4-(2-hydroxy-ethyl)-2-(4-chlorophenyl)-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one | 501675-34-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(2-hydroxy-ethyl)-2-(4-chlorophenyl)-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one
• 英文别名: 4-(2-hydroxyethyl)-5-methyl-2-(4-chlorophenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one；2-(4-Chlorophenyl)-4-(2-hydroxyethyl)-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one；2-(4-chlorophenyl)-4-(2-hydroxyethyl)-5-methyl-1,2,4-triazol-3-one
• CAS: 501675-34-9
• 化学式: C₁₁H₁₂ClN₃O₂
• 分子量: 253.688
• InChiKey: WHYWIJROTDEAPX-UHFFFAOYSA-N

物化性质

• 熔点：
  120-122 °C(Solv: ethanol (64-17-5))
• 沸点：
  389.2±52.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  56.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2-hydroxy-ethyl)-2-(4-chlorophenyl)-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one 在 potassium carbonate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-(2-(4-chlorophenoxy)ethyl)-2-(4-chlorophenyl)-5-methyl-2H-1,2,4-triazol-3(4H)-one
  参考文献：
  名称：

  Synthesis, characterization and in vitro anticancer evaluation of novel 1,2,4-triazolin-3-one derivatives

  摘要：

  A series of novel 2-(4-chlorophenyl)-5-methyl-4-(2-amine/oxy-ethyl)-2,4-dihydro-[1,2,4]triazol-3-one (5a-t) were synthesized and in vitro anticancerous action of the resulting compounds was studied against NCI-60 Human Tumor Cell Line at a single high dose (10(-5) M) concentration for primary cytotoxicity assay. Among the tested compounds (5a-e, 5g-h, 5k, 5p), the compound 5g (NSC: 761736/1) was further evaluated for five dose criteria at five different minimal concentrations against the full panel of 60 human tumor cell lines which exhibited activity against Leukemia (GI(50): 1.10 mu M), Non-Small Cell Lung Cancer (GI(50): 1.00 mu M), Renal Cancer (GI(50): 1.00 mu M), Colon Cancer (GI(50): 1.66 mu M), CNS Cancer (GI(50): 1.36 mu M), Melanoma (GI(50): 1.82 mu M), Ovarian Cancer (GI(50): 1.64 mu M) and Breast Cancer (GI(50): 1.69 mu M). (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.004
• 作为产物：
  描述：

  3-(4-氯苯基)-1,2,3-氧杂二氮唑-3-鎓-5-酸内盐 在 溴 作用下， 生成 4-(2-hydroxy-ethyl)-2-(4-chlorophenyl)-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one
  参考文献：
  名称：

  Synthesis, characterization and in vitro anticancer evaluation of novel 1,2,4-triazolin-3-one derivatives

  摘要：

  A series of novel 2-(4-chlorophenyl)-5-methyl-4-(2-amine/oxy-ethyl)-2,4-dihydro-[1,2,4]triazol-3-one (5a-t) were synthesized and in vitro anticancerous action of the resulting compounds was studied against NCI-60 Human Tumor Cell Line at a single high dose (10(-5) M) concentration for primary cytotoxicity assay. Among the tested compounds (5a-e, 5g-h, 5k, 5p), the compound 5g (NSC: 761736/1) was further evaluated for five dose criteria at five different minimal concentrations against the full panel of 60 human tumor cell lines which exhibited activity against Leukemia (GI(50): 1.10 mu M), Non-Small Cell Lung Cancer (GI(50): 1.00 mu M), Renal Cancer (GI(50): 1.00 mu M), Colon Cancer (GI(50): 1.66 mu M), CNS Cancer (GI(50): 1.36 mu M), Melanoma (GI(50): 1.82 mu M), Ovarian Cancer (GI(50): 1.64 mu M) and Breast Cancer (GI(50): 1.69 mu M). (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.004

文献信息

• A simple and efficient synthesis of novel N,N′-bis (1H-pyrrol-1-yl)-1-[2-(2-aryl-5-methyl-3-oxo-2,4-dihydro-3H-1,2,4-triazol-4-yl)ethyl]-1H-1,2,3-triazole-4,5-dicarboxamides
  作者：Prashant R. Latthe、Vinay A. Sunagar、Bharati V. Badami

  DOI：10.1002/jhet.5570440620

  日期：2007.11

  thyl-2,4-dihydro-3H-1,2,4-triazolin-3-ones 2a-g which were converted to the azido compounds 6a-g. These azides on 1,3-dipolar cycloaddition with DMAD afforded the dimethyl-1-[2-(2-aryl-5-methyl-3-oxo-1,2,4-triazol-4-yl)ethyl]-1H-1,2,3-triazol-4,5-dicarboxylates 7a-g which on conversion to bishydrazides 8a-g and further cyclisation with 2,5-hexanedione afforded the title compounds 9a-g. This new short

  3-芳基-5-甲基-1,3,4-恶二唑啉-2-酮1a-g与乙醇胺的一锅反应生成4-（2-羟乙基）-2-芳基-5-甲基-2,4 -二氢-3 H -1,2,4-三唑啉-3-酮2a-g，其被转化为叠氮基化合物6a-g。这些叠氮化物与DMAD在1，3-偶极环加成上得到二甲基-1- [2-（2-芳基-5-甲基-3-氧代-1,2,4-三唑-4-基）乙基] -1 H -1,2,3-三唑-4,5-二羧酸酯7a-g，将其转化为二酰肼8a-g，并进一步用2,5-己二酮环化，得到标题化合物9a-g。迄今为止尚不为人知的双-（三唑啉酮-三唑）乙烷的新的短路线涉及温和且收敛的1，3-偶极环加成反应，产生了总体上良好的产物收率。