2-amino-6-chloro-7-methyl-7H-purine | 38119-33-4

• 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: 2-amino-6-chloro-7-methyl-7H-purine
• 英文别名: 6-chloro-7-methyl-7H-purin-2-amine；2-amino-6-chloro-7-methylpurine；6-chloro-7-methyl-7H-purin-2-ylamine；2-Amino-6-chlor-7-methyl-purin；6-chloro-7-methylpurin-2-amine
• CAS: 38119-33-4
• 化学式: C₆H₆ClN₅
• 分子量: 183.6
• InChiKey: BVZVAMWFBOLXDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  69.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-amino-6-chloro-7-methyl-7H-purine 在 sodium hydroxide 、 硫脲 作用下， 以 乙醇 为溶剂， 反应 12.33h， 生成 2-amino-6-methylthio-7-methylpurine
  参考文献：
  名称：

  天然嘌呤代谢产物含硫衍生物的合成及辐射防护性能

  摘要：

  鉴于氯在 7-甲基腺嘌呤中的低反应性，这些化合物被转化为它们的盐 (II, III)。质子化时带正电的碳正离子的形成增强了分子的亲电性，并促进了氯被硫置换。除 2-硫腺嘌呤 (IV) 外，盐 (II) 与硫脲缩合得到一些硫化物 (V)。2-氨基-6-氯-7-甲基嘌呤(IX)得到6-硫-7-甲基鸟嘌呤(X)和2-氨基-6-甲硫-7-甲基嘌呤(XI)。

  DOI：

  10.1007/bf00776334
• 作为产物：
  描述：

  氯甲烷 、 2-氨基-6-氯嘌呤 在 四丁基氢氧化铵 作用下， 以 水 、 乙腈 为溶剂， 反应 0.5h， 以48%的产率得到6-氯-9-甲基-9H-嘌呤-2-胺
  参考文献：
  名称：

  微波辐照下嘌呤的区域选择性烷基化反应

  摘要：

  通常在阴离子形成后通过用碱和烷基卤处理进行的嘌呤烷基化是复杂的，并且在最好的情况下，获得了N-烷基化化合物的混合物。嘌呤衍生物可以从N -7 和N -9 的烷基化中获得。在这项工作中，对反应条件进行了优化，以区域选择性地获得N -9 的烷基化产物。已经尝试了不同的碱，氢氧化四丁基铵产生了最好的结果。反应取决于所使用的碱和溶剂的类型，并且在使用微波辐照的帮助下显着改善，这也通过减少副产物的形成而显着减少了反应时间。

  DOI：

  10.1002/jhet.4407

文献信息

• Tricyclic Purine Analogs Derived from 2-Amino-6-chloropurine and 2,6-Diaminopurine and Their Methylated Quaternary Salts
  作者：Kateřina Hořejší、Radek Pohl、Antonín Holý

  DOI：10.1135/cccc20060077

  日期：——

  A novel series of tricyclic, etheno-bridged purine analogs was sythesized from 2-amino-6-(substituted amino)-9-methylpurines by cyclization with chloroacetaldehyde, with particular focus on the regioselectivity of the cyclization reaction and fluorescence properties. The analogs as well as the starting purines were alkylated with iodomethane, affording a new class of quaternary salts with potential biological activity. Neither significant fluorescence nor cytostatic effect was found.

  一系列新型三环、乙烯桥联嘌呤类似物从2-氨基-6-(取代氨基)-9-甲基嘌呤通过与氯乙醛环化合成，特别关注环化反应的区域选择性和荧光性质。这些类似物以及起始嘌呤均与碘甲烷烷基化，形成一类具有潜在生物活性的季铵盐。未发现显著的荧光或细胞静止效应。
• [EN] HIV REPLICATION INHIBITING PURINE DERIVATIVES<br/>[FR] DERIVES DE PURINE SERVANT A INHIBER LA REPLICATION DU VIH
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2005028479A3

  公开（公告）日：2005-06-16
• The discovery of purine-based agents targeting triple-negative breast cancer and the αB-crystallin/VEGF protein–protein interaction
  作者：Nelly A. Fosu-Mensah、Wen Jiang、Andrea Brancale、Jun Cai、Andrew D. Westwell

  DOI：10.1007/s00044-018-2275-9

  日期：2019.2

  Oestrogen receptor-negative breast cancer, particularly subtypes such as triple-negative breast cancer (TNBC, around 10-15% of cases), are characterised by poor long-term survival, poor response to therapy and early progression to metastasis. Purine-based compounds represent a privileged scaffold in anticancer drug design, with several clinically approved and experimental agents in clinical development comprising a purine core structure. In this study, a series of new purine-based compounds were synthesised; seven of the new analogues were found to significantly reduce the in vitro viability of TNBC cell lines (MDA-MB-231 and MDA-MB-436) with IC50 values of 50M. In previous work, we have proposed a new concept for targeting angiogenesis driving TNBC progression, by disrupting the protein-protein interaction between the molecular chaperone B-crystallin (CRYAB) and VEGF. Since previous clinical studies applying anti-VEGF therapy to TNBC patients have met with limited success, we were interested to test our most promising purine analogues against CRYAB/VEGF, using a custom-designed cell-based CRYAB/VEGF(165) interaction assay platform. Analogues 4e and 4f significantly reduced the interaction between CRYAB/VEGF(165), and compound 4e (100M) was also found to decrease the levels of soluble VEGF expressed by MDA-MB-231 cells by 40%. In conclusion, these promising early activity profiles warrant further investigation to validate this concept.
• Jakobsen, Erik; Gundersen, Lise-Lotte, Heterocycles, 2000, vol. 53, # 4, p. 935 - 940
  作者：Jakobsen, Erik、Gundersen, Lise-Lotte

  DOI：——

  日期：——
• HIV REPLICATION INHIBITING PURINE DERIVATIVES
  申请人：Janssen Pharmaceutica NV

  公开号：EP1668011B1

  公开（公告）日：2011-03-02