(3aR)-5-iodo-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-ol | 166828-10-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR)-5-iodo-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-ol
• 英文别名: 5-iodo-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol；(3aS,4R,6aR)-5-iodo-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-ol
• CAS: 166828-10-0
• 化学式: C₈H₁₁IO₃
• 分子量: 282.078
• InChiKey: CHZQPISQCHBLHW-DSYKOEDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3aR)-5-iodo-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-ol 在 咪唑 、 正丁基锂 、 四丁基氟化铵 、 N-氟代双苯磺酰胺 作用下， 以 四氢呋喃 、 hexanes 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.67h， 生成 (3AS,4R,6AR)-5-氟代-2,2-二甲基-3A,6A-二氢-4H-环戊二烯[D][1,3]二氧六环-4-醇
  参考文献：
  名称：

  AHCY HYDROLASE INHIBITORS FOR TREATMENT OF HYPER HOMOCYSTEINEMIA

  摘要：

  本发明涉及式(I)的AHCY抑制剂，对于治疗高同型半胱氨酸水平疾病（如阿尔茨海默病）具有益处。该发明还涉及包含这些化合物的药物组合物，以及在治疗高同型半胱氨酸水平疾病中使用这些化合物和组合物。

  公开号：

  US20110160229A1
• 作为产物：
  描述：

  (3AS,4S,6AR)-2,2-二甲基-3A,6A-二氢-4H-环戊[D][1,3]二噁酚-4-醇 在 吡啶 、 sodium tetrahydroborate 、 cerium(III) chloride 、 碘 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 72.08h， 生成 (3aR)-5-iodo-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-ol
  参考文献：
  名称：

  AHCY HYDROLASE INHIBITORS FOR TREATMENT OF HYPER HOMOCYSTEINEMIA

  摘要：

  本发明涉及式(I)的AHCY抑制剂，对于治疗高同型半胱氨酸水平疾病（如阿尔茨海默病）具有益处。该发明还涉及包含这些化合物的药物组合物，以及在治疗高同型半胱氨酸水平疾病中使用这些化合物和组合物。

  公开号：

  US20110160229A1

文献信息

• 5′-Nor-3-Deaza-1′,6′-Isoneplanocin, the Synthesis and Antiviral Study
  作者：Qi Chen、Stewart W. Schneller、Chong Liu、Kathryn L. Jones、Tyler Singer

  DOI：10.3390/molecules25173865

  日期：——

  have been studied as a source for new antiviral agents. A convenient synthesis of C-5′-truncated 3-deaza-1′,6′-isoneplanocin, which combines the features of antiviral candidates 5′-noraristeromycin and 3-deaza-1′,6′-isoneplanocin is reported from (−)-cyclopentenone to give the two C-4′ epimers of 5′-nor-3-deaza isoneplanocin. Antiviral assays showed activity against the JC virus (EC50 = 1.12 µM for (4′R)-8;

  arbocyclic nucleosides aristeromycin 和 neplanocin 已被研究作为新的抗病毒药物的来源。据报道，C-5'-截短的 3-deaza-1',6'-isoneplanocin 的方便合成结合了抗病毒候选药物 5'-noraristeromycin 和 3-deaza-1',6'-isoneplanocin 的特征，来自 (- )-环戊烯酮产生 5'-nor-3-deaza isoneplanocin 的两个 C-4' 差向异构体。抗病毒分析显示对 JC 病毒有活性（对于 (4'R)-8，EC50 = 1.12 µM；对于 (4'S)-7，EC50 = 59.14 µM），并且两种化合物对几种 DNA 和 RNA 病毒均无活性。两种化合物均缺乏细胞毒性。
• AHCY hydrolase inhibitors for treatment of hyper homocysteinemia
  申请人：Converso Antonella

  公开号：US08629275B2

  公开（公告）日：2014-01-14

  The present invention is directed to AHCY inhibitors of formula (I): which are useful in the treatment of diseases characterized by high homocysteine levels, such as Alzheimer's disease. The invention is also directed to pharmaceutical compositions comprising the compounds, and to the use of the compounds and compositions in the treatment of diseases characterized by high homocysteine levels.

  本发明涉及公式(I)的AHCY抑制剂，其可用于治疗高同型半胱氨酸水平的疾病，如阿尔茨海默病。本发明还涉及包含该化合物的制药组合物，以及在治疗高同型半胱氨酸水平的疾病中使用该化合物和组合物的方法。
• Design and Synthesis of Bicyclo[4.3.0]nonene Nucleoside Analogues
  作者：Stephan Scheeff、Yan Wang、Mao-Yun Lyu、Behzad Nasiri Ahmadabadi、Sam Chun Kit Hau、Tony K. C. Hui、Yufeng Zhang、Zhong Zuo、Renee Wan Yi Chan、Billy Wai-Lung Ng

  DOI：10.1021/acs.orglett.3c03590

  日期：2023.12.22

  Nucleoside analogues are effective antiviral agents, and the continuous emergence of pathogenic viruses demands the development of novel and structurally diverse analogues. Here, we present the design and synthesis of novel nucleoside analogues with a carbobicyclic core, which mimics the conformation of natural ribonucleosides. Employing a divergent synthetic route featuring an intermolecular Diels–Alder

  核苷类似物是有效的抗病毒药物，病原病毒的不断出现需要开发新型且结构多样的类似物。在这里，我们展示了具有碳双环核心的新型核苷类似物的设计和合成，它模仿了天然核糖核苷的构象。采用分子间狄尔斯-阿尔德反应的不同合成路线，我们成功合成了对呼吸道合胞病毒具有高效抗病毒功效的碳双环核苷类似物。
• 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.
• Synthesis of Halogenated 9-(Dihydroxycyclopent-4′-enyl) Adenines and Their Inhibitory Activities Against<i>S</i>-Adenosylhomocysteine Hydrolase
  作者：Lak Shin Jeong、Jae Gyu Park、Won Jun Choi、Hyung Ryong Moon、Kang Man Lee、Hea Ok Kim、Hee-Doo Kim、Moon Woo Chun、Hea-Young Park、Kilhyoun Kim、Yhun Y. Sheen

  DOI：10.1081/ncn-120022686

  日期：2003.10

  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.