C-(5-Nitro-thiophen-3-yl)-methylamine | 771582-78-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: C-(5-Nitro-thiophen-3-yl)-methylamine
• 英文别名: (5-Nitrothiophen-3-yl)methanamine
• CAS: 771582-78-6
• 化学式: C₅H₆N₂O₂S
• 分子量: 158.181
• InChiKey: USVXNAIIFNGSGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  C-(5-Nitro-thiophen-3-yl)-methylamine 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 25.0 ℃ 、413.69 kPa 条件下， 反应 32.0h， 生成 (S)-1-[(R)-3-(3,4-Dichloro-phenyl)-2-phenylmethanesulfonylamino-propionyl]-pyrrolidine-2-carboxylic acid (5-amino-thiophen-3-ylmethyl)-amide
  参考文献：
  名称：

  Discovery of a Novel, Selective, and Orally Bioavailable Class of Thrombin Inhibitors Incorporating Aminopyridyl Moieties at the P1 Position

  摘要：

  A novel class of thrombin inhibitors incorporating aminopyridyl moieties at the P1 position has been discovered. Four of these thrombin inhibitors (13b,c,e and 14d) showed nanomolar potency (K-i 0.8-12 nM), 300-1500-fold selectivity for thrombin compared with trypsin, and good oral bioavailability (F = 40-76%) in rats or dogs. The neutral Fl was expected to increase metabolic stability and oral absorption. Identification of this novel aminopyridyl group at Fl was a key step in our search for a clinical candidate.

  DOI：

  10.1021/jm970493r
• 作为产物：
  描述：

  2-硝基噻吩-4-腈 在 盐酸 、 硼烷 作用下， 生成 C-(5-Nitro-thiophen-3-yl)-methylamine
  参考文献：
  名称：

  Discovery of a Novel, Selective, and Orally Bioavailable Class of Thrombin Inhibitors Incorporating Aminopyridyl Moieties at the P1 Position

  摘要：

  A novel class of thrombin inhibitors incorporating aminopyridyl moieties at the P1 position has been discovered. Four of these thrombin inhibitors (13b,c,e and 14d) showed nanomolar potency (K-i 0.8-12 nM), 300-1500-fold selectivity for thrombin compared with trypsin, and good oral bioavailability (F = 40-76%) in rats or dogs. The neutral Fl was expected to increase metabolic stability and oral absorption. Identification of this novel aminopyridyl group at Fl was a key step in our search for a clinical candidate.

  DOI：

  10.1021/jm970493r

文献信息

• Discovery of a Novel, Selective, and Orally Bioavailable Class of Thrombin Inhibitors Incorporating Aminopyridyl Moieties at the P1 Position
  作者：Dong-Mei Feng、Stephen J. Gardell、S. Dale Lewis、Mark G. Bock、Zhongguo Chen、Roger M. Freidinger、Adel M. Naylor-Olsen、Harri G. Ramjit、Richard Woltmann、Elizabeth P. Baskin、Joseph J. Lynch、Robert Lucas、Jules A. Shafer、Kimberley B. Dancheck、I-Wu Chen、Shi-Shan Mao、Julie A. Krueger、Timothy R. Hare、Anne M. Mulichak、Joseph P. Vacca

  DOI：10.1021/jm970493r

  日期：1997.11.1

  A novel class of thrombin inhibitors incorporating aminopyridyl moieties at the P1 position has been discovered. Four of these thrombin inhibitors (13b,c,e and 14d) showed nanomolar potency (K-i 0.8-12 nM), 300-1500-fold selectivity for thrombin compared with trypsin, and good oral bioavailability (F = 40-76%) in rats or dogs. The neutral Fl was expected to increase metabolic stability and oral absorption. Identification of this novel aminopyridyl group at Fl was a key step in our search for a clinical candidate.