2-chloro-6-(cyclohexylamino)-9-(2'-deoxy-β-D-erythro-pentofuranosyl)-9H-purine | 146196-11-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2-chloro-6-(cyclohexylamino)-9-(2'-deoxy-β-D-erythro-pentofuranosyl)-9H-purine
• 英文别名: 2-chloro-6-cyclohexylamino-9-(2'-deoxy-β-D-erythro-pentofuranosyl)-9H-purine；6-cyclohexylamino-2-chloro-9-(2'-deoxy-β-D-ribofuranosyl)purine；(2R,3S,5R)-5-[2-chloro-6-(cyclohexylamino)purin-9-yl]-2-(hydroxymethyl)oxolan-3-ol
• CAS: 146196-11-4
• 化学式: C₁₆H₂₂ClN₅O₃
• 分子量: 367.835
• InChiKey: AGLVJWCZPBFXMM-QJPTWQEYSA-N

物化性质

• 沸点：
  624.6±65.0 °C(Predicted)
• 密度：
  1.70±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-chloro-6-(cyclohexylamino)-9-(2'-deoxy-β-D-erythro-pentofuranosyl)-9H-purine 在 溶剂黄146 作用下， 以 水 为溶剂， 生成 2-chloro-N-cyclohexyl-9H-purin-6-amine
  参考文献：
  名称：

  Determination Of 2-Chloro-2′-deoxyadenosine (Antileukemic Agent) and Related Compounds by Electrochemical Method

  摘要：

  Electrochemical method for determination of 2-chloro-2'-deoxyadenosine and related compounds modified in exocyclic 6-NH2 group is described. Electrochemical detection of investigated compounds, based on the electrooxidation process of the adenine moiety, has been performed in aqueous solutions, in the pH range 2-9, on a glassy carbon electrode.

  DOI：

  10.1080/15257779908041649
• 作为产物：
  描述：

  2,6-二氯-9-(3,5-二-O-对甲苯甲酰基-2-脱氧-beta-D-赤式-呋喃戊糖基)嘌呤 在 氨 作用下， 以 甲醇 为溶剂， 反应 80.0h， 生成 2-chloro-6-(cyclohexylamino)-9-(2'-deoxy-β-D-erythro-pentofuranosyl)-9H-purine
  参考文献：
  名称：

  N-Cycloalkyl Derivatives of Adenosine and 1-Deazaadenosine as Agonists and Partial Agonists of the A₁ Adenosine Receptor

  摘要：

  A number of cycloalkyl substituents (from C-3 to C-8) have been int-reduced on the 6-amino group of adenosine, 1-deazaadenosine, and 2'-deoxyadenosine, bearing or not a chlorine atom at the 2-position, to evaluate the influence on the A(1) and A(2A) affinity of steric hindrance and lipophilicity. Furthermore, the guanosine 5'-triphosphate (GTP) shift and the maximal induction of guanosine 5'-(gamma-thio)triphosphate ([S-35]GTP gamma S) binding to G proteins in rat brain membranes were used to determine the intrinsic activity of these nucleosides at the A(1) adenosine receptor. All compounds of the ribose-bearing series proved to be full agonists, the 1-deaza derivatives showing affinities for the Al receptor about 10-fold lower than the corresponding adenosines. On the other hand, all the 2'-deoxyribose derivatives bind to the A(1) receptor with affinities in the high nanomolar range, with the 2-chloro substituted compounds showing slightly higher affinities than the 2-unsubstituted counterparts. In terms of the potencies, the most potent compounds proved to be those bearing four- and five-membered rings. Both GTP shifts and [S-35]-GTP gamma S experiments showed that most of the 2'-deoxyadenosine derivatives are partial agonists, The 2'-deoxyadenosine derivatives which were identified as partial agonists consistently detected fewer Az receptors in the high-affinity state than full agonists. However, it is worthwhile noting that there was not a simple Linear relationship between receptor occupancy and activation. These results indicate that a critical density of A(1) adenosine receptors in the high-affinity state is required for G protein activation.

  DOI：

  10.1021/jm9911231

文献信息

• Base-Modified Nucleosides Related to 2-Chloro-2?-deoxyadenosine
  作者：Zygmunt Kazimierczuk、Juhani A. Vilpo、Frank Seela

  DOI：10.1002/hlca.19920750715

  日期：1992.11.11

  Derivatives of 2-chloro-2′-deoxyadenosine (1a) containing secondary 6-NH2 groups (5a-c) or a 8-Br substituent (9) were synthesized. They were tested together with ring-modified congeners containing a pyrrolo[2,3-b]pyridine, pyrrolo[3,2-c]pyridine, or pyrazolo[3,4-d]pyrimidine ring system as inhibitors of various leukemic cell lines. Only the 8-Br derivatives 9 showed inhibitory activity, whereas the

  合成了含有仲6-NH 2基团（5a-c）或8-Br取代基（9）的2-氯-2'-脱氧腺苷（1a）的衍生物。将它们与含有吡咯并[2,3- b ]吡啶，吡咯并[3,2- c ]吡啶或吡唑并[3,4- d ]嘧啶环系统作为各种白血病细胞系抑制剂的环修饰同类物一起进行了测试。。仅8-Br衍生物9表现出抑制活性，而碱基修饰的同类物没有活性。化合物1a在ap K a = 1.4（2'-脱氧腺苷在p K a= 3.8）。质子化发生在N（7），而不是在dA观察到的N（1）。
• US6498241B1
  申请人：——

  公开号：US6498241B1

  公开（公告）日：2002-12-24