N-formyl-L-alanine-(1S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester | 1072902-73-8

• 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: N-formyl-L-alanine-(1S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester
• 英文别名: [(2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl] (2S)-2-formamidopropanoate
• CAS: 1072902-73-8
• 化学式: C₂₆H₄₇NO₅
• 分子量: 453.663
• InChiKey: XDDBYWHHMMLVGR-ZJZGAYNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  32
• 可旋转键数：
  21
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  L-alanine-(1S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester 、 甲乙酐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以21%的产率得到N-formyl-L-alanine-(1S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester
  参考文献：
  名称：

  Tetrahydrolipstatin Analogues as Modulators of Endocannabinoid 2-Arachidonoylglycerol Metabolism

  摘要：

  formation or hydrolysis of the endocannabinoid 2-arachidonoylglycerol (2-AG). Three of the novel compounds, i.e., 11, 13, and 15, inhibited 2-AG formation via the diacylglycerol lipase a (DAGL alpha) with IC50 values lower than 50 nM (IC50 of THL = 1 mu M) and were between 23- and 375-fold selective vs 2-AG hydrolysis by rnonoacylglycerol lipase (MAGL) Lis well as vs cannabinoid CB1 and CB2 receptors and anandamide hydrolysis by fatty acid amide hydrolase (FAAH). Three other THL analogues, i.e., 14, 16, and 18, were slightly more potent than THL against DAGL alpha and appreciably selective vs MAGL, CB receptors, and FAAH (15-26-fold). One compound, i.e., 8, was a potent inhibitor of MAGL-like activity (IC50 = 0.41 mu M), and relatively (similar to 7-fold) selective vs the other targets tested.

  DOI：

  10.1021/jm800978m

文献信息

• NOVEL METHOD FOR THE ASYMMETRIC SYNTHESIS OF BETA-LACTONE COMPOUNDS
  申请人：Smith Jeffrey W.

  公开号：US20100173982A1

  公开（公告）日：2010-07-08

  The present invention features methods of treating a cancer in a subject by administering an effective amount of a beta-lactone to the subject. The invention also features methods of inhibiting angiogenesis in a subject by administering an effective amount of an inhibitor of fatty acid synthase to the subject. These methods can be used to treat a variety of cancers and other diseases and conditions. The invention also features methods of identifying beta-lactones and other compounds that can be used in the methods of the invention for the treatment of tumors, inhibition of angiogenesis, and the treatment of diseases and conditions that involve pathological angiogenesis. The invention also features methods of synthesizing beta-lactones and features novel beta-lactone compounds.

  本发明涉及通过向受试者施用有效量的β-内酰胺来治疗癌症的方法。本发明还涉及通过向受试者施用脂肪酸合成酶抑制剂的有效量来抑制血管生成的方法。这些方法可用于治疗各种癌症和其他疾病和病况。本发明还涉及识别β-内酰胺和其他化合物的方法，这些化合物可用于本发明的治疗肿瘤、抑制血管生成以及涉及病理性血管生成的疾病和病况的方法。本发明还涉及β-内酰胺的合成方法和新型β-内酰胺化合物。
• US7728153B2
  申请人：——

  公开号：US7728153B2

  公开（公告）日：2010-06-01
• US7799826B2
  申请人：——

  公开号：US7799826B2

  公开（公告）日：2010-09-21
• US8124794B2
  申请人：——

  公开号：US8124794B2

  公开（公告）日：2012-02-28
• Tetrahydrolipstatin Analogues as Modulators of Endocannabinoid 2-Arachidonoylglycerol Metabolism
  作者：Giorgio Ortar、Tiziana Bisogno、Alessia Ligresti、Enrico Morera、Marianna Nalli、Vincenzo Di Marzo

  DOI：10.1021/jm800978m

  日期：2008.11.13

  formation or hydrolysis of the endocannabinoid 2-arachidonoylglycerol (2-AG). Three of the novel compounds, i.e., 11, 13, and 15, inhibited 2-AG formation via the diacylglycerol lipase a (DAGL alpha) with IC50 values lower than 50 nM (IC50 of THL = 1 mu M) and were between 23- and 375-fold selective vs 2-AG hydrolysis by rnonoacylglycerol lipase (MAGL) Lis well as vs cannabinoid CB1 and CB2 receptors and anandamide hydrolysis by fatty acid amide hydrolase (FAAH). Three other THL analogues, i.e., 14, 16, and 18, were slightly more potent than THL against DAGL alpha and appreciably selective vs MAGL, CB receptors, and FAAH (15-26-fold). One compound, i.e., 8, was a potent inhibitor of MAGL-like activity (IC50 = 0.41 mu M), and relatively (similar to 7-fold) selective vs the other targets tested.