4-amino-2-<(4-methyl-1-piperazinyl)methyl>phenol trihydrochloride | 86260-80-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-amino-2-<(4-methyl-1-piperazinyl)methyl>phenol trihydrochloride
• 英文别名: 4-amino-2-<(4-methyl-1-piperazinyl)methyl>phenol；4-amino-2-[(4-methyl-1-piperazinyl)methyl]phenol
• CAS: 86260-80-2
• 化学式: C₁₂H₁₉N₃O*ClH
• 分子量: 257.763
• InChiKey: MEMKEJMFTBMRAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.14
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.73
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-(4-benzoylphenyl)-N'-<4-hydroxy-6-(trifluoromethyl)-2-pyrimidinyl>guanidine 、 4-amino-2-<(4-methyl-1-piperazinyl)methyl>phenol trihydrochloride 在 三氯氧磷 作用下， 生成 N-(4-Benzoyl-phenyl)-N'-{4-[4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl)-phenylamino]-6-trifluoromethyl-pyrimidin-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

文献信息

• Synthesis and biological evaluation of a novel structural type of serotonin 5-HT3 receptor antagonists
  作者：Ramachandran Venkatesha Perumal、Radhakrishnan Mahesh

  DOI：10.1016/j.bmcl.2006.02.006

  日期：2006.5

  A series of novel 3-substituted quinoxalin-2-carboxamides were designed as per the pharmacophoric requirement for 5-HT(3) receptor antagonists and prepared by microwave irradiation and also by conventional method. The compounds were characterized by spectral data (IR, (1)H NMR, and MS) and the purity was ascertained by microanalysis. The synthesized compounds were evaluated for 5-HT(3) antagonisms

  根据药效学要求，对5-HT（3）受体拮抗剂设计了一系列新型的3-取代的喹喔啉-2-羧酰胺，并通过微波辐射和常规方法制备。通过光谱数据（IR，（1）H NMR和MS）表征化合物，并通过微量分析确定纯度。评价了合成的化合物对5-HT（3）激动剂2-甲基-5-HT的豚鼠回肠纵向肌肉-肠系膜丛制备中的5-HT（3）拮抗作用。在测试化合物中，N- 3-[（4-甲基哌嗪-1-基）甲基] -4-羟基苯基} -3-甲氧基喹喔啉-2-碳氧酰胺4e显示出最有利的5-HT（3）受体拮抗作用。
• Pharmacophore Based Synthesis of 3-Chloroquinoxaline-2-carboxamides as Serotonin3 (5-HT3) Receptor Antagonist
  作者：Radhakrishnan Mahesh、Ramachandran Venkatesha Perumal、Pandi Vijaya Pandi

  DOI：10.1248/bpb.27.1403

  日期：——

  A series of 3-chloroquinoxaline-2-carboxamides were designed and prepared by the condensation of 3-chloro-2-quinoxaloylchloride with appropriate Mannich bases of the p-aminophenol in the microwave environment. The synthesized compounds were evaluated for serotonin3 (5-HT3) receptor antagonistic activities in longitudinal muscle-myenteric plexus (LMMP) preparation from guinea pig ileum against the 5-HT3 agonist, 2-methyl-5-HT. Compound 3g exhibited comparable 5-HT3 antagonistic activity (pA2 6.4) to that of standard antagonist Ondansetron (pA2 6.9), while the other compounds exhibited mild to moderate 5-HT3 antagonistic activities.

  在微波环境下，通过 3-氯-2-喹喔啉盐酸盐与对氨基苯酚的适当曼尼希碱缩合，设计并制备了一系列 3-氯喹喔啉-2-羧酰胺。评估了合成化合物在豚鼠回肠纵肌-肠肌丛（LMMP）制备过程中对 5-HT3 激动剂 2-甲基-5-HT 的 5-羟色胺3（5-HT3）受体拮抗活性。化合物 3g 的 5-HT3 拮抗活性（pA2 6.4）与标准拮抗剂昂丹司琼（pA2 6.9）相当，而其他化合物则表现出轻度至中度的 5-HT3 拮抗活性。
• El-Telbany, Pharmazie, 1980, vol. 35, # 5-6, p. 326 - 327
  作者：El-Telbany

  DOI：——

  日期：——
• N2-1H-Benzimidazol-2-yl-N4-phenyl-2,4-pyrimidinediamines and N2-1H-benzimidazol-2-yl-5,6,7,8-tetrahydro-N4-phenyl-2,4-quinazolinediamines as potential antifilarial agents
  作者：Mario M. Angelo、Daniel Ortwine、Donald F. Worth、Leslie M. Werbel

  DOI：10.1021/jm00363a017

  日期：1983.9

  A series of N2-1H-benzimidazol-2-yl-N4-phenyl-2,4-pyrimidinediamines and N2-1H-benzimidazol-2-yl-5,6,7,8-tetrahydro-N4-phenyl-2,4-quinazolinediamines (XI) was synthesized for antifilarial evaluation. Condensation of the requisite beta-keto ester (VI) with N-cyanoguanidine afforded 2-pyrimidinylcyanamides (VIIa,b) and (5,6,7,8-tetrahydro-4-hydroxy-2-quinazolinyl)cyanamide (VIIc). Reaction of VII with a substituted o-phenylenediamine gave 2-(1H-benzimidazol-2-ylamino)-4-pyrimidinols and 2-[(5,6-dichloro-1H-benzimidazol-2-yl)amino]-5,6,7, 8-tetrahydro-4-quinazolinol (IX). Chlorination with phosphoryl chloride, followed by condensation with the appropriate substituted benzenamine, gave the desired N2-1H-benzimidazol-2-yl-N4-phenyl-2,4-pyrimidinediamines and N2-1H-benzimidazol-2-yl-5,6,7,8-tetrahydro-N4-phenyl-2,4-quinazolinediamines (XI). None of these compounds possessed antifilarial activity against Litomosoides carinii or Brugia pahangi infections in jirds.