methyl 4-fluoro-3-methylbenzoyl acetate | 146299-76-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-fluoro-3-methylbenzoyl acetate
• 英文别名: Methyl 4-fluoro-3-methylbenzoylacetate；methyl 3-(4-fluoro-3-methylphenyl)-3-oxopropanoate
• CAS: 146299-76-5
• 化学式: C₁₁H₁₁FO₃
• 分子量: 210.205
• InChiKey: CYWPJNPOYPCNFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-fluoro-3-methylbenzoyl acetate 在 sodium tetrahydroborate 、 三氟化硼乙醚 、 苄基三甲基氢氧化铵 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 Methyl 2-(4-fluoro-3-methylphenyl)-4-hydroxy-6, 6-dimethyl-cyclohex-2-en-1-carboxylate
  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 、 碳酸二甲酯 在 sodium hydride 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以75%的产率得到methyl 4-fluoro-3-methylbenzoyl acetate
  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：Rorer Pharmaceutical Corporation

  公开号：US04939143A1

  公开（公告）日：1990-07-03

  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. Pharmaceutical compositions containing said compounds and method of inhibiting the biosynthesis of cholesterol therewith are also disclosed.

  本发明涉及一种新型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，化学式如下：##STR1## 以及相应的开环羟基酸及其药学上可接受的盐。还揭示了含有该化合物的制药组合物以及用其抑制胆固醇生物合成的方法。
• US4939143A
  申请人：——

  公开号：US4939143A

  公开（公告）日：1990-07-03
• US5001144A
  申请人：——

  公开号：US5001144A

  公开（公告）日：1991-03-19
• US5132312A
  申请人：——

  公开号：US5132312A

  公开（公告）日：1992-07-21
• [EN] SUBSTITUTED CYCLOHEXENE DERIVATIVES AS HMG-CoA REDUCTASE INHIBITORS
  申请人：RORER INTERNATIONAL (OVERSEAS) INC.

  公开号：WO1991004736A1

  公开（公告）日：1991-04-18

  (EN) Disclosed are novel 3-hydroxy-3-methylglutaryl-coenzyme A reductase inhibitors useful as antihypercholesterolemic agents represented by formula (I), and the corresponding ring-opened hydroxy acids derived therefrom and pharmaceutically acceptable salts thereof. Pharmaceutical compositions containing said compounds and method of inhibiting the biosynthesis of cholesterol therewith are also disclosed.(FR) Nouveaux inhibiteurs de réductase de 3-hydroxy-3-méthylglutaryle-coenzyme A, utiles en tant qu'agents antihypercholestérolémiques représentés par la formule (I), et les acides d'hydroxy décyclisés correspondants dérivés desdits inhibiteurs, ainsi que leurs sels pharmaceutiquement acceptables. Des compositions pharmaceutiques contenant lesdits composés et un procédé d'inhibition de la biosynthèse du cholestérol à l'aide desdites compositions sont également décrits.