1,3-二甲基-7-丙基嘌呤-2,6-二酮 | 27760-74-3

• 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: 1,3-二甲基-7-丙基嘌呤-2,6-二酮
• 英文名称: 7-Propyltheophylline
• 英文别名: 1,3-dimethyl-7-n-propylxanthine；7-propyl-theophylline；1,3-dimethyl-7-propyl-3,7-dihydro-purine-2,6-dione；1,3-Dimethyl-7-propyl-3,7-dihydro-purin-2,6-dion；7-Propyl-theophyllin；Theophylline, n-propyl derivative；1,3-dimethyl-7-propylpurine-2,6-dione
• CAS: 27760-74-3
• 化学式: C₁₀H₁₄N₄O₂
• mdl: MFCD01631099
• 分子量: 222.247
• InChiKey: HGFWMGARSDHJFP-UHFFFAOYSA-N

物化性质

• 沸点：
  363.42°C (rough estimate)
• 密度：
  1.2042 (rough estimate)
• 保留指数：
  1997

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 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

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  羟丙茶碱	proxyphylline	603-00-9	C10H14N4O3	238.246
  ——	7-allyl-1,3-dimethylxanthine	61444-26-6	C10H12N4O2	220.231
  茶碱	theophylline	58-55-9	C7H8N4O2	180.166

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  3-甲基-7-丙基黄嘌呤	3-methyl-7-propyl-xanthine	55242-64-3	C9H12N4O2	208.22
  ——	1-[4-(4-methoxyphenoxy)butyl]-3-methyl-7-propylxanthine	117835-22-0	C20H26N4O4	386.451
  ——	1-[6-(4-methoxyphenoxy)hexyl]-3-methyl-7-propylxanthine	117835-23-1	C22H30N4O4	414.505
  ——	1-[6-(4-chlorophenoxy)hexyl]-3-methyl-7-propylxanthine	117835-24-2	C21H27ClN4O3	418.923
  可可碱	theobromine /	83-67-0	C7H8N4O2	180.166
  1-氨基-3-甲基-7-丙基黄嘌呤	1-amino-3-methyl-7-propylxanthine	117835-15-1	C9H13N5O2	223.235
  ——	1,3-dimethyl-8-phenyl-7-n-propylxanthine	249929-64-4	C16H18N4O2	298.345

反应信息

• 作为反应物：
  描述：

  1,3-二甲基-7-丙基嘌呤-2,6-二酮 在 一水合肼 作用下， 反应 8.0h， 以42%的产率得到1-氨基-3-甲基-7-丙基黄嘌呤
  参考文献：
  名称：

  Synthesis of imidazo(4,5-c)(1,2,6)thiadiazine 2-oxides from hydrolytes of xanthines and determination of their vasodilating activity.

  摘要：

  合成了新型的1, 3, 6, 7-四氢-7-氧代噁唑并[4, 5-c][1, 2, 6]硫二嗪2-氧化物衍生物（2a-q），反应的原料为通过碱性水解获得的1, 3, 7-三取代黄嘌呤衍生物（3）与SOCl2反应，产率为42-93%。用SO2Cl2对2进行氯化得到5-氯衍生物（10a, d, i-q），但产率较低。与苯甲酰氯衍生物（14）反应得到3, 7-二氢-6H-嘌呤-6-酮衍生物（15a-d）。在2和10中，具有苯氧烷基团位于l位的化合物在自发性高血压大鼠的肠系膜动脉上表现出强效的血管扩张活性。特别是，具有1-[6-(4-氯苯氧)己基]-6-丙基（2o），6-己基-1-[6-(4-甲氧基苯氧)己基]（2p），1-[6-(4-氯苯氧)己基]-6-己基（2q），5-氯-1-[6-(4-氯苯氧)己基]-6-甲基（101），5-氯-1-[4-(4-甲氧基苯氧)-丁基]-6-丙基（10m），5-氯-1-[6-(4-甲氧基苯氧)己基]-6-丙基（10n），或5-氯-1-[6-(4-氯苯氧)己基]-6-丙基（10o）取代基的ED50值在10^-7 M的数量级。

  DOI：

  10.1248/cpb.36.877
• 作为产物：
  描述：

  7-allyl-1,3-dimethylxanthine 在 palladium on activated charcoal 氢气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 以85%的产率得到1,3-二甲基-7-丙基嘌呤-2,6-二酮
  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。
• Double C−H Activation: The Palladium-Catalyzed Direct C-Arylation of Xanthines with Arenes
  作者：Chandi C. Malakar、Dietmar Schmidt、Jürgen Conrad、Uwe Beifuss

  DOI：10.1021/ol200065s

  日期：2011.3.18

  The novel Pd-catalyzed C(sp2)−H/C(sp2)−H cross-coupling of unactivated xanthines with unactivated arenes utilizing a combination of Ag(I) and O2 as oxidants exclusively yields C-8 arylated xanthines in a single synthetic operation.

  利用Ag（I）和O 2作为氧化剂，新型Pd催化未活化的黄嘌呤与未活化的芳烃的C（sp 2）-H / C（sp 2）-H交叉偶联，在C芳基化的黄嘌呤中仅产生C-8芳基化的黄嘌呤。单个合成操作。
• 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。
• Caffeine demethylate gene-containing DNA fragment and microbial process
  申请人：Amano Pharmaceutical Co., Ltd.

  公开号：US05550041A1

  公开（公告）日：1996-08-27

  A DNA fragment containing a caffeine demethylase gene produced by a microorganism belonging to the genus Pseudomonas and capable of assimilating caffeine and a process for producing a 3-methyl-7-alkylxanthine comprising cultivating a novel bacterium strain of the genus Pseudomonas having been transformed with a recombinant DNA having integrated therein the above-mentioned DNA fragment in a nutrient culture medium containing a 1,3-dimethyl-7-alkylxanthine to produce a 3-methyl-7-alkylxanthine in the culture and recovering the produced 3-methyl-7-alkylxanthine from the culture are disclosed, as well as a process for producing 3-methyl-7-propylxanthine, comprising cultivating a microorganism capable of converting 1,3-dimethyl-7-propylxanthine to 3-methyl-7-propylxanthine or a mutant thereof in a nutrient culture medium containing 1,3-dimethyl-7-propylxanthine, to produce 3-methyl-7-propylxanthine in the culture and recovering the produced 3-methyl-7-propylxanthine from the culture.

  本文披露了一种含有咖啡因去甲基化酶基因的DNA片段，该基因由属于假单胞菌属的微生物产生，并且能够同化咖啡因的过程。还披露了一种生产3-甲基-7-烷基茶碱的方法，包括在营养培养基中培养已经被转化为含有上述DNA片段的重组DNA的假单胞菌属的新菌株，该培养基含有1,3-二甲基-7-烷基茶碱，以在培养中产生3-甲基-7-烷基茶碱，并从培养物中回收产生的3-甲基-7-烷基茶碱。此外，还披露了一种生产3-甲基-7-丙基茶碱的方法，包括在营养培养基中培养能够将1,3-二甲基-7-丙基茶碱转化为3-甲基-7-丙基茶碱或其突变体的微生物，以在培养中产生3-甲基-7-丙基茶碱，并从培养物中回收产生的3-甲基-7-丙基茶碱。
• ANTI-INFLAMMATORY PHOSPHONATE COMPOUNDS
  申请人：Cannizzaro Carina

  公开号：US20090247488A1

  公开（公告）日：2009-10-01

  The invention is related to phosphorus substituted anti-inflammatory compounds, compositions containing such compounds, and therapeutic methods that include the administration of such compounds, as well as to processes and intermediates useful for preparing such compounds.

  本发明涉及磷取代的抗炎化合物、含有这种化合物的组合物、包括给药这种化合物的治疗方法，以及用于制备这种化合物的有用过程和中间体。