N-(2-amino-4-methoxyphenyl)-2,2,2-trifluoroacetoamide | 128897-59-6

• 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-(2-amino-4-methoxyphenyl)-2,2,2-trifluoroacetoamide
• 英文别名: N-(2-amino-4-methoxyphenyl)-2,2,2-trifluoroacetamide
• CAS: 128897-59-6
• 化学式: C₉H₉F₃N₂O₂
• 分子量: 234.178
• InChiKey: DQMDTLPVZKIYOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(2-amino-4-methoxyphenyl)-2,2,2-trifluoroacetoamide 在 氢氧化钾 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 3.25h， 生成 2,2,2-Trifluoro-1-[6-methoxy-3-(piperidin-1-ylmethyl)-2-sulfanylidenebenzimidazol-1-yl]ethanone
  参考文献：
  名称：

  Joshi, Krishna C.; Misra, Ram A.; Jain, Renuka, Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 409 - 412

  摘要：

  DOI：
• 作为产物：
  描述：

  2,2,2-三氟-4’-甲氧基乙酰苯胺 在 盐酸 、 硫酸 、 硝酸 、 铁粉 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 1.5h， 生成 N-(2-amino-4-methoxyphenyl)-2,2,2-trifluoroacetoamide
  参考文献：
  名称：

  Joshi, Krishna C.; Misra, Ram A.; Jain, Renuka, Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 409 - 412

  摘要：

  DOI：

文献信息

• Rapid one-pot preparation of 2-substituted benzimidazoles from 2-nitroanilines using microwave conditions
  作者：David S. VanVliet、Paul Gillespie、Jan J. Scicinski

  DOI：10.1016/j.tetlet.2005.07.130

  日期：2005.9

  A high yielding one-pot procedure for the generation of 2-substituted benzimidazoles directly from 2-nitroanilines by in situ reduction and cyclization using a microwave procedure is described.

  描述了一种高产率的一锅法，该方法通过微波还原法原位还原和环化直接从2-硝基苯胺生成2-取代的苯并咪唑。
• Discovery of <i>N</i>-[2-Hydroxy-6-(4-methoxybenzamido)phenyl]-4- (4-methyl-1,4-diazepan-1-yl)benzamide (Darexaban, YM150) as a Potent and Orally Available Factor Xa Inhibitor
  作者：Fukushi Hirayama、Hiroyuki Koshio、Tsukasa Ishihara、Shunichiro Hachiya、Keizo Sugasawa、Yuji Koga、Norio Seki、Ryouta Shiraki、Takeshi Shigenaga、Yoshiyuki Iwatsuki、Yumiko Moritani、Kenichi Mori、Takeshi Kadokura、Tomihisa Kawasaki、Yuzo Matsumoto、Shuichi Sakamoto、Shin-ichi Tsukamoto

  DOI：10.1021/jm200868m

  日期：2011.12.8

  Inhibitors of factor Xa (FXa), a crucial serine protease in the coagulation cascade, have attracted a great deal of attention as a target for developing antithrombotic agents. We previously reported findings from our optimization study of a high-throughput screening (HTS) derived lead compound la that resulted in the discovery of potent amidine-containing FXa inhibitors represented by compound 2. We also conducted an alternative optimization study of la without incorporating a strong basic amidine group, which generally has an adverse effect on the pharmacokinetic profile after oral administration. Replacement of 4-methoxybenzene with a 1,4-benzodiazepine structure and introduction of a hydroxy group at the central benzene led to the discovery of the potent and orally effective factor Xa inhibitor 14i (darexaban, YM150). Subsequent extensive study revealed a unique aspect to the pharmacokinetic profile of this compound, wherein the hydroxy moiety of 141 is rapidly transformed into its glucuronide conjugate 16 (YM-222714) as an active metabolite after oral administration and it plays a major role in expression of potent anticoagulant activity in plasma. The distinctive, potent activity of inhibitor 14i after oral dosing was explained by this unique pharmacokinetic profile and its favorable membrane permeability. Compound 14i is currently undergoing clinical development for prevention and treatment of thromboembolic diseases.
• JOSHI, KRISHNA C.;MISRA, RAM A.;JAIN, RENUKA;SHARMA, KANTI, J. HETEROCYCL. CHEM., 26,(1989) N, C. 409-412
  作者：JOSHI, KRISHNA C.、MISRA, RAM A.、JAIN, RENUKA、SHARMA, KANTI

  DOI：——

  日期：——