2-(methylsulfonylamino)acetophenone thiosemicarbazone | 546112-33-8

• 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: 2-(methylsulfonylamino)acetophenone thiosemicarbazone
• 英文别名: [[2-(Methanesulfonamido)-1-phenylethylidene]amino]thiourea；[[2-(methanesulfonamido)-1-phenylethylidene]amino]thiourea
• CAS: 546112-33-8
• 化学式: C₁₀H₁₄N₄O₂S₂
• 分子量: 286.379
• InChiKey: YCPYYCDTCOHSCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  137
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(methylsulfonylamino)acetophenone thiosemicarbazone 、 三甲基乙酰氯 在 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 3.6h， 以22%的产率得到N-[5-amino-3-(2,2-dimethylpropionyl)-2-phenyl-2,3-dihydro[1,3,4]thiadiazol-2-ylmethyl]methanesulfonamide
  参考文献：
  名称：

  Thiadiazoline derivatives for treating cancer

  摘要：

  公开号：

  EP1454903B9
• 作为产物：
  描述：

  thioacetic hydrazide 、 N-(2-氧代-2-苯基乙基)甲磺酰胺 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 生成 2-(methylsulfonylamino)acetophenone thiosemicarbazone
  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

• EP1671957
  申请人：——

  公开号：——

  公开（公告）日：——
• Thiadiazoline derivatives for treating cancer
  申请人：Kyowa Hakko Kirin Co., Ltd.

  公开号：EP1454903B9

  公开（公告）日：2011-10-05
• M-STAGE KINESIN INHIBITOR
  申请人：Kyowa Hakko Kirin Co., Ltd.

  公开号：EP1616866B1

  公开（公告）日：2011-12-14
• Synthetic studies on mitotic kinesin Eg5 inhibitors: Synthesis and structure–activity relationships of novel 2,4,5-substituted-1,3,4-thiadiazoline derivatives
  作者：Junichiro Yamamoto、Nobuyoshi Amishiro、Kazuhiko Kato、Yoshihisa Ohta、Yoji Ino、Mitsuharu Araki、Tetsuya Tsujita、Seiho Okamoto、Takeshi Takahashi、Hideaki Kusaka、Shiro Akinaga、Yoshinori Yamashita、Ryuichiro Nakai、Chikara Murakata

  DOI：10.1016/j.bmcl.2014.06.034

  日期：2014.8

  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.