(2E,6E)-2,6-bis((1-methyl-1H-pyrazol-5-yl)methylene)cyclohexanone | 1578301-18-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (2E,6E)-2,6-bis((1-methyl-1H-pyrazol-5-yl)methylene)cyclohexanone
• 英文别名: (2E,6E)-2,6-bis[(2-methylpyrazol-3-yl)methylidene]cyclohexan-1-one
• CAS: 1578301-18-4
• 化学式: C₁₆H₁₈N₄O
• 分子量: 282.345
• InChiKey: AWSHHJOEAWWDPS-DCIPZJNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  52.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  环己酮 、 1-甲基-1H-吡唑-5-甲醛 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以97%的产率得到(2E,6E)-2,6-bis((1-methyl-1H-pyrazol-5-yl)methylene)cyclohexanone
  参考文献：
  名称：

  Design, synthesis, and evaluation of novel heteroaromatic analogs of curcumin as anti-cancer agents

  摘要：

  To improve the potential of curcumin to treat advanced hormone-refractory prostate cancer, three series (A-C) of heteroaromatic analogs (thirty two compounds) with different monoketone linkers have been synthesized and evaluated for cytotoxicity against two human androgen-independent prostate cancer cell lines (PC-3 and DU-145). Among them, thirty analogs are more potent than curcumin against PC-3 cells, and twenty one analogs are more cytotoxic towards DU-145 cells relative to curcumin. The most potent compounds (44, 45, 51, and 52) also showed impressive cytotoxicity against three other metastatic cancer cell lines (MDA-MB-231, HeLa, and A549), with IC50 values ranging from 50 nM to 390 nM. All four most potent analogs exhibited no apparent cytotoxicity towards the MCF-10A normal mammary epithelial cells. Taken together, selective enhancement of cell death in prostate cancer cell lines and other aggressive cancer cell lines suggests that nitrogen-containing heteroaromatic rings are promising bio-isosteres of the substituted phenyl ring in curcumin. Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2014.01.041