(3S,6S)-3-benzyl-6-isobutyl-1,4-dimethylpiperazine-2,5-dione | 1242265-12-8

• 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: (3S,6S)-3-benzyl-6-isobutyl-1,4-dimethylpiperazine-2,5-dione
• 英文别名: (3S,6S)-3-benzyl-6-isobutyl-1,4-dimethyl-2,5-diketopiperazine；(3S,6S)-3-benzyl-1,4-dimethyl-6-(2-methylpropyl)piperazine-2,5-dione
• CAS: 1242265-12-8
• 化学式: C₁₇H₂₄N₂O₂
• 分子量: 288.39
• InChiKey: FWZDZRSWOPZMHW-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  methyl methyl-L-leucinate hydrochloride 在 sodium hydride 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.92h， 生成 (3S,6S)-3-benzyl-6-isobutyl-1,4-dimethylpiperazine-2,5-dione
  参考文献：
  名称：

  N4-methylation changes the conformation of (3S,6S)-3-alkyl-6-benzylpiperazine-2,5-diones from folded to extended

  摘要：

  N4-methylation of (3S,6S)-3-alkyl-6-benzylpiperazine-2,5-diones (S,S)-1a-c was found to change their folded conformation to an extended conformation. Conformational aspects of N1- and/or N4-methylated (S,S)-1a-c were revealed by single crystal X-ray crystallography and H-1 NMR spectroscopy. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2016.03.019

文献信息

• Study of intramolecular aminolysis in peptides containing N-alkylamino acids at position 2
  作者：Vladimir V. Ryakhovsky、Andrey S. Ivanov

  DOI：10.1016/j.tet.2012.06.056

  日期：2012.9

  IA more strongly than aqueous ammonia, while tertiary amines were less effective. Peptides with methionine-S-oxide residues were more labile than the unoxidized analogs, suggesting intramolecular assistance of the S-oxide group in aminolysis. Surprisingly, intermediate compounds of the formula Boc–Met-MeXaa-Sar–NHR underwent rapid cleavage (endopeptolysis) upon attempted acidolytic deprotection.

  许多肽和蛋白质，含Ñ α -烷基氨基酸（包括脯氨酸）在所述第二位置，很容易发生分子内氨解（IA）具有N-末端二肽序列的消除2,5-二酮哌嗪（DKP）。我们合成了一系列短肽，在2位含有N-烷基氨基酸，并研究了它们在乙酸和胺存在下的稳定性。在第二侧链和第三个氨基酸残基，并且烷基化在存在Ñ α第三氨基酸残基的减慢IA。ñ α-第一个氨基酸残基中的烷基残基仅在包含三个或更多个残基的肽中阻碍IA。第一个氨基酸的侧链没有显着影响裂解率。乙酸比氨水对IA的促进作用更强，而叔胺的效果较差。具有蛋氨酸-S-氧化物残基的肽比未氧化的类似物更不稳定，这表明在氨解中S-氧化物基团的分子内辅助。出人意料的是，式Boc–Met-MeXaa-Sar–NHR的中间体化合物在尝试进行酸解脱保护后迅速裂解（内肽水解）。
• 2,5-Diketopiperazine Derivatives as Potential Anti-Influenza (H5N2) Agents: Synthesis, Biological Evaluation, and Molecular Docking Study
  作者：Chanakan Winyakul、Weerachai Phutdhawong、Poomipat Tamdee、Jitnapa Sirirak、Thongchai Taechowisan、Waya S. Phutdhawong

  DOI：10.3390/molecules27134200

  日期：——

  2,5-Diketopiperazine derivatives, consisting of benzylidene and alkylidene substituents at 3 and 6 positions, have been considered as a core structure for their antiviral activities. Herein, the novel N-substituted 2,5-Diketopiperazine derivatives were successfully prepared and their antiviral activities against influenza virus were evaluated by monitoring viral propagation in embryonated chicken eggs. It was found that (3Z,6Z)-3-benzylidene-6-(2-methyl propylidene)-4-substituted-2,5-Diketopiperazines (13b–d), (3Z,6E)-3-benzylidene-6-(2-methylpropyli dene)-1-(1-ethyl pyrrolidine)-2,5-Diketopiperazine (14c), and Lansai-C exhibited negative results in influenza virus propagation at a concentration of 25 µg/mL. Additionally, molecular docking study revealed that 13b–d and 14c bound in 430-cavity of neuraminidase from H5N2 avian influenza virus and the synthesized derivatives also strongly interacted with the key amino acid residues, including Arg371, Pro326, Ile427, and Thr439.

  2,5-二酮哌嗪衍生物是由苯甲醛和烷基甲醛取代3和6位置而成的核心结构，具有抗病毒活性。本研究成功合成了新型N取代的2,5-二酮哌嗪衍生物，并通过监测在鸡胚中的病毒传播评估了它们对流感病毒的抗病毒活性。结果发现，在25 µg/mL浓度下，(3Z,6Z)-3-苯甲醛基-6-(2-甲基丙烯基)-4-取代-2,5-二酮哌嗪衍生物(13b–d)、(3Z,6E)-3-苯甲醛基-6-(2-甲基丙烯基)-1-(1-乙基吡咯烷)-2,5-二酮哌嗪衍生物(14c)和Lansai-C在流感病毒传播方面呈现负效果。此外，分子对接研究揭示出13b–d和14c在H5N2禽流感病毒神经氨酸酶的430腔中结合，并且合成的衍生物也与关键氨基酸残基（包括Arg371、Pro326、Ile427和Thr439）强烈相互作用。