4-amino-N,N,3-trimethylbenzenesulfonamide | 57946-91-5

• 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: 4-amino-N,N,3-trimethylbenzenesulfonamide
• CAS: 57946-91-5
• 化学式: C₉H₁₄N₂O₂S
• 分子量: 214.288
• InChiKey: OGJLVYJNUNZJAA-UHFFFAOYSA-N

物化性质

• 沸点：
  369.7±52.0 °C(Predicted)
• 密度：
  1.234±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-amino-N,N,3-trimethylbenzenesulfonamide 、 [4-chloro-2-(3-fluoro-5-trifluoromethylbenzoyl)phenoxy]acetic acid 在 碳酸氢钠 作用下， 以 丙酮 为溶剂， 反应 2.5h， 以42%的产率得到2-[4-chloro-2-[3-fluoro-5-(trifluoromethyl)benzoyl]phenoxy]-N-[4-(dimethylsulfamoyl)-2-methyl-phenyl]acetamide
  参考文献：
  名称：

  Structure−Activity Relationship Studies of Novel Benzophenones Leading to the Discovery of a Potent, Next Generation HIV Nonnucleoside Reverse Transcriptase Inhibitor

  摘要：

  Despite the progress of the past two decades, there is still considerable need for safe, efficacious drugs that target human immunodeficiency virus (HIV). This is particularly true for the growing number of patients infected with virus resistant to currently approved HIV drugs. Our high throughput screening effort identified a benzophenone template as a potential nonnucleoside reverse transcriptase inhibitor (NNRTI). This manuscript describes our extensive exploration of the benzophenone structure-activity relationships, which culminated in the identification of several compounds with very potent inhibition of both wild type and clinically relevant NNRTI-resistant mutant strains of HIV. These potent inhibitors include 70h (GW678248), which has in vitro antiviral assay IC50 values of 0.5 nM against wild-type HIV, 1 nM against the K103N mutant associated with clinical resistance to efavirenz, and 0.7 nM against the Y181C mutant associated with clinical resistance to nevirapine. Compound 70h has also demonstrated relatively low clearance in intravenous pharmacokinetic studies in three species, and it is the active component of a drug candidate which has progressed to phase 2 clinical studies.

  DOI：

  10.1021/jm050670l
• 作为产物：
  描述：

  2-氨基甲苯-5-磺酸 在 palladium on activated charcoal 氯化亚砜 、 氢气 、 sodium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 20.0 ℃ 、275.79 kPa 条件下， 反应 80.5h， 生成 4-amino-N,N,3-trimethylbenzenesulfonamide
  参考文献：
  名称：

  Structure−Activity Relationship Studies of Novel Benzophenones Leading to the Discovery of a Potent, Next Generation HIV Nonnucleoside Reverse Transcriptase Inhibitor

  摘要：

  Despite the progress of the past two decades, there is still considerable need for safe, efficacious drugs that target human immunodeficiency virus (HIV). This is particularly true for the growing number of patients infected with virus resistant to currently approved HIV drugs. Our high throughput screening effort identified a benzophenone template as a potential nonnucleoside reverse transcriptase inhibitor (NNRTI). This manuscript describes our extensive exploration of the benzophenone structure-activity relationships, which culminated in the identification of several compounds with very potent inhibition of both wild type and clinically relevant NNRTI-resistant mutant strains of HIV. These potent inhibitors include 70h (GW678248), which has in vitro antiviral assay IC50 values of 0.5 nM against wild-type HIV, 1 nM against the K103N mutant associated with clinical resistance to efavirenz, and 0.7 nM against the Y181C mutant associated with clinical resistance to nevirapine. Compound 70h has also demonstrated relatively low clearance in intravenous pharmacokinetic studies in three species, and it is the active component of a drug candidate which has progressed to phase 2 clinical studies.

  DOI：

  10.1021/jm050670l

文献信息

• Method comprising the use of N-substituted perfluoroalkyanesulfonamides as herbicidal and plant growth modifying agents, and composition
  申请人：MINNESOTA MINING AND MANUFACTURING COMPANY

  公开号：US03920444A1

  公开（公告）日：1975-11-18

  N-Substituted perfluoroalkanesulfonamides of the formula:

  N-取代的全氟烷磺酰胺的化学式：
• [EN] BENZOPHENONES AS INHIBITORS OF REVERSE TRANSCRIPTASE<br/>[FR] BENZOPHENONES AGISSANT COMME INHIBITEURS DE LA TRANSCRIPTASE INVERSE
  申请人：GLAXO GROUP LTD

  公开号：WO2001017982A1

  公开（公告）日：2001-03-15

  The present invention includes benzophenone compounds (I) which are useful in the treatment of HIV infections.

  本发明包括苯甲酮化合物（I），其在治疗HIV感染方面具有用处。
• Benzophenones as inhibitors of reverse transcriptase
  申请人：GLAXO GROUP LIMITED

  公开号：EP1710238A1

  公开（公告）日：2006-10-11

  The present invention includes benzophenone compounds (I) which are useful in the treatment of HIV infections.

  本发明包括二苯甲酮化合物 (I)，它们可用于 治疗艾滋病病毒感染。
• BENZOPHENONES AS INHIBITORS OF REVERSE TRANSCRIPTASE
  申请人：GLAXO GROUP LIMITED

  公开号：EP1208091B1

  公开（公告）日：2006-05-03
• US7273863B1
  申请人：——

  公开号：US7273863B1

  公开（公告）日：2007-09-25