2-chloro-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide | 53297-88-4

• 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: 2-chloro-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide
• 英文别名: N-[4-(aminosulfonyl)-2-methylphenyl]-2-chloroacetamide；2-Chloro-N-(2-methyl-4-sulphamoylphenyl)-acetamide；2-chloro-N-(2-methyl-4-sulfamoylphenyl)acetamide
• CAS: 53297-88-4
• 化学式: C₉H₁₁ClN₂O₃S
• 分子量: 262.717
• InChiKey: UTVZWVRTUIUNLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  97.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-chloro-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide 在 苯胺 作用下， 生成 2-Phenylamino-N-(2-methyl-4-sulphamoylphenyl)-acetamide
  参考文献：
  名称：

  Sulphamoylphenyl-imidazolidinones

  摘要：

  通过将N-磺胺基苯基取代的α-氨基乙酰胺与甲醛或碳酸的活性衍生物环化，或者通过将N-卤磺酰基苯基取代的咪唑烷酮与氨反应，制备具有有用抗癫痫活性的N-磺胺基苯基取代的咪唑烷酮。

  公开号：

  US03963706A1
• 作为产物：
  描述：

  3-甲基-4-氨基苯磺酰胺 、 氯乙酰氯 反应 0.5h， 以to yield 11 g, m.p. 193°-194°的产率得到2-chloro-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide
  参考文献：
  名称：

  Sulphamoylphenyl-imidazolidinones

  摘要：

  具有有用的抗癫痫活性的N-磺酰基苯基取代咪唑啉-4-酮通过将N-磺酰基苯基取代的α-氨基乙酰胺与甲醛或碳酸的反应性衍生物环化，或通过将N-卤代磺酰基苯基取代的咪唑啉-4-酮与氨反应制备。

  公开号：

  US03963706A1
• 作为试剂：
  描述：

  N-[4-(aminosulfonyl)-2-methylphenyl]-2-bromoacetamide 在 2-chloro-N-(2-methyl-4-sulfamoyl-phenyl)-acetamide 、 potassium carbonate 、 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 42.0h， 生成 2-[4-chloro-2-(3-chloro-5-methyl-benzoyl)phenoxy]-N-(2-methyl-4-sulfamoyl-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

文献信息

• S-TRIAZOLYL ALPHA-MERCAPTO ACETANILIDES AS INHIBITORS OF HIV REVERSE TRANSCRIPTASE
  申请人：Ardea Biosciences, Inc.

  公开号：US20180002296A1

  公开（公告）日：2018-01-04

  A series of S-triazolyl α-mercaptoacetanilides having general structure (1) are provided, where Q is CO 2 H, CONR 2 , SO 3 H, or SO 2 NR 2 . The compounds inhibit several variants of the reverse transcriptase of HIV, and are useful in the treatment of HIV infections.

  提供一系列具有通用结构（1）的S-三唑基α-巯基乙酰苯胺，其中Q为CO2H，CONR2，SO3H或SO2NR2。这些化合物抑制HIV的多种逆转录酶变异体，并可用于治疗HIV感染。
• S-TRIAZOLE ALPHA-MERCAPTOACETANILIDES AS INHIBITORS OF HIV REVERSE TRANSCRIPTASE
  申请人：Girardet Jean-Luc

  公开号：US20100267724A2

  公开（公告）日：2010-10-21

  A series of S-triazolyl α-mercaptoacetanilides having general structure (1) are provided, where Q is CO 2 H, CONR 2 , SO 3 H, or SO 2 NR 2 . The compounds inhibit several variants of the reverse transcriptase of HIV, and are useful in the treatment of HIV infections.

  提供了一系列具有通用结构（1）的S-三唑基α-巯基乙酰苯胺类化合物，其中Q为CO2H，CONR2，SO3H或SO2NR2。这些化合物抑制了HIV的几种逆转录酶变体，并在治疗HIV感染方面有用。
• Triazolyl alpha -mercaptoacetanilides as inhibitors of HIV reverse transcriptase
  申请人：Ardea Biosciences, Inc.

  公开号：EP2609917A1

  公开（公告）日：2013-07-03

  A series of S-triazolyl α-mercaptoacetanilides having general structure (I) are provided, where Q is CO2H, CONR2, SO3H,or SO2NR2. The compounds inhibit several variants of the reverse transcriptase of HIV, and are useful in the treatment of HIV infections.

  提供了一系列具有一般结构（I）的S-三唑基α-巯基乙酰苯胺，其中Q为CO2H，CONR2，SO3H或SO2NR2。这些化合物抑制了HIV的多种逆转录酶变体，并可用于治疗HIV感染。
• S-Triazolyl Alpha-Mercaptoacetanilides as Inhibitors of Hiv Reverse Transcriptase
  申请人：Girardet Jean-Luc

  公开号：US20080176850A1

  公开（公告）日：2008-07-24

  A series of S-triazolyl α-mercaptoacetanilides having general structure (1) are provided, where Q is CO 2 H, CONR 2 , SO 3 H, or SO 2 NR 2 . The compounds inhibit several variants of the reverse transcriptase of HIV, and are useful in the treatment of HIV infections.

  提供了一系列具有一般结构（1）的S-三唑基α-巯基乙酰苯胺，其中Q为CO2H，CONR2，SO3H或SO2NR2。这些化合物抑制了HIV的几种反转录酶变体，并可用于治疗HIV感染。
• S-TRIAZOLE ALPHA- MERCAPTOACETANILIDES AS INHIBITORS OF HIV REVERSE TRANSCRIPTASE
  申请人：Girardet Jean-Luc

  公开号：US20110190491A1

  公开（公告）日：2011-08-04

  A series of S-triazolyl α-mercaptoacetanilides having general structure (1) are provided, where Q is CO 2 H, CONR 2 , SO 3 H, or SO 2 NR 2 . The compounds inhibit several variants of the reverse transcriptase of HIV, and are useful in the treatment of HIV infections.

  提供了一系列具有一般结构（1）的S-三唑基α-巯基乙酰苯胺，其中Q为CO2H，CONR2，SO3H或SO2NR2。这些化合物抑制了HIV的几种逆转录酶变体，并且可用于治疗HIV感染。