N-邻甲苯胍盐酸盐 | 6976-05-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-邻甲苯胍盐酸盐
• 英文名称: o-tolyl-guanidine; hydrochloride
• 英文别名: o-Tolyl-guanidin; Hydrochlorid；N-o-tolyl-guanidine hydrochloride；2-(2-methylphenyl)guanidine;hydrochloride
• CAS: 6976-05-2
• 化学式: C₈H₁₁N₃*ClH
• 分子量: 185.656
• InChiKey: RMMCGTVQUBUJFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.72
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  64.4
• 氢给体数：
  3
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-邻甲苯胍盐酸盐 、 (Z)-3-(dimethylamino)-1-(pyridin-2-yl)prop-2-en-1-one 在 potassium carbonate 作用下， 以 乙二醇甲醚 为溶剂， 反应 25.0h， 以55%的产率得到(4-Pyridin-2-yl-pyrimidin-2-yl)-o-tolyl-amine
  参考文献：
  名称：

  Preparation of substituted N-phenyl-4-aryl-2-pyrimidinamines as mediator release inhibitors

  摘要：

  The role of immunologically released mediators, such as histamine, leukotrienes, and platelet-activating factor, is well-established for asthma and other allergic disorders. Developing therapeutic agents which would block mediator release from mast cells and other relevant cell types would provide a rational approach to asthma therapy. Using human basophil as a screen, a series of 4-aryl-2-(phenylamino)pyrimidines was found which inhibited mediator release. These compounds were prepared by condensing acetyl heterocycles with dimethylformamide dimethyl acetal to form enaminones which are cyclized with aryl guanidines to give pyrimidines. After examining a large number of analogs, N-[3-(1H-imidazol-1-yl)phenyl]-4-(2-pyridinyl)-2-pyrimidinamine (1-27) was chosen for toxicological evaluation.

  DOI：

  10.1021/jm00071a002
• 作为产物：
  描述：

  氰胺 、 邻甲苯胺 在 盐酸 作用下， 以 乙醚 、 melt 为溶剂， 以96 %的产率得到N-邻甲苯胍盐酸盐
  参考文献：
  名称：

  二茂铁修饰的伊马替尼和尼罗替尼类似物作为有效的抗癌药物

  摘要：

  二茂铁的独特特性和开发靶向抗癌药物的需求激发了二茂铁基修饰酪氨酸激酶抑制剂的设计、合成和生物学评价，通过用二茂铁基取代伊马替尼和尼洛替尼通用结构中的吡啶基部分。使用伊马替尼作为参考药物，合成了一系列七种新的二茂铁类似物，并在一组 bcr-abl 阳性人类恶性细胞系中评估了它们的抗癌活性。茂金属对恶性细胞生长表现出剂量依赖性抑制作用，并具有不同的抗白血病活性。最有效的类似物是化合物9和15a ，显示出与参考相当甚至更优异的功效。他们的癌症选择性指数显示出良好的选择性特征，表明与正常小鼠相比， 15a对恶性转化的 K-562 细胞的优先活性高出 250 倍，LAMA-84 白血病模型中的9的优先活性甚至高出两倍（500）成纤维细胞系。

  DOI：

  10.1039/d3md00030c

文献信息

• TETRA-AZA-HETEROCYCLES AS PHOSPHATIDYLINOSITOL-3-KINASES (PI3-KINASES) INHIBITOR
  申请人：Boehringer Ingelheim International GmbH

  公开号：EP2350084B1

  公开（公告）日：2015-06-24
• US4324801A
  申请人：——

  公开号：US4324801A

  公开（公告）日：1982-04-13
• Preparation of substituted N-phenyl-4-aryl-2-pyrimidinamines as mediator release inhibitors
  作者：Rolf Paul、William A. Hallett、John W. Hanifin、Marvin F. Reich、Bernard D. Johnson、Robert H. Lenhard、John P. Dusza、Suresh S. Kerwar、Yang I Lin

  DOI：10.1021/jm00071a002

  日期：1993.9

  The role of immunologically released mediators, such as histamine, leukotrienes, and platelet-activating factor, is well-established for asthma and other allergic disorders. Developing therapeutic agents which would block mediator release from mast cells and other relevant cell types would provide a rational approach to asthma therapy. Using human basophil as a screen, a series of 4-aryl-2-(phenylamino)pyrimidines was found which inhibited mediator release. These compounds were prepared by condensing acetyl heterocycles with dimethylformamide dimethyl acetal to form enaminones which are cyclized with aryl guanidines to give pyrimidines. After examining a large number of analogs, N-[3-(1H-imidazol-1-yl)phenyl]-4-(2-pyridinyl)-2-pyrimidinamine (1-27) was chosen for toxicological evaluation.
• Ferrocene modified analogues of imatinib and nilotinib as potent anti-cancer agents
  作者：Irena Philipova、Rositsa Mihaylova、Georgi Momekov、Rostislava Angelova、Georgi Stavrakov

  DOI：10.1039/d3md00030c

  日期：——

  development of targeted anticancer drugs inspired the design, synthesis and biological evaluation of ferrocenyl modified tyrosine kinase inhibitors by replacing the pyridyl moiety in imatinib and nilotinib generalized structures with a ferrocenyl group. A series of seven new ferrocene analogues were synthesized and evaluated for their anticancer activity in a panel of bcr–abl positive human malignant cell

  二茂铁的独特特性和开发靶向抗癌药物的需求激发了二茂铁基修饰酪氨酸激酶抑制剂的设计、合成和生物学评价，通过用二茂铁基取代伊马替尼和尼洛替尼通用结构中的吡啶基部分。使用伊马替尼作为参考药物，合成了一系列七种新的二茂铁类似物，并在一组 bcr-abl 阳性人类恶性细胞系中评估了它们的抗癌活性。茂金属对恶性细胞生长表现出剂量依赖性抑制作用，并具有不同的抗白血病活性。最有效的类似物是化合物9和15a ，显示出与参考相当甚至更优异的功效。他们的癌症选择性指数显示出良好的选择性特征，表明与正常小鼠相比， 15a对恶性转化的 K-562 细胞的优先活性高出 250 倍，LAMA-84 白血病模型中的9的优先活性甚至高出两倍（500）成纤维细胞系。