N-(4-amino-2,6-dioxo-1,3-dipropylpyrimidin-5-yl)tricyclo[3.3.1.03,7]nonane-3-carboxamide | 136199-22-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(4-amino-2,6-dioxo-1,3-dipropylpyrimidin-5-yl)tricyclo[3.3.1.03,7]nonane-3-carboxamide
• CAS: 136199-22-9
• 化学式: C₂₀H₃₀N₄O₃
• 分子量: 374.483
• InChiKey: FBCJZBZQGOZHEJ-UHFFFAOYSA-N

物化性质

• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  95.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-amino-2,6-dioxo-1,3-dipropylpyrimidin-5-yl)tricyclo[3.3.1.03,7]nonane-3-carboxamide 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 10.0h， 生成 KW-3902; HMR-4902; 1,3-二丙基-8-(3-正金刚烷基)黄嘌呤
  参考文献：
  名称：

  8-Polycycloalkyl-1,3-dipropylxanthines as potent and selective antagonists for A1-adenosine receptors

  摘要：

  With the aim of characterizing the hydrophobic interactions between xanthines and the A1 receptor site, 1,3-dipropyl-8-substituted xanthines were synthesized. Introduction of a quaternary carbon and the conformationally restricted cyclopentyl moiety into the 8-position of xanthines enhanced the adenosine A1 antagonism. 1,3-Dipropyl-8-(3-noradamantyl)xanthine (42) was identified to be a selective and the most potent A1 receptor antagonist reported to date. Under our structure-activity relationship, the 8-substituent of xanthine antagonists and the N6-substituent of adenosine agonists appears to bind to the same region of the A1 receptor.

  DOI：

  10.1021/jm00083a018
• 作为产物：
  描述：

  5,6-二氨基-1,3-二丙基嘧啶-2,4(1H,3H)-二酮 、 3-降金刚烷碳酰氯 在 吡啶 作用下， 反应 1.0h， 生成 N-(4-amino-2,6-dioxo-1,3-dipropylpyrimidin-5-yl)tricyclo[3.3.1.03,7]nonane-3-carboxamide
  参考文献：
  名称：

  8-Polycycloalkyl-1,3-dipropylxanthines as potent and selective antagonists for A1-adenosine receptors

  摘要：

  With the aim of characterizing the hydrophobic interactions between xanthines and the A1 receptor site, 1,3-dipropyl-8-substituted xanthines were synthesized. Introduction of a quaternary carbon and the conformationally restricted cyclopentyl moiety into the 8-position of xanthines enhanced the adenosine A1 antagonism. 1,3-Dipropyl-8-(3-noradamantyl)xanthine (42) was identified to be a selective and the most potent A1 receptor antagonist reported to date. Under our structure-activity relationship, the 8-substituent of xanthine antagonists and the N6-substituent of adenosine agonists appears to bind to the same region of the A1 receptor.

  DOI：

  10.1021/jm00083a018

文献信息

• Xanthine compounds
  申请人：KYOWA HAKKO KOGYO CO., LTD.

  公开号：EP0415456A2

  公开（公告）日：1991-03-06

  Novel xanthine compounds represented by the following formula: wherein each of R¹, R² and R³ independently represents a hydrogen atom or a lower alkyl group; each of X¹ and X² independently represents an oxygen or sulfur atom; represents a single bond or a double bond; Y represents a single bond or an alkylene group, n represents 0 or 1, each of W¹ and W² independently represents a hydrogen atom, a lower alkyl or amino group, Z represents -CH₂-, -O-, -S- or -NH-residues; provided that when Q is then R¹, R² and R³ are not simultaneously methyl; and physiologically acceptable salts thereof have a diuretic effect, a renal-protecting effect and/or a bronchodilatory effect. The compounds are useful as a diuretic, a renal-­protecting agent and /or bronchodilator.

  由下式代表的新型黄嘌呤化合物： 其中 R¹、R² 和 R³ 各自独立地代表氢原子或低级烷基； X¹和X²各自独立地代表氧原子或硫原子； 代表单键或双键； Y代表单键或亚烷基，n代表0或1，W¹和W²各自独立地代表氢原子、低级烷基或氨基，Z代表-CH₂-、-O-、-S-或-NH-残基；条件是当Q是 则 R¹、R² 和 R³ 不同时为甲基；其生理上可接受的盐类具有利尿作用、肾保护作用和/或支气管扩张作用。 这些化合物可用作利尿剂、肾保护剂和/或支气管扩张剂。
• PROCESS FOR PRODUCING XANTHINE DERIVATIVE
  申请人：KYOWA HAKKO KOGYO CO., LTD.

  公开号：EP0711772A1

  公开（公告）日：1996-05-15

  The present invention relates to a process for producing a xanthine derivative represented by formula (II), comprising converting a xanthine derivative represented by formula (I) hereinafter, referred to as Compound (I)}: (wherein R¹ and R² independently represent hydrogen, or hydroxy-substituted, oxo-substituted, or unsubstituted lower alkyl) into a xanthine derivative represented by formula (II) hereinafter, referred to as Compound (II)}: (wherein R³ and R⁴ independently represent hydrogen, or hydroxy-substituted, oxo-substituted, or unsubstituted lower alkyl; R⁵ and R⁶ independently represent hydrogen, hydroxy, or oxo; with the proviso that R⁵ and R⁶ are both hydrogen, at least one of R³ and R⁴ is hydroxy-substituted or oxo-substituted lower alkyl; and X and Y both represent hydrogen or are combined with each other to form a single bond) in the presence of an enzyme source for catalyzing hydroxylation or carbonylation of Compound (I) into Compound (II), and collecting the produced Compound (II).

  本发明涉及一种生产式（II）代表的黄嘌呤衍生物的工艺，包括将式（I）代表的黄嘌呤衍生物以下简称化合物（I）}进行转化： (其中R¹和R²独立地代表氢，或羟基取代的、氧代取代的或未取代的低级烷基）转化为式（II）代表的黄嘌呤衍生物以下简称化合物（II）}： (其中 R³ 和 R⁴ 独立地代表氢，或羟基取代、氧代取代或未取代的低级烷基；R⁵ 和 R⁶ 独立地代表氢、羟基或氧代；但 R⁵ 和 R⁶ 都是氢，R³ 和 R⁴ 中至少有一个是羟基取代或氧代取代的低级烷基；以及 X 和 Y 均代表氢或彼此结合形成单键），在酶源存在下催化化合物 (I) 的羟基化或羰基化转化为化合物 (II)，并收集生成的化合物 (II)。
• US5290782A
  申请人：——

  公开号：US5290782A

  公开（公告）日：1994-03-01
• US5525607A
  申请人：——

  公开号：US5525607A

  公开（公告）日：1996-06-11
• US6107064A
  申请人：——

  公开号：US6107064A

  公开（公告）日：2000-08-22