(2R,3S)-2,3-epoxy-4-oxo-dodecanamide | 17397-90-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: (2R,3S)-2,3-epoxy-4-oxo-dodecanamide
• 英文别名: (+)-Tetrahydrocerulenin；(+)-(2R,3S)-tetrahydrocerulenin；(2R,3S)-3-nonanoyloxirane-2-carboxamide
• CAS: 17397-90-9
• 化学式: C₁₂H₂₁NO₃
• 分子量: 227.304
• InChiKey: OKJJXKSUEUHANI-GHMZBOCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  72.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2R,3R)-3-[(1S)-1-hydroxynonyl]oxirane-2-carboxamide 在 sodium acetate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以65%的产率得到(2R,3S)-2,3-epoxy-4-oxo-dodecanamide
  参考文献：
  名称：

  A novel stereoselective synthesis of (+)-cerulenin and (+)-tetrahydrocerulenin

  摘要：

  An antibiotic natural (+)-cerulenin and (+)-tetrahydrocerulenin have been synthesized, based on successive alkylation and reduction of chiral cyclic imide with C2-symmetry derived from D-tartaric acid.

  DOI：

  10.1016/s0040-4039(00)93599-8

文献信息

• Syntheses of Cerulenin and Its Analogs. I. Cerulenin and Its Analogs with Modified Side Chain.
  作者：Naoko MORISAKI、Hiroshi FUNABASHI、Jun FURUKAWA、Rumiko SHIMAZAWA、Akira KANEMATSU、Toshiaki ANDO、Shigenobu OKUDA、Shigeo IWASAKI

  DOI：10.1248/cpb.40.2945

  日期：——

  Optically active cerulenin 1, a potent inhibitor of fatty acid synthetase, was prepared via the condensation of the epoxy aldehyde 8 and the alkenyl lithium 16. In order to evaluate the effects of (E, E)-1, 4-double bounds of the cerulenin side chain on the interaction with the enzyme, a series of optically active cerulenin analogs 32a-i with modified side chains and tetrahydrocerulenin 3 were synthesized by similar procedures.

  通过环氧醛8与烯基锂16的缩合反应，制备了具有光学活性的西鲁莱宁1，这是一种强效脂肪酸合成酶抑制剂。为了评估西鲁莱宁侧链上的(E, E)-1, 4-双键对其与酶相互作用的影响，采用类似方法合成了具有修饰侧链的一组光学活性西鲁莱宁类似物32a-i及四氢西鲁莱宁3，并进行了系统研究。
• Novel autophagy modulators: Design and synthesis of (+)-epogymnolactam analogues and structure-activity relationship
  作者：Kazuki Ueda、Yuji Okado、Kengo Shigetomi、Makoto Ubukata

  DOI：10.1016/j.bmc.2018.09.013

  日期：2018.10

  from a culture of Gymnopus sp. in our laboratory. To determine structure-activity relationships among (+)-epogymnolactam analogues comparing with cerulenin (2), we synthesized 5 analogues including (−)-epogymnolactam (3) having each different functional group, and 3 analogues with different side-chain lengths. Five analogues, 3, 4, 5, 6, and 7 did not significantly increase the ratio of LC3-II to LC3-I

  （+）-Epogymnolactam（1）被发现作为一种新的自噬诱导剂，来自Gymnopus sp。的培养。在我们的实验室。为确定（+）-环氧ym内酰胺类似物与铜绿素（2）之间的构效关系，我们合成了5种类似物，其中包括（-）-环氧ym内酰胺（3）每个具有不同的官能团，以及3个类似的侧链长度不同。五个类似物，3，4，5，6，和7没有显著增加LC3-II的比例LC3-I如在NIH3T3细胞中自噬标记物。这些结果表明（2 R，3小号） -环氧基团和环状顺式-形式（图1b）的1是用于活性自噬诱导重要。己基类似物（8）以及1具有丁基侧链剂量依赖性地增加LC3-II的到LC3-I的比率，而辛基类似物（9）和2而降低的比率。癸基类似物（10）的比例没有变化。虽然8似乎是一个极好的自噬诱导剂，它剂量依赖性地增加SQSTM1（P62）作为的情况下2，而1表现出p62的轻微剂量依赖性降低，这是自噬蛋白降解的指
• Treatment of viral infections by modulation of host cell metabolic pathways
  申请人：THE TRUSTEES OF PRINCETON UNIVERSITY

  公开号：EP2581081A2

  公开（公告）日：2013-04-17

  Alterations of certain metabolite concentrations and fluxes that occur in response to viral infection are described. Host cell enzymes in the involved metabolic pathways are selected as targets for intervention; i.e., to restore metabolic flux to disadvantage viral replication, or to further derange metabolic flux resulting in "suicide" of viral-infected cells (but not uninfected cells) in order to limit viral propagation. While any of the enzymes in the relevant metabolic pathway can be selected, pivotal enzymes at key control points in these metabolic pathways are preferred as candidate antiviral drug targets. Inhibitors of these enzymes are used to reverse, or redirect, the effects of the viral infection. Drug candidates are tested for antiviral activity using screening assays in vitro and host cells, as well as in animal models.; Animal models are then used to test efficacy of candidate compounds in preventing and treating viral infections. The antiviral activity of enzyme inhibitors is demonstrated.

  描述了病毒感染时某些代谢物浓度和通量的变化。所涉及的代谢途径中的宿主细胞酶被选为干预目标；即恢复代谢通量以不利于病毒复制，或进一步改变代谢通量导致病毒感染细胞（而非未感染细胞）"自杀 "以限制病毒传播。虽然可以选择相关代谢途径中的任何一种酶，但这些代谢途径关键控制点上的关键酶更适合作为候选的抗病毒药物靶点。这些酶的抑制剂可用于逆转或重定向病毒感染的影响。候选药物通过体外和宿主细胞以及动物模型中的筛选试验进行抗病毒活性测试；然后用动物模型测试候选化合物在预防和治疗病毒感染方面的疗效。展示酶抑制剂的抗病毒活性。
• Compositions and methods for inhibiting platelet activation and thrombosis
  申请人：Beth Israel Deaconess Medical Center

  公开号：US20040147540A1

  公开（公告）日：2004-07-29

  The invention provides methods and compositions for reducing platelet activation, platelet aggregation and thrombosis. The invention further provides compositions and methods for treating or preventing diseases or disorders in which the pathology of the disease or disorder involves one or more of platelet activation, platelet aggregation and thrombus formation. The invention additionally relates to the use of protein palmitoylation inhibitors for the reduction of platelet activation, platelet aggregation and thrombosis, as well as to the use of protein palmitoylation as a target for the identification of inhibitors of platelet activation, platelet aggregation and thrombosis.

  本发明提供了减少血小板活化、血小板聚集和血栓形成的方法和组合物。本发明进一步提供了用于治疗或预防疾病或失调的组合物和方法，其中疾病或失调的病理涉及血小板活化、血小板聚集和血栓形成中的一种或多种。本发明还涉及使用蛋白棕榈酰化抑制剂降低血小板活化、血小板聚集和血栓形成，以及使用蛋白棕榈酰化作为靶点鉴定血小板活化、血小板聚集和血栓形成抑制剂。
• Synthesis of optically active butenolides via chromium alkoxycarbene complexes: total synthesis of (+)-tetrahydrocerulenin and two butenolides from the marine sponge Plakortis lita
  作者：Michael Miller、Louis S. Hegedus

  DOI：10.1021/jo00076a044

  日期：1993.11

  Optically active butenolides were synthesized from the corresponding cyclobutanones, derived from the photolysis of chromium alkoxycarbene complexes and optically active ene-carbamates. The cyclobutanones were oxidized (Baeyer-Villiger) to the corresponding lactones, and subsequent base-induced elimination of the beta-oxazolidinone ring provided optically active butenolides efficiently. The butenolides were utilized in the syntheses of (+)-tetrahydrocerulenin and two marine natural products.