(1S,3R)-1-hydroxy-3-(ethyl-carboxymethoxy)-4-cyclopentene | 426225-69-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1S,3R)-1-hydroxy-3-(ethyl-carboxymethoxy)-4-cyclopentene
• 英文别名: ethyl 2-[(1R,4S)-4-hydroxycyclopent-2-en-1-yl]oxyacetate
• CAS: 426225-69-6
• 化学式: C₉H₁₄O₄
• 分子量: 186.208
• InChiKey: FUPYYGUVNAYNPU-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,3R)-1-hydroxy-3-(ethyl-carboxymethoxy)-4-cyclopentene 在 sodium methylate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 生成 (1R,3R)-1-hydroxy-3-(methyl-carboxymethoxy)-4-cyclopentene
  参考文献：
  名称：

  Hydroxamate based inhibitors of adenylyl cyclase. Part 2: The effect of cyclic linkers on P-site binding

  摘要：

  The adenylyl cyclases (ACs) are a family of enzymes that are key elements of 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 purine binding site (P-site) followed by metal mediated cyclization with loss of pyrophosphate. Previous work in our group identified novel inhibitors which possess an adenine ring joined to a metal-coordinating hydroxamic acid through flexible linkers. Considering the spatial positioning of the metals with respect to the adenine binding site coupled with potentially favorable entropic factors, conformational restriction of the tether through a stereochemistry based SAR employing a rigid cyclic scaffold was explored. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00654-6
• 作为产物：
  描述：

  2-环戊烯-1-醇,4-[[(1,1-二甲基乙基)二甲基甲硅烷基]氧代]-,(1R,4S)- 在 dirhodium tetraacetate 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 (1S,3R)-1-hydroxy-3-(ethyl-carboxymethoxy)-4-cyclopentene
  参考文献：
  名称：

  Hydroxamate based inhibitors of adenylyl cyclase. Part 2: The effect of cyclic linkers on P-site binding

  摘要：

  The adenylyl cyclases (ACs) are a family of enzymes that are key elements of 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 purine binding site (P-site) followed by metal mediated cyclization with loss of pyrophosphate. Previous work in our group identified novel inhibitors which possess an adenine ring joined to a metal-coordinating hydroxamic acid through flexible linkers. Considering the spatial positioning of the metals with respect to the adenine binding site coupled with potentially favorable entropic factors, conformational restriction of the tether through a stereochemistry based SAR employing a rigid cyclic scaffold was explored. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00654-6

文献信息

• Regulation of type 5 adenylyl cyclase for treatment of neurodegenerative and cardiac diseases
  申请人：Vatner F. Stephen

  公开号：US20060252774A1

  公开（公告）日：2006-11-09

  The invention concerns pharmaceutical compositions that contain a compound or compounds that can effectively regulate the activity of Type 5 Adenylyl Cyclase and methods for treatment of neurological diseases and disorders, as well as motor function loss therefrom, as well as treatment for cardiac conditions and diseases including conditions characterized by abnormal heart rate.

  这项发明涉及含有一种或多种能够有效调节第5型腺苷酸环化酶活性的化合物的药物组合物，以及治疗神经系统疾病和障碍、以及由此引起的运动功能丧失的方法，以及用于治疗心脏疾病和疾病的方法，包括以异常心率为特征的情况。
• Hydroxamate based inhibitors of adenylyl cyclase. Part 2: The effect of cyclic linkers on P-site binding
  作者：Daniel E Levy、Ming Bao、James E Tomlinson、Robert M Scarborough

  DOI：10.1016/s0960-894x(02)00654-6

  日期：2002.11

  The adenylyl cyclases (ACs) are a family of enzymes that are key elements of 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 purine binding site (P-site) followed by metal mediated cyclization with loss of pyrophosphate. Previous work in our group identified novel inhibitors which possess an adenine ring joined to a metal-coordinating hydroxamic acid through flexible linkers. Considering the spatial positioning of the metals with respect to the adenine binding site coupled with potentially favorable entropic factors, conformational restriction of the tether through a stereochemistry based SAR employing a rigid cyclic scaffold was explored. (C) 2002 Elsevier Science Ltd. All rights reserved.