N-octanoyl imidazole | 17450-31-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-octanoyl imidazole
• 英文别名: N-octanoyl-imidazole；1-octanoylimidazole；N-octanoylimidazole；octanoylimidazole；1-octanoyl-1H-imidazole；1-Octanoyl-1H-imidazol；1H-Imidazole, 1-(1-oxooctyl)-；1-imidazol-1-yloctan-1-one
• CAS: 17450-31-6
• 化学式: C₁₁H₁₈N₂O
• 分子量: 194.277
• InChiKey: RMNNQHPVYVFFMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-octanoyl imidazole 在 titanium(III) chloride 、 二丁基镁 、 sodium acetate 、 sodium nitrite 作用下， 以 水 、 丙酸 、 丙酮 、 乙腈 为溶剂， 反应 21.5h， 生成 tert-butyl 2,3-dioxodecanoate
  参考文献：
  名称：

  Titanium(III)-mediated synthesis of a 1,2,3-tricarbonyl moiety from an .alpha.-oximido-.beta.-keto ester: application to the synthesis of the carbacephem nucleus

  摘要：

  A general procedure for the conversion of alpha-oximido-beta-keto esters into vicinal tricarbonyl moieties by TiCl3 in aqueous, buffered (pH 5) conditions with acetone cosolvent was demonstrated. As applied to N-hydroxy beta-lactam 17, which contained an alpha-oximido-beta-keto ester side chain, these combined reductive and hydrolytic conditions effected simultaneous tricarbonyl formation and beta-lactam N-O bond reduction. Vicinal tricarbonyl-containing N-unsubstituted beta-lactam 18 was a direct precursor to semifunctionalized carbacephem 1.

  DOI：

  10.1021/jo00039a009
• 作为产物：
  描述：

  咪唑 、 辛酰氯 以 四氢呋喃 为溶剂， 生成 N-octanoyl imidazole
  参考文献：
  名称：

  酰基咪唑对芳香族酮的电还原酰化

  摘要：

  在氯代三甲基硅烷的存在下，通过电还原作用实现芳族酮与酰基咪唑的分子间还原偶联，得到α-三甲基甲硅烷氧基酮和酯。使用Bu 4 NPF 6作为支持电解质和THF中的Pb阴极可获得最佳结果。通过在THF中用TBAF处理，将含α-三甲基甲硅烷氧基的产物转化为相应的α-羟基酮和酯。该方法对于δ-和ε-酮基酰基咪唑的分子内还原偶联也是有效的。

  DOI：

  10.1021/jo051498w

文献信息

• Modular synthesis and biological activity of pyridyl-based analogs of the potent Class I Histone Deacetylase Inhibitor Largazole
  作者：Dane J. Clausen、William B. Smith、Brandon E. Haines、Olaf Wiest、James E. Bradner、Robert M. Williams

  DOI：10.1016/j.bmc.2015.03.063

  日期：2015.8

  The formation of a series of analogs containing a pyridine moiety in place of the natural thiazole heterocycle, based on the potent, naturally occurring HDAC inhibitor Largazole has been accomplished. The synthetic strategy was designed modularly to access multiple inhibitors with different aryl functionalities containing both the natural depsipeptide and peptide isostere variant of the macrocycle

  基于有效的天然存在的HDAC抑制剂拉尔加唑，已经形成了一系列取代基，其包含吡啶部分代替天然噻唑杂环。模块化设计了合成策略，以获取具有不同芳基官能团的多种抑制剂，这些抑制剂同时包含大环化合物的天然十肽和肽等排异构体。本文描述了HDAC抑制剂文库的细胞毒性和生化活性。
• [EN] METHOD FOR PREPARING LARGAZOLE ANALOGS AND USES THEREOF<br/>[FR] PROCÉDÉ DE PRÉPARATION DE PARTICULES CREUSES ET LEURS UTILISATIONS
  申请人：UNIV COLORADO STATE RES FOUND

  公开号：WO2016144665A1

  公开（公告）日：2016-09-15

  Analogs of largazole are described herein. Methods of treating cancer and blood disorders using largazole and largazole analogs and pharmaceutical compositions comprising the same are additionally described herein. Methods for preparing largazole analogs are likewise described.

  本文描述了类似largazole的类似物。此外，还描述了使用largazole和largazole类似物治疗癌症和血液疾病的方法，以及包含它们的药物组合物。同样描述了制备largazole类似物的方法。
• Selective Acylation of Nucleosides, Nucleotides, and Glycerol-3-phosphocholine in Water
  作者：Matthew Powner、Christian Fernández-García

  DOI：10.1055/s-0036-1588626

  日期：——

  2′,3′,5′-tri-O-acetyl-nucleosides in water has been developed. Furthermore, a long-chain selective glycerol-3-phosphocholine diacylation is elucidated. These reactions are environmentally benign, rapid, high yielding, and the products are readily purified. Importantly, this reaction may indicate a prebiotically plausible reaction pathway for the selective acylation of key metabolites to facilitate their

  2',3'-二-O-乙酰基-核苷酸-5'-磷酸、2',3'-二-O-乙酰-核苷酸-5'-三磷酸和2',3',5的方便选择性合成'-tri-O-乙酰基-核苷在水中得到了开发。此外，还阐明了长链选择性甘油-3-磷酸胆碱二酰化。这些反应对环境无害、快速、收率高，并且产物易于纯化。重要的是，该反应可能表明关键代谢物的选择性酰化以促进它们并入原代谢中的益生元似是而非的反应途径。
• Length-Selective Synthesis of Acylglycerol-Phosphates through Energy-Dissipative Cycling
  作者：Claudia Bonfio、Cécile Caumes、Colm D. Duffy、Bhavesh H. Patel、Claudia Percivalle、Maria Tsanakopoulou、John D. Sutherland

  DOI：10.1021/jacs.8b12331

  日期：2019.3.6

  Starting with a mixture of activated carboxylic acids of different lengths, iterative cycling of acylation and hydrolysis steps allowed for the selection of longer-chain acylglycerol-phosphates. Our results suggest that a selection pathway based on energy-dissipative cycling could have driven the selective synthesis of phospholipids on early Earth.

  生命起源研究的主要目的是寻找从益生元化学到新生生物学的合理转变序列。在这种情况下，了解早期地球上磷脂膜是如何以及何时出现的，对于阐明导致原始细胞出现的益生元途径至关重要。在这里，我们表明将 glycerol-2-phosphate 暴露于酰化剂会导致形成 acylglycerol-phosphates 库。发现中链酰基甘油磷酸酯自组装成囊泡，在各种条件下稳定，并能够保留单核苷酸和寡核苷酸。从不同长度的活化羧酸混合物开始，酰化和水解步骤的迭代循环允许选择更长链的酰基甘油-磷酸酯。
• Biosynthesis of Branched-chain Fatty Acid in<i>Bacilli</i>: FabD (malonyl-CoA:ACP transacylase) Is Not Essential for<i>In Vitro</i>Biosynthesis of Branched-chain Fatty Acids
  作者：Hirosuke OKU、Naoya FUTAMORI、Kenichi MASUDA、Yumiko SHIMABUKURO、Tomoyo OMINE、Hironori IWASAKI

  DOI：10.1271/bbb.67.2106

  日期：2003.1

  It was found that the partially purified β-ketoacyl-ACP synthase of Bacillus insolitus did not require the addition of FabD (malonyl-CoA:ACP transacylase, MAT) for the activity assay. This study therefore examined the necessity of FabD protein for in vitro branched-chain fatty acid (BCFA) biosynthesis by crude fatty acid synthetases (FAS) of Bacilli. To discover the involvement of FabD in the BCFA biosynthesis, the protein was removed from the crude FAS by immunoprecipitation. The His-tag fusion protein FabD of Bacillus subtilis was expressed in Escherichia coli and used for the preparation of antibody. The rabbit antibody raised against the expressed fusion protein specifically recognized the FabD in the crude FAS of B. subtilis. Evaluation of the efficacy of the immunoprecipitation showed that a trace of FabD protein was present in the antibody-treated crude FAS. However, this complete removal of FabD from the crude FAS did not abolish its BCFA biosynthesis, but only reduced the level to 50-60% of the control level for acyl-CoA primer and to 80% for α-keto-β-methylvalerate primer. Furthermore, the FabD concentration did not necessarily correlate with the MAT specific activity in the enzyme fractions, suggesting the presence of another enzyme source of MAT activity. This study, therefore, suggests that FabD is not the sole enzyme source of MAT for in vitro BCFA biosynthesis, and implies the existence of a functional connection between fatty acid biosynthesis and another metabolic pathway.

  研究发现，不完全纯化的无枝菌酸菌β-酮脂酰ACP合酶（Bacillus insolitus）在活性测定时不需要添加FabD（丙二酸单酰-CoA:ACP转酰酶，MAT）。因此，本研究探讨了杆状菌粗脂肪酸合成酶（FAS）体外支链脂肪酸（BCFA）生物合成中FabD蛋白的必要性。为了探索FabD在BCFA生物合成中的作用，通过免疫沉淀法从粗FAS中去除该蛋白。将枯草芽孢杆菌的His标签融合蛋白FabD在大肠杆菌中表达，并用其制备抗体。针对表达的融合蛋白免疫兔子得到的抗体能特异性地识别枯草芽孢杆菌粗FAS中的FabD。免疫沉淀法效力评估显示，经抗体处理的粗FAS中仅残留极少量的FabD蛋白。然而，从粗FAS中完全去除FabD并未使其BCFA生物合成失活，仅使其活性降低，对于酰基-CoA引物降至对照组的50-60%，对于α-酮基-β-甲基戊酸引物降至80%。此外，FabD浓度与酶组分中MAT的特异性活性并不一定相关，表明存在另一种MAT活性的酶源。因此，本研究认为，FabD不是体外BCFA生物合成中MAT唯一的酶源，并暗示脂肪酸生物合成与其他代谢途径之间存在功能联系。