3,5-bis(N-pyrrolidinylmethyl)-4-hydroxyaniline | 85236-51-7

• 物质功能分类: 有机原料 - 杂环化合物
• 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: 3,5-bis(N-pyrrolidinylmethyl)-4-hydroxyaniline
• 英文别名: 2,6-bis<(N-pyrrolidinyl)methyl>-4-aminophenol；4-amino-2,6-bis(pyrrolidin-1'-ylmethyl)phenol；2,6-bis-(1-pyrrolidinomethyl)-4-aminophenol；4-Amino-2,6-bis(pyrrolidin-1-ylmethyl)phenol
• CAS: 85236-51-7
• 化学式: C₁₆H₂₅N₃O
• 分子量: 275.394
• InChiKey: ZCVLBPMYDFQUBD-UHFFFAOYSA-N

物化性质

• 熔点：
  218-219 °C
• 沸点：
  429.3±45.0 °C(Predicted)
• 密度：
  1.210±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  52.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-bis(N-pyrrolidinylmethyl)-4-hydroxyaniline 生成 N-[4-hydroxy-3,5-bis(pyrrolidin-1-ylmethyl)phenyl]-2-(trifluoromethyl)benzamide;dihydrochloride
  参考文献：
  名称：

  STOUT, D. M.;MATIER, W. L.

  摘要：

  DOI：
• 作为产物：
  描述：

  对乙酰氨基酚 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 3,5-bis(N-pyrrolidinylmethyl)-4-hydroxyaniline
  参考文献：
  名称：

  Synthesis and antiarrhythmic and parasympatholytic properties of substituted phenols. 1. Heteroarylamine derivatives

  摘要：

  Twenty-four structural derivatives of the antiarrhythmic drug changrolin were synthesized and tested for antiarrhythmic and parasympatholytic activities. It was found that while the bis(pyrrolidinylmethyl)phenol pattern of changrolin appeared to be optimal in this series, a wide latitude existed for the heteroaryl substituent for maintaining good antiarrhythmic activity. Further, the antiarrhythmic and parasympatholytic activities tended to exhibit parallel changes.

  DOI：

  10.1021/jm00360a005

文献信息

• Potential Antimalarials. IX. Di-mannich Bases of 4-(7′-trifluoro-methylquinazolin-4′-ylamino)phenol and 4-(7′-Trifluoromethylquinolin-4′-ylamino)phenol
  作者：GB Barlin、C Jiravinyu

  DOI：10.1071/ch9900311

  日期：——

  Syntheses are reported for a series of di-Mannich bases of 4-(7′-trifluoromethylquinazolin-4′-ylamino)phenol derived from 4-chloro-7-trifluoromethylquinazoline with the di-Mannich bases of 4-aminophenol. Some analogous quinolines were prepared similarly. When tested for antimalarial activity against Plasmodium falciparum in vitro, the quinazolines were rather less active than the corresponding quinolines.

  报告了一系列 4-(7′-三氟甲基喹唑啉-4′-基氨基)苯酚二曼尼希碱的合成，这些苯酚二曼尼希碱来自 4-氯-7-三氟甲基喹唑啉和 4-氨基苯酚的二曼尼希碱。一些类似的喹啉类化合物也是用类似方法制备的。在对恶性疟原虫进行体外抗疟活性测试时，这些喹唑啉类化合物的活性比相应的喹啉类化合物低。
• Phthalazine compounds, compositions and use
  申请人：American Hospital Supply Corporation

  公开号：US04466965A1

  公开（公告）日：1984-08-21

  The present invention relates to new compounds of the formula ##STR1## alkylene, or --S-- where R.sub.1 is hydrogen, alkyl, or aryl; W is hydrogen, hydroxy, amino, alkyloxy, aryloxy, O-alkyl, or O-aralkyl; (Y).sub.A is --CH.sub.2 NR.sub.2 R.sub.3 where R.sub.2 and R.sub.3 may be hydrogen, substituted alkyls, aryls, or together with N form a 5 to 7 membered heterocyclic group; and Ar is a substituted or unsubstituted heteroaryl. These compounds are useful in the treatment of various cardiac arrhythmias.

  本发明涉及新化合物，其化学式为##STR1##其中R.sub.1为氢、烷基或芳基；W为氢、羟基、氨基、烷氧基、芳氧基、O-烷基或O-芳基；(Y).sub.A为--CH.sub.2 NR.sub.2 R.sub.3，其中R.sub.2和R.sub.3可以是氢、取代烷基、芳基，或与N一起形成5到7元杂环基；Ar为取代或未取代的杂芳基。这些化合物在治疗各种心律失常中有用。
• N-substituted benzyl or phenyl aromatic sulfamides compounds and the use thereof
  申请人：Shanghai Institute of Materia Medica Chinese Academy of Science

  公开号：US06605635B1

  公开（公告）日：2003-08-12

  N-(3,5-bis-disubstituted aminomethyl-4-hydroxy)benzyl aromatic sulfonamides and N-(3,5-bis-disubstituted aminomethyl-4-hydroxy)phenyl aromatic sulfonamides compounds in accordance with the animal test, are active in the prevention and the treatment of cardiac arrhythmia. These compounds are prepared as corresponding diamines by the condensation of optionally substituted aromatic sulfochlorides with p-hydroxybenzylamine, p-aminophenol, or the like, which followed by the Mannich reaction of the resulted corresponding aromatic sulfamides with formaldehyde and secondary amines; or directly obtained by the reaction of the aromatic sulfamides with 4-amino-2,6-bis-disubstituted aminomethylphenol. Subsequently, the diamines are reacted with various acids to provide their salts.

  根据动物测试，N-(3,5-双取代氨甲基-4-羟基)苯甲醇磺酰胺和N-(3,5-双取代氨甲基-4-羟基)苯基磺酰胺化合物在预防和治疗心律失常方面具有活性。这些化合物通过选择性取代的芳香基磺酰氯与对羟基苯甲胺、对氨基苯酚等缩合生成相应的二胺，然后将所得的芳香基磺酰胺与甲醛和二级胺进行Mannich反应制备；或直接与4-氨基-2,6-双取代氨甲基苯酚反应得到。随后，这些二胺与不同的酸反应形成它们的盐。
• Heteroaryl substituted aminomethyl benzene derivatives, compositions and use
  申请人：THE DU PONT MERCK PHARMACEUTICAL COMPANY

  公开号：EP0310155A1

  公开（公告）日：1989-04-05

  New compounds of the formula (I) where X is straight-chained alkylene, or -S- wherein R1 is hydrogen, aryl, or lower alkyl; W is hydrogen, hydroxy, amino, , 0-alkyl, alkylsulfonamide or O-aralkyl; (Y)A is positioned ortho to W and is an aminoalkyl having the formula -CH2NR2R3, wherein R2 and R3 are the same or different and may be hydrogen, lower alkyl, hydroxyalkyl, cycloalkyl, alkoxyalkyl, alkoxyaryl, aryl, heteroaryl, or R2 and R3 may together with N form a 5 to 7 membered heterocyclic group optionally including oxygen, nitrogen, or sulfur as a second hetero-atom, and A is 1 or 2; N and M are independently from O to about 5; and Ar is a substituted or unsubstituted pyridine optionally fused with one or more heteroaryls and pharmaceutically acceptable salts of such compounds are useful in the treatment of various cardiac arrhythmias.

  式 (I) 的新化合物 其中 X 是 直链亚烷基，或 -S- 其中 R1 是氢、芳基或低级烷基；W 是氢、羟基、氨基、 其中 R2 和 R3 相同或不同，可以是氢、低级烷基、羟基烷基、环烷基、烷氧基烷基、烷氧基芳基、芳基、杂芳基，或 R2 和 R3 可与 N 一起形成 5 至 7 个成员的杂环基团，任选包括氧、氮或硫作为第二个杂原子，且 A 为 1 或 2；N 和 M 独立地从 O 到约 5；Ar 是取代或未取代的吡啶，可选与一个或多个杂芳基融合，此类化合物的药学上可接受的盐类可用于治疗各种心律失常。
• N-SUBSTITUTED BENZYL OR PHENYL AROMATIC SULFAMIDES COMPOUNDS AND THE USE THEREOF
  申请人：SHANGHAI INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF SCIENCES

  公开号：EP1245561A1

  公开（公告）日：2002-10-02

  N-(3,5-bis-disubstituted aminomethyl-4-hydroxy)benzyl aromatic sulfonamides and N-(3,5-bis-disubstituted aminomethyl-4-hydroxy)phenyl aromatic sulfonamides compounds in accordance with the animal test, are active in the prevention and the treatment of cardiac arrhythmia. These compounds are prepared as corresponding diamines by the condensation of optionally substituted aromatic sulfochlorides with p-hydroxybenzylamine, p-aminophenol, or the like, which followed by the Mannich reaction of the resulted corresponding aromatic sulfamides with formaldehyde and secondary amines; or directly obtained by the reaction of the aromatic sulfamides with 4-amino-2,6-bis-disubstituted aminomethylphenol. Subsequently, the diamines are reacted with various acids to provide their salts.

  根据动物试验，N-(3,5-二取代氨甲基-4-羟基)苄基芳香族磺酰胺和 N-(3,5-二取代氨甲基-4-羟基)苯基芳香族磺酰胺化合物在预防和治疗心律失常方面具有活性。这些化合物是通过任选取代的芳香族磺酰氯与对羟基苄胺、对氨基苯酚或类似物缩合，然后将生成的相应芳香族磺酰胺与甲醛和仲胺进行曼尼希反应制备成相应的二胺；或者直接通过芳香族磺酰胺与 4-氨基-2,6-二取代氨甲基苯酚反应制备成二胺。随后，二胺与各种酸反应生成它们的盐。