N-环丙基-1-[(2-氟苯基)磺酰]-1H-吡咯-2-甲酰胺 | 180905-88-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-环丙基-1-[(2-氟苯基)磺酰]-1H-吡咯-2-甲酰胺
• 英文名称: 1-(2-fluorobenzenesulfonyl)-1H-pyrrole-2-(N-cyclopropyl)carboxyamide
• 英文别名: 1H-Pyrrole-2-carboxamide, N-cyclopropyl-1-((2-fluorophenyl)sulfonyl)-；N-cyclopropyl-1-(2-fluorophenyl)sulfonylpyrrole-2-carboxamide
• CAS: 180905-88-8
• 化学式: C₁₄H₁₃FN₂O₃S
• 分子量: 308.333
• InChiKey: PPAQVZQZRLFVBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  76.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-环丙基-1-[(2-氟苯基)磺酰]-1H-吡咯-2-甲酰胺 在 copper(l) iodide 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 以80%的产率得到5-Cyclopropyl-10,10-dioxo-pyrrolo[1,2-b][1,2,5]benzothiadiazepin-4-one
  参考文献：
  名称：

  5H-pyrrolo[1,2-b][1,2,5]benzothiadiazepines (PBTDs): A novel class of non-nucleoside reverse transcriptase inhibitors

  摘要：

  With the aim of developing novel inhibitors of human immunodeficiency virus, various derivatives (10-17) related to SH-pyrrolo[1,2-b][1,2,5]benzothiadiazepine (PBTD) were prepared and tested in vitro. The title tricyclic derivatives were obtained by intramolecular cyclization of the open-chain intermediate arylpyrrylsulfones, followed by N-alkylation at position 10. Among test derivatives some 10-alkyl-5H-pyrrolo[1,2-b][1,2,5]benzothiadiazepin-11(10H)-one-5,5-dioxides were found to exert potent and specific activity against HIV-1. In particular, 7-chloro derivatives 11i and j showed a potency comparable to that of nevirapine. However, when the chloro atom was shifted to the 8 position, the related products were scarcely active or totally inactive. Replacement of the pyrrole with pyrrolidine led to inactive products and the reduction of SO2 to S strongly diminished the antiviral potency. PBTD derivatives active in cell cultures were also inhibitory to the recombinant HIV-1 RT in enzyme assays, thus allowing the conclusion that PBTDs are a new class of non-nucleoside reverse transcriptase inhibitors (NNRTIs). Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00075-2
• 作为产物：
  描述：

  2-氟苯磺酰氯 在 4-二甲氨基吡啶 、 氢氧化钾 、 18-冠醚-6 、 potassium tert-butylate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 21.75h， 生成 N-环丙基-1-[(2-氟苯基)磺酰]-1H-吡咯-2-甲酰胺
  参考文献：
  名称：

  5H-pyrrolo[1,2-b][1,2,5]benzothiadiazepines (PBTDs): A novel class of non-nucleoside reverse transcriptase inhibitors

  摘要：

  With the aim of developing novel inhibitors of human immunodeficiency virus, various derivatives (10-17) related to SH-pyrrolo[1,2-b][1,2,5]benzothiadiazepine (PBTD) were prepared and tested in vitro. The title tricyclic derivatives were obtained by intramolecular cyclization of the open-chain intermediate arylpyrrylsulfones, followed by N-alkylation at position 10. Among test derivatives some 10-alkyl-5H-pyrrolo[1,2-b][1,2,5]benzothiadiazepin-11(10H)-one-5,5-dioxides were found to exert potent and specific activity against HIV-1. In particular, 7-chloro derivatives 11i and j showed a potency comparable to that of nevirapine. However, when the chloro atom was shifted to the 8 position, the related products were scarcely active or totally inactive. Replacement of the pyrrole with pyrrolidine led to inactive products and the reduction of SO2 to S strongly diminished the antiviral potency. PBTD derivatives active in cell cultures were also inhibitory to the recombinant HIV-1 RT in enzyme assays, thus allowing the conclusion that PBTDs are a new class of non-nucleoside reverse transcriptase inhibitors (NNRTIs). Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00075-2