N-(3,4-Dichloro-phenyl)-N'-(4-hydroxy-5,6,7,8-tetrahydro-quinazolin-2-yl)-guanidine | 86177-03-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: N-(3,4-Dichloro-phenyl)-N'-(4-hydroxy-5,6,7,8-tetrahydro-quinazolin-2-yl)-guanidine
• CAS: 86177-03-9
• 化学式: C₁₅H₁₅Cl₂N₅O
• 分子量: 352.223
• InChiKey: QMLIAZCOLMUARM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.83
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  93.92
• 氢给体数：
  4.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-(3,4-Dichloro-phenyl)-N'-(4-hydroxy-5,6,7,8-tetrahydro-quinazolin-2-yl)-guanidine 、 5-amino-N,N-diethyl-2-ethoxybenzenemethanamine dihydrochloride 在 sodium hydroxide 、 三氯氧磷 作用下， 生成 1-(3,4-Dichlorophenyl)-2-[4-[3-(diethylaminomethyl)-4-ethoxyanilino]-5,6,7,8-tetrahydroquinazolin-2-yl]guanidine
  参考文献：
  名称：

  Synthesis and antifilarial activity of N-[4-[[4-alkoxy-3-[(dialkylamino)methyl]phenyl]amino]-2-pyrimidinyl]-N'-phenylguanidines

  摘要：

  A series of N-[4-[[4-alkoxy-3-[(dialkylamino)methyl]phenyl]amino]- 2-pyrimidinyl]-N'-phenylguanidines have been synthesized for antifilarial evaluation. Reaction of the appropriate benzenamines with N-cyanoguanidine, followed by condensation of the resultant N-phenylimidodicarbonimidic diamides (V) with ethyl 4,4,4-trifluoro-3-oxobutanoate provided the intermediate N-(4-hydroxy-2-pyrimidinyl)-N'-phenylguanidines VIa. Alternatively, compounds VIa were synthesized by reaction of the requisite beta-keto esters (VII) with N-cyanoguanidine to give the (4-hydroxy-2-pyrimidinyl)cyanamides (VIII), followed by treatment with the desired benzenamines. Chlorination with POCl3 and condensation with the appropriate benzenamines (IX) generated the desired guanidines (X). Antifilarial activity was confined to adult Litomosoides carinii infections, and a structure-activity relationship for this activity is discussed. Lack of activity against L. carinii microfilaria and adult Brugia pahangi infections preclude further work in this area pending evaluation in additional experimental models.

  DOI：

  10.1021/jm00363a010
• 作为产物：
  描述：

  、 3,4-二氯苯胺 在 盐酸 、 乙二醇乙醚 作用下， 以 水 为溶剂， 以52%的产率得到N-(3,4-Dichloro-phenyl)-N'-(4-hydroxy-5,6,7,8-tetrahydro-quinazolin-2-yl)-guanidine
  参考文献：
  名称：

  Synthesis and antifilarial activity of N-[4-[[4-alkoxy-3-[(dialkylamino)methyl]phenyl]amino]-2-pyrimidinyl]-N'-phenylguanidines

  摘要：

  A series of N-[4-[[4-alkoxy-3-[(dialkylamino)methyl]phenyl]amino]- 2-pyrimidinyl]-N'-phenylguanidines have been synthesized for antifilarial evaluation. Reaction of the appropriate benzenamines with N-cyanoguanidine, followed by condensation of the resultant N-phenylimidodicarbonimidic diamides (V) with ethyl 4,4,4-trifluoro-3-oxobutanoate provided the intermediate N-(4-hydroxy-2-pyrimidinyl)-N'-phenylguanidines VIa. Alternatively, compounds VIa were synthesized by reaction of the requisite beta-keto esters (VII) with N-cyanoguanidine to give the (4-hydroxy-2-pyrimidinyl)cyanamides (VIII), followed by treatment with the desired benzenamines. Chlorination with POCl3 and condensation with the appropriate benzenamines (IX) generated the desired guanidines (X). Antifilarial activity was confined to adult Litomosoides carinii infections, and a structure-activity relationship for this activity is discussed. Lack of activity against L. carinii microfilaria and adult Brugia pahangi infections preclude further work in this area pending evaluation in additional experimental models.

  DOI：

  10.1021/jm00363a010