triisopropyl {[4-(2,4,5-trifluorophenyl)cyclohex-1-en-1-yl]oxy}silane | 874359-97-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: triisopropyl {[4-(2,4,5-trifluorophenyl)cyclohex-1-en-1-yl]oxy}silane
• 英文别名: Triisopropyl{[4-(2,4,5-trifluorophenyl)cyclohex-1-en-1-yl]oxy}silane；tri(propan-2-yl)-[4-(2,4,5-trifluorophenyl)cyclohexen-1-yl]oxysilane
• CAS: 874359-97-4
• 化学式: C₂₁H₃₁F₃OSi
• 分子量: 384.557
• InChiKey: UQZXNPNCZUPQKC-UHFFFAOYSA-N

物化性质

• 沸点：
  360.0±42.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.45
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  triisopropyl {[4-(2,4,5-trifluorophenyl)cyclohex-1-en-1-yl]oxy}silane 在 lithium aluminium tetrahydride 、 decaborane 、 叠氮基三甲基硅烷 、 亚碘酰苯 、 氢氟酸 作用下， 以 甲醇 为溶剂， 生成 tert-butyl [(1S,2R,5S)-5-[3-(trifluoromethyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-2-(2,4,5-trifluorophenyl)cyclohexyl]carbamate
  参考文献：
  名称：

  Rational design of a novel, potent, and orally bioavailable cyclohexylamine DPP-4 inhibitor by application of molecular modeling and X-ray crystallography of sitagliptin

  摘要：

  Molecular modeling was used to design a rigid analog of sitagliptin 1. The X-ray crystal structure of sitagliptin bound to DPP-4 suggested that the central beta-amino butyl amide moiety could be replaced with a cyclohexylamine group. This was confirmed by structural analysis and the resulting analog 2a was synthesized and found to be a potent DPP-4 inhibitor (IC50 = 21 nM) with excellent in vivo activity and pharmacokinetic profile. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.03.095
• 作为产物：
  描述：

  8-(2,4,5-trifluorophenyl)-1,4-dioxaspiro[4.5]dec-7-ene 在 palladium on activated charcoal 氢气 作用下， 生成 triisopropyl {[4-(2,4,5-trifluorophenyl)cyclohex-1-en-1-yl]oxy}silane
  参考文献：
  名称：

  Rational design of a novel, potent, and orally bioavailable cyclohexylamine DPP-4 inhibitor by application of molecular modeling and X-ray crystallography of sitagliptin

  摘要：

  Molecular modeling was used to design a rigid analog of sitagliptin 1. The X-ray crystal structure of sitagliptin bound to DPP-4 suggested that the central beta-amino butyl amide moiety could be replaced with a cyclohexylamine group. This was confirmed by structural analysis and the resulting analog 2a was synthesized and found to be a potent DPP-4 inhibitor (IC50 = 21 nM) with excellent in vivo activity and pharmacokinetic profile. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.03.095

文献信息

• [EN] AMINOCYCLOHEXANES AS DIPEPTIDYL PEPTIDASE-IV INHIBITORS FOR THE TREATMENT OR PREVENTION OF DIABETES<br/>[FR] AMINOCYCLOHEXANES EN TANT QU'INHIBITEURS DE DIPEPTIDYL PEPTIDASE-IV POUR LE TRAITEMENT OU LA PRÉVENTION DE DIABÈTES
  申请人：MERCK & CO INC

  公开号：WO2006009886A1

  公开（公告）日：2006-01-26

  The present invention is directed to novel substituted aminocyclohexanes which are inhibitors of the dipeptidyl peptidase-IV enzyme ('DPP-IV inhibitors') and which are useful in the treatment or prevention of diseases in which the dipeptidyl peptidase-IV enzyme is involved, such as diabetes and particularly Type 2 diabetes. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which the dipeptidyl peptidase-IV enzyme is involved.

  本发明涉及一种新型的取代氨基环己烷，它们是二肽基肽酶-IV酶（'DPP-IV抑制剂'）的抑制剂，并且在治疗或预防涉及二肽基肽酶-IV酶的疾病中具有用处，如糖尿病，特别是2型糖尿病。该发明还涉及包含这些化合物的药物组合物以及在预防或治疗涉及二肽基肽酶-IV酶的这类疾病中使用这些化合物和组合物。
• Aminocyclohexanes as Dipeptidyl Peptidase-Iv Inhibitors for the Treatment or Prevention of Diabetes
  申请人：Biftu Tesfaye

  公开号：US20070254865A1

  公开（公告）日：2007-11-01

  The present invention is directed to novel substituted aminocyclohexanes which are inhibitors of the dipeptidyl peptidase-IV enzyme (“DPP-IV inhibitors”) and which are useful in the treatment or prevention of diseases in which the dipeptidyl peptidase-IV enzyme is involved, such as diabetes and particularly Type 2 diabetes. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which the dipeptidyl peptidase-IV enzyme is involved.

  本发明涉及新型的取代氨基环己烷，其为二肽基肽酶-IV酶（“DPP-IV抑制剂”）的抑制剂，并且对于二肽基肽酶-IV酶参与的疾病，例如糖尿病和特别是2型糖尿病的治疗或预防有用。该发明还涉及包含这些化合物的制药组合物以及在预防或治疗二肽基肽酶-IV酶参与的这些疾病中使用这些化合物和组合物。
• Aminocyclohexanes as Dipeptidyl Peptidase-IV Inhibitors for the Treatment or Prevention of Diabetes
  申请人：Biftu Tesfaye

  公开号：US20090270467A1

  公开（公告）日：2009-10-29

  The present invention is directed to novel substituted aminocyclohexanes of structural formula (I) which are inhibitors of the dipeptidyl peptidase-IV enzyme and which are useful in the treatment or prevention of diseases in which the dipeptidyl peptidase-IV enzyme is involved, such as diabetes and particularly Type 2 diabetes. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which the dipeptidyl peptidase-IV enzyme is involved.

  本发明涉及结构式（I）的新型取代氨基环己烷，其是二肽基肽酶-IV酶的抑制剂，并且对于涉及二肽基肽酶-IV酶的疾病的治疗或预防，例如糖尿病，特别是2型糖尿病，具有用途。本发明还涉及包含这些化合物的制药组合物以及这些化合物和组合物在预防或治疗涉及二肽基肽酶-IV酶的疾病中的使用。
• TRICYCLIC HETEROAROMATIC COMPOUNDS AS DIPEPTIDYL PEPTIDASE-IV INHIBITORS FOR THE TREATMENT OR PREVENTION OF DIABETES
  申请人：Cox Jason M.

  公开号：US20100056550A1

  公开（公告）日：2010-03-04

  The present invention is directed to novel substituted tricyclic heteroaromatic compounds of structural formula (I) which are inhibitors of the dipeptidyl peptidase-IV enzyme and which are useful in the treatment or prevention of diseases in which the dipeptidyl peptidase-IV enzyme is involved, such as diabetes and particularly Type 2 diabetes. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which the dipeptidyl peptidase-IV enzyme is involved.

  本发明涉及结构式(I)的新型取代三环杂芳烃化合物，其为二肽基肽酶-IV酶的抑制剂，可用于治疗或预防二肽基肽酶-IV酶参与的疾病，如糖尿病，特别是2型糖尿病。本发明还涉及包含这些化合物的制药组合物以及在预防或治疗二肽基肽酶-IV酶参与的此类疾病中使用这些化合物和组合物的方法。
• Aminocyclohexanes as Dipeptidyl Peptidase-IV for the Treatment or Prevention of Diabetes
  申请人：Biftu Tesfaye

  公开号：US20090105284A1

  公开（公告）日：2009-04-23

  The present invention is directed to novel substituted aminocyclohexanes which are inhibitors of the dipeptidyl peptidase-IV enzyme (“DPP-IV inhibitors”) and which are useful in the treatment or prevention of diseases in which the dipeptidyl peptidase-IV enzyme is involved, such as diabetes and particularly Type 2 diabetes. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which the dipeptidyl peptidase-IV enzyme is involved.

  本发明涉及一种新型的取代氨基环己烷化合物，它们是二肽基肽酶-IV酶（“DPP-IV抑制剂”）的抑制剂，可用于治疗或预防二肽基肽酶-IV酶参与的疾病，如糖尿病，特别是2型糖尿病。本发明还涉及包含这些化合物的制药组合物以及在预防或治疗二肽基肽酶-IV酶参与的疾病中使用这些化合物和组合物的方法。