N-[2-[(Aminothioxomethyl)hydrazono]-2-phenylethyl]acetamide | 218767-48-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[2-[(Aminothioxomethyl)hydrazono]-2-phenylethyl]acetamide
• 英文别名: N-[2-(carbamothioylhydrazinylidene)-2-phenylethyl]acetamide
• CAS: 218767-48-7
• 化学式: C₁₁H₁₄N₄OS
• 分子量: 250.324
• InChiKey: QXDHPPFFDIBUAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[2-[(Aminothioxomethyl)hydrazono]-2-phenylethyl]acetamide 、 三甲基乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 C₂₁H₃₀N₄O₃S
  参考文献：
  名称：

  Synthetic studies on mitotic kinesin Eg5 inhibitors: Synthesis and structure–activity relationships of novel 2,4,5-substituted-1,3,4-thiadiazoline derivatives

  摘要：

  The 2,4,5-substituted-1,3,4-thiadiazoline derivative 1a has been identified as a new class of mitotic kinesin Eg5 inhibitor. With the aim of enhancement of the mitotic phase accumulation activity, structure optimization of side chains at the 2-, 4-, and 5-positions of the 1,3,4-thiadiazoline ring of 1a was performed. The introduction of sulfonylamino group at the side chain at the 5-position and bulky acyl group at the 2- and 4-position contributed to a significant increase in the mitotic phase accumulation activity and Eg5 inhibitory activity. As a result, a series of optically active compounds exhibited an increased antitumor activity in a human ovarian cancer xenograft mouse model that was induced by oral administration.

  DOI：

  10.1016/j.bmcl.2014.06.034
• 作为产物：
  描述：

  2-氨基苯乙酮盐酸盐 在 盐酸 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 N-[2-[(Aminothioxomethyl)hydrazono]-2-phenylethyl]acetamide
  参考文献：
  名称：

  Synthetic studies on mitotic kinesin Eg5 inhibitors: Synthesis and structure–activity relationships of novel 2,4,5-substituted-1,3,4-thiadiazoline derivatives

  摘要：

  The 2,4,5-substituted-1,3,4-thiadiazoline derivative 1a has been identified as a new class of mitotic kinesin Eg5 inhibitor. With the aim of enhancement of the mitotic phase accumulation activity, structure optimization of side chains at the 2-, 4-, and 5-positions of the 1,3,4-thiadiazoline ring of 1a was performed. The introduction of sulfonylamino group at the side chain at the 5-position and bulky acyl group at the 2- and 4-position contributed to a significant increase in the mitotic phase accumulation activity and Eg5 inhibitory activity. As a result, a series of optically active compounds exhibited an increased antitumor activity in a human ovarian cancer xenograft mouse model that was induced by oral administration.

  DOI：

  10.1016/j.bmcl.2014.06.034

文献信息

• Elevation of HDL cholesterol by N-[2-[(aminothioxomethyl)
  申请人：American Home Products Corp.

  公开号：US06049006A1

  公开（公告）日：2000-04-11

  This invention relates to the treatment of atherosclerosis via raising the level of HDL cholesterol by administration of a compound of the formula ##STR1## wherein: R.sup.1, R.sup.2, and R.sup.3 are independently hydrogen, C.sub.1 -C.sub.6 alkyl or --(CH.sub.2).sub.0-6 Ph where Ph is phenyl optionally substituted by halogen, cyano, nitro, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, trifluoromethyl, C.sub.1 -C.sub.6 alkoxycarbonyl, --CO.sub.2 H or OH; R.sup.4 is hydrogen or C.sub.1 -C.sub.6 alkyl; R.sup.5 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.8 cycloalkyl, or --(CH.sub.2).sub.0-6 Ar.sup.1 where Ar.sup.1 is phenyl naphthyl, furanyl, pyridinyl or thienyl and Ar.sup.1 can be optionally substituted by halogen, cyano, nitro, C.sub.1 -C.sub.6 alkyl, phenyl, C.sub.1 -C.sub.6 alkoxy, phenoxy, tifluoromethyl, C.sub.1 -C.sub.6 alkoxycarbonyl, --CO.sub.2 H or OH; and Ar is phenyl, naphthyl, furanyl, pyridinyl or thienyl or Ar is optionally substituted by halogen, cyano, nitro, C.sub.1 -C.sub.6 alkyl, phenyl, C.sub.1 -C.sub.6 alkoxy, phenoxy, tifluoromethyl, C.sub.1 -C.sub.6 alkoxycarbonyl, --CO.sub.2 H or OH.

  该发明涉及通过给予公式##STR1##中的化合物提高HDL胆固醇水平来治疗动脉粥样硬化，其中：R.sup.1、R.sup.2和R.sup.3独立地表示氢、C.sub.1-C.sub.6烷基或--(CH.sub.2).sub.0-6 Ph，其中Ph是苯基，可选地被卤素、氰基、硝基、C.sub.1-C.sub.6烷基、C.sub.1-C.sub.6烷氧基、三氟甲基、C.sub.1-C.sub.6烷氧羰基、--CO.sub.2H或OH取代；R.sup.4表示氢或C.sub.1-C.sub.6烷基；R.sup.5表示氢、C.sub.1-C.sub.6烷基、C.sub.3-C.sub.8环烷基或--(CH.sub.2).sub.0-6 Ar.sup.1，其中Ar.sup.1是苯基萘基、呋喃基、吡啶基或噻吩基，Ar.sup.1可以被卤素、氰基、硝基、C.sub.1-C.sub.6烷基、苯基、C.sub.1-C.sub.6烷氧基、苯氧基、三氟甲基、C.sub.1-C.sub.6烷氧羰基、--CO.sub.2H或OH取代；Ar是苯基、萘基、呋喃基、吡啶基或噻吩基，或Ar可被卤素、氰基、硝基、C.sub.1-C.sub.6烷基、苯基、C.sub.1-C.sub.6烷氧基、苯氧基、三氟甲基、C.sub.1-C.sub.6烷氧羰基、--CO.sub.2H或OH取代。