(1'S,4'R)-4'-(6-chloropurin-9-yl)-1'-methoxycarbonyl-cyclopent-2'-ene | 288866-42-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: (1'S,4'R)-4'-(6-chloropurin-9-yl)-1'-methoxycarbonyl-cyclopent-2'-ene
• 英文别名: (1R,3S)-1-[9-(1-chloroadenenyl)]-3-methylcarboxy-4-cyclopentene；methyl (1S,4R)-4-(6-chloropurin-9-yl)cyclopent-2-ene-1-carboxylate
• CAS: 288866-42-2
• 化学式: C₁₂H₁₁ClN₄O₂
• 分子量: 278.698
• InChiKey: OUVRSHUFVJAKPU-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  69.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1'S,4'R)-4'-(6-chloropurin-9-yl)-1'-methoxycarbonyl-cyclopent-2'-ene 在 四氧化锇 、 N-甲基吲哚酮 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以74%的产率得到
  参考文献：
  名称：

  钯催化碳核苷的对映选择性合成

  摘要：

  已开发出用于对映选择性合成多种碳核苷的一般策略。关键步骤是 Pd(0) 催化的 cis-3,5-dibenzoyloxycyclopent-2-ene 10a 与核碱基的对映选择性烯丙基胺化。使用鸟嘌呤衍生的核碱基 13 和手性配体 9，获得了 93-96% 的 ee，而 6-氯嘌呤和手性配体 8 获得了 94% 的 ee。该反应之后是与苯磺酰基（硝基）甲烷 6 进行第二次 Pd（0）催化的烯丙基烷基化反应。由此获得的硝基砜用作多用途中间体，用于发散合成，其中苯磺酰基（硝基）甲基是羟甲基侧链。使用鸟嘌呤衍生的核碱基 13，从 10a 仅通过四步即可获得 (-)-卡波韦。以 6-氯嘌呤作为腺嘌呤等价物，

  DOI：

  10.1021/ja9938837
• 作为产物：
  描述：

  (1S,4R)-4-甲基环戊-2-烯甲酸甲酯盐酸盐 在 甲烷磺酸 、 三乙胺 、 tin(ll) chloride 作用下， 以 乙醇 为溶剂， 反应 8.83h， 生成 (1'S,4'R)-4'-(6-chloropurin-9-yl)-1'-methoxycarbonyl-cyclopent-2'-ene
  参考文献：
  名称：

  Metal Coordination-Based Inhibitors of Adenylyl Cyclase:  Novel Potent P-Site Antagonists

  摘要：

  The adenylyl cyclases (ACS) are a family of intracellular enzymes associated with signal transduction by virtue of their ability to convert ATP to cAMP. The catalytic mechanism of this transformation proceeds through initial binding of ATP to the so-called purine binding site (P-site) of the enzyme followed by metal-mediated cyclization with loss of pyrophosphate. Crystallographic analysis of ACs with known inhibitors reveals the presence of two metals in the active site. Presently, nine isoforms of adenylyl cyclase are known, and unique isoform combinations are expressed in a tissue-specific manner. The development of isoform-specific inhibitors of adenylyl cyclase may prove to be a useful strategy toward the design of unique signal transduction inhibitors. To develop novel AC inhibitors, we have chosen an approach to inhibitor design utilizing an adenine ring system joined to a metal-coordinating hydroxamic acid via various linkers. Previous work in our group has validated this approach and identified novel inhibitors that possess an adenine ring joined to a metal-coordinating hydroxamic acid through flexible acyclic linkers (Levy, D. E., et al. Bioorg. Med. Chem. Lett. 2002, 12, 30853088). Subsequent studies have focused on the introduction of conformational restrictions into the tether of the inhibitors with the goal of increasing potency (Levy, D. E., et al. Bioorg. Med. Chem. Lett. 2002, 12, 3089-3092). Building upon the favorable spatial positioning of the adenine and hydroxamate groups coupled with potentially favorable entropic factors, the unit joining the carbocycle to the hydroxamate was explored further and a stereochemical-based SAR was elucidated, leading to a new series of highly potent AC inhibitors.

  DOI：

  10.1021/jm0205604