lovastatin | 237073-61-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: lovastatin
• 英文别名: (S)-2-methyl-butyric acid (1S,3R,7S,8S,8aR)-8-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-napthalen-1-yl ester；6(R)-[2[ 8(S)-(2-methylbutyryloxy)-2 (S),6(R)-dimethyl-1,2,6,7,8,8a(R)-hexahydronaphthyl-1 (S)]ethyl]-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one；(1S,3R,7S,8S,8aR)-8-(2-((2R,4R)-4-Hydroxy-6-oxotetrahydro-2H-pyran-2-yl)ethyl)-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2-methylbutanoate；[(1S,3R,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] 2-methylbutanoate
• CAS: 237073-61-9
• 化学式: C₂₄H₃₆O₅
• 分子量: 404.547
• InChiKey: PCZOHLXUXFIOCF-SGFUJYLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  lovastatin 生成 莫那可林J
  参考文献：
  名称：

  WILLARD, A. K.

  摘要：

  DOI：
• 作为产物：
  描述：

  Ammonium-7-[1,2,6,7,8,8a(R)-hexahydro-2(S),6(R),dimethyl-8(S)-(2-methylbutyryloxy)-1(S)-naphthyl]-3(R),5(R)-dihydroxyheptanoate 以 水 、 溶剂黄146 为溶剂， 以92%的产率得到lovastatin
  参考文献：
  名称：

  Process of lactonization in the preparation of statins

  摘要：

  一种改进的乳酸化过程用于制备他汀类药物（例如，HMG--CoA还原酶抑制剂洛伐他汀和辛伐他汀），采用非常温和的反应条件。改进的过程包括处理他汀类药物的开环羟基酸形式，使用过量的乙酸，在缺乏强酸催化剂的情况下在温和加热条件下（例如，室温至55摄氏度），并向反应混合物中添加抗溶剂，从而导致他汀类药物以内酯形式从反应混合物中结晶。乙酸既作为溶剂又作为乳酸化反应的催化剂。

  公开号：

  US05917058A1

文献信息

• Process for Preparing Substantially Pure Simvastatin
  申请人：Chatterjee Sugata

  公开号：US20110282074A1

  公开（公告）日：2011-11-17

  This invention relates to an improved process for preparing substantially pure simvastatin (I), chemically known as (1S,3R,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxotetrahydro-2-H-pyran-2-yl]ethyl]-3 ,7-dimeth-yl-1,2,3,7,8,8a-Hexahydronaphthalen-1-yl2,2-dimethyl butanoate, which comprises of: a) treating lovastatin (II) with an alkali metal hydroxide in a chosen suitable alcoholic solvent followed by relactonization to obtain the diol lactone intermediate (III) in a single vessel. b) selective silylation of 4-hydroxy group of diol lactone intermediate (III) with a chosen suitable silylating reagent to obtain mono silylated intermediate diol lactone (IV). c) acylation of the mono silylated intermediate (IV) to form silylated simvastatin (V) Or optionally, preparing silylated simvastatin (V) starting from Lovastatin (II) without isolating diol lactone (III) and monosilylated diol lactone (IV) and d) finally, removal of the silyl protecting group on silylated simvastatin (V) followed by purification to provide substantially pure simvastatin (I).

  这项发明涉及一种改进的制备基本纯度辛伐他汀（I）的过程，化学名称为（1S,3R,7S,8S,8aR）-8-[2-[(2R,4R)-4-羟基-6-氧代四氢-2-H-吡喃-2-基]乙基]-3,7-二甲基-1,2,3,7,8,8a-六氢萘-1-基2,2-二甲基丁酸酯，包括：a）用碱金属氢氧化物在选择的适宜醇溶剂中处理洛伐他汀（II），然后重新内酯化以获得二醇内酯中间体（III）在单个容器中。b）用选择的适宜硅化试剂选择性硅化二醇内酯中间体（III）的4-羟基以获得单硅化中间二醇内酯（IV）。c）酰化单硅化中间体（IV）以形成硅化辛伐他汀（V）。或者，从洛伐他汀（II）开始制备硅化辛伐他汀（V），而不用分离二醇内酯（III）和单硅化二醇内酯（IV），d）最后，去除硅化辛伐他汀（V）上的硅保护基，然后经过纯化以提供基本纯度辛伐他汀（I）。
• Croos-B Structure Binding Compounds
  申请人：Gebbink Martijn Frans Ben Gerard

  公开号：US20080267948A1

  公开（公告）日：2008-10-30

  The invention relates to the field of biochemistry, biophysical chemistry, molecular biology, structural biology and medicine. More in particular, the invention relates to cross-β structure conformation. Even more particular, the invention relates to compounds capable of binding to a compound with cross-β structure conformation, i.e. cross-β structure binding compounds and uses thereof.

  本发明涉及生物化学、生物物理化学、分子生物学、结构生物学和医学领域。更具体地说，本发明涉及交叉β结构构象。更具体地说，本发明涉及能够结合具有交叉β结构构象的化合物的化合物，即交叉β结构结合化合物及其用途。
• 3,5,N-TRIHYDROXY-ALKANAMIDE AND DERIVATIVES: METHOD FOR MAKING SAME AND USE THEREOF
  申请人：Academia Sinica

  公开号：US20150148360A1

  公开（公告）日：2015-05-28

  The present invention provides novel compounds of Formula (I), and pharmaceutically compositions thereof. Compounds of Formula (I) are inhibitors of histone deacetylases (HDACs) and 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase (HMGR). Also provided are methods of using the compounds and pharmaceutical compositions for inhibiting the activity of HDACs and HMGR, treating diseases associated with HDACs or HMGR (e.g., cancer, hypercholesterolemia, an acute or chronic inflammatory disease, autoimmune disease, allergic disease, pathogen infection, neurodegenerative disease, and a disease associated with oxidative stress), or inhibiting drug resistance of cancer cells.

  本发明提供了公式（I）的新型化合物及其药物组合物。公式（I）的化合物是组蛋白去乙酰化酶（HDACs）和3-羟基-3-甲基戊二酰辅酶A（HMG-CoA）还原酶（HMGR）的抑制剂。还提供了使用这些化合物和药物组合物的方法，用于抑制HDACs和HMGR的活性，治疗与HDACs或HMGR相关的疾病（例如癌症，高胆固醇血症，急性或慢性炎症性疾病，自身免疫疾病，过敏疾病，病原体感染，神经退行性疾病和与氧化应激相关的疾病），或抑制癌细胞的耐药性。
• PROCESS FOR SELECTIVE LACTONIZATION
  申请人：KANEKA CORPORATION

  公开号：EP1110959A1

  公开（公告）日：2001-06-27

  The invention has its object to provide a method of lactonization for a compound of the general formula (1) in which the dimer formation reaction can be drastically inhibited. The invention provides a process for producing a compound of the general formula (2)    comprising lactonizing a compound of the general formula (1) under conditions such that the solubility of the compound of the general formula (1) and/or the compound of the general formula (2) is not more than 0.5 w/w % to thereby give a compound of the general formula (2) with a dimer content of not more than 0.3 mole %.

  本发明的目的是提供一种通式（1）化合物的内酯化方法，在该方法中，二聚物形成反应可被大大抑制。 本发明提供了一种通式（2）化合物的生产工艺 包括在通式(1)化合物和/或通式(2)化合物的溶解度不超过 0.5 w/w%的条件下对通式(1)化合物进行内酯化，从而得到二聚物含量不超过 0.3 摩尔%的通式(2)化合物。
• METHODS FOR CRYSTALLIZATION OF HYDROXYCARBOXYLIC ACIDS
  申请人：KANEKA CORPORATION

  公开号：EP1323701B1

  公开（公告）日：2009-07-15