(5S)-5-(chloromethyl)oxolan-2-one | 179797-19-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (5S)-5-(chloromethyl)oxolan-2-one
• CAS: 179797-19-4
• 化学式: C₅H₇ClO₂
• 分子量: 134.562
• InChiKey: HPLJEKXDAFHJPD-BYPYZUCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5S)-5-(chloromethyl)oxolan-2-one 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 以84%的产率得到(S)-5-Chloromethyl-tetrahydro-furan-2-ol
  参考文献：
  名称：

  具有组胺H（1）受体拮抗剂活性的5-脂氧合酶抑制剂。

  摘要：

  设计了一系列具有5-脂氧合酶（5-LO）抑制和组胺H（1）受体拮抗剂活性的新型化合物，用于治疗哮喘。这些双功能化合物分别通过连接5-LO和H（1）药效团，N-羟基脲和二苯甲基哌嗪制备。观察到了一系列的体外活性，呋喃类似物10在动物模型中证明了这两种活性。将观察到的活性与单功能药物进行比较。

  DOI：

  10.1016/j.bmcl.2004.02.005
• 作为产物：
  描述：

  (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 在 吡啶 、 氯化亚砜 作用下， 以90%的产率得到(5S)-5-(chloromethyl)oxolan-2-one
  参考文献：
  名称：

  具有组胺H（1）受体拮抗剂活性的5-脂氧合酶抑制剂。

  摘要：

  设计了一系列具有5-脂氧合酶（5-LO）抑制和组胺H（1）受体拮抗剂活性的新型化合物，用于治疗哮喘。这些双功能化合物分别通过连接5-LO和H（1）药效团，N-羟基脲和二苯甲基哌嗪制备。观察到了一系列的体外活性，呋喃类似物10在动物模型中证明了这两种活性。将观察到的活性与单功能药物进行比较。

  DOI：

  10.1016/j.bmcl.2004.02.005

文献信息

• Fused pyrazole derivatives and methods of treatment of metabolic-related disorders thereof
  申请人：Boatman Douglas P.

  公开号：US20060205955A1

  公开（公告）日：2006-09-14

  The present invention relates to certain fused pyrazole derivatives of Formula (Ia), and pharmaceutically acceptable salts thereof, which exhibit useful pharmacological properties, for example, as agonists for the RUP25 receptor. Also provided by the present invention are pharmaceutical compositions containing compounds of the invention, and methods of using the compounds and compositions of the invention in the treatment of metabolic-related disorders, including dyslipidemia, atherosclerosis, coronary heart disease, insulin resistance, type 2 diabetes, Syndrome-X and the like. In addition, the present invention also provides for the use of the compounds of the invention in combination with other active agents such as those belonging to the class of α-glucosidase inhibitors, aldose reductase inhibitors, biguanides, HMG-CoA reductase inhibitors, squalene synthesis inhibitors, fibrates, LDL catabolism enhancers, angiotensin converting enzyme (ACE) inhibitors, insulin secretion enhancers, DP receptor antagonists, and the like.

  本发明涉及某些融合吡唑衍生物的化合物（Ia）及其药学上可接受的盐，这些化合物展现出有用的药理特性，例如作为RUP25受体激动剂。本发明还提供了含有本发明化合物的药物组合物，以及使用这些化合物和组合物治疗代谢相关疾病的方法，包括血脂异常、动脉粥样硬化、冠心病、胰岛素抵抗、2型糖尿病、X综合症等。此外，本发明还提供了在与其他活性剂结合使用的本发明化合物的用途，例如属于α-葡萄糖苷酶抑制剂、醛糖还原酶抑制剂、双胍类药物、HMG-CoA还原酶抑制剂、角鲨烯合成抑制剂、贝特类药物、LDL降解增强剂、血管紧张素转换酶（ACE）抑制剂、胰岛素分泌增强剂、DP受体拮抗剂等类别的其他活性剂。
• FUSED PYRAZOLE DERIVATIVES AND METHODS OF TREATMENT OF METABOLIC-RELATED DISORDERS THEREOF
  申请人：Boatman P. Douglas

  公开号：US20090258892A1

  公开（公告）日：2009-10-15

  The present invention relates to certain fused pyrazole derivatives of Formula (Ia), and pharmaceutically acceptable salts thereof, which exhibit useful pharmacological properties, for example, as agonists for the RUP25 receptor. Also provided by the present invention are pharmaceutical compositions containing compounds of the invention, and methods of using the compounds and compositions of the invention in the treatment of metabolic-related disorders, including dyslipidemia, atherosclerosis, coronary heart disease, insulin resistance, type 2 diabetes, Syndrome-X and the like. In addition, the present invention also provides for the use of the compounds of the invention in combination with other active agents such as those belonging to the class of α-glucosidase inhibitors, aldose reductase inhibitors, biguanides, HMG-CoA reductase inhibitors, squalene synthesis inhibitors, fibrates, LDL catabolism enhancers, angiotensin converting enzyme (ACE) inhibitors, insulin secretion enhancers, DP receptor antagonists, and the like.

  本发明涉及公式（Ia）的某些融合吡唑衍生物及其药学上可接受的盐，其具有有用的药理特性，例如作为RUP25受体激动剂。本发明还提供了包含该化合物的制药组合物，并且提供了使用该化合物和组合物治疗代谢相关疾病的方法，包括脂质代谢异常、动脉硬化、冠心病、胰岛素抵抗、2型糖尿病、X综合症等。此外，本发明还提供了将该化合物与其他活性剂（例如属于α-葡萄糖苷酶抑制剂、醛糖还原酶抑制剂、双胍类、HMG-CoA还原酶抑制剂、角鲨烷合成抑制剂、纤维酸类、LDL降解增强剂、血管紧张素转换酶（ACE）抑制剂、胰岛素分泌增强剂、DP受体拮抗剂等类别）组合使用的用途。
• A Direct Method for the Conversion of Terminal Epoxides into γ-Butanolides
  作者：Mohammad Movassaghi、Eric N. Jacobsen

  DOI：10.1021/ja025604c

  日期：2002.3.1

  A new and efficient process for the conversion of terminal epoxides to gamma-butanolides is described involving Lewis acid promoted epoxide ring-opening by 1-morpholino-2-trimethylsilyl acetylene. Addition of a terminal epoxide to a solution of the ynamine and boron trifluoride diethyl etherate in dichloromethane at 0 degrees C rapidly affords a cyclic keteneaminal that can be hydrolyzed and protodesilylated under mild conditions to provide the corresponding gamma-butanolide in high yield. The net transformation is equivalent to an acetate enolate opening of terminal epoxides. The formation of a cyclic keteneaminal as the direct addition product was observed by monitoring of the reaction by IR and NMR spectroscopy. Functionalized gamma-lactones were prepared by the interception of the reactive cyclic keteneaminal prior to hydrolysis. Reactions with enantiomerically enriched terminal epoxides provide the corresponding gamma-butanolides without loss of optical activity. The compatibility of the present methodology with a wide range of functional groups is noteworthy.
• US7241792B2
  申请人：——

  公开号：US7241792B2

  公开（公告）日：2007-07-10
• US7612106B2
  申请人：——

  公开号：US7612106B2

  公开（公告）日：2009-11-03