8-<4-<<<<4-(carboxymethyl)anilino>carbonyl>methyl>oxy>phenyl>-1,3-diethylxanthine methyl ester | 104576-52-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 8-<4-<<<<4-(carboxymethyl)anilino>carbonyl>methyl>oxy>phenyl>-1,3-diethylxanthine methyl ester
• 英文别名: 8-[4-[[[[(4-Carboxymethyl)anilino]carbonyl]methyl]oxy]-phenyl]-1,3-diethylxanthine Methyl Ester；(4-{2-[4-(1,3-Diethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)-phenoxy]-acetylamino}-phenyl)-acetic acid methyl ester；methyl 2-[4-[[2-[4-(1,3-diethyl-2,6-dioxo-7H-purin-8-yl)phenoxy]acetyl]amino]phenyl]acetate
• CAS: 104576-52-5
• 化学式: C₂₆H₂₇N₅O₆
• 分子量: 505.53
• InChiKey: IBIUZSLPYZDABK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  134
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  8-<4-<<<<4-(carboxymethyl)anilino>carbonyl>methyl>oxy>phenyl>-1,3-diethylxanthine methyl ester 、 乙二胺 以77%的产率得到N-{4-[(2-Amino-ethylcarbamoyl)-methyl]-phenyl}-2-[4-(1,3-diethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)-phenoxy]-acetamide
  参考文献：
  名称：

  Xanthine functionalized congeners as potent ligands at A2-adenosine receptors

  摘要：

  Amide derivatives of a carboxylic acid congener of 1,3-dialkylxanthine, having a 4-[(carboxymethyl)oxy]phenyl substituent at the 8-position, have been synthesized in order to identify potent antagonists at A2-adenosine receptors stimulatory to adenylate cyclase in platelets. Distal structural features of amide-linked chains and the size of the 1,3-dialkyl groups have been varied. 1,3-Diethyl groups, more than 1,3-dimethyl or 1,3-dipropyl groups, favor A2 potency, even in the presence of extended chains attached at the 8-(p-substituted-phenyl) position. Polar groups, such as amines, on the chain simultaneously enhance water solubility and A2 potency. Among the most potent A2 ligands are an amine congener, 8-[4-[[[[(2-aminoethyl)amino]carbonyl]methyl]oxy]phenyl]- 1,3-diethylxanthine, and its D-lysyl conjugate, which have KB values of 21 and 23 nM, respectively, for the antagonism of N-ethyl-adenosine-5'-uronamide-stimulated adenylate cyclase activity in human platelet membranes. Strategies for the selection and tritiation of new radioligands for use in competitive binding assays at A2-adenosine receptors have been considered.

  DOI：

  10.1021/jm00384a037
• 作为产物：
  描述：

  (4-氨基-苯基)-乙酸 甲酯 盐酸盐 、 2-[4-(1,3-diethyl-2,6-dioxo-7H-purin-8-yl)phenoxy]acetic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以92%的产率得到8-<4-<<<<4-(carboxymethyl)anilino>carbonyl>methyl>oxy>phenyl>-1,3-diethylxanthine methyl ester
  参考文献：
  名称：

  Xanthine functionalized congeners as potent ligands at A2-adenosine receptors

  摘要：

  Amide derivatives of a carboxylic acid congener of 1,3-dialkylxanthine, having a 4-[(carboxymethyl)oxy]phenyl substituent at the 8-position, have been synthesized in order to identify potent antagonists at A2-adenosine receptors stimulatory to adenylate cyclase in platelets. Distal structural features of amide-linked chains and the size of the 1,3-dialkyl groups have been varied. 1,3-Diethyl groups, more than 1,3-dimethyl or 1,3-dipropyl groups, favor A2 potency, even in the presence of extended chains attached at the 8-(p-substituted-phenyl) position. Polar groups, such as amines, on the chain simultaneously enhance water solubility and A2 potency. Among the most potent A2 ligands are an amine congener, 8-[4-[[[[(2-aminoethyl)amino]carbonyl]methyl]oxy]phenyl]- 1,3-diethylxanthine, and its D-lysyl conjugate, which have KB values of 21 and 23 nM, respectively, for the antagonism of N-ethyl-adenosine-5'-uronamide-stimulated adenylate cyclase activity in human platelet membranes. Strategies for the selection and tritiation of new radioligands for use in competitive binding assays at A2-adenosine receptors have been considered.

  DOI：

  10.1021/jm00384a037

文献信息

• US4968672A
  申请人：——

  公开号：US4968672A

  公开（公告）日：1990-11-06
• Xanthine functionalized congeners as potent ligands at A2-adenosine receptors
  作者：Kenneth A. Jacobson、Dieter Ukena、William Padgett、John W. Daly、Kenneth L. Kirk

  DOI：10.1021/jm00384a037

  日期：1987.1

  Amide derivatives of a carboxylic acid congener of 1,3-dialkylxanthine, having a 4-[(carboxymethyl)oxy]phenyl substituent at the 8-position, have been synthesized in order to identify potent antagonists at A2-adenosine receptors stimulatory to adenylate cyclase in platelets. Distal structural features of amide-linked chains and the size of the 1,3-dialkyl groups have been varied. 1,3-Diethyl groups, more than 1,3-dimethyl or 1,3-dipropyl groups, favor A2 potency, even in the presence of extended chains attached at the 8-(p-substituted-phenyl) position. Polar groups, such as amines, on the chain simultaneously enhance water solubility and A2 potency. Among the most potent A2 ligands are an amine congener, 8-[4-[[[[(2-aminoethyl)amino]carbonyl]methyl]oxy]phenyl]- 1,3-diethylxanthine, and its D-lysyl conjugate, which have KB values of 21 and 23 nM, respectively, for the antagonism of N-ethyl-adenosine-5'-uronamide-stimulated adenylate cyclase activity in human platelet membranes. Strategies for the selection and tritiation of new radioligands for use in competitive binding assays at A2-adenosine receptors have been considered.