2-(4-Chloro-2-methyl-phenylamino)-6-trifluoromethyl-nicotinic acid | 741265-22-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-(4-Chloro-2-methyl-phenylamino)-6-trifluoromethyl-nicotinic acid
• CAS: 741265-22-5
• 化学式: C₁₄H₁₀ClF₃N₂O₂
• 分子量: 330.694
• InChiKey: LIVNBSBLAOKUFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  62.22
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3,4-二甲氧基苯胺 、 2-(4-Chloro-2-methyl-phenylamino)-6-trifluoromethyl-nicotinic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙腈 为溶剂， 反应 24.5h， 以86%的产率得到2-((4-chloro-2-methylphenyl)amino)-N-(3,4-dimethoxyphenyl)-6-(trifluoromethyl)nicotinamide
  参考文献：
  名称：

  2-芳基氨基-6-三氟甲基-3-吡啶羧酸的酯和酰胺衍生物的合成和抗肿瘤活性评估。

  摘要：

  描述了2-芳基氨基-6-三氟甲基-3-吡啶羧酸8-58的酯和酰胺衍生物的合成和抗肿瘤活性。美国国家癌症研究所（NCI）评估了三氟甲基吡啶衍生物8-58对人肿瘤细胞系的抗癌活性。它们中的大多数具有令人鼓舞的抗癌活性，其GI（50）值在低微摩尔至纳摩尔浓度范围内。3,4,5-三甲氧基苯基酰胺44活性最高，目前正由NCI生物评估委员会审查，以进行可能的进一步研究。

  DOI：

  10.1016/j.bmc.2007.11.069
• 作为产物：
  描述：

  4-氯-2-甲基苯胺 在 硫酸 作用下， 以 水 、 乙腈 为溶剂， 反应 108.0h， 生成 2-(4-Chloro-2-methyl-phenylamino)-6-trifluoromethyl-nicotinic acid
  参考文献：
  名称：

  Synthesis of new 2-arylamino-6-trifluoromethylpyridine-3-carboxylic acid derivatives and investigation of their analgesic activity

  摘要：

  A new series of 2-arylamino-6-trifluoromethyl-3-carboxylic acid derivatives was synthesized and assayed in vivo for their analgesic properties by means of writhing test in rats. When compared to aspirin, ibuprofen and flufenamic acid some of the new compounds exhibited a comparable or improved analgesic activity and a lower ulcerogenic effect. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.05.025

文献信息

• Synthesis and evaluation of anticancer activity of 2-arylamino-6-trifluoromethyl-3-(hydrazonocarbonyl)pyridines
  作者：Valentina Onnis、Maria T. Cocco、Roberta Fadda、Cenzo Congiu

  DOI：10.1016/j.bmc.2009.07.066

  日期：2009.9.1

  The synthesis and anticancer activity of 2-arylamino-6-trifluoromethyl-3-(hydrazonocarbonyl)pyridines is described. The new trifluoromethylpyridine derivatives were evaluated for their anticancer activity toward human cancer cell lines by the National Cancer Institute (NCI). Most of them had excellent growth inhibition activity, having GI(50) values in the low micromolar to nanomolar concentration range. The most potent 2,6-dichlorobenzaldehydehydrazone 29 inhibited the growth of all tested cancer cell lines with nanomolar potency, and did not show animal toxicity. Hydrazone 29 has been selected by the Biological Evaluation Committee of NCI for testing in vivo Hollow Fiber Assay. (C) 2009 Elsevier Ltd. All rights reserved.