(2R,3S,4S)-3-ethyl-4-(2-hydroxy-tridecyl)-oxetan-2-one | 1151391-93-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R,3S,4S)-3-ethyl-4-(2-hydroxy-tridecyl)-oxetan-2-one
• 英文别名: (3S,4S)-3-ethyl-4-[(2R)-2-hydroxytridecyl]oxetan-2-one
• CAS: 1151391-93-3
• 化学式: C₁₈H₃₄O₃
• 分子量: 298.466
• InChiKey: OLQWKGFSXJCZAZ-IKGGRYGDSA-N

物化性质

• 沸点：
  414.7±18.0 °C(predicted)
• 密度：
  0.953±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  21
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-甲酰甘氨酸 、 (2R,3S,4S)-3-ethyl-4-(2-hydroxy-tridecyl)-oxetan-2-one 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 xylene 、 二氯甲烷 为溶剂， 反应 13.0h， 以99%的产率得到(R)-1-((2S,3S)-3-ethyl-4-oxooxetan-2-yl)tridecan-2-yl-methanamido ethanoate ester
  参考文献：
  名称：

  BETA-LACTONE COMPOUNDS

  摘要：

  本发明提供具有一般结构A的化合物，或其药学上可接受的衍生物：其中R是烷基基团，R1包括至少一种从烷基、烯基、芳基、杂环、羟基、酯、酰胺、醛基和卤素组成的基团。

  公开号：

  US20090124681A1
• 作为产物：
  描述：

  (R)-3-(tert-butyldimethylsiloxy)tetradecanal 以58%的产率得到(2R,3S,4S)-3-ethyl-4-(2-hydroxy-tridecyl)-oxetan-2-one
  参考文献：
  名称：

  BETA-LACTONE COMPOUNDS

  摘要：

  本发明提供具有一般结构A的化合物，或其药学上可接受的衍生物：其中R是烷基基团，R1包括至少一种从烷基、烯基、芳基、杂环、羟基、酯、酰胺、醛基和卤素组成的基团。

  公开号：

  US20090124681A1

文献信息

• Beta-lactone compounds
  申请人：Burnham Institute for Medical Research

  公开号：US08258321B2

  公开（公告）日：2012-09-04

  The present invention provides compounds having the general structure A, or a pharmaceutically acceptable derivatives thereof: wherein R is an alkyl group, and R1 comprises at least one moiety selected from a group consisting of an alkyl, an alkenyl, an aryl, a heterocycle, hydroxyl, ester, amido, aldehyde, and a halogen.

  本发明提供具有一般结构A或其药学上可接受的衍生物的化合物：其中R为烷基，R1包括至少一种从烷基，烯基，芳基，杂环，羟基，酯，酰胺，醛和卤素组成的基团。
• Synthesis of Novel β-Lactone Inhibitors of Fatty Acid Synthase
  作者：Robyn D. Richardson、Gil Ma、Yatsandra Oyola、Manuel Zancanella、Lynn M. Knowles、Piotr Cieplak、Daniel Romo、Jeffrey W. Smith

  DOI：10.1021/jm800321h

  日期：2008.9.11

  Fatty acid synthase (FAS) is necessary for growth and survival of tumor cells and is a promising drug target for oncology. Here, we report oil the syntheses and activity of novel inhibitors of the thioesterase domain of FAS. Using the structure of orlistat as a starting point, which contains a beta-lactone as the central pharmacophore, 28 novel congeners were synthesized and examined. Structural features such as the length of the alpha- and beta-alkyl chains, their chemical composition, and arnino ester substitutions were altered and tile resulting compounds explored for inhibitory activity toward the thioesterase domain of FAS. Nineteen congeners show improved potency for FAS in biochemical assays relative to orlistat. Three of that subset, including the natural product valilactone, also display all increased potency in inducing tumor cell death and improved solubility compared to orlistat. These findings Support the idea that all orlistat congener can be optimized for use in a preclinical drug design and for clinical drug development.
• US8258321B2
  申请人：——

  公开号：US8258321B2

  公开（公告）日：2012-09-04
• [EN] BETA-LACTONE COMPOUNDS<br/>[FR] COMPOSÉS DE BÊTA-LACTONE
  申请人：BURNHAM INST MEDICAL RESEARCH

  公开号：WO2009059046A1

  公开（公告）日：2009-05-07

  The present invention provides compounds having the general structure A3 or a pharmaceutically acceptable derivatives thereof: wherein R is an alkyl group, and Ri comprises at least one moiety selected from a group consisting of an alkyl, an alkenyl, an aryl, a heterocycle, hydroxyl, ester, amido, aldehyde, and a halogen.
• [EN] METHOD AND COMPOSITIONS FOR TREATING OBESITY AND INSULIN RESISTANCE<br/>[FR] MÉTHODE ET COMPOSITIONS DE TRAITEMENT DE L'OBÉSITÉ ET DE LA RÉSISTANCE À L'INSULINE
  申请人：OKLAHOMA MED RES FOUND

  公开号：WO2019112996A1

  公开（公告）日：2019-06-13

  The present invention provides a method of treating obesity in a patient by upregulation of mitochondrial chaperones comprising the steps of: providing a pharmaceutically effective amount of a cDNA composition encoding one or more cellular proteins to increase the one or more cellular proteins in the cell and reduced adiposity in the patient.