3,7-dimethyl-1-(4-oxo-pentyl)-3,7-dihydro-purine-2,6-dione | 10226-60-5

• 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: 3,7-dimethyl-1-(4-oxo-pentyl)-3,7-dihydro-purine-2,6-dione
• 英文别名: 1-(2-Keto-5-pentyl)-3,7-dimethylxanthine；3,7-Dimethyl-1-(4-oxopentyl)purine-2,6-dione
• CAS: 10226-60-5
• 化学式: C₁₂H₁₆N₄O₃
• 分子量: 264.284
• InChiKey: NSVYGIIKCJGYIO-UHFFFAOYSA-N

物化性质

• 沸点：
  508.6±56.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  75.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,7-dimethyl-1-(4-oxo-pentyl)-3,7-dihydro-purine-2,6-dione 在 sodium tetrahydroborate 作用下， 以 甲醇 、 乙醚 为溶剂， 生成 1-(4-羟基戊基)-3,7-二甲基-1H-嘌呤-2,6-(2H,6H)-二酮
  参考文献：
  名称：

  Potentiation of cADPR-Induced Ca²⁺-Release by Methylxanthine Analogues

  摘要：

  Caffeine and other methylxanthines are known to induce Ca2+-release from intracellular stores via the ryanodine receptor. In the present work, a range of caffeine analogues, in which methyl groups at the 1 and 7 positions were replaced with alkyl chains containing different functional groups (oxo, hydroxyl, propargyl, ester, and acids), were synthesized. These compounds were then screened for their ability to potentiate Ca2+-release induced by cADPR (an endogenous modulator of ryanodine receptors) in sea urchin egg homogenates. Two of the synthesized methylxanthines, 1,3-dimethyl-7-(7-hydroxyoctyl)xanthine (37) and 3-methyl-7-(7-oxooctyl)-1-propargylxanthine (66), were shown to be more potent than caffeine in potentiating cADPR-induced Ca2+-release, while 1,3-dimethyl-7-(5-ethylcarboxypentyl)xanthine (14) was shown to be more efficacious. The development of new methylxanthine analogues may lead to a better understanding of ryanodine receptor function and could possibly provide novel therapeutic agents.

  DOI：

  10.1021/jm980469t
• 作为产物：
  描述：

  5-Tosyloxy-2,2-ethylenedioxypentane 在 盐酸 、 甲醇 、 potassium carbonate 作用下， 反应 1.0h， 生成 3,7-dimethyl-1-(4-oxo-pentyl)-3,7-dihydro-purine-2,6-dione
  参考文献：
  名称：

  Potentiation of cADPR-Induced Ca²⁺-Release by Methylxanthine Analogues

  摘要：

  Caffeine and other methylxanthines are known to induce Ca2+-release from intracellular stores via the ryanodine receptor. In the present work, a range of caffeine analogues, in which methyl groups at the 1 and 7 positions were replaced with alkyl chains containing different functional groups (oxo, hydroxyl, propargyl, ester, and acids), were synthesized. These compounds were then screened for their ability to potentiate Ca2+-release induced by cADPR (an endogenous modulator of ryanodine receptors) in sea urchin egg homogenates. Two of the synthesized methylxanthines, 1,3-dimethyl-7-(7-hydroxyoctyl)xanthine (37) and 3-methyl-7-(7-oxooctyl)-1-propargylxanthine (66), were shown to be more potent than caffeine in potentiating cADPR-induced Ca2+-release, while 1,3-dimethyl-7-(5-ethylcarboxypentyl)xanthine (14) was shown to be more efficacious. The development of new methylxanthine analogues may lead to a better understanding of ryanodine receptor function and could possibly provide novel therapeutic agents.

  DOI：

  10.1021/jm980469t

文献信息

• Studies on xanthine derivatives. II. Synthesis of 1,2,3,7-tetrahydro-6H-purin-6-ones from xanthine hydrolyzates.
  作者：TSUTOMU OHSAKI、TAKEO KURIKI、TAISEI UEDA、JINSAKU SAKAKIBARA

  DOI：10.1248/cpb.34.36

  日期：——

  Intramolecular cyclization of caffeidine homologues (2a and 2b) in the presence of ethanolic hydrogen chloride gave 9-oxo-1H-pyrrolo[1, 2-α]purine (4a) and 11-oxo-1H-azepino[1, 2-α]purine (4b) derivatives, both containing a 1, 2, 3, 7-tetrahydro-6H-purin-6-one ring system. Purine ring system compounds, 2-monosubstituted (7) and 2, 2, -disubstituted (8) 1, 2, 3, 7-tetrahydro-6H-purin-6-ones, were synthesized by intermolecular cyclization between caffeidine and aldehydes (5) or ketones (6) in the presence of acid catalysts. Pyrolysis of 4, 7, 8, 9, 9a, 11-hexahydro-1, 4, 9a-trimethyl-5, 11-dioxo-1H, 5H-imidazo[4, 5-f]pyrrolo[2, 1-b][1, 3, 5]-oxadiazocine hydrochloride (9·HCl) derived from a urea derivative (3a) afforded 4a and 1, 4-dimethyl-4, 5-dihydro-5, 7-dioxo-1H, 7H-imidazo[4, 5-d][1, 3]oxazine (11). Many of these compounds (4, 7 and 8) showed relaxing activity against KCl-induced contraction of arterial strips isolated from the rabbit mesenterium, and potent activity was observed in the case of 71.

  在乙醇氢氯酸存在下，咖啡啶同系物（2a和2b）发生分子内环化，生成含有1,2,3,7-四氢-6H-嘌呤-6-酮环系的9-氧代-1H-吡咯并[1,2-α]嘌呤（4a）和11-氧代-1H-氮杂庚英并[1,2-α]嘌呤（4b）衍生物。通过咖啡啶与醛（5）或酮（6）在酸催化剂作用下的分子间环化反应合成了含有嘌呤环系的化合物，即2-单取代（7）和2,2-二取代（8）的1,2,3,7-四氢-6H-嘌呤-6-酮。从脲衍生物（3a）衍生得到的4,7,8,9,9a,11-六氢-1,4,9a-三甲基-5,11-二氧代-1H,5H-咪唑并[4,5-f]吡咯并[2,1-b][1,3,5]-氧二唑盐酸盐（9·HCl）的热解产物为4a和1,4-二甲基-4,5-二氢-5,7-二氧代-1H,7H-咪唑并[4,5-d][1,3]恶唑（11）。这些化合物中的许多（4,7和8）显示出对来自兔肠系膜的动脉条在氯化钾诱导的收缩中具有松弛活性，其中71表现出了强效活性。
• Compounds having antiplatelet aggregation activity, and pharmaceutical
  申请人：Ellem Industria Farmaceutica S.p.A.

  公开号：US04737502A1

  公开（公告）日：1988-04-12

  Compounds of general formula (I) ##STR1## wherein: m is zero or 1; n is zero, 1, 2, 3 or 4; A is a 3,7-dimethylxanthine-1-yl or 1,3-dimethylxanthine-7-yl residue; show marked anti-platelet activity.

  通式（I）的复合物如下：##STR1## 其中：m为零或1；n为零、1、2、3或4；A为3,7-二甲基黄嘌呤-1-基或1,3-二甲基黄嘌呤-7-基残基；具有明显的抗血小板活性。
• Photoredox Catalysis-Enabled C–H Difluoromethylation of Heteroarenes with Pentacoordinate Phosphorane as the Reagent
  作者：Huanhuan Song、Jingwen Li、Yinbin Zhang、Ke Chen、Le Liu、Junjie Zhang、Xin-Hua Duan、Mingyou Hu

  DOI：10.1021/acs.joc.3c01336

  日期：2023.8.18

  broad applications in numerous bioactive molecules. Herein, we report photoredox catalysis-induced direct C–H difluoromethylation of heterocycles by using bis(difluoromethyl) pentacoordinate phosphorane (PPh3(CF2H)2, 1) as the reagent. A variety of heterocycles, such as quinoxalin-2(1H)-one, thiophene, indole, and coumarin, are readily tailored with a difluoromethyl group. The method is featured as transition-metal-free

  二氟甲基化杂环化合物已在众多生物活性分子中得到广泛应用。在此，我们报道了使用双（二氟甲基）五配位正膦（PPh 3 (CF 2 H) 2 , 1）作为试剂，光氧化还原催化诱导杂环的直接C-H二氟甲基化。多种杂环化合物，例如喹喔啉-2(1H ) -酮、噻吩、吲哚和香豆素，很容易用二氟甲基进行定制。该方法以有机化合物赤藓红B为催化剂，O 2为氧化剂，具有无过渡金属的特点。
• Compounds having antiplatelet aggregation activity, a process for the preparation thereof and pharmaceutical compositions containing them
  申请人：ELLEM INDUSTRIA FARMACEUTICA S.p.A.

  公开号：EP0198190A2

  公开（公告）日：1986-10-22

  Compounds of general formula (I) wherein: · m is zero or 1; · n is zero, 1, 2, 3 or 4; · A is a 3,7-dimethylxanthine-1-yl or 1,3-dimethylxanthine-7-yl residue; show marked anti-platelet activity.

  通式（I）的化合物，其中：- m 为零或 1；- n 为零、1、2、3 或 4；- A 为 3,7-二甲基黄嘌呤-1-基或 1,3-二甲基黄嘌呤-7-基残基；具有明显的抗血小板活性。
• US4737502A
  申请人：——

  公开号：US4737502A

  公开（公告）日：1988-04-12