(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 | 663190-27-0

• 物质功能分类: 化学试剂 - 有机试剂 - 烯烃（环状与无环状）
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (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
• 英文名称: 5-fluoro-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol
• 英文别名: (3aS,4R,6aR)-5-fluoro-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-ol；(3aS,4R,6aR)-5-Fluoro-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-ol
• CAS: 663190-27-0
• 化学式: C₈H₁₁FO₃
• 分子量: 174.172
• InChiKey: KXHQSLVTKGWHSK-DSYKOEDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 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：
  4

反应信息

• 作为反应物：
  描述：

  (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 在 18-crown-8 、 potassium carbonate 作用下， 生成 9-(5-fluoro-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl)-9H-purin-6-ylamine
  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
• 作为产物：
  描述：

  在 N-碘代丁二酰亚胺 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 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：

  对映体 4'-截短的 6'-fluoro-3-deazaneplanocin 及其 3-溴衍生物：合成和抗病毒特性，包括埃博拉病毒和马尔堡病毒

  摘要：

  为了增加含氟腺嘌呤衍生的碳环核苷抗病毒候选药物的文库，d- like 和l -like 6'-fluoro-3-deazaneplanocin 及其缺乏 4'-羟基亚甲基取代基的 3-溴衍生物（2 / 3和4 / 5，分别）。它们的合成是从d-核糖通过开发比文献建议的更容易的前体途径完成的。该2 / 4 d样对显示显著抗费罗维里的性质，同时对映异构体升样同源3 / 5不活跃。目标化合物2 / 4对麻疹和诺如病毒也有活性。的效果2 / 4的作用是氟腺嘌呤衍生碳环核苷的进一步的证据可以在抗病毒药物发现播放。此外，它们合成的简单性使它们具有更有效的类似物和放大优化。2 / 3和4 / 5没有其他相关的抗病毒特性（3 / 5 的BK 多瘤病毒除外）。

  DOI：

  10.1016/j.bmcl.2021.127985

文献信息

• AHCY HYDROLASE INHIBITORS FOR TREATMENT OF HYPER HOMOCYSTEINEMIA
  申请人：Converso Antonella

  公开号：US20110160229A1

  公开（公告）日：2011-06-30

  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。
• 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。
• 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.
• Truncated Fluorocyclopentenyl Pyrimidines as <i>S</i>-Adenosylhomocysteine Hydrolase Inhibitors
  作者：Yeon Hee Park、Won Jun Choi、Amol S. Tipnis、Kang Man Lee、Lak Shin Jeong

  DOI：10.1080/15257770903054316

  日期：2009.8.11

  On the basis of inhibitory activity of truncated cyclopentenyl cytosine against S-adenosylhomocysteine hydrolase (SAH), its fluorocyclopentenyl Pyrimidine derivatives were efficiently synthesized from D-ribose via electrophilic fluorination as a key step. The final nucleosides were evaluated for SAH inhibitory activity, among which the uracil derivative 9 showed significant inhibitory activity (IC50 = 8.53 mu M). They were also evaluated for cytotoxic effects in several human cancer cell lines such as fibro sarcoma, stomach cancer, Leukemia, and colon cancer, but they did not show any cytotoxic effects up to 100 mu M, indicating that 4'-hydroxymethyl groups are essential for the anticancer activity.
• US8629275B2
  申请人：——

  公开号：US8629275B2

  公开（公告）日：2014-01-14