(S)-1-(4-异丙基苯基)乙胺盐酸盐

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: (S)-1-(4-异丙基苯基)乙胺盐酸盐
• 英文名称: (S)-1-(4-isopropylphenyl)ethylamine hydrochloride
• 英文别名: (S)-1-(4-isopropylphenyl)ethan-1-amine hydrochloride；(1S)-1-[4-(propan-2-yl)phenyl]ethan-1-aminium chloride；(1S)-1-[4-(propan-2-yl)phenyl]ethan-1-amine monohydrochloride salt；(S)-1-(4-isopropylphenyl)ethanamine hydrochloride；[(1S)-1-(4-propan-2-ylphenyl)ethyl]azanium;chloride
• 化学式: C₁₁H₁₇N*ClH
• mdl: MFCD16295045
• 分子量: 199.724
• InChiKey: LMSMWEMLBQTBPN-FVGYRXGTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.76
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  26
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-((2'-(tert-butoxycarbonyl)biphenyl-4-yl)methyl)-2,3-dimethyl-1H-indole-5-carboxylic acid 、 (S)-1-(4-异丙基苯基)乙胺盐酸盐 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 反应 0.58h， 生成
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Indole Biphenylcarboxylic Acids as PPARγ Antagonists

  摘要：

  The thiazolidinediones (TZD) typified by rosiglitazone are the only approved therapeutics targeting PPAR gamma for the treatment of type-2 diabetes (T2DM). Unfortunately, despite robust insulin sensitizing properties, they are accompanied by a number of severe side effects including congestive heart failure, edema, weight gain, and osteoporosis. We recently identified PPAR gamma antagonists that bind reversibly with high affinity but do not induce transactivation of the receptor, yet they act as insulin sensitizers in mouse models of diabetes (SR1664).(1) This Letter details our synthetic exploration around this novel series of PPAR gamma antagonists based on an N-biphenylmethylindole scaffold. Structure-activity relationship studies led to the identification of compound 46 as a high affinity PPAR gamma antagonist that exhibits antidiabetic properties following oral administration in diet-induced obese mice.

  DOI：

  10.1021/acsmedchemlett.5b00218
• 作为产物：
  描述：

  在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 生成 (S)-1-(4-异丙基苯基)乙胺盐酸盐
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Indole Biphenylcarboxylic Acids as PPARγ Antagonists

  摘要：

  The thiazolidinediones (TZD) typified by rosiglitazone are the only approved therapeutics targeting PPAR gamma for the treatment of type-2 diabetes (T2DM). Unfortunately, despite robust insulin sensitizing properties, they are accompanied by a number of severe side effects including congestive heart failure, edema, weight gain, and osteoporosis. We recently identified PPAR gamma antagonists that bind reversibly with high affinity but do not induce transactivation of the receptor, yet they act as insulin sensitizers in mouse models of diabetes (SR1664).(1) This Letter details our synthetic exploration around this novel series of PPAR gamma antagonists based on an N-biphenylmethylindole scaffold. Structure-activity relationship studies led to the identification of compound 46 as a high affinity PPAR gamma antagonist that exhibits antidiabetic properties following oral administration in diet-induced obese mice.

  DOI：

  10.1021/acsmedchemlett.5b00218