cis ethyl 4-(piperidin-4-yloxy)cyclohexanecarboxylate | 1415573-47-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: cis ethyl 4-(piperidin-4-yloxy)cyclohexanecarboxylate
• CAS: 1415573-47-5
• 化学式: C₁₄H₂₅NO₃
• 分子量: 255.357
• InChiKey: HMYDLDVGFJPFQL-TXEJJXNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.88
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  47.56
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-chloro-2-(6-fluoropyridin-3-yl)-1H-benzo[d]imidazole 、 cis ethyl 4-(piperidin-4-yloxy)cyclohexanecarboxylate 在 碳酸氢钠 作用下， 以 二甲基亚砜 为溶剂， 以130 mg的产率得到cis-ethyl 4-((1-(5-(5-chloro-1H-benzo[d]imidazol-2-yl)pyridin-2-yl)piperidin-4-yl)oxy)cyclohexanecarboxylate
  参考文献：
  名称：

  Discovery of a Potent and Selective DGAT1 Inhibitor with a Piperidinyl-oxy-cyclohexanecarboxylic Acid Moiety

  摘要：

  We report the discovery of a novel series of DGAT1 inhibitors in the benzimidazole class with a piperdinyl-oxy-cyclohexanecarboxylic acid moiety. This novel series possesses significantly improved selectivity against the A(2A) receptor, no ACAT1 off-target activity at 10 mu M, and higher aqueous solubility and free fraction in plasma as compared to the previously reported pyridyl-oxy-cyclohexanecarboxylic acid series. In particular, 5B was shown to possess an excellent selectivity profile by screening it against a panel of more than 100 biological targets. Compound 5B significantly reduces lipid excursion in LTT in mouse and rat, demonstrates DGAT1 mediated reduction of food intake and body weight in mice, is negative in a 3-strain Ames test, and appears to distribute preferentially in the liver and the intestine in mice. We believe this lead series possesses significant potential to identify optimized compounds for clinical development.

  DOI：

  10.1021/ml5003426
• 作为产物：
  描述：

  4-羟基吡啶 在 platinum(IV) oxide 偶氮二甲酸二异丙酯 、 氢气 、 溶剂黄146 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 cis ethyl 4-(piperidin-4-yloxy)cyclohexanecarboxylate
  参考文献：
  名称：

  [EN] IMIDAZOLE DERIVATIVES
  [FR] DÉRIVÉS D'IMIDAZOLE

  摘要：

  本文描述了式(I)的化合物。式(I)的化合物作为DGAT1抑制剂，可用于预防、治疗或作为高脂血症、糖尿病和肥胖的治疗药物。

  公开号：

  WO2012164071A1

文献信息

• A biocatalytic/reductive etherification approach to substituted piperidinyl ethers
  作者：Jeffrey T. Kuethe、Jacob M. Janey、Matthew Truppo、Juan Arredondo、Tao Li、Kelvin Yong、Shuwen He

  DOI：10.1016/j.tet.2014.04.064

  日期：2014.7

  synthetically useful protocol has been developed for the preparation of highly functionalized piperidinyl ethers. Biocatalytic reduction of cyclhexanones 7, 10, and 14 allows for the preparation of both cis- and trans diastereomers with an extremely high degree of stereochemical control. Reductive etherification of the corresponding trimethylsilylethers with 1-(benzyloxycarbonyl)-4-piperidinone 17 in the presence

  已经开发出用于制备高度官能化的哌啶基醚的合成上有用的方案。生物催化还原cyclhexanones的7，10，和14允许用于制备两者的顺式-和反式非对映体具有极高程度的立体化学控制的。相应的三甲基甲硅烷基醚与1-（苄氧羰基）-4-哌啶酮17的还原醚化在三乙基硅烷和催化TMSO-Tf的存在下，以良好或优异的收率提供了所需的哌啶基醚。最终，氮保护基的湿解产生了接近定量产率的哌啶基醚。还介绍了该方法在一系列哌啶醚中的应用，包括二苯基吡咯啉和依巴斯汀的核心骨架。
• IMIDAZOLE DERIVATIVES
  申请人：DeVita Robert J.

  公开号：US20140088124A1

  公开（公告）日：2014-03-27

  Described herein are compounds of formula (I), The compounds of formula I act as DGAT1 inhibitors and can be useful in preventing, treating or acting as a remedial agent for hyperlipidemia, diabetes mellitus and obesity.

  本文描述了化学式（I）的化合物。化合物I的作用是DGAT1抑制剂，可以用于预防，治疗或作为治疗高脂血症，糖尿病和肥胖症的药物。