1,3,7-trimethyl-8-(3-phenylpropylthio)-1H-purine-2,6(3H,7H)-dione | 908823-08-5

• 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: 1,3,7-trimethyl-8-(3-phenylpropylthio)-1H-purine-2,6(3H,7H)-dione
• 英文别名: 8-[(Phenylpropyl)Sulfanyl]Caffeine；1,3,7-trimethyl-8-(3-phenylpropylsulfanyl)purine-2,6-dione
• CAS: 908823-08-5
• 化学式: C₁₇H₂₀N₄O₂S
• 分子量: 344.437
• InChiKey: AYQZKQHEXAMKFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  83.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  咖啡因 在 氯 、 sodium hydroxide 作用下， 以 乙醇 、 氯仿 、 水 为溶剂， 反应 1.0h， 生成 1,3,7-trimethyl-8-(3-phenylpropylthio)-1H-purine-2,6(3H,7H)-dione
  参考文献：
  名称：

  Inhibition of monoamine oxidase by 8-[(phenylethyl)sulfanyl]caffeine analogues

  摘要：

  In a previous study we have investigated the monoamine oxidase (MAO) inhibitory properties of a series of 8-sulfanylcaffeine analogues. Among the compounds studied, 8-[(phenylethyl) sulfanyl] caffeine (IC50 = 0.223 mu M) was found to be a particularly potent inhibitor of the type B MAO isoform. In an attempt to discover potent MAO inhibitors and to further examine the structure-activity relationships (SAR) of MAO inhibition by 8-sulfanylcaffeine analogues, in the present study a series of 8-[(phenylethyl)sulfanyl] caffeine analogues were synthesized and evaluated as inhibitors of human MAO-A and -B. The results document that substitution on C3 and C4 of the phenyl ring with alkyl groups and halogens yields 8-[( phenylethyl) sulfanyl] caffeine analogues which are potent and selective MAO-B inhibitors with IC50 values ranging from 0.017 to 0.125 mu M. The MAO inhibitory properties of a series of 8-sulfinylcaffeine analogues were also examined. The results show that, compared to the corresponding 8-sulfanylcaffeine analogues, the 8-sulfinylcaffeins are weaker MAO-B inhibitors. Both the 8-sulfanylcaffeine and 8-sulfinylcaffeine analogues were found to be weak MAO-A inhibitors. This study also reports the MAO inhibition properties of selected 8-[(phenylpropyl) sulfanyl] caffeine analogues. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.10.005

文献信息

• Two-step three-component process for one-pot synthesis of 8-alkylmercaptocaffeine derivatives
  作者：M. N. Soltani Rad、S. Maghsoudi

  DOI：10.1039/c6ra17814f

  日期：——

  A highly efficient, odourless and two-step three-component process for one-pot synthesis of some 8-alkylmercaptocaffeine derivatives has been described. The catalyst-free three-component reaction of alkyl bromides, thiourea, and 8-bromocaffeine gave 8-alkylmercaptocaffeine products in excellent to quantitative yields. In addition, the impact of parameters on sample reaction is discussed.

  已经描述了一种高效，无味，两步三组分法，用于一锅合成一些8-烷基巯基咖啡因衍生物。烷基溴，硫脲和8-溴咖啡因的无催化剂三组分反应以优异的定量收率得到了8-烷基巯基咖啡因产物。此外，还讨论了参数对样品反应的影响。
• 8-Alkylmercaptocaffeine derivatives: antioxidant, molecular docking, and in-vitro cytotoxicity studies
  作者：Saman Sargazi、Sheida Shahraki、Omolbanin Shahraki、Farshid Zargari、Roghayeh Sheervalilou、Saeid Maghsoudi、Mohammad Navid Soltani Rad、Ramin Saravani

  DOI：10.1016/j.bioorg.2021.104900

  日期：2021.6

  damage (P > 0.05). Computational studies showed that H-bond formation between the nitrogen atom in pyrazolo[4,3-D] pyrimidine moiety with Gln817 and creating a hydrophobic cavity result in the stability of the alkyl group in the PDE5A active site. We found that synthesized 8-alkylmercaptocaffeine derivatives induced cell death in different cancer cells through the cGMP pathway. These findings will help

  由于其独特的药理特性，甲基黄嘌呤被认为是具有广泛药用范围的治疗剂。在本报告中，我们旨在检查先前合成的 8-烷基巯基咖啡因衍生物的一些生物学效应。在恶性 A549、MCF7 和 C152 细胞系中测量了 8-烷基巯基咖啡因衍生物的细胞毒性和抗氧化活性。使用比色竞争 ELISA 试剂盒进行 cGMP 水平和 caspase-3 活性的评估。计算方法被用来发现合成化合物的抑制机制。在十二种合成的衍生物中，带有丙基、庚基和 3-甲基-丁基部分的三种化合物（C1、C5 和 C7）对所有研究的细胞系都显示出更高和更理想的细胞毒活性（IC50 < 100 µM）。此外，C5 在 MCF-7 细胞中协同增强顺铂诱导的细胞毒性（CI < 1）。在所有研究的细胞系中，C5 和 C7 在特定时间间隔显着增加 caspase-3 活性和细胞内 cGMP 水平（P < 0.05）。然而，这些衍生物并未增加LDH渗漏（P
• Inhibition of monoamine oxidase by 8-[(phenylethyl)sulfanyl]caffeine analogues
  作者：Samantha Mostert、Wayne Mentz、Anél Petzer、Jacobus J. Bergh、Jacobus P. Petzer

  DOI：10.1016/j.bmc.2012.10.005

  日期：2012.12

  In a previous study we have investigated the monoamine oxidase (MAO) inhibitory properties of a series of 8-sulfanylcaffeine analogues. Among the compounds studied, 8-[(phenylethyl) sulfanyl] caffeine (IC50 = 0.223 mu M) was found to be a particularly potent inhibitor of the type B MAO isoform. In an attempt to discover potent MAO inhibitors and to further examine the structure-activity relationships (SAR) of MAO inhibition by 8-sulfanylcaffeine analogues, in the present study a series of 8-[(phenylethyl)sulfanyl] caffeine analogues were synthesized and evaluated as inhibitors of human MAO-A and -B. The results document that substitution on C3 and C4 of the phenyl ring with alkyl groups and halogens yields 8-[( phenylethyl) sulfanyl] caffeine analogues which are potent and selective MAO-B inhibitors with IC50 values ranging from 0.017 to 0.125 mu M. The MAO inhibitory properties of a series of 8-sulfinylcaffeine analogues were also examined. The results show that, compared to the corresponding 8-sulfanylcaffeine analogues, the 8-sulfinylcaffeins are weaker MAO-B inhibitors. Both the 8-sulfanylcaffeine and 8-sulfinylcaffeine analogues were found to be weak MAO-A inhibitors. This study also reports the MAO inhibition properties of selected 8-[(phenylpropyl) sulfanyl] caffeine analogues. (C) 2012 Elsevier Ltd. All rights reserved.