3-bromomethyl-4-(4-fluorophenylthio)-6,7,8-trifluoroquinoline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-bromomethyl-4-(4-fluorophenylthio)-6,7,8-trifluoroquinoline
• 英文别名: 3-(Bromomethyl)-6,7,8-trifluoro-4-(4-fluorophenyl)sulfanylquinoline；3-(bromomethyl)-6,7,8-trifluoro-4-(4-fluorophenyl)sulfanylquinoline
• 化学式: C₁₆H₈BrF₄NS
• 分子量: 402.21
• InChiKey: STLKUNSNSHASAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  38.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-bromomethyl-4-(4-fluorophenylthio)-6,7,8-trifluoroquinoline 在 2,2,6,6-四甲基哌啶 、 盐酸 、 正丁基锂 、 水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 2-甲基四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 7.0h， 生成
  参考文献：
  名称：

  Development of a Practical and Efficient Synthesis of SIPI-4884, a HMG CoA Reductase Inhibitor for the Treatment of Hypercholesterolemia

  摘要：

  An improved process of the novel HMG CoA reductase inhibitor SIPI-4884 has been developed for early preclinical pharmacology and safety studies, and it was made up with an efficient nine-step and scalable process. Significant improvements in the nucleophilic substitution, reduction, Wittig-Horner reaction, and preparation of calcium salt were demonstrated. The overall yield was improved to 17.2%.

  DOI：

  10.1021/op400060z
• 作为产物：
  描述：

  ethyl 4-chloro-6,7,8-trifluoroquinoline-3-carboxylate 在 三溴化磷 、 二异丁基氢化铝 、 碳酸氢钠 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 28.0h， 生成 3-bromomethyl-4-(4-fluorophenylthio)-6,7,8-trifluoroquinoline
  参考文献：
  名称：

  Development of a Practical and Efficient Synthesis of SIPI-4884, a HMG CoA Reductase Inhibitor for the Treatment of Hypercholesterolemia

  摘要：

  An improved process of the novel HMG CoA reductase inhibitor SIPI-4884 has been developed for early preclinical pharmacology and safety studies, and it was made up with an efficient nine-step and scalable process. Significant improvements in the nucleophilic substitution, reduction, Wittig-Horner reaction, and preparation of calcium salt were demonstrated. The overall yield was improved to 17.2%.

  DOI：

  10.1021/op400060z

文献信息

• Synthesis and HMG CoA reductase inhibition of 4-thiophenyl quinolines as potential hypocholesterolemic agents
  作者：Zhengyan Cai、Weicheng Zhou、Lixin Sun

  DOI：10.1016/j.bmc.2007.08.044

  日期：2007.12

  8-trisubstituted-4-chloro-quinoline-3-carboxylates by several reactions and evaluated for their ability to inhibit the rat HMG CoA reductase in vitro. It was found that substitution with a variety of thiophenyl groups at position 4 in quinoline resulted in retention or enhancement of the inhibition and the preferable groups were 4-isopropyl-thiophenyl and 3-methoxy-thiophenyl. (4R,6S)-6-[(E)-2-(6,7,8-trifluoro-4

  由6,7,8-三取代-4-氯喹啉-3-羧酸乙酯经数个反应合成了一系列新颖的基于4-硫代苯基喹啉的甲羟戊酸内酯衍生物，并评估了它们在体外抑制大鼠HMG CoA还原酶的能力。 。发现在喹啉的4位上被各种硫代苯基取代会导致抑制作用的保持或增强，优选的基团是4-异丙基-硫代苯基和3-甲氧基-硫代苯基。（4R，6S）-6-[（E）-2-（6,7,8-三氟-4-异丙基硫代苯基-喹啉-3-基）-乙烯基]-3,4,5,6-四氢-4-羟基-2H-吡喃-2-酮（A16）和（4R，6S）-6-[（E）-2-（6-氟-4,7-二-（3-甲氧基-硫代苯基）-喹啉-3 -基）-乙烯基] -3,4，5，
• Development of a Practical and Efficient Synthesis of SIPI-4884, a HMG CoA Reductase Inhibitor for the Treatment of Hypercholesterolemia
  作者：Qun Hao、Jing Pan、Yongjia Li、Zhengyan Cai、Weicheng Zhou

  DOI：10.1021/op400060z

  日期：2013.6.21

  An improved process of the novel HMG CoA reductase inhibitor SIPI-4884 has been developed for early preclinical pharmacology and safety studies, and it was made up with an efficient nine-step and scalable process. Significant improvements in the nucleophilic substitution, reduction, Wittig-Horner reaction, and preparation of calcium salt were demonstrated. The overall yield was improved to 17.2%.