1,3-二氢-6-(甲基硫代)-2H-嘌呤-2-酮 | 22514-96-1

• 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: 1,3-二氢-6-(甲基硫代)-2H-嘌呤-2-酮
• 中文别名: 6-甲硫基-2-羟基嘌呤
• 英文名称: 2-hydroxy-6-methylthiopurine
• 英文别名: 2-Hydroxy-6-methylmercapto-purin；6-methylsulfanyl-3,7-dihydropurin-2-one
• CAS: 22514-96-1
• 化学式: C₆H₆N₄OS
• mdl: MFCD24394208
• 分子量: 182.206
• InChiKey: GSIUARFGUJCVDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  95.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-(R)-4-Amino-2-methyl-pent-2-en-1-ol 、 1,3-二氢-6-(甲基硫代)-2H-嘌呤-2-酮 在 三乙胺 作用下， 以 正丁醇 为溶剂， 反应 3.0h， 以90%的产率得到(1'R)-2-hydroxy-1'-methylzeatin
  参考文献：
  名称：

  Synthesis and Absolute Configuration of the Green Alga Cytokinin 2-Hydroxy-1'-methylzeatin

  摘要：

  The correctness of the gross structure of the marine green alga cytokinin 2-hydroxy-1'-methylzeatin (1) has been confirmed as a result of the chiral syntheses of (1'R)-1 and (1'S)-1. An indirect comparison of the cytokinin activity of the natural cytokinin with those of the synthetic enantiomers suggests that the R configuration may be assigned to the natural one unless it would be racemic.

  DOI：

  10.3987/com-91-5920

文献信息

• NOVEL KINASE MODULATORS
  申请人：MUTHUPPALANIAPPAN Meyyappan

  公开号：US20110118257A1

  公开（公告）日：2011-05-19

  The present invention provides PI3K protein kinase modulators, methods of preparing them, pharmaceutical compositions containing them and methods of treatment, prevention and/or amelioration of kinase mediated diseases or disorders with them.

  本发明提供了PI3K蛋白激酶调节剂，其制备方法，含有它们的药物组合物，以及使用它们进行激酶介导的疾病或紊乱的治疗、预防和/或改善的方法。
• NOVEL COMPOUNDS AS MODULATORS OF PROTEIN KINASES
  申请人：NAGARATHNAM Dhanapalan

  公开号：US20120289496A1

  公开（公告）日：2012-11-15

  The present invention provides PI3K protein kinase modulators, methods of preparing them, pharmaceutical compositions containing them and methods of treatment, prevention and/or amelioration of kinase mediated diseases or disorders with them.

  本发明提供了PI3K蛋白激酶调节剂，其制备方法，含有它们的药物组合物，以及使用它们进行治疗、预防和/或改善激酶介导的疾病或紊乱的方法。
• Purines. LV. Syntheses and Cytokinin Activities of Some Adenine and Adenosine Derivatives Related to 1'-Methylzeatin.
  作者：Tozo FUJII、Masashi OHBA、Hitoshi KAWAMURA、Tsuyoshi HANEISHI、Satoshi MATSUBARA

  DOI：10.1248/cpb.41.1362

  日期：——

  (1'S)-1-Methyl-cis-zeatin [(1'S)-2] and its 9-β-D-ribofuranoside [(1"S)-4] were synthesized from L-alanine through [S-(Z)]-4-amino-2-methyl-2-penten-1-ol ethanedioate [(S)-3]. Condensations of 2-hydroxy-6-methylthiopurine (16) with the trans-isomeric amine salt [(S)-15], its enantiomer [(R)-15], and the racemic modification [(±)-15] furnished (1'S)-, (1'R)-, and (±)-2-hydroxy-1'-methyl-trans-zeatine (6), respectively. A similar condensation of 16 with methylamine yielded 2-hydroxy-N6-methyladenine (7). These adenine derivatives were tested for cytokinin activity in the tobacco callus bioassay, and the order of their activity was (1'R)-6>(±)-6>(1'S)-2>7; on the other hand, (1"S)-4 and (1'S)-6 were completely inactive at 0.1-100μM and 0.01-10μM concentrations, respectively. As a result of the above syntheses of (1'R)-6, (1'S)-6, (±)-6, and 7, the gross structures of a marine green alga cytokinin and of a blue coral cytokinin were established to be 6 and 7, respectively.

  以L-丙氨酸为原料，通过[S-(Z)]合成(1'S)-1-甲基-顺式玉米素[(1'S)-2]及其9-β-D-呋喃核苷[(1"S)-4] -4-氨基-2-甲基-2-戊烯-1-醇乙二酸酯[(S)-3] 2-羟基-6-甲基硫嘌呤(16)与反式异构胺盐[(S)-15]、其对映体[(R)-15]和外消旋体[(±)-15]提供(1'S)-、(1'R)-和(± )-2-羟基-1'-甲基-反式-玉米丁(6)，分别用甲胺进行类似的缩合，得到2-羟基-N6-甲基腺嘌呤(7)。烟草愈伤组织生物测定中的细胞分裂素活性，其活性顺序为(1'R)-6>(±)-6>(1'S)-2>7；另一方面，(1"S)-4和(1'S)-6 分别在 0.1-100μM 和 0.01-10μM 浓度下完全失活。作为(1'R)-6、(1'S)-6、(±)-6和7的上述合成的结果，海洋绿藻细胞分裂素和蓝珊瑚细胞分裂素的总体结构被确定为分别为6和7。
• Structures of cytokinins influence synergistic production of ethylene
  作者：Yeong-Biau Yu、Shang Fa Yang、Joseph Corse、Judy A. Kuhnle、Sui-Sheng Hua

  DOI：10.1016/0031-9422(81)80002-7

  日期：1981.1

  Abstract Twenty-five naturally occurring cytokinins and structurally related compounds were tested for their ability to promote ethylene production synergistica

  摘要 测试了 25 种天然存在的细胞分裂素和结构相关化合物促进乙烯产生协同作用的能力。
• INHIBITORS OF HUMAN PHOSPHATIDYLINOSITOL 3-KINASE DELTA
  申请人：Sadhu Chanchal

  公开号：US20120172591A1

  公开（公告）日：2012-07-05

  Methods of inhibiting phosphatidylinositol 3-kinase delta isoform (PI3Kδ) activity, and methods of treating diseases, such as disorders of immunity and inflammation, in which PI3Kδ plays a role in leukocyte function are disclosed. Preferably, the methods employ active agents that selectively inhibit PI3Kδ, while not significantly inhibiting activity of other PI3K isoforms. Compounds are provided that inhibit PI3Kδ activity, including compounds that selectively inhibit PI3Kδ activity. Methods of using PI3Kδ inhibitory compounds to inhibit cancer cell growth or proliferation are also provided. Accordingly, the invention provides methods of using PI3Kδ inhibitory compounds to inhibit PI3Kδ-mediated processes in vitro and in vivo.

  本发明揭示了抑制磷脂酰肌醇3-激酶δ亚型（PI3Kδ）活性的方法，以及治疗免疫和炎症等疾病的方法，其中PI3Kδ在白细胞功能中发挥作用。优选地，这些方法采用能够选择性地抑制PI3Kδ而不显著抑制其他PI3K亚型活性的活性剂。提供了抑制PI3Kδ活性的化合物，包括选择性抑制PI3Kδ活性的化合物。还提供了使用PI3Kδ抑制剂化合物抑制癌细胞生长或增殖的方法。因此，本发明提供了使用PI3Kδ抑制剂化合物在体外和体内抑制PI3Kδ介导的过程的方法。