5-bromo-2,2-dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one | 663190-22-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-bromo-2,2-dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one
• 英文别名: (3aR,6aR)-5-bromo-2,2-dimethyl-3a,6a-dihydrocyclopenta[d][1,3]dioxol-4-one
• CAS: 663190-22-5
• 化学式: C₈H₉BrO₃
• 分子量: 233.062
• InChiKey: CMLPHFHICUGUMV-IYSWYEEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-bromo-2,2-dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one 在 吡啶 、 sodium tetrahydroborate 、 二甲基硫 、 对甲苯磺酸 、 臭氧 作用下， 以 丙酮 为溶剂， 生成 methyl(2R,3R,4S,5S)-3,4-dimethylmethylenedioxy-5-methoxy-2,3,4,5-tetrahydrofuran-2-carboxylate
  参考文献：
  名称：

  Chemoenzymic Synthesis of 4-Substituted Riboses. S-(4'-Methyladenosyl)-L-homocysteine

  摘要：

  The synthesis of 4-C-methyl-D-ribose, 4-C-methyl-D-ribose, D-ribose-4-d, and L-ribose derivatives as well as the title nucleoside by a chemoenzymatic strategy beginning from cyclopentadiene is described.

  DOI：

  10.1021/jo00099a005
• 作为产物：
  描述：

  (-)-(3Ar,6ar)-3a,6a-二氢-2,2-二甲基-4H-环戊并-1,3-二氧代-4-酮 在 溴 、 三乙胺 作用下， 以87%的产率得到5-bromo-2,2-dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one
  参考文献：
  名称：

  Synthesis of Halogenated 9-(Dihydroxycyclopent-4′-enyl) Adenines and Their Inhibitory Activities AgainstS-Adenosylhomocysteine Hydrolase

  摘要：

  Novel halovinyl analogues of neplanocin A without 4'-hydroxymethyl group were easily synthesized starting from D-ribose via cyclopentenone 5 as a key intermediate and their inhibitory activity against SAH hydrolase was assayed.

  DOI：

  10.1081/ncn-120022686

文献信息

• X-ray Crystal Structure and Binding Mode Analysis of Human <i>S</i>-Adenosylhomocysteine Hydrolase Complexed with Novel Mechanism-Based Inhibitors, Haloneplanocin A Analogues
  作者：Kang Man Lee、Won Jun Choi、Yoonji Lee、Hyun Joo Lee、Long Xuan Zhao、Hyuk Woo Lee、Jae Gyu Park、Hea Ok Kim、Kwang Yeon Hwang、Yong-Seok Heo、Sun Choi、Lak Shin Jeong

  DOI：10.1021/jm1010836

  日期：2011.2.24

  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.