2-Isopropyl-3-[4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenyl]-3H-imidazole-4-carbaldehyde | 444622-08-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-Isopropyl-3-[4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenyl]-3H-imidazole-4-carbaldehyde
• 英文别名: 3-[4-(1,1,1,3,3,3-Hexafluoro-2-hydroxypropan-2-yl)phenyl]-2-propan-2-ylimidazole-4-carbaldehyde；3-[4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl]-2-propan-2-ylimidazole-4-carbaldehyde
• CAS: 444622-08-6
• 化学式: C₁₆H₁₄F₆N₂O₂
• 分子量: 380.29
• InChiKey: NIQLNFJHGCXEGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.1
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-Isopropyl-3-[4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenyl]-3H-imidazole-4-carbaldehyde 在 sodium tetrahydroborate 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 6-((1-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)-2-isopropyl-1H-imidazol-5-yl)methoxy)hexanenitrile
  参考文献：
  名称：

  Design and synthesis of heterocyclic malonyl-CoA decarboxylase inhibitors

  摘要：

  We have previously reported the discovery of small molecule inhibitors of malonyl-CoA decarboxylase (MCD) as novel metabolic modulators, which inhibited fatty acid oxidation and consequently increased the glucose oxidation rates in the isolated working rat hearts. MCD inhibitors were also shown to improve cardiac efficiency in rat and pig demand-induced ischemic models through the mechanism-based modulation of energy metabolism. Herein, we describe the design and synthesis of a series of novel heterocyclic MCD inhibitors with a preference for substituted imidazole and isoxazole. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.020
• 作为产物：
  描述：

  2-(4-氨基苯)-1,1,1,3,3,3-六氟-2-丙醇 在 potassium carbonate 作用下， 以 氯仿 为溶剂， 生成 2-Isopropyl-3-[4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenyl]-3H-imidazole-4-carbaldehyde
  参考文献：
  名称：

  Design and synthesis of heterocyclic malonyl-CoA decarboxylase inhibitors

  摘要：

  We have previously reported the discovery of small molecule inhibitors of malonyl-CoA decarboxylase (MCD) as novel metabolic modulators, which inhibited fatty acid oxidation and consequently increased the glucose oxidation rates in the isolated working rat hearts. MCD inhibitors were also shown to improve cardiac efficiency in rat and pig demand-induced ischemic models through the mechanism-based modulation of energy metabolism. Herein, we describe the design and synthesis of a series of novel heterocyclic MCD inhibitors with a preference for substituted imidazole and isoxazole. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.020

文献信息

• Methods for the treatment of diseases using malonyl-coa decarbox ylase inhibitors
  申请人：——

  公开号：US20040087627A1

  公开（公告）日：2004-05-06

  The present invention relates to methods for the prophylaxis, management and treatment of certain diseases modulated by the inhibition of the enzyme malonyl-coenzyme A decarboxylase (malonyl-CoA decarboxylase, MCD) by the administration of a composition containing as an active ingredient a compound according to Formula I. In particular, the invention relates to methods for the prophylaxis, management and treatment of cardiovascular diseases, diabetes, acidosis, cancers, and obesity through the administration of a compound which inhibits malonyl-coenzyme A decarboxylase activity. The present invention also includes within its scope the novel process for the preparation of certain compounds. 1

  本发明涉及通过给予含有化合物I的活性成分的组合物来抑制麦芽酰辅酶A脱羧酶（malonyl-CoA脱羧酶，MCD）的方法，用于预防、管理和治疗某些由该酶抑制调节的疾病。特别地，本发明涉及通过给予抑制麦芽酰辅酶A脱羧酶活性的化合物来预防、管理和治疗心血管疾病、糖尿病、酸中毒、癌症和肥胖症的方法。本发明还包括其范围内的新型化合物制备方法。1
• METHODS FOR THE TREATMENT OF DISEASES USING MALONYL-COA DECARBOX YLASE INHIBITORS
  申请人：CHUGAI SEIYAKU KABUSHIKI KAISHA

  公开号：EP1353662A2

  公开（公告）日：2003-10-22
• JP2004521113A
  申请人：——

  公开号：JP2004521113A

  公开（公告）日：2004-07-15
• マロニル−ＣｏＡ脱炭酸酵素阻害剤を用いた疾患の治療法
  申请人：中外製薬株式会社

  公开号：JP4503232B2

  公开（公告）日：2004-07-15
• [EN] METHODS FOR THE TREATMENT OF DISEASES USING MALONYL-COA DECARBOX YLASE INHIBITORS<br/>[FR] PROCEDES RELATIFS AU TRAITEMENT DE MALADIES PAR LE BIAIS D'INHIBITEURS DE MALONYL-COA DECARBOXYLASE
  申请人：CHUGAI PHARMACEUTICAL CO LTD

  公开号：WO2002058690A2

  公开（公告）日：2002-08-01

  The present invention relates to methods for the prophylaxis, management and treatment of certain diseases modulated by the inhibition of the enzyme malonyl-coenzyme A decarboxylase (malonyl-CoA decarboxylase, MCD) by the administration of a composition containing as an active ingredient a compound according to Formula I. In particular, the invention relates to methods for the prophylaxis, management and treatment of cardiovascular diseases, diabetes, acidosis, cancers, and obesity through the administration of a compound which inhibits malonyl-coenzyme A decarboxylase activity. The present invention also includes within its scope the novel process for the preparation of certain compounds.