitors based on an imidazole-amide biarylether scaffold has been identified and shown to possess potent antiviral activity against HIV-1, including the NNRTI-resistant Y188L mutated virus. X-ray crystallography of inhibitors bound to reverse transcriptase, including a structure of the Y188L RT protein, was used extensively to help identify and optimize the key hydrogen-bonding motif. This led directly to the design of compound 43 that exhibits remarkable antiviral activity (EC50 < 1 nM) against a wide range of NNRTI-resistant viruses and a favorable pharmacokinetic profile across multiple species.