3-(3-chloro-5-hydroxyphenyl)-N-(2-(4-methylpiperazin-1-yl)ethyl)-4-(pyridin-4-yl)-1H-pyrazole-1-carboxamide | 1286232-29-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(3-chloro-5-hydroxyphenyl)-N-(2-(4-methylpiperazin-1-yl)ethyl)-4-(pyridin-4-yl)-1H-pyrazole-1-carboxamide
• 英文别名: 3-(3-chloro-5-hydroxyphenyl)-N-[2-(4-methylpiperazin-1-yl)ethyl]-4-pyridin-4-ylpyrazole-1-carboxamide
• CAS: 1286232-29-8
• 化学式: C₂₂H₂₅ClN₆O₂
• 分子量: 440.933
• InChiKey: WXTFPPNCJYIMDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  86.5
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3,5-二氯苯甲酸 在 六甲基磷酰三胺 、 三氟二甲基硫醚络合物 、 sodium methylate 、 一水合肼 、 三乙胺 、 乙酰氯 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 82.0h， 生成 3-(3-chloro-5-hydroxyphenyl)-N-(2-(4-methylpiperazin-1-yl)ethyl)-4-(pyridin-4-yl)-1H-pyrazole-1-carboxamide
  参考文献：
  名称：

  1H-Pyrazole-1-carboxamide 衍生物的合成及其对黑色素瘤细胞系的抗增殖活性

  摘要：

  描述了一系列新的 1H - 吡唑 - 1 - 甲酰胺衍生物的合成。测试了它们对 A375 人黑色素瘤细胞系的抗增殖活性，并研究了替代物对二芳基吡唑支架的影响。药理结果表明，与索拉非尼相比，大多数新合成的化合物对 A375 表现出中等活性。在所有这些衍生物中，具有 N-甲基哌嗪基和酚基部分的化合物 IIe 对 A375 人黑色素瘤细胞系显示出最有效的抗增殖活性。

  DOI：

  10.1002/ardp.201000057

文献信息

• Antiproliferative Diarylpyrazole Derivatives as Dual Inhibitors of the ERK Pathway and COX-2
  作者：Mohammed I. El-Gamal、Hong Seok Choi、Kyung Ho Yoo、Daejin Baek、Chang-Hyun Oh

  DOI：10.1111/cbdd.12186

  日期：2013.9

  A series of 3,4‐diarylpyrazole‐1‐carboxamide derivatives was designed and synthesized. A selected group of the target compounds was tested for in vitro antiproliferative activities over a panel of 60 cancer cell lines at the National Cancer Institute (NCI, Bethesda, MD, USA) at a single‐dose concentration of 10 μm, and the four most active compounds 9a, 9l, 9n, and 10o were further tested in a five‐dose testing mode to determine their IC50 values over the 60 cell lines. In addition, a selected group of target compounds were tested for inhibitory effect over cyclooxygenase isozymes. Compounds 9a, 9l, 9n, and 10o were also tested for MEK and ERK kinase inhibitory activity using Western blot assay. Compound 10o was selective toward melanoma cell line subpanel, and its antiproliferative activity may be attributed to selective cyclooxygenase‐2 inhibition and ERK pathway inhibition.
• Synthesis of 1H-Pyrazole-1-carboxamide Derivatives and Their Antiproliferative Activity against Melanoma Cell Line
  作者：Mohammed I. El-Gamal、Tae Bo Sim、Jun Hee Hong、Jung-Hyuck Cho、Kyung Ho Yoo、Chang-Hyun Oh

  DOI：10.1002/ardp.201000057

  日期：2011.3

  Synthesis of a new series of 1H‐pyrazole‐1‐carboxamide derivatives is described. Their antiproliferative activity against A375 human melanoma cell line was tested and the effect of substituents on the diarylpyrazole scaffold was investigated. The pharmacological results indicated that most of the newly synthesized compounds showed moderate activity against A375, compared with sorafenib. Among all of

  描述了一系列新的 1H - 吡唑 - 1 - 甲酰胺衍生物的合成。测试了它们对 A375 人黑色素瘤细胞系的抗增殖活性，并研究了替代物对二芳基吡唑支架的影响。药理结果表明，与索拉非尼相比，大多数新合成的化合物对 A375 表现出中等活性。在所有这些衍生物中，具有 N-甲基哌嗪基和酚基部分的化合物 IIe 对 A375 人黑色素瘤细胞系显示出最有效的抗增殖活性。