1-N-丙基-3,7-二甲基黄嘌呤 | 63906-63-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 1-N-丙基-3,7-二甲基黄嘌呤
• 英文名称: 3,7-Dimethyl-1-propylxanthine
• 英文别名: 3,7-dimethyl-1-propyl-1H-purine-2,6-(2H,6H)-dione；1-propyl-3,7-dimethylxanthine；3,7-dimethyl-1-propyl-3,7-dihydro-purine-2,6-dione；3,7-Dimethyl-1-propyl-3,7-dihydro-purin-2,6-dion；Theobromine, 1-propyl-；3,7-dimethyl-1-propylpurine-2,6-dione
• CAS: 63906-63-8
• 化学式: C₁₀H₁₄N₄O₂
• mdl: MFCD01682413
• 分子量: 222.247
• InChiKey: XJKSERUTELYNMR-UHFFFAOYSA-N

物化性质

• 沸点：
  363.42°C (rough estimate)
• 密度：
  1.2042 (rough estimate)
• 溶解度：
  0.06 M
• 保留指数：
  1996

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  58.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1-N-丙基-3,7-二甲基黄嘌呤 在 phosphate buffer 、 葡萄糖 、 咖啡因 、 mixed culture of Klebsiella and Rhodococcus 作用下， 反应 12.0h， 生成 1-Propyl-3,7-dimethyluric acid
  参考文献：
  名称：

  Highly efficient C-8 oxidation of substituted xanthines with substitution at the 1-, 3-, and 7- positions using biocatalysts

  摘要：

  由克雷伯氏菌属和红球菌属菌株组成的细菌群能将 1-、3- 和 7-取代的黄嘌呤定量转化为各自的 8-氧代化合物。

  DOI：

  10.1039/a900089e
• 作为产物：
  描述：

  可可碱 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.58h， 生成 1-N-丙基-3,7-二甲基黄嘌呤
  参考文献：
  名称：

  Analogs of caffeine and theophylline: effect of structural alterations on affinity at adenosine receptors

  摘要：

  A variety of analogues of caffeine and theophylline in which the 1-,3-, and 7-methyl substituents have been replaced with n-propyl, allyl, propargyl, and isobutyl and, in a few cases, with chloroethyl, hydroxyethyl, or benzyl were assessed for potency and selectivity as antagonists at A1- and A2-adenosine receptors in brain tissue. Caffeine and theophylline are nonselective for these receptors. Nearly all of the 22 analogues of caffeine are more potent than caffeine itself at adenosine receptors. Replacement of the 1-methyl moiety with n-propyl, allyl, or propargyl substituent has little effect on potency at the A1 receptor while enhancing potency about 7- to 10-fold at the A2 receptor. 3,7-Di-methyl-1-propylxanthine is only slightly (1.4-fold) more potent than caffeine at the A1 receptor while being 10-fold more potent at the A2 receptor. 1,3-Di-n-propyl-7-methylxanthine is also selective for the A2 receptor, being 8-fold more potent than caffeine at the A1 receptor and 40-fold more potent at the A2 receptor. A number of other caffeine analogues including 3,7-dimethyl-1-n-propylxanthine, 7-allyl-1,3-dimethylxanthine, and 1,3-dimethyl-7-propargylxanthine are also somewhat selective for the A2 receptor. The most potent caffeine analogue was 1,3-di-n-propyl-7-propargylxanthine, which was about 100-fold more potent than caffeine at both A1 and A2 receptors. The 10 theophylline analogues were relatively nonselective except for the 1-ethyl analogue and the 1,3-diallyl analogue, which were selective for the A2 receptor, and the 1,3-di-n-propyl, 1,3-diisobutyl, and 1,3-dibenzyl analogues, which were somewhat selective for the A1 receptor. 1,3-Di-n-propylxanthine was 20-fold more potent than theophylline at the A1 receptor and 5-fold more potent at the A2 receptor.

  DOI：

  10.1021/jm00157a035

文献信息

• Palladium-catalyzed C–H olefination of uracils and caffeines using molecular oxygen as the sole oxidant
  作者：Xinyu Zhang、Lv Su、Lin Qiu、Zhenwei Fan、Xiaofeng Zhang、Shen Lin、Qiufeng Huang

  DOI：10.1039/c7ob00616k

  日期：——

  The palladium-catalyzed oxidative C–H olefination of uracils or caffeines with alkenes using an atmospheric pressure of molecular oxygen as the sole oxidant has been disclosed. This novel strategy offers an efficient and environmentally friendly method to biologically important C5-alkene uracil derivatives or C8-alkene caffeine derivatives.

  已经公开了使用大气压下的分子氧作为唯一的氧化剂，钯催化尿烷或咖啡因与烯烃的钯催化氧化CH烯化反应。这种新颖的策略为生物学上重要的C5-烯烃尿嘧啶衍生物或C8烯烃咖啡因衍生物提供了一种有效且环保的方法。
• 一种8-酯基咖啡因衍生物的制备方法
  申请人：福建师范大学

  公开号：CN104892610B

  公开（公告）日：2016-08-24

  本发明公开了一种8‑酯基咖啡因衍生物的制备方法，包括如下步骤：在CO气氛中将咖啡因类化合物、醇、催化剂、氧化剂放入有机溶剂中进行C‑H键直接羰基化反应，反应完成后通过柱层析分离得到8‑酯基咖啡因衍生物。本发明对咖啡因C‑H键直接进行羰基化反应，避免原料预功能化，且使用CO作为碳源，具有很高原子经济性，符合现代绿色化学发展要求，同时制备得到的8‑酯基咖啡因衍生物具有潜在的药用价值。
• Compositions and methods for treating disorders associated with salt or fluid retention
  申请人：Ironwood Pharmaceuticals, Inc.

  公开号：EP2671584A2

  公开（公告）日：2013-12-11

  Methods for reducing the risk of or treating a disorder associated with fluid and/or salt retention in a patient are described. The methods include administering to the patient an agent selected from: a) an agent that reduces sodium absorption in the intestine; b) an agent that increases anion secretion in the intestine; or c) an agent that both reduces sodium absorption in the intestine and increases anion secretion in the intestine.

  本文描述了降低患者发生与体液和/或盐潴留有关的疾病的风险或治疗这种疾病的方法。这些方法包括向患者施用选自以下几种的制剂：a) 减少肠道钠吸收的制剂；b) 增加肠道阴离子分泌的制剂；或 c) 既减少肠道钠吸收又增加肠道阴离子分泌的制剂。
• Adeno-associated virus-delivered ribozyme compositions and methods for the treatment of retinal diseases
  申请人：Lewin S. Alfred

  公开号：US20050096282A1

  公开（公告）日：2005-05-05

  Disclosed are ribozymes, as well as compositions, vectors, virus particles, host cells, and therapeutic kits comprising them useful in the treatment of diseases of the eye, including retinopathy and macular degeneration, and the amelioration of symptoms of such diseases including loss of vision, retinitis, and blindness.

  所公开的是核糖酶，以及由其组成的组合物、载体、病毒颗粒、宿主细胞和治疗试剂盒，它们可用于治疗眼部疾病，包括视网膜病变和黄斑变性，以及改善此类疾病的症状，包括视力丧失、视网膜炎和失明。
• [EN] NUCLEOSIDE DERIVATIVE FOR PREVENTING AND TREATING INFLAMMATION AND APPLICATION THEREOF<br/>[FR] DÉRIVÉ NUCLÉOSIDIQUE DESTINÉ À LA PRÉVENTION ET AU TRAITEMENT D'UNE INFLAMMATION ET SON UTILISATION<br/>[ZH] 防治炎症反应的核苷类衍生物及其应用
  申请人：WEST CHINA HOSPITAL OF SICHUAN UNIV

  公开号：WO2020192665A1

  公开（公告）日：2020-10-01

  本发明提供了一类防治炎症反应的核苷类衍生物，以及该衍生物在制备防治炎症疾病的药物中的应用。本发明提供的防治炎症反应的核苷类衍生物能够明显改善胰腺炎、肝炎、关节炎等病情，改善器官受损和炎性指标，效果优于阳性对照药吲哚美辛。相比于传统抗炎药物阿司匹林、布洛芬、吲哚美辛、保泰松、双氯芬酸、吡罗昔康以及糖皮质激素，本发明提供的防治炎症反应的核苷类衍生物具有副作用明显更小的优势。