1-benzyl-3-butylxanthine | 161419-61-0

• 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: 1-benzyl-3-butylxanthine
• 英文别名: 3-Butyl-1-(phenylmethyl)-3,7-dihydro-1H-purine-2,6-dione；1-benzyl-3-butyl-7H-purine-2,6-dione
• CAS: 161419-61-0
• 化学式: C₁₆H₁₈N₄O₂
• 分子量: 298.345
• InChiKey: XHLOBEVLJHFXCR-UHFFFAOYSA-N

物化性质

• 沸点：
  549.9±52.0 °C(Predicted)
• 密度：
  1.286±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  69.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-benzyl-3-butylxanthine 在 N-氯代丁二酰亚胺 作用下， 以 乙腈 为溶剂， 反应 0.17h， 生成 3-butyl-8-chloro-1-(phenylmethyl)-3,7-dihydro-1H-purine-2,6-dione
  参考文献：
  名称：

  WO2007/17265

  摘要：

  公开号：
• 作为产物：
  描述：

  3-butyl-1,7-bis(phenylmethyl)-3,7-dihydro-1H-purine-2,6-dione 在 氢氧化钯 氢气 、 溶剂黄146 作用下， 以 溶剂黄146 为溶剂， 反应 32.0h， 生成 1-benzyl-3-butylxanthine
  参考文献：
  名称：

  XANTHINE DERIVATIVES AS SELECTIVE HM74A AGONISTS

  摘要：

  本发明涉及黄嘌呤衍生物化合物，制造该衍生物的过程，含有活性化合物的药物配方以及化合物在治疗中的应用，例如，在治疗HM74A受体欠活化导致疾病或激活受体将有益的疾病治疗中的应用。

  公开号：

  US20100099690A1

文献信息

• Structure-Activity Relationships of 1,3-Dialkylxanthine Derivatives at Rat A3 Adenosine Receptors
  作者：Hea Ok Kim、Xiao-duo Ji、Neli Melman、Mark E. Olah、Gary L. Stiles、Kenneth A. Jacobson

  DOI：10.1021/jm00046a022

  日期：1994.9

  respectively. A synthetic strategy for introducing multiple carboxylate groups at the 8-position using iminodiacetic acid derivatives was explored. The presence of a sulfonate, a carboxylate, or multiple carboxylate groups did not result in a significant enhancement of affinity at rat A3 receptors, although as previously observed an anionic group tended to diminish potency at A1 and A2a receptors. The rat

  合成了在 8 位取代基上含有羧酸和其他带电基团的 1,3-二烷基黄嘌呤类似物。使用新的放射性配体 [125I]AB-MECA (N6-(4-amino-3-iodobenzyl)adenosine-5'-N-甲基糖醛酰胺），并分别使用 [3H]PIA 和 [3H]CGS 21680 作用于大鼠脑 A1 和 A2a 受体。探索了使用亚氨基二乙酸衍生物在 8 位引入多个羧酸酯基团的合成策略。磺酸盐、羧酸盐或多个羧酸盐基团的存在不会导致对大鼠 A3 受体的亲和力显着增强，尽管如前所述，阴离子基团倾向于降低对 A1 和 A2a 受体的效力。大鼠 A3 受体亲和力不高度依赖于羧酸盐基团与黄嘌呤药效团的距离。2-Thio 与 2-oxo 取代有利于 A3 效力，8-烷基与 8-芳基取代有利于 A3 选择性，尽管很少有衍生物对大鼠 A3 受体具有真正的选择性。1,3-Dimethyl-8-(3-carb
• Novel Compounds 737
  申请人：Cheng Leifeng

  公开号：US20090023704A1

  公开（公告）日：2009-01-22

  The present invention relates to novel xanthine compounds of the general formula (I) wherein R 1 , R 2 , R 3 and R 4 are as defined, having a positive allosteric GABA B receptor (GBR) modulator effect, methods for the preparation of said compounds and to their use, optionally in combination with a GABA B agonist, for the inhibition of transient lower esophageal sphincter relaxations, for the treatment of gastroesophageal reflux disease, as well as for the treatment of functional gastrointestinal disorders and irritable bowel syndrome (IBS).

  本发明涉及一种新型黄嘌呤化合物，其通式为（I），其中R1，R2，R3和R4如定义所述，具有正向变构GABAB受体（GBR）调节剂效应，以及制备所述化合物的方法和它们的用途，可选与GABAB激动剂结合，用于抑制短暂性下食管括约肌松弛，治疗胃食管反流病，以及用于治疗功能性胃肠疾病和肠易激综合征（IBS）。
• Selective Ligands for Rat A3 Adenosine Receptors: Structure-Activity Relationships of 1,3-Dialkylxanthine 7-Riboside Derivatives
  作者：Hea Ok Kim、Xiao-duo Ji、Neli Melman、Mark E. Olah、Gary L. Stiles、Kenneth A. Jacobson

  DOI：10.1021/jm00049a021

  日期：1994.11

  1,3-Dibutylxanthine 7-riboside has been found to be a partial agonist at A(3) adenosine receptors (van Galen et al. Mol. Pharmacol. 1994, 45, 1101-1111). 1,3-Dialkylxanthine 7-riboside analogues modified at the 1-, 3-, and 8-purine positions and at the ribose 5'-position were synthesized. The nucleoside analogues were examined for affinity in radioligand binding assays at rat brain A(3) adenosine receptors stably expressed in CHO cells, using the radioligand [[I-125]-4-amino- 3-iodobenzyl]adenosine-5'-N-methyluronamide (AB-MECA). Affinity was assayed at rat brain A(1) and A(2a) receptors using [H-3]PIA and [H-3]CGS 21680, respectively. The affinity of xanthine 7-ribosides at A(3) receptors depended on the 1,3-dialkyl substituents in the order: Pent greater than or equal to. Bu >> Hx > Pr approximate to Me. 1,3-Dipentylxanthine 7-riboside was slightly selective for A(3) receptors (2-fold vs A(1) and 10-fold vs A(2a)). 8-Methoxy substitution was tolerated at A(3) receptors. 2-Thio vs 2-oxo substitution increased potency at all three subtypes and slightly increased A(3) vs A(1) selectivity. The 5'-uronamide modification, which was previously found to enhance A(3) selectivity in N-6-benzyladenosine derivatives, was also incorporated into the xanthine 7-ribosides, with similar results. The affinity of 1,3-dialkylxanthine 7-riboside 5'-uronamides at A(3) receptors depended on the N-alkyluronamide substituent in the order: MeNH > EtNH >> NH2 >> Me(2)N. Affinity of the 5'-uronamides at A(3) receptors was dependent on the 1,3-dialkyl substitution in the order: Bu > Pent > Hex. 1,3-Dibutylxanthine 7-riboside 5'-N-methylcarboxamide, with a K-i value of 229 nM at A(3) receptors, was 160-fold selective for rat A(3) vs A(1) receptors and > 400-fold selective vs A(2a) receptors. This derivative acted as a full agonist in the A(3) receptor-mediated inhibition of adenylate cyclase.
• A 3 ADENOSINE RECEPTOR AGONISTS
  申请人：THE UNITED STATES OF AMERICA, as represented by the Secretary of the Department of Health and Human Services

  公开号：EP0708781A1

  公开（公告）日：1996-05-01
• XANTHINE COMPOUNDS HAVING A POSITIVE ALLOSTERIC GABAB RECEPTOR MODULATOR EFFECT
  申请人：AstraZeneca AB

  公开号：EP2146996A1

  公开（公告）日：2010-01-27