methanesulfonic acid 6-benzyloxymethyl-5-iodo-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl ester | 643760-44-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methanesulfonic acid 6-benzyloxymethyl-5-iodo-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl ester
• 英文别名: [(3aR,6R,6aR)-5-iodo-2,2-dimethyl-4-(phenylmethoxymethyl)-6,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-6-yl] methanesulfonate
• CAS: 643760-44-5
• 化学式: C₁₇H₂₁IO₆S
• 分子量: 480.321
• InChiKey: SAQCCJHIKYWHKB-OWCLPIDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  79.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methanesulfonic acid 6-benzyloxymethyl-5-iodo-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl ester 在 18-冠醚-6 、 三氯化硼 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 1.5h， 生成 5-(6-amino-purin-9-yl)-4-iodo-3-hydroxymethyl-cyclopent-3-ene-1,2-diol
  参考文献：
  名称：

  X-ray Crystal Structure and Binding Mode Analysis of Human S-Adenosylhomocysteine Hydrolase Complexed with Novel Mechanism-Based Inhibitors, Haloneplanocin A Analogues

  摘要：

  The X-ray crystal structure of human S-adenosylhomocysteine (AdoHcy) hydrolase was first determined as a tetrameric form bound with the novel mechanism-based inhibitor fluoroneplanocin A (4b). The crystallized enzyme complex showed the closed conformation and turned out to be the intermediate of mechanism-based inhibition. It confirmed that the cofactor depletion by 3'-oxidation of fluoroneplanocin A contributes to the enzyme inhibition along with the irreversible covalent modification of AdoHcy hydrolase. In addition, a series of haloneplanocin A analogues (4b-e and 5b-e) were designed and synthesized to characterize the binding role and reactivity of the halogen substituents and the 4'-CH2OH group. The biological evaluation and molecular modeling studies identified the key pharmacophores and structural requirements for the inhibitor binding of AdoHcy hydrolase. The inhibitory activity was decreased as the size of the halogen atom increased and/or if the 4'-CH2OH group was absent. These results could be utilized to design new therapeutic agents operating via AdoHcy hydrolase inhibition.

  DOI：

  10.1021/jm1010836
• 作为产物：
  描述：

  (4R,5R)-3-benzyloxymethyl-4,5-isopropylidenedioxycyclopent-2-enone 在 吡啶 、 sodium tetrahydroborate 、 cerium(III) chloride 、 碘 、 三乙胺 作用下， 以 四氯化碳 为溶剂， 反应 7.0h， 生成 methanesulfonic acid 6-benzyloxymethyl-5-iodo-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl ester
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Halo-neplanocin A as Novel Mechanism-Based Inhibitors ofS-Adenosylhomocysteine Hydrolase

  摘要：

  Halogenated analogues of neplanocin A were synthesized from the key intermediate 1, among which fluoro-neplanocin A was found to be novel mechanism-based irreversible inhibitor of S-Adenosylhomocysteine hydrolase.

  DOI：

  10.1081/ncn-120021961