methyl 4-amino-6-(p-tolylamino)-1,3,5-triazine-2-carboxylate | 93002-59-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: methyl 4-amino-6-(p-tolylamino)-1,3,5-triazine-2-carboxylate
• 英文别名: 4-Amino-6-p-toluidino-s-triazin-carbonsaeure-(2)-methylester；4-amino-6-(4-methyl-anilino)-[1,3,5]triazine-2-carboxylic acid methyl ester；amino-p-toluidino-[1,3,5]triazine-2-carboxylic acid methyl ester；Amino-p-toluidino-[1,3,5]triazin-2-carbonsaeure-methylester；Methyl 4-amino-6-(4-methylanilino)-1,3,5-triazine-2-carboxylate；methyl 4-amino-6-(4-methylanilino)-1,3,5-triazine-2-carboxylate
• CAS: 93002-59-6
• 化学式: C₁₂H₁₃N₅O₂
• 分子量: 259.268
• InChiKey: FNHFJBIGOBWPED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 4-amino-6-(p-tolylamino)-1,3,5-triazine-2-carboxylate 在 盐酸 作用下， 生成 N2-对甲苯-1,3,5-三嗪-2,4-二胺
  参考文献：
  名称：

  Age-Related Increase of Brain Cyclooxygenase Activity and Dietary Modulation of Oxidative Status

  摘要：

  Several studies have demonstrated that inhibitors of cyclooxygenase (COX) attenuate various neuronal injuries and age-dependent demented conditions. From these findings, we proposed to test the effect of age on COX activity and its. possible suppression by the antiaging action of dietary restriction in the rat brain. The status of reactive oxygen species (ROS) was also assessed to correlate with COX activity to delineate the underlying mechanism of the altered COX activity during aging. These results showed that COX activity significantly increased in 24-month-old rats compared with 6-month-old rats in an ad libitum group. Interestingly, mRNA and protein levels of COX-2 showed little corresponding age-related change. The formation of ROS was found to increase gradually with age in ad libitum fed rats. However, dietary restriction suppressed the increase at the age of 24 months. To substantiate the relationship between ROS and COX activity when the rats were 24 months of age, we conducted in vitro experiments with a C6 glioma cell line. Together, it is concluded that increased COX activity with age is due to the activation of COX catalytic reaction by ROS without increased gene expression of COX-2 and that it is related to the increased pro-oxidant status in aged rats.

  DOI：

  10.1093/gerona/56.10.b426
• 作为产物：
  描述：

  乙烷,三氯氟- 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 27.0h， 生成 methyl 4-amino-6-(p-tolylamino)-1,3,5-triazine-2-carboxylate
  参考文献：
  名称：

  Optimised synthesis of diamino-triazinylmethyl benzoates as inhibitors of Rad6B ubiquitin conjugating enzyme

  摘要：

  DOI：

  10.1016/j.tetlet.2014.10.122

文献信息

• Synthesis and in vitro anticancer evaluation of some 4,6-diamino-1,3,5-triazine-2-carbohydrazides as Rad6 ubiquitin conjugating enzyme inhibitors
  作者：Hend Kothayer、Sebastian M. Spencer、Kaushlendra Tripathi、Andrew D. Westwell、Komaraiah Palle

  DOI：10.1016/j.bmcl.2016.02.085

  日期：2016.4

  abbreviate our compound names as 'new triazines', have been synthesized, based on the previously reported Rad6B-inhibitory diamino-triazinylmethyl benzoate anticancer agents TZ9 and 4-amino-N'-phenyl-6-(arylamino)-1,3,5-triazine-2-carbohydrazides. Synthesis of the target compounds was readily accomplished in two steps from either bis-aryl/aryl biguanides via reaction of phenylhydrazine or hydrazinehydrate

  4-氨基-6-（芳基氨基）-1,3,5-三嗪-2-碳酰肼（3a-e）和N'-苯基-4,6-双（芳基氨基）-1,3,5-三嗪系列为方便读者阅读，我们合成了-2-碳酰肼（6a-e），根据先前报道的Rad6B抑制性二氨基三嗪基甲基苯甲酸酯苯甲酸酯类抗癌剂TZ9和4-氨基合成了我们的化合物名称“新三嗪”。 -N′-苯基-6-（芳基氨基）-1,3,5-三嗪-2-碳酰肼。通过苯肼或肼与关键的4-氨基-6-双（芳基氨基）/（芳基氨基）-1,3,5-三嗪- 2-羧酸盐中间体。评估了这些新的三嗪衍生物抑制Rad6B泛素结合的能力以及针对几种人类癌细胞系的体外抗癌活性：卵巢癌（OV90和A2780），肺部（H1299和A549），乳腺（MCF-7和MDA-MB231） MTS分析检测结肠癌和结肠癌（HT29）细胞。与先前报道的选择性Rad6抑制剂TZ9相比，所有10种新的三嗪均表现出优异的Rad6B抑制活性。
• Design, synthesis and in vitro anticancer evaluation of 4,6-diamino-1,3,5-triazine-2-carbohydrazides and -carboxamides
  作者：Hend Kothayer、Abdalla A. Elshanawani、Mansour E. Abu Kull、Osama I. El-Sabbagh、Malathy P.V. Shekhar、Andrea Brancale、Arwyn T. Jones、Andrew D. Westwell

  DOI：10.1016/j.bmcl.2013.09.087

  日期：2013.12

  Series of substituted 4,6-diamino-1,3,5-triazine-2-carbohydrazides and -carboxamides have been synthesised, based on molecular modelling of candidate structures related to the previously reported Rad6B-inhibitory diamino-triazinylmethyl benzoate anticancer agents TZ8 and TZ9. Synthesis of the target compounds was readily accomplished in two steps from aryl biguanides via reaction of phenylhydrazine or benzylamines with key 4-amino-6-(arylamino)-1,3,5-triazine-2-carboxylate intermediates. These new triazine derivatives were tested for in vitro anticancer activity against the Rad6B expressing human breast cancer cell lines MDA-MB-231 and MCF-7. Active compounds, such as the triazinyl-carbohydrazides 3a-e, were found to exhibit low micromolar IC50 values particularly in the Rad6B-overexpressing MDA-MB-231 cell line. (C) 2013 Elsevier Ltd. All rights reserved.
• Optimised synthesis of diamino-triazinylmethyl benzoates as inhibitors of Rad6B ubiquitin conjugating enzyme
  作者：Hend Kothayer、Matteo Morelli、Ghali Brahemi、Abdalla A. Elshanawani、Mansour E. Abu Kull、Osama I. El-Sabbagh、Malathy P.V. Shekhar、Andrew D. Westwell

  DOI：10.1016/j.tetlet.2014.10.122

  日期：2014.12
• Age-Related Increase of Brain Cyclooxygenase Activity and Dietary Modulation of Oxidative Status
  作者：B. S. Baek、J. W. Kim、J. H. Lee、H. J. Kwon、N. D. Kim、H. S. Kang、M. A. Yoo、B. P. Yu、H. Y. Chung

  DOI：10.1093/gerona/56.10.b426

  日期：2001.10.1

  Several studies have demonstrated that inhibitors of cyclooxygenase (COX) attenuate various neuronal injuries and age-dependent demented conditions. From these findings, we proposed to test the effect of age on COX activity and its. possible suppression by the antiaging action of dietary restriction in the rat brain. The status of reactive oxygen species (ROS) was also assessed to correlate with COX activity to delineate the underlying mechanism of the altered COX activity during aging. These results showed that COX activity significantly increased in 24-month-old rats compared with 6-month-old rats in an ad libitum group. Interestingly, mRNA and protein levels of COX-2 showed little corresponding age-related change. The formation of ROS was found to increase gradually with age in ad libitum fed rats. However, dietary restriction suppressed the increase at the age of 24 months. To substantiate the relationship between ROS and COX activity when the rats were 24 months of age, we conducted in vitro experiments with a C6 glioma cell line. Together, it is concluded that increased COX activity with age is due to the activation of COX catalytic reaction by ROS without increased gene expression of COX-2 and that it is related to the increased pro-oxidant status in aged rats.