2-cyclohexyl-N-[(Z)-1,3-benzodioxole-5-ylmethylidene]hydrazinecarbothioamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 2-cyclohexyl-N-[(Z)-1,3-benzodioxole-5-ylmethylidene]hydrazinecarbothioamide
• 英文别名: 1-[(Z)-1,3-benzodioxol-5-ylmethylideneamino]-3-cyclohexylthiourea
• 化学式: C₁₅H₁₉N₃O₂S
• 分子量: 305.401
• InChiKey: CLTZTXNVQYXKIO-SXGWCWSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  87
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  胡椒醛 、 4-环己基-3-硫代氨基脲 在 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以70%的产率得到2-cyclohexyl-N-[(Z)-1,3-benzodioxole-5-ylmethylidene]hydrazinecarbothioamide
  参考文献：
  名称：

  Targeting HER-2 over expressed breast cancer cells with 2-cyclohexyl-N-[(Z)-(substituted phenyl/furan-2-yl/thiophene-2-yl)methylidene]hydrazinecarbothioamide

  摘要：

  Cyclohexyl thiosemicarbazone derivatives (C1-14) were synthesized, characterized and evaluated against HER-2 over expressed breast cancer cells. The synthesized compounds were screened in vitro against four breast cancer cell lines; SKBr-3, MCF-7, MDA-MB-468 and MDA-MB-231. All the compounds showed activity against HER-2 over expressed SKBr-3 cells with (IC50 = 25.6 +/- 0.07 mu M-61.6 +/- 0.4 mu M). The most active compounds inhibit ALDH(+) breast cancer stem cells more effectively than the cancer stem cells specific agent Salinomycin. Immunohistochemistry staining also confirmed that these compounds inhibit the expression of HER-2 on SKBr-3 cells. Compound C2 significantly inhibited the cell migration and cell adhesion of breast cancer cell lines. Compound C2 was found to most active compound of this series targeting HER-2 over expressed breast cancer cells. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.11.009

文献信息

• Targeting HER-2 over expressed breast cancer cells with 2-cyclohexyl-N-[(Z)-(substituted phenyl/furan-2-yl/thiophene-2-yl)methylidene]hydrazinecarbothioamide
  作者：Mashooq Ahmad Bhat、Abdullah Al-Dhfyan、Azmat Ali Khan、Nouf Al-Harbi、P.S. Manogaran、Amer M. Alanazi、Hoong-Kun Fun、Mohamed A. Al-Omar

  DOI：10.1016/j.bmcl.2014.11.009

  日期：2015.1

  Cyclohexyl thiosemicarbazone derivatives (C1-14) were synthesized, characterized and evaluated against HER-2 over expressed breast cancer cells. The synthesized compounds were screened in vitro against four breast cancer cell lines; SKBr-3, MCF-7, MDA-MB-468 and MDA-MB-231. All the compounds showed activity against HER-2 over expressed SKBr-3 cells with (IC50 = 25.6 +/- 0.07 mu M-61.6 +/- 0.4 mu M). The most active compounds inhibit ALDH(+) breast cancer stem cells more effectively than the cancer stem cells specific agent Salinomycin. Immunohistochemistry staining also confirmed that these compounds inhibit the expression of HER-2 on SKBr-3 cells. Compound C2 significantly inhibited the cell migration and cell adhesion of breast cancer cell lines. Compound C2 was found to most active compound of this series targeting HER-2 over expressed breast cancer cells. (C) 2014 Elsevier Ltd. All rights reserved.