6-((2-methylbenzyl)thio)-9H-purine | 5069-73-8

• 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: 6-((2-methylbenzyl)thio)-9H-purine
• 英文别名: 6-[(2-methylbenzyl)thio]purine；6-(2-methyl-benzylsulfanyl)-7(9)H-purine；6-(o-Methylbenzylthio)purin；6-[(2-methylphenyl)methylsulfanyl]-7H-purine
• CAS: 5069-73-8
• 化学式: C₁₃H₁₂N₄S
• 分子量: 256.331
• InChiKey: ZSISWONFONJBBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  79.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为产物：
  描述：

  在 盐酸 作用下， 以 甲醇 为溶剂， 以60 %的产率得到6-((2-methylbenzyl)thio)-9H-purine
  参考文献：
  名称：

  Mitsunobu 反应对 6-硫嘌呤衍生物的烷基化

  摘要：

  摘要 据报道，通过 Mitsunobu 反应，硫嘌呤衍生物与醇的烷基化反应收率适中。将该方法应用于多种硫嘌呤和硫嘌呤核苷衍生物的合成。

  DOI：

  10.1080/15257770.2022.2163501

文献信息

• Synthesis, Anti-cancer Activity and Mechanism Study of 6-Mercapto-purine Derivatives
  作者：Yu-qin Ma、Xing Yan、Rong Du、Xiao-guang Yang、Yu-xin Li、Ying Gao、Wen-liang Li

  DOI：10.2174/1570180812666150821003536

  日期：2016.6.18

  (NMSP) which possessing a β-naphthalene, showed better anti-cancer activity than other compounds, with an IC50 value 6.09µg/mL. NMSP could induce S phase cell cycle arrest and apoptosis in HepG2 cells. Western blot analysis indicated that NMSP induced apoptosis is mitochondria-dependent. The novel 6-MP derivative discovered in this study is a promising drug candidate to be used as an anti-cancer agent.

  6-巯基嘌呤（6-MP）是第一种抑制癌细胞的活性代谢物抑制剂。这项研究的目的是研究6-MP衍生物的生物活性并发现新的抗癌药。合成了四个6-巯基嘌呤（6-MP）衍生物，并对其抗癌活性进行了分析。所有这些化合物均显示出对HepG2和A2780癌细胞的抗增殖作用。在合成的衍生物中，具有β-萘的6-（（萘-2-基甲基）硫基）-9H-嘌呤（NMSP）具有比其他化合物更好的抗癌活性，其IC 50为值6.09μg/ mL。NMSP可以诱导HepG2细胞S期细胞周期停滞和凋亡。Western印迹分析表明，NMSP诱导的细胞凋亡是线粒体依赖性的。在这项研究中发现的新型6-MP衍生物是有望用作抗癌药物的候选药物。
• Antimycobacterial Agents. 1. Thio Analogues of Purine
  作者：Ashish K. Pathak、Vibha Pathak、Lainne E. Seitz、William J. Suling、Robert C. Reynolds

  DOI：10.1021/jm030389b

  日期：2004.1.1

  Thio analogues of purine, pyridine, and pyrimidine were prepared based on the initial activity screening of several analogues of these heterocycles against Mycobacterium tuberculosis (Mtb). Certain 6-thio-substituted purine analogues described herein showed moderate to good inhibitory activity. In particular, two purine analogues 9-(ethylcarboxymethyl)-6-(decylthio)9H-purine (20) and 9-(ethylcarboxymethyl)-6-(dodecylthio)-9H-purine (21) exhibited MIC values of 1.56 and 0.78 mug/mL respectively against the Mtb H(37)Rv strain. N-9-Substitution apparently enhances the antimycobacterial activity in the purine series described herein.
• Ma, Yu-Qin; Yan, Xing; Du, Rong, Letters in drug design and discovery, 2016, vol. 13, # 6, p. 570 - 576
  作者：Ma, Yu-Qin、Yan, Xing、Du, Rong、Yang, Xiao-Guang、Li, Yu-Xin、Gao, Ying、Li, Wen-Liang

  DOI：——

  日期：——
• Alkylation of 6-thiopurine derivatives by the Mitsunobu reaction
  作者：Rafael Dias do Espírito Santo、Bianca Nascimento Monteiro da Silva、Jaime A. Rabi、Vagner D. Pinho

  DOI：10.1080/15257770.2022.2163501

  日期：——

  Abstract Alkylation of thiopurine derivatives with alcohols by the Mitsunobu reaction are reported in moderated to good yields. The method was applied in synthesis of number of thiopurine and thiopurine ribosides derivatives.

  摘要 据报道，通过 Mitsunobu 反应，硫嘌呤衍生物与醇的烷基化反应收率适中。将该方法应用于多种硫嘌呤和硫嘌呤核苷衍生物的合成。