methyl (4R,5S)-5-[(tert-butoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)cyclohex-1-ene-1-carboxylate | 913623-66-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (4R,5S)-5-[(tert-butoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)cyclohex-1-ene-1-carboxylate
• 英文别名: Methyl(4r,5s)-5-[(tert-butoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)cyclohex-1-ene-1-carboxylate；methyl (4R,5S)-5-[(2-methylpropan-2-yl)oxycarbonylamino]-4-(2,4,5-trifluorophenyl)cyclohexene-1-carboxylate
• CAS: 913623-66-2
• 化学式: C₁₉H₂₂F₃NO₄
• 分子量: 385.383
• InChiKey: AOVTYUYMLWMSGN-BZNIZROVSA-N

物化性质

• 沸点：
  427.2±45.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (4R,5S)-5-[(tert-butoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)cyclohex-1-ene-1-carboxylate 在 sodium hydroxide 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 ((4R,5S)-5-amino-4-(2,4,5-trifluorophenyl)cyclohex-1-enyl)(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)methanone
  参考文献：
  名称：

  Discovery of ((4R,5S)-5-Amino-4-(2,4,5- trifluorophenyl)cyclohex-1-enyl)-(3- (trifluoromethyl)-5,6-dihydro- [1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)methanone (ABT-341), a Highly Potent, Selective, Orally Efficacious, and Safe Dipeptidyl Peptidase IV Inhibitor for the Treatment of Type 2 Diabetes

  摘要：

  Dipeptidyl peptidase IV (DPP4) deactivates glucose-regulating hormones such as GLP-1 and GIP, thus, DPP4 inhibition has become a useful therapy for type 2 diabetes. Optimization of the high-throughput screening lead 6 led to the discovery of 25 (ABT-341), a highly potent, selective, and orally bioavailable DPP4 inhibitor. When dosed orally, 25 dose-dependently reduced glucose excursion in ZDF rats. Amide 25 is safe in a battery of in vitro and in vivo tests and may represent a new therapeutic agent for the treatment of type 2 diabetes.

  DOI：

  10.1021/jm060955d
• 作为产物：
  描述：

  在 bis-triphenylphosphine-palladium(II) chloride sodium chlorite 、 甲酸 、 三正丁胺 、 戴斯-马丁氧化剂 、 天然橡胶 作用下， 以 四氢呋喃 、 甲醇 、 phosphate buffer 、 乙醚 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.67h， 生成 methyl (4R,5S)-5-[(tert-butoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)cyclohex-1-ene-1-carboxylate
  参考文献：
  名称：

  Discovery of ((4R,5S)-5-Amino-4-(2,4,5- trifluorophenyl)cyclohex-1-enyl)-(3- (trifluoromethyl)-5,6-dihydro- [1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)methanone (ABT-341), a Highly Potent, Selective, Orally Efficacious, and Safe Dipeptidyl Peptidase IV Inhibitor for the Treatment of Type 2 Diabetes

  摘要：

  Dipeptidyl peptidase IV (DPP4) deactivates glucose-regulating hormones such as GLP-1 and GIP, thus, DPP4 inhibition has become a useful therapy for type 2 diabetes. Optimization of the high-throughput screening lead 6 led to the discovery of 25 (ABT-341), a highly potent, selective, and orally bioavailable DPP4 inhibitor. When dosed orally, 25 dose-dependently reduced glucose excursion in ZDF rats. Amide 25 is safe in a battery of in vitro and in vivo tests and may represent a new therapeutic agent for the treatment of type 2 diabetes.

  DOI：

  10.1021/jm060955d

文献信息

• Pharmaceutical compositions as inhibitors of dipeptidyl peptidase-IV (DPP-IV)
  申请人：Pei Zhonghua

  公开号：US20070049596A1

  公开（公告）日：2007-03-01

  The present invention relates to compounds, which inhibit dipeptidyl peptidase IV (DPP-IV) and are useful for the prevention or treatment of diabetes, especially type II, as well as hyperglycemia, metabolic syndrome, hyperinsulinemia, obesity, atherosclerosis, various immunomodulatory diseases, and other diseases.

  本发明涉及一种抑制二肽基肽酶IV（DPP-IV）的化合物，可用于预防或治疗糖尿病，特别是II型糖尿病，以及高血糖、代谢综合征、高胰岛素血症、肥胖、动脉粥样硬化、各种免疫调节性疾病和其他疾病。
• US7834012B2
  申请人：——

  公开号：US7834012B2

  公开（公告）日：2010-11-16