3-(2-(4-fluoro-3-methylphenyl)-4-(t-butyldimethylsilyl)oxy-6,6-dimethylcyclohex-1-en-1-yl)propenal | 129084-05-5

• 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: 3-(2-(4-fluoro-3-methylphenyl)-4-(t-butyldimethylsilyl)oxy-6,6-dimethylcyclohex-1-en-1-yl)propenal
• 英文别名: (E)-3-[2-(4-fluoro-3-methylphenyl)-4-t-butyldimethylsiloxy-6,6-dimethylcyclohex-1-en-1-yl]propenal；(E)-3-{2-(4-fluoro-3-methylphenyl)-4-(t-butyldimethyl-sily-oxy)-6,6-dimethylcyclohexen-1-yl}propenal；(E)-3-[4-[tert-butyl(dimethyl)silyl]oxy-2-(4-fluoro-3-methylphenyl)-6,6-dimethylcyclohexen-1-yl]prop-2-enal
• CAS: 129084-05-5
• 化学式: C₂₄H₃₅FO₂Si
• 分子量: 402.625
• InChiKey: CMPYQTQXYPZQHA-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.85
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-(4-fluoro-3-methylphenyl)-4-(t-butyldimethylsilyl)oxy-6,6-dimethylcyclohex-1-en-1-yl)propenal 在 吡啶 、 咪唑 、 sodium hydroxide 、 sodium tetrahydroborate 、 三乙基硼 、 四丁基氟化铵 、 双氧水 、 氯甲酸乙酯 、 溶剂黄146 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 10.0h， 生成 (trans)-(E)-6-<2-<2-(4-fluoro-3-methylphenyl)-4-(R,S)-ethoxycarbonyloxy-6,6-dimethylcyclohex-1-en-1-yl>ethenyl>-4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one
  参考文献：
  名称：

  Inhibitors of HMG-CoA reductase. Biological effects of A 6-[2-[2-(4-fluoro-3-methylphenyl)-4-substituted cyclohexe-1-en-1-yl]ethenyl]-4-hydroxy-3,4,5,6-tetrahydro-2h-pyran-2-one

  摘要：

  We report on a series of potent inhibitors of HMG-CoA reductase (HMGR) that were designed to examine the biological consequences that result from molecular changes in RG 12561. The introduction of functional groups on the cyclohexene nucleus of RG 12561 and the resulting inhibitor-enzyme interactions at remote binding sites of HMGR are discussed. Cellular membrane permeability may also contribute to potency. The HMGR inhibitory activity was measured utilizing solubilized enzyme. The compounds were evaluated as inhibitors of sterol biosynthesis in vitro using liver slices and in vivo after oral administration to the rat.

  DOI：

  10.1016/0223-5234(92)90095-i
• 作为产物：
  描述：

  4-氟-3-甲基苯乙酮 在 咪唑 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 三氟化硼乙醚 、 potassium tert-butylate 、 水 、 三氧化硫吡啶 、 silica gel 、 苄基三甲基氢氧化铵 、 sodium hydride 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 28.0h， 生成 3-(2-(4-fluoro-3-methylphenyl)-4-(t-butyldimethylsilyl)oxy-6,6-dimethylcyclohex-1-en-1-yl)propenal
  参考文献：
  名称：

  Inhibitors of HMG-CoA reductase. Biological effects of A 6-[2-[2-(4-fluoro-3-methylphenyl)-4-substituted cyclohexe-1-en-1-yl]ethenyl]-4-hydroxy-3,4,5,6-tetrahydro-2h-pyran-2-one

  摘要：

  We report on a series of potent inhibitors of HMG-CoA reductase (HMGR) that were designed to examine the biological consequences that result from molecular changes in RG 12561. The introduction of functional groups on the cyclohexene nucleus of RG 12561 and the resulting inhibitor-enzyme interactions at remote binding sites of HMGR are discussed. Cellular membrane permeability may also contribute to potency. The HMGR inhibitory activity was measured utilizing solubilized enzyme. The compounds were evaluated as inhibitors of sterol biosynthesis in vitro using liver slices and in vivo after oral administration to the rat.

  DOI：

  10.1016/0223-5234(92)90095-i

文献信息

• Substituted cyclohexene derivatives as HMG-CoA reductase inhibitors
  申请人：Rhone-Poulenc Rorer Pharmaceuticals Inc.

  公开号：US05001144A1

  公开（公告）日：1991-03-19

  Disclosed are novel 3-hydroxy-3-methylglutaryl-coenzyme A reductase inhibitors useful as antihypercholesterolemic agents represented by the formula ##STR1## and the corresponding ring-opened hydroxy acids derived therefrom and pharmaceutically acceptable salts thereof. Phamaceutical compositions containing said compounds and method of inhibiting the biosynthesis of cholesterol therewith are also disclosed.

  本发明涉及一种新颖的3-羟基-3-甲基戊二酰辅酶A还原酶抑制剂，其可用作抗高胆固醇药物，其化学式如下：##STR1##以及由此衍生的相应的开环羟基酸及其药学上可接受的盐。本发明还涉及含有上述化合物的制药组合物以及利用其抑制胆固醇生物合成的方法。
• REGAN, JOHN R.;NEUENSCHWANDER, KENT W.
  作者：REGAN, JOHN R.、NEUENSCHWANDER, KENT W.

  DOI：——

  日期：——
• Inhibitors of HMG-CoA reductase. Biological effects of A 6-[2-[2-(4-fluoro-3-methylphenyl)-4-substituted cyclohexe-1-en-1-yl]ethenyl]-4-hydroxy-3,4,5,6-tetrahydro-2h-pyran-2-one
  作者：JR Regan、JG Bruno、K Gustafson、D Amin、K Neuenschwander、M Perrone

  DOI：10.1016/0223-5234(92)90095-i

  日期：1992.10

  We report on a series of potent inhibitors of HMG-CoA reductase (HMGR) that were designed to examine the biological consequences that result from molecular changes in RG 12561. The introduction of functional groups on the cyclohexene nucleus of RG 12561 and the resulting inhibitor-enzyme interactions at remote binding sites of HMGR are discussed. Cellular membrane permeability may also contribute to potency. The HMGR inhibitory activity was measured utilizing solubilized enzyme. The compounds were evaluated as inhibitors of sterol biosynthesis in vitro using liver slices and in vivo after oral administration to the rat.