1-[2-(3,4-dichloro-phenylamino)-4-methyl-thiazole-5-yl]-3-(3,4-methylenedioxyphenyl)-propen-1-one | 1257438-53-1

• 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: 1-[2-(3,4-dichloro-phenylamino)-4-methyl-thiazole-5-yl]-3-(3,4-methylenedioxyphenyl)-propen-1-one
• 英文别名: (E)-3-(1,3-benzodioxol-5-yl)-1-[2-(3,4-dichloroanilino)-4-methyl-thiazol-5-yl]prop-2-en-1-one；(E)-3-(1,3-benzodioxol-5-yl)-1-[2-(3,4-dichloroanilino)-4-methyl-1,3-thiazol-5-yl]prop-2-en-1-one
• CAS: 1257438-53-1
• 化学式: C₂₀H₁₄Cl₂N₂O₃S
• 分子量: 433.315
• InChiKey: HUWFWRBOYDPAPI-QHHAFSJGSA-N

物化性质

• 熔点：
  237-239 °C(Solvent: Tetrahydrofuran; Ethyl acetate)
• 沸点：
  605.5±65.0 °C(predicted)
• 密度：
  1.494±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  88.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  胡椒醛 、 1-(2-(3,4-dichlorophenylamino)-4-methylthiazol-5-yl)ethanone 在 potassium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以45%的产率得到1-[2-(3,4-dichloro-phenylamino)-4-methyl-thiazole-5-yl]-3-(3,4-methylenedioxyphenyl)-propen-1-one
  参考文献：
  名称：

  Synthesis and anticancer evaluation of thiazolyl–chalcones

  摘要：

  Thirty-seven (E)-1-(4-methyl-2-arylaminothiazol-5-yl)-3-arylprop-2-en-1-ones were synthesized via Claisen-Schmidt condensation of 1-(4-methyl-2-(arylamino)thiazol-5-yl) ethanone with the corresponding arylaldehydes. All these thiazolyl-chalcones were characterized and evaluated by MTT assay on human cancer cell lines BGC-823, PC-3, NCI-H460, BEL-7402 in vitro. Compounds 5, 8, 26, 37 and 41 are effective against cancer cell lines with IC(50)s below 10 mu M. The antitumor activity in ICR mice bearing sarcoma 180 tumors indicates compounds 10 and 41 have moderate in vivo activity with 22-25% tumor-weight inhibition. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.09.041

文献信息

• Synthesis and anticancer evaluation of thiazolyl–chalcones
  作者：Hai-Bo Shi、Shi-Jie Zhang、Qiu-Fu Ge、Dian-Wu Guo、Chao-Ming Cai、Wei-Xiao Hu

  DOI：10.1016/j.bmcl.2010.09.041

  日期：2010.11

  Thirty-seven (E)-1-(4-methyl-2-arylaminothiazol-5-yl)-3-arylprop-2-en-1-ones were synthesized via Claisen-Schmidt condensation of 1-(4-methyl-2-(arylamino)thiazol-5-yl) ethanone with the corresponding arylaldehydes. All these thiazolyl-chalcones were characterized and evaluated by MTT assay on human cancer cell lines BGC-823, PC-3, NCI-H460, BEL-7402 in vitro. Compounds 5, 8, 26, 37 and 41 are effective against cancer cell lines with IC(50)s below 10 mu M. The antitumor activity in ICR mice bearing sarcoma 180 tumors indicates compounds 10 and 41 have moderate in vivo activity with 22-25% tumor-weight inhibition. (C) 2010 Elsevier Ltd. All rights reserved.