1-(3'-chlorophenyl)-2-phenyl-4,6-diamino-1,2-dihydro-1,3,5-triazine hydrochloride | 1931-13-1

• 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: 1-(3'-chlorophenyl)-2-phenyl-4,6-diamino-1,2-dihydro-1,3,5-triazine hydrochloride
• 英文别名: 1-(3-chlorophenyl)-2-phenyl-2H-1,3,5-triazine-4,6-diamine;hydrochloride
• CAS: 1931-13-1
• 化学式: C₁₅H₁₄ClN₅*ClH
• 分子量: 336.224
• InChiKey: SQEPHEIDBIBQJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.08
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  79.4
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(3'-chlorophenyl)-2-phenyl-4,6-diamino-1,2-dihydro-1,3,5-triazine hydrochloride 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 以2.1 g的产率得到N²-(3-chlorophenyl)-6-phenyl-5,6-dihydro-1,3,5-triazine-2,4-diamine
  参考文献：
  名称：

  一锅法合成 N2,6-diaryl-5,6-dihydro-1,3,5-triazine-2,4-diamines 并系统评估它们在晶体中承载乙醇的能力†

  摘要：

  使用 1,6-二芳基的三组分合成开发了一种方便的一锅法制备N 2 ,6-二芳基-5,6-二氢-1,3,5-三嗪-2,4-二胺-1,6-dihydro-1,3,5-triazine-2,4-diamines，然后将它们的 Dimroth 重排为所需的产物。制备的化合物以乙醇包合物(1:1)的形式从乙醇中结晶出来。几种产品的 X 射线晶体学证实采用了 5,6-二氢互变异构体。对选定化合物的热分析和粉末 X 射线衍射实验表明，晶体的热去溶剂化是不可逆的。

  DOI：

  10.1039/c9ra08795h
• 作为产物：
  描述：

  苯甲醛 、 二聚氰胺 、 3-氯苯胺 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 1-(3'-chlorophenyl)-2-phenyl-4,6-diamino-1,2-dihydro-1,3,5-triazine hydrochloride
  参考文献：
  名称：

  一锅法合成 N2,6-diaryl-5,6-dihydro-1,3,5-triazine-2,4-diamines 并系统评估它们在晶体中承载乙醇的能力†

  摘要：

  使用 1,6-二芳基的三组分合成开发了一种方便的一锅法制备N 2 ,6-二芳基-5,6-二氢-1,3,5-三嗪-2,4-二胺-1,6-dihydro-1,3,5-triazine-2,4-diamines，然后将它们的 Dimroth 重排为所需的产物。制备的化合物以乙醇包合物(1:1)的形式从乙醇中结晶出来。几种产品的 X 射线晶体学证实采用了 5,6-二氢互变异构体。对选定化合物的热分析和粉末 X 射线衍射实验表明，晶体的热去溶剂化是不可逆的。

  DOI：

  10.1039/c9ra08795h

文献信息

• Dihydrofolate reductase inhibitors
  申请人：——

  公开号：US20030203908A1

  公开（公告）日：2003-10-30

  A compound of formula (I) or (II), wherein X is hydrogen, halogen, alkyl, aralkyl,aryloxy, arylalkoxy or alkoxy, Y is hydrogen, halogen, alkyl, aralkyl, aryloxy, arylalkoxy or alkoxy, or formula (a) wherein A and B are different and one of A and B is CH 2 and the other is O, NH, or S or A and B are both CH 2 or CH═, and R a , R b , and R c are the same or different and are hydrogen, halogen, alkyl, alkoxy, aryloxy, aralkyl or arylalkoxy. R 1 is hydrogen, and R 2 is hydrogen, C 1 -C 6 alkyl or aryl which is unsubstituted or substituted by halogen, cyano, hydroxy, C 1 -C 6 alkyl, which is unsubstituted or substituted by halogen, cyano, hydroxy, C 1 -C 6 alkoxy, aralkyl, aryloxy or aryl, C 1 -C 6 alkoxy, aralkyl, arylalkoxy, aryloxy or aryl, which is unsubstituted or substituted by halogen, cyano, hydroxy, C 1 -C 6 alkyl or C 1 -C 6 alkoxy; and pharmaceutically acceptable salts thereof; with the proviso that when R 2 is phenyl and Y is hydrogen, X is not chlorine. 1

  化合物的化学式(I)或(II)，其中X为氢、卤素、烷基、芳基烷基、芳氧基、芳基烷氧基或烷氧基，Y为氢、卤素、烷基、芳基烷基、芳氧基、芳基烷氧基或烷氧基，或者化学式(a)中A和B不同，A和B中之一为CH2，另一个为O、NH或S，或者A和B都为 或CH═，而Ra、Rb和Rc相同或不同，分别为氢、卤素、烷基、烷氧基、芳氧基、芳基烷基或芳基烷氧基。R1为氢，R2为氢、C1-C6烷基或芳基，未被卤素、氰基、羟基、C1-C6烷基（未被卤素、氰基、羟基、C1-C6烷氧基、芳基烷基、芳氧基或芳基取代）取代或取代的烷基、芳基烷基、芳基烷氧基、芳氧基或芳基，未被卤素、氰基、羟基、C1-C6烷基或C1-C6烷氧基取代或取代的烷基、芳基烷基、芳基烷氧基、芳氧基或芳基；以及其药学上可接受的盐；但当R2为苯基且Y为氢时，X不为氯。
• Development of a Lead Inhibitor for the A16V+S108T Mutant of Dihydrofolate Reductase from the Cycloguanil-Resistant Strain (T9/94) of <i>Plasmodium falciparum</i>^†
  作者：Yongyuth Yuthavong、Tirayut Vilaivan、Netnapa Chareonsethakul、Sumalee Kamchonwongpaisan、Worachart Sirawaraporn、Rachel Quarrell、Gordon Lowe

  DOI：10.1021/jm0009181

  日期：2000.7.1

  The Ala16Val+Ser108Thr (A16V+S108T) mutant of the Plasmodium falciparum dihydrofolate reductase (DHFR) is a key mutant responsible for cycloguanil-resistant malaria due to steric interaction between Val-16 and one of the C-2 methyl groups of cycloguanil. 4,6-Diamino-1,2-dihydrotriazines have been prepared, in which both methyl groups of cycloguanil are replaced by H or by H and an alkyl or phenyl group, and their inhibition constants against wild-type and mutant DHFR determined. The S108T mutation is considered to decrease cycloguanil binding further through the effect on the orientation of the p-chlorophenyl group. By moving the p-chloro-substituent to the m-position in the chlorophenyl group, the activity against the A16V+S108T mutant enzyme is improved, and this effect is reinforced by the p-chloro substituent in the 3,4-dichlorophenyl group. A lead compound has been found with inhibitory activity similar to that of cycloguanil against the wild-type DHFR and about 120-fold more effective than cycloguanil against the A16V+S108T mutant enzyme. The activity of this compound against P. falciparum clone (T9/94 RC17) which harbors the A16V+S108T DHFR is about 85-fold greater than cycloguanil.