7-[5-cyclopropylcarbamoyl-3-(4-fluorophenyl)-1-isopropyl-4-phenyl-1H-pyrrol-2-yl]-3-hydroxy-5-oxo-hept-6-enoic acid methyl ester | 950599-92-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 7-[5-cyclopropylcarbamoyl-3-(4-fluorophenyl)-1-isopropyl-4-phenyl-1H-pyrrol-2-yl]-3-hydroxy-5-oxo-hept-6-enoic acid methyl ester
• 英文别名: methyl (E,3R)-7-[5-(cyclopropylcarbamoyl)-3-(4-fluorophenyl)-4-phenyl-1-propan-2-ylpyrrol-2-yl]-3-hydroxy-5-oxohept-6-enoate
• CAS: 950599-92-5
• 化学式: C₃₁H₃₃FN₂O₅
• 分子量: 532.612
• InChiKey: QQCOTAIIZMJYNX-KVACCUTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  97.6
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-[5-cyclopropylcarbamoyl-3-(4-fluorophenyl)-1-isopropyl-4-phenyl-1H-pyrrol-2-yl]-3-hydroxy-5-oxo-hept-6-enoic acid methyl ester 在 palladium on activated charcoal sodium tetrahydroborate 、 二乙基甲氧基硼烷 、 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 5.0h， 生成 7-[5-cyclopropylcarbamoyl-3-(4-fluorophenyl)-1-isopropyl-4-phenyl-1H-pyrrol-2-yl]-3,5-dihydroxy-heptanoic acid methyl ester
  参考文献：
  名称：

  Design and synthesis of hepatoselective, pyrrole-based HMG-CoA reductase inhibitors

  摘要：

  This manuscript describes the design and synthesis of a series of pyrrole-based inhibitors of HMG-CoA reductase for the treatment of hypercholesterolemia. Analogs were optimized using structure-based design and physical property considerations resulting in the identification of 44, a hepatoselective HMG-CoA reductase inhibitor with excellent acute and chronic efficacy in a pre-clinical animal models. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.096
• 作为产物：
  描述：

  4-(4-fluoro-phenyl)-5-formyl-1-isopropyl-3-phenyl-1H-pyrrole-2-carboxylic acid ethyl ester 在 sodium hydroxide 、 氯化亚砜 、 氢氟酸 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 、 乙腈 为溶剂， 反应 64.0h， 生成 7-[5-cyclopropylcarbamoyl-3-(4-fluorophenyl)-1-isopropyl-4-phenyl-1H-pyrrol-2-yl]-3-hydroxy-5-oxo-hept-6-enoic acid methyl ester
  参考文献：
  名称：

  Design and synthesis of hepatoselective, pyrrole-based HMG-CoA reductase inhibitors

  摘要：

  This manuscript describes the design and synthesis of a series of pyrrole-based inhibitors of HMG-CoA reductase for the treatment of hypercholesterolemia. Analogs were optimized using structure-based design and physical property considerations resulting in the identification of 44, a hepatoselective HMG-CoA reductase inhibitor with excellent acute and chronic efficacy in a pre-clinical animal models. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.096

文献信息

• Design and synthesis of hepatoselective, pyrrole-based HMG-CoA reductase inhibitors
  作者：Jeffrey A. Pfefferkorn、Yuntao Song、Kuai-Lin Sun、Steven R. Miller、Bharat K. Trivedi、Chulho Choi、Roderick J. Sorenson、Larry D. Bratton、Paul C. Unangst、Scott D. Larsen、Toni-Jo Poel、Xue-Min Cheng、Chitase Lee、Noe Erasga、Bruce Auerbach、Valerie Askew、Lisa Dillon、Jeffrey C. Hanselman、Zhiwu Lin、Gina Lu、Andrew Robertson、Karl Olsen、Thomas Mertz、Catherine Sekerke、Alexander Pavlovsky、Melissa S. Harris、Graeme Bainbridge、Nicole Caspers、Huifen Chen、Matthias Eberstadt

  DOI：10.1016/j.bmcl.2007.05.096

  日期：2007.8

  This manuscript describes the design and synthesis of a series of pyrrole-based inhibitors of HMG-CoA reductase for the treatment of hypercholesterolemia. Analogs were optimized using structure-based design and physical property considerations resulting in the identification of 44, a hepatoselective HMG-CoA reductase inhibitor with excellent acute and chronic efficacy in a pre-clinical animal models. (c) 2007 Elsevier Ltd. All rights reserved.