3-(1-amino-cyclohexyl)-propan-1-ol | 6339-94-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-(1-amino-cyclohexyl)-propan-1-ol
• 英文别名: 3-(1-Aminocyclohexyl)propan-1-ol
• CAS: 6339-94-2
• 化学式: C₉H₁₉NO
• 分子量: 157.256
• InChiKey: XBZKGBLCDQHZOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-bromoacetyl)-pyrrolidine-2,5-cis-dicarbonitrile 、 3-(1-amino-cyclohexyl)-propan-1-ol 以 乙腈 为溶剂， 反应 48.0h， 生成 (2R,5S)-1-(2-(1-(3-hydroxypropyl)cyclohexylamino)acetyl)pyrrolidine-2,5-dicarbonitrile
  参考文献：
  名称：

  cis-2,5-Dicyanopyrrolidine Inhibitors of Dipeptidyl Peptidase IV:  Synthesis and in Vitro, in Vivo, and X-ray Crystallographic Characterization

  摘要：

  Inhibitors of the glucagon-like peptide-1 (GLP-1) degrading enzyme dipeptidyl peptidase IV (DPP-IV) have been shown to be effective treatments for type 2 diabetes in animal models and in human subjects. A novel series of cis-2,5-dicyanopyrrolidine alpha-amino amides were synthesized and evaluated as inhibitors of dipeptidyl peptidase IV (DPP-IV) for the treatment of type 2 diabetes. 1-({[1-(Hydroxymethyl) cyclopentyl] amino}acetyl) pyrrolidine-2,5-cis-dicarbonitrile (1c) is an achiral, slow-binding (time-dependent) inhibitor of DPP-IV that is selective for DPP-IV over other DPP isozymes and proline specific serine proteases, and which has oral bioavailability in preclinical species and in vivo efficacy in animal models. The mode of binding of the cis-2,5-dicyanopyrrolidine moiety was determined by X-ray crystallography. The hydrochloride salt of 1c was further profiled for development as a potential new treatment for type 2 diabetes.

  DOI：

  10.1021/jm0600085
• 作为产物：
  描述：

  硝基环己烷 在 lithium aluminium tetrahydride 、 乙醚 、 苄基三甲基氢氧化铵 作用下， 生成 3-(1-amino-cyclohexyl)-propan-1-ol
  参考文献：
  名称：

  Notes - Synthesis of Spirolactams from Nitrocycloalkanes

  摘要：

  DOI：

  10.1021/jo01358a606

文献信息

• Notes - Synthesis of Spirolactams from Nitrocycloalkanes
  作者：R. Hill

  DOI：10.1021/jo01358a606

  日期：1957.7
• <i>cis</i>-2,5-Dicyanopyrrolidine Inhibitors of Dipeptidyl Peptidase IV:  Synthesis and in Vitro, in Vivo, and X-ray Crystallographic Characterization
  作者：Stephen W. Wright、Mark J. Ammirati、Kim M. Andrews、Anne M. Brodeur、Dennis E. Danley、Shawn D. Doran、Jay S. Lillquist、Lester D. McClure、R. Kirk McPherson、Stephen J. Orena、Janice C. Parker、Jana Polivkova、Xiayang Qiu、Walter C. Soeller、Carolyn B. Soglia、Judith L. Treadway、Maria A. VanVolkenburg、Hong Wang、Donald C. Wilder、Thanh V. Olson

  DOI：10.1021/jm0600085

  日期：2006.6.1

  Inhibitors of the glucagon-like peptide-1 (GLP-1) degrading enzyme dipeptidyl peptidase IV (DPP-IV) have been shown to be effective treatments for type 2 diabetes in animal models and in human subjects. A novel series of cis-2,5-dicyanopyrrolidine alpha-amino amides were synthesized and evaluated as inhibitors of dipeptidyl peptidase IV (DPP-IV) for the treatment of type 2 diabetes. 1-([1-(Hydroxymethyl) cyclopentyl] amino}acetyl) pyrrolidine-2,5-cis-dicarbonitrile (1c) is an achiral, slow-binding (time-dependent) inhibitor of DPP-IV that is selective for DPP-IV over other DPP isozymes and proline specific serine proteases, and which has oral bioavailability in preclinical species and in vivo efficacy in animal models. The mode of binding of the cis-2,5-dicyanopyrrolidine moiety was determined by X-ray crystallography. The hydrochloride salt of 1c was further profiled for development as a potential new treatment for type 2 diabetes.