(2R,3S,4S)-4-(2-hydroxy-tridecyl)-3-methyl-oxetan-2-one | 1151392-01-6

• 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)-4-(2-hydroxy-tridecyl)-3-methyl-oxetan-2-one
• 英文别名: (3S,4S)-4-[(2R)-2-hydroxytridecyl]-3-methyloxetan-2-one
• CAS: 1151392-01-6
• 化学式: C₁₇H₃₂O₃
• 分子量: 284.439
• InChiKey: VSJZYCXVQANSKF-XHSDSOJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  20
• 可旋转键数：
  12
• 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

• 作为产物：
  描述：

  2-[(E)-1-(tert-Butyl-dimethyl-silanyloxy)-propenylsulfanyl]-pyridine 、 (R)-3-(tert-butyldimethylsiloxy)tetradecanal 在 zinc(II) chloride 、 氢氟酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 60.0h， 生成 (2R,3S,4S)-4-(2-hydroxy-tridecyl)-3-methyl-oxetan-2-one 、 (3R,4R)-4-[(2R)-2-hydroxytridecyl]-3-methyloxetan-2-one
  参考文献：
  名称：

  Synthesis of Novel β-Lactone Inhibitors of Fatty Acid Synthase

  摘要：

  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.

  DOI：

  10.1021/jm800321h

文献信息

• BETA-LACTONE COMPOUNDS
  申请人：Smith Jeffrey W.

  公开号：US20090124681A1

  公开（公告）日：2009-05-14

  The present invention provides compounds having the general structure A, or a pharmaceutically acceptable derivatives thereof: wherein R is an alkyl group, and R 1 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。
• PREPARATION METHOD OF (3S,4S)-3-HEXYL-4-((R)-2-HYDROXYTRIDECYL)-OXETAN-2-0NE AND THE PRODUCT OF THAT METHOD
  申请人：Qin Yong

  公开号：US20110046400A1

  公开（公告）日：2011-02-24

  The present invention relates to a method for the preparation of (3S,4S)-3-hexyl-4-((R)-2-hydroxytridecyl)-oxetan-2-one and a product of the method. The method includes the following steps: a) reducing a substance represented by formula (II) to obtain a substance represented by formula (III), and then oxidizing the substance represented by formula (III) to form a substance represented by formula (IV); b) acylating n-octanoic acid to obtain n-octanoyl chloride using thionyl dichloride, then condensing the obtained n-octanoyl chloride with 2-mercapto-pyridine under basic condition to form a substance represented by formula (V), and then converting the substance represented by formula (V) to a substance represented by formula (VI); c) reacting the substance obtained in the step a) with the substance obtained in the step b) under catalytic condition of Lewis acid to generate a substance represented by formula (VII), and then reacting with a Lewis acid. The meanings of the signs in these formulas are the same as those in the description.

  本发明涉及一种制备(3S,4S)-3-己基-4-[(R)-2-羟基十三烷基]-氧杂环戊烷-2-酮及其制备方法的产品。该方法包括以下步骤：a) 还原式（II）所表示的物质以获得式（III）所表示的物质，然后氧化式（III）所表示的物质以形成式（IV）所表示的物质；b) 用氯化硫酰将正辛酸酰化为正辛酰氯，然后在碱性条件下将所得的正辛酰氯与2-巯基吡啶缩合以形成式（V）所表示的物质，然后将式（V）所表示的物质转化为式（VI）所表示的物质；c) 在Lewis酸的催化条件下将步骤a)中获得的物质与步骤b)中获得的物质反应以生成式（VII）所表示的物质，然后与Lewis酸反应。这些公式中符号的含义与说明中的相同。
• Oxetanone
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0185359B1

  公开（公告）日：1991-12-04
• US4931463A
  申请人：——

  公开号：US4931463A

  公开（公告）日：1990-06-05
• US5175186A
  申请人：——

  公开号：US5175186A

  公开（公告）日：1992-12-29