(E)-3-[1-Benzothiazol-2-yl-5-(4-fluoro-phenyl)-3-isopropyl-1H-pyrazol-4-yl]-acrylic acid ethyl ester | 133258-54-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (E)-3-[1-Benzothiazol-2-yl-5-(4-fluoro-phenyl)-3-isopropyl-1H-pyrazol-4-yl]-acrylic acid ethyl ester
• 英文别名: ethyl (E)-3-[1-(1,3-benzothiazol-2-yl)-5-(4-fluorophenyl)-3-propan-2-ylpyrazol-4-yl]prop-2-enoate
• CAS: 133258-54-5
• 化学式: C₂₄H₂₂FN₃O₂S
• 分子量: 435.522
• InChiKey: IOWYAWYVWUJLMR-BUHFOSPRSA-N

物化性质

• 沸点：
  613.9±65.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  85.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-3-[1-Benzothiazol-2-yl-5-(4-fluoro-phenyl)-3-isopropyl-1H-pyrazol-4-yl]-acrylic acid ethyl ester 在 manganese(IV) oxide 、 sodium tetrahydroborate 、 正丁基锂 、 三乙基硼 、 sodium hydride 、 二异丁基氢化铝 、 三甲基乙酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 31.08h， 生成 (R*,S*,trans)-7-[1-(2-Benzothiazolyl)-5-(4-fluorophenyl)-3-(1-methylethyl)-1H-pyrazol-4-yl]-3,5-dihydroxy-6-heptenoic acid, ethyl ester
  参考文献：
  名称：

  Inhibitors of cholesterol biosynthesis. 6. trans-6-[2-(2-N-heteroaryl-3,5-disubstituted-pyrazol-4-yl)ethyl/ethenyl]tetrahydro-4-hydroxy-2H-pyran-2-ones

  摘要：

  A series of N-heteroaryl-substituted mevalonolactones were prepared and evaluated for their ability to inhibit the enzyme HMG-CoA reductase both in vitro and in vivo, and to lower plasma cholesterol in a hypercholesterolemic dog model. The goal of the strategy employed was to design an inhibitor which possessed the pharmacological properties of lovastatin (1), and the physicochemical properties (increased hydrophilicity) of pravastatin (2). Two compounds 20a and 20b, were more potent than lovastatin at inhibiting cholesterol biosynthesis both in vitro and in vivo. In terms of plasma cholesterol lowering, 20a was much more efficacious than lovastatin. In addition to possessing increased biological activity, these compounds are significantly less lipophilic than lovastatin, in fact, 20b has a CLOGP value comparable to pravastatin.

  DOI：

  10.1021/jm00089a022
• 作为产物：
  描述：

  2-[5-(4-Fluorophenyl)-3-(1-methylethyl)-1H-pyrazol-1-yl]benzothiazole 在 N-溴代丁二酰亚胺(NBS) 、 bis(triphenylphosphine)palladium(II)-chloride 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (E)-3-[1-Benzothiazol-2-yl-5-(4-fluoro-phenyl)-3-isopropyl-1H-pyrazol-4-yl]-acrylic acid ethyl ester
  参考文献：
  名称：

  Inhibitors of cholesterol biosynthesis. 6. trans-6-[2-(2-N-heteroaryl-3,5-disubstituted-pyrazol-4-yl)ethyl/ethenyl]tetrahydro-4-hydroxy-2H-pyran-2-ones

  摘要：

  A series of N-heteroaryl-substituted mevalonolactones were prepared and evaluated for their ability to inhibit the enzyme HMG-CoA reductase both in vitro and in vivo, and to lower plasma cholesterol in a hypercholesterolemic dog model. The goal of the strategy employed was to design an inhibitor which possessed the pharmacological properties of lovastatin (1), and the physicochemical properties (increased hydrophilicity) of pravastatin (2). Two compounds 20a and 20b, were more potent than lovastatin at inhibiting cholesterol biosynthesis both in vitro and in vivo. In terms of plasma cholesterol lowering, 20a was much more efficacious than lovastatin. In addition to possessing increased biological activity, these compounds are significantly less lipophilic than lovastatin, in fact, 20b has a CLOGP value comparable to pravastatin.

  DOI：

  10.1021/jm00089a022

文献信息

• PICARD, JOSEPH A.;ROTH, BRUCE D.;SLISKOVIC, DRAGO R.
  作者：PICARD, JOSEPH A.、ROTH, BRUCE D.、SLISKOVIC, DRAGO R.

  DOI：——

  日期：——