[2-氧代-2-(2-氧代环戊基)乙基]乙酸酯 | 118790-18-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: [2-氧代-2-(2-氧代环戊基)乙基]乙酸酯
• 英文名称: acetoxyacetyl cyclopentanone
• 英文别名: 2-Oxo-2-(2-oxocyclopentyl)ethyl acetate；[2-oxo-2-(2-oxocyclopentyl)ethyl] acetate
• CAS: 118790-18-4
• 化学式: C₉H₁₂O₄
• 分子量: 184.192
• InChiKey: GNLWFDSMCVUEJF-UHFFFAOYSA-N

物化性质

• 沸点：
  125 °C(Press: 0.5 Torr)
• 密度：
  1.204±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [2-氧代-2-(2-氧代环戊基)乙基]乙酸酯 在 Raney nickel W₄ 氢气 作用下， 以 乙醇 为溶剂， 60.0 ℃ 、10.13 MPa 条件下， 反应 6.0h， 生成 [2-Hydroxy-2-(2-hydroxycyclopentyl)ethyl] acetate
  参考文献：
  名称：

  Dolmazon, Rene, Journal of Heterocyclic Chemistry, 1988, vol. 25, # 2, p. 751 - 757

  摘要：

  DOI：
• 作为产物：
  描述：

  环戊酮 、 乙酰氧基乙酰氯 在 吗啉 作用下， 以 苯 为溶剂， 以53%的产率得到[2-氧代-2-(2-氧代环戊基)乙基]乙酸酯
  参考文献：
  名称：

  HMG-CoA reductase inhibitors: design, synthesis, and biological activity of tetrahydroindazole-substituted 3,5-dihydroxy-6-heptenoic acid sodium salts

  摘要：

  Compounds comprising a series of 7-[2-(4-fluorophenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-3,5-dihydroxy-6-heptenoic acid sodium salts (18) were synthesized and tested for their ability to inhibit HMG-CoA reductase in a partially purified enzyme preparation and cholesterol biosynthesis from acetate in cultured HEP-G2 cells. Changing the size of the saturated ring of the tetrahydroindazole nucleus did not improve potency, but incorporation of substituents at the 7-position resulted in up to 1700-fold improvement in inhibitory potency. Structure-activity studies revealed that the most potent compounds possess a substituted benzyl group at the 7-position, with a preference for steric bulk at the para position of the benzene ring. The most potent enzyme inhibitor (18t, IC50 = 3.0 nM) is approximately 3-fold more potent than lovastatin sodium salt (2). The most potent cholesterol biosynthesis inhibitor in HEP-G2 cells (18q, IC50 = 0.078 muM) is slightly less potent than 2 (sodium salt). Molecular modeling studies suggested that, when compared to the parent compound (18b) lacking the appropriate 7-substituent, 18t overlaps better with 2 and literature inhibitors 5 and 6 in a hydrophobic binding region adjacent to the enzyme active site.

  DOI：

  10.1021/jm00075a024

文献信息

• Tetrahydroindazole, tetrahydrocyclopentapyrazole, and hexahydrocycloheptapyrazole compounds and their use as HMG-COA reductase inhibitors
  申请人：ORTHO PHARMACEUTICAL CORPORATION

  公开号：EP0529854A2

  公开（公告）日：1993-03-03

  Compounds of the general formula I : are disclosed as useful in the treatment or prevention of hypercholesterolemia, hyperlipoproteinemia and atherosclerosis. Novel intermediate compounds used to make the compound of formula I are also disclosed.

  通式 I 的化合物 ： 公开了用于治疗或预防高胆固醇血症、高脂蛋白血症和动脉粥样硬化的化合物。还公开了用于制造式 I 化合物的新型中间体化合物。
• DOLMAZON, RENE, J. HETEROCYCL. CHEM., 25,(1988) N 3, C. 751-757
  作者：DOLMAZON, RENE

  DOI：——

  日期：——
• US5134155A
  申请人：——

  公开号：US5134155A

  公开（公告）日：1992-07-28
• US5250561A
  申请人：——

  公开号：US5250561A

  公开（公告）日：1993-10-05
• US5315012A
  申请人：——

  公开号：US5315012A

  公开（公告）日：1994-05-24