methyl 5-(benzylamino)-5-oxopentanoate

• 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: methyl 5-(benzylamino)-5-oxopentanoate
• 英文别名: 4-benzylcarbamoylbutyric acid methyl ester
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: NCEPAHZHUZEWBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 5-(benzylamino)-5-oxopentanoate 在 sodium hydride 作用下， 以 甲苯 、 mineral oil 为溶剂， 反应 3.0h， 以65%的产率得到N-苄基-2,6-哌啶二酮
  参考文献：
  名称：

  Antiproliferative and antibacterial activity of some glutarimide derivatives

  摘要：

  Antiproliferative and antibacterial activities of nine glutarimide derivatives (1-9) were reported. Cytotoxicity of compounds was tested toward three human cancer cell lines, HeLa, K562 and MDA-MB-453 by MTT assay. Compound 7 (2-benzyl-2-azaspiro[5.11] heptadecane-1,3,7-trione), containing 12-membered ketone ring, was found to be the most potent toward all tested cell lines (IC50 = 9-27 mu M). Preliminary screening of antibacterial activity by a disk diffusion method showed that Gram-positive bacteria were more susceptible to the tested compounds than Gram-negative bacteria. Minimum inhibitory concentration (MIC) determined by a broth microdilution method confirmed that compounds 1, 2, 4, 6-8 and 9 inhibited the growth of all tested Gram-positive and some of the Gram-negative bacteria. The best antibacterial potential was achieved with compound 9 (ethyl 4-(1-benzyl-2,6-dioxopiperidin-3-yl) butanoate) against Bacillus cereus (MIC 0.625 mg/mL; 1.97 x 10(-3) mol/L). Distinction between more and less active/inactive compounds was assessed from the pharmacophoric patterns obtained by molecular interaction fields.

  DOI：

  10.3109/14756366.2015.1070844
• 作为产物：
  描述：

  戊二酸酐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 5-(benzylamino)-5-oxopentanoate
  参考文献：
  名称：

  Antiproliferative and antibacterial activity of some glutarimide derivatives

  摘要：

  Antiproliferative and antibacterial activities of nine glutarimide derivatives (1-9) were reported. Cytotoxicity of compounds was tested toward three human cancer cell lines, HeLa, K562 and MDA-MB-453 by MTT assay. Compound 7 (2-benzyl-2-azaspiro[5.11] heptadecane-1,3,7-trione), containing 12-membered ketone ring, was found to be the most potent toward all tested cell lines (IC50 = 9-27 mu M). Preliminary screening of antibacterial activity by a disk diffusion method showed that Gram-positive bacteria were more susceptible to the tested compounds than Gram-negative bacteria. Minimum inhibitory concentration (MIC) determined by a broth microdilution method confirmed that compounds 1, 2, 4, 6-8 and 9 inhibited the growth of all tested Gram-positive and some of the Gram-negative bacteria. The best antibacterial potential was achieved with compound 9 (ethyl 4-(1-benzyl-2,6-dioxopiperidin-3-yl) butanoate) against Bacillus cereus (MIC 0.625 mg/mL; 1.97 x 10(-3) mol/L). Distinction between more and less active/inactive compounds was assessed from the pharmacophoric patterns obtained by molecular interaction fields.

  DOI：

  10.3109/14756366.2015.1070844

文献信息

• Specificity of DNA Alkylation by 1-(2-Chloroethyl)-3-alkyl-3-acyltriazenes Depends on the Structure of the Acyl Group:  Kinetic and Product Studies
  作者：Marilyn B. Kroeger Smith、Brigitte F. Schmidt、Grzegorz Czerwinski、Lisa A. Taneyhill、Emily J. Snyder、Adam M. Kline、Christopher J. Michejda、Richard H. Smith

  DOI：10.1021/tx950155y

  日期：1996.1.1

  principal reaction product. In the absence of esterase, the order of DNA alkylation for all of the acyltriazenes did not correlate with their respective rates of decomposition, leading to the conclusion that the triazenes did not decompose by the expected mode of uncatalyzed N(2)-N(3) heterolyic cleavage. The major DNA alkylation product from the N(3)-methyltriazenes was 7-methylguanine, instead of the expected

  单独研究了小牛胸腺DNA与十个具有不同酰基侧链结构的1-（2-氯乙基）-3-烷基-3-酰基苯甲酰氮的反应，或在pH 7.0磷酸盐缓冲液中在猪肝酯酶存在下的反应。在几种关键的三氮烯中，酰基取代基包含一个游离的羧酸基团。在反应混合物中存在酯酶的情况下，所得的DNA烷基化水平可能与三氮烯分解的动力学速率相关。在这些条件下，主要的分解途径涉及母体三氮烯的脱酰作用并最终产生链烷重氮离子。该中间体随后将DNA-鸟嘌呤烷基化，得到7-烷基鸟嘌呤作为主要反应产物。在没有酯酶的情况下，DNA烷基化的顺序对所有的acyltriazenes都不与它们各自的分解速率相关，从而得出结论，三氮烯不会被未催化的N（2）-N（3）杂多裂解的预期模式分解。N（3）-甲基三氮烯的主要DNA烷基化产物是7-甲基鸟嘌呤，而不是预期的7-（氯乙基）-和7-（羟乙基）鸟嘌呤，这表明酰基正在被水解。但是，与预测相反，在该位置具有N（3
• Spiroaziridination of Cycloalkylidene Esters under High Pressure
  作者：Alexandre Rulev、Jacques Maddaluno

  DOI：10.1002/1099-0690(200107)2001:13<2569::aid-ejoc2569>3.0.co;2-1

  日期：2001.7

  The reaction between primary amines and 2-bromo-2-(cycloalkylidene)acetates in alcohol under high pressure provides the expected spiroaziridines in good yields and diastereomeric excesses. With bulky or aromatic amines, this reaction competes with the migration of the double bond, which, migrating from an exo to an endocyclic position, provides an intermediate allylic α-bromo ester, immediately converted

  伯胺和 2-溴-2-(亚环烷基) 乙酸酯在高压下在醇中的反应以良好的产率和非对映体过量提供了预期的螺氮丙啶。对于体积大的或芳香胺，该反应与双键的迁移竞争，双键从外环位置迁移到环内位置，提供中间烯丙基 α-溴酯，立即转化为 α-氨基酯。还可以开发串联版本，将相同的高压条件应用于 1,4-双-环己叉乙酸酯。相应的双螺氮丙啶以良好的收率和适度的脱色获得。然而，该反应在使用 2-氯-2-(环亚丙基)乙酸酯时没有成功，其仅以低产率产生戊二酸衍生物。