8-(1-hydroxyethyl)3,7-trimethyl-3,7-dihydro-1H-purine-2,6-dione | 32086-89-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 8-(1-hydroxyethyl)3,7-trimethyl-3,7-dihydro-1H-purine-2,6-dione
• 英文别名: 8-(1-hydroxyethyl)-1,3,7-trimethyl-3,7-dihydro-1H-purine-2,6-dione；8-(1-hydroxyethyl)-caffeine；8-(1-hydroxy-ethyl)-1,3,7-trimethyl-3,7-dihydro-purine-2,6-dione；8-(1-Hydroxy-aethyl)-1,3,7-trimethyl-3,7-dihydro-purin-2,6-dion；8-alpha-Hydroxyethylcaffeine；8-(1-hydroxyethyl)-1,3,7-trimethylpurine-2,6-dione
• CAS: 32086-89-8
• 化学式: C₁₀H₁₄N₄O₃
• 分子量: 238.246
• InChiKey: JFHMEXPYFAUGEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  78.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-(1-hydroxyethyl)3,7-trimethyl-3,7-dihydro-1H-purine-2,6-dione 在 叔丁基过氧化氢 作用下， 以 癸烷 为溶剂， 以96%的产率得到8-acetyl-1,3,7-trimethyl-3,7-dihydro-1H-purine-2,6-dione
  参考文献：
  名称：

  天然存在的甲基黄嘌呤的C8-类似物的微波辅助修饰合成：合成，生物学评估及其实际应用。

  摘要：

  C8-咖啡因2 /可可碱3 /茶碱4与取代的脂肪族醇11a-lvia CH键活化的高效，微波辅助，无氧化剂交叉，无过渡金属的交叉脱氢Csp2-Csp3偶联，用于制备系列使用微波辐射已开发出可替代的C 8-（羟甲基）咖啡因12a-1 /可可碱13a-c /茶碱14a-b，其产率高达98％。该反应在叔丁基过氧化氢（TBHP）的存在下，在溶剂分解条件下于120°C进行20分钟，以良好至极好的收率，反应生成相应的取代的C8-（羟甲基）-甲基黄嘌呤衍生物。良好的底物范围，对照实验，克级合成和实用的合成转化进一步凸显了该方法的实用性。这些C8-（羟甲基）咖啡因12a-1

  DOI：

  10.1016/j.fitote.2020.104533
• 作为产物：
  描述：

  1,3,7-trimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purine-8-carboxylic acid amide 在 乙醚 、 aluminum isopropoxide 、 异丙醇 、 三氯氧磷 、 苯 作用下， 生成 8-(1-hydroxyethyl)3,7-trimethyl-3,7-dihydro-1H-purine-2,6-dione
  参考文献：
  名称：

  [嘌呤衍生物的基本取代。一世]。

  摘要：

  DOI：

  10.1002/ardp.19562890902

文献信息

• Reduction‐Triggered Doxorubicin Delivery by Self‐Assembled Nanospheres of Lipoylated Caffeine
  作者：Krishan Kumar、Bharti Rajesh Kumar Shyamlal、Rajbala Verma、Paturu Kondaiah、Sandeep Chaudhary

  DOI：10.1002/cmdc.202000070

  日期：2020.5.6

  hydroxyethyl derivative of caffeine. In water, CAFF-LA self-assembles into nanospheres with an average size of 155 nm, as evidenced from dynamic light scattering and electron microscopy studies. The nanospheres are stable in serum and could be disintegrated upon exposure to the reducing environment of dithiothreitol (DTT; 10 mM) and glutathione (GSH; 10 mM). These nanospheres easily encapsulate the chemotherapy

  这项研究报告了一种新的两亲生物共轭物（CAFF-LA），其衍生自咖啡因的羟乙基衍生物的脂酰化。在水中，CAFF-LA自组装成平均大小为155 nm的纳米球，这通过动态光散射和电子显微镜研究得到了证明。纳米球在血清中是稳定的，并且在暴露于二硫苏糖醇（DTT； 10 mM）和谷胱甘肽（GSH； 10 mM）的还原环境中时可能崩解。这些纳米球易于封装化疗药物阿霉素（DOX），并证明可有效转运至耐阿霉素的宫颈癌（HeLa）细胞，与自由药物相比，已观察到明显的细胞凋亡诱导作用和IC50明显降低。
• Caffeine derivatives
  申请人：Societa' Farmaceutici Italia S.p.A.

  公开号：US03975389A1

  公开（公告）日：1976-08-17

  New derivatives of caffeine are disclosed having the formula: ##SPC1## Where R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are selected from the group consisting of hydrogen, chlorine, bromine, an alkyl or an alkoxy radical containing from 1 to 4 carbon atoms. They are made by transforming 8-.alpha. hydroxyethyl caffeine into the corresponding 8-.alpha.-chloroethyl caffeine by the action of a suitable chlorinating agent such as thionyl chloride, reacting the product so obtained in a suitable solvent such as anhydrous dimethylformamide at a temperature from 40.degree. to 110.degree. C and for a period of time from 1 to 5 hours with the sodium or potassium salt of a nicotinic acid of the formula: ##SPC2## Where R.sub.1, R.sub.2, R.sub.3 and R.sub.4 have the above-mentioned meanings, and crystallizing the resulting product from a suitable solvent, such as ethanol. These new compounds have broncholitic activity.

  公开了咖啡因的新衍生物，其化学式为：##SPC1##其中R.sub.1、R.sub.2、R.sub.3和R.sub.4从氢、氯、溴、含有1至4个碳原子的烷基或烷氧基的群中选择。它们通过将8-α-羟乙基咖啡因转化为相应的8-α-氯乙基咖啡因，使用适当的氯化剂（如亚磺酰氯），在适当的溶剂（如无水二甲基甲酰胺）中，在40℃至110℃的温度下反应1至5小时，与烟酸钠或烟酸钾的盐反应，其化学式为：##SPC2##其中R.sub.1、R.sub.2、R.sub.3和R.sub.4具有上述含义，并从适当的溶剂（如乙醇）中结晶得到产物。这些新化合物具有支气管扩张活性。
• Free radical polymerization of caffeine-containing methacrylate monomers
  作者：Ashley M. Nelson、Sean T. Hemp、Jessica Chau、Timothy E. Long

  DOI：10.1002/pola.27756

  日期：2015.12.15

  ABSTRACTThe incorporation of acrylic functionality into caffeine enables the preparation of a vast array of novel thermoplastics and thermosets. A two‐step derivatization provided a novel caffeine‐containing methacrylate monomer capable of free radical polymerization. Copolymers of 2‐ethylhexyl methacrylate and caffeine methacrylate (CMA) allowed for a systematic study of the effect of covalently bound caffeine on polymer properties. 1H NMR and UV‐vis spectroscopy confirmed caffeine incorporation at 5 and 13 mol %, and SEC revealed the formation of high molecular weight (co)polymers (>40,000 g/mol). CMA incorporation resulted in a multistep degradation profile with initial mass loss closely correlating to caffeine content. Differential scanning calorimetry, rheological, and thermomechanical analysis demonstrated that relatively low levels of CMA increased the glass transition temperature, resulting in higher moduli and elucidating the benefits of incorporating caffeine into polymers. © 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2015, 53, 2829–2837
• Erndt, Aleksander; Fiedorowicz, Maciej; Kostuch, Andrzej, Liebigs Annalen der Chemie, 1993, # 10, p. 1043 - 1046
  作者：Erndt, Aleksander、Fiedorowicz, Maciej、Kostuch, Andrzej、Para, Andrzej

  DOI：——

  日期：——
• Benzophenone-Photosensitized Reactions of Xanthinic Compounds. A Mechanistic Study
  作者：Daniel H. Murgida、Pedro F. Aramendía、Rosa Erra-Balsells

  DOI：10.1111/j.1751-1097.1998.tb09444.x

  日期：1998.5

  Photosensitized reaction of xanthinic compounds (XH) as caffeine (CF), theobromine (TB) and theophylline (TF) by benzophenone (BZ) in ethanol solution was investigated. In the three cases four main reaction products (benzopinacol; diphenylcarbinol; 1,1-diphenyl-1,2-propanediol and 8-[1-(1-hydroxyethyl)] xanthine) were identified and then characterized by melting point, H-1 NMR, C-13 NMR and mass spectrometry. The quenching of triplet BZ by the three XH was detected and a thorough kinetic analysis was performed. Caffeine produces mainly physical quenching, while TF reacts by N-H hydrogen abstraction. For TB both mechanisms are operative. Heats of reactions were calculated for chosen reactive steps of the mechanism by the PM3 method. They provide additional support to the proposed reaction scheme. We demonstrate that the mechanism leading to XP formation does not proceed through the X . radical directly obtained by H abstraction. An alternative reaction path through an intermediate radical originated on the addition of ethanol radical to XH is proposed. Redox potentials for the oxidation of XH were estimated by cyclic voltametry and by using the Rehm-Weller equation the redox quenching of triplet BZ by XH was discarded.