(S)-1,4-diacetyl-3-methylpiperazine-2,5-dione | 74124-56-4

• 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: (S)-1,4-diacetyl-3-methylpiperazine-2,5-dione
• 英文别名: (3S)-1,4-diacetyl-3-methylpiperazine-2,5-dione
• CAS: 74124-56-4
• 化学式: C₉H₁₂N₂O₄
• 分子量: 212.205
• InChiKey: BCCGVIDADIROFB-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-1,4-diacetyl-3-methylpiperazine-2,5-dione 在 palladium on activated charcoal 盐酸 、 potassium tert-butylate 、 氢气 作用下， 以 二氯甲烷 、 乙酸乙酯 、 叔丁醇 为溶剂， 反应 2.5h， 生成 N-(1H-indol-2-ylcarbonyl)-L-alanine
  参考文献：
  名称：

  From cyclic dehydrodipeptides to uncommon acyclic peptide mimetics

  摘要：

  1-Acetyl-3 -arylmethylene-2,5-piperazinediones gave N-3-arylpyruvylamino esters by acid-promoted alcoholysis under thermal conditions or microwave irradiation. Compounds obtained from 1-acetyl-3-(o-nitro)arylmethylene-2,5-piperazinediones gave, after reduction of the nitro group and spontaneous cyclization, N-2-indolylcarbonylamino acid derivatives. A similar alcoholysis/reduction sequence applied to dehydrodipeptides bearing a 3(4)-nitroaryl substituent gave N-3(4)-aminophenyi-alpha-ketopropionylamino acid derivatives. Coupling of the free amino group with Boc-protected amino acids gave tripeptide mimetics with a 6-aminoindole-2-carboxylic or a 3(4)-aminophenyl-alpha-ketopropionic acid as the second residue. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.07.095
• 作为产物：
  描述：

  L-alanylglycine methyl ester trifluoroacetate 在 N-甲基吗啉 、 溶剂黄146 作用下， 以 仲丁醇 为溶剂， 反应 10.0h， 生成 (S)-1,4-diacetyl-3-methylpiperazine-2,5-dione
  参考文献：
  名称：

  Synthesis and anti-cancer activity of naturally occurring 2,5-diketopiperazines

  摘要：

  Three naturally occurring oxyprenylated diketopiperazines were synthesized and preliminarily tested as growth inhibitory agents in vitro against various cancer cell lines. The compounds were tested on six human cancer cell lines with different sensitivity to proapoptotic stimuli using the MTT colorimetric assay. The data revealed that of the chemicals under study only deoxymicelianamide (11) displayed the highest activity, recording mean IC50 growth inhibitory values ranging from 2 to 23 mu M. A comparative study with the non-geranylated saturated derivative of (11) revealed the importance of the presence of the geranyloxy side chain and the exocyclic 2,5-DPK double bond moiety for the observed activity. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.fitote.2014.07.010

文献信息

• Microwave-Assisted, Solvent-Free Synthesis of Several Quinazoline Alkaloid Frameworks
  作者：J. Menéndez、Pilar Cledera、Juan Sánchez、Esmeralda Caballero、Tamara Yates、Elena Ramírez、Carmen Avendaño、M. Ramos

  DOI：10.1055/s-2007-990818

  日期：2007.11

  Microwave irradiation leads to a considerable improvement of the cyclocondensation between anthranilic acid and lactim ethers derived from piperazine-2,5-diones in terms of reaction times, yields, and stereocenter integrity. This reaction has been used to prepare some derivatives of the pyrazino[2,1-b]quinazoline-3,6-dione system present in many quinazoline alkaloids. It could also be applied to the synthesis of compounds containing the complete hexacyclic ring system of the anti-MDR natural product N-acetyl­ardeemin, and other comprising the pentacyclic framework of circumdatin E. The microwave-assisted reaction was also much better than the thermal one when applied to a bis-lactim ether, leading to the corresponding pentacyclic pyrazino[2,1-b:5,4-b′]diquinazoline-8,16-dione in excellent yield.

  微波辐照显著改善了邻氨基苯甲酸与来自哌嗪-2,5-二酮的乳酰亚胺醚之间的环加成反应，在反应时间、产率和立体中心完整性方面均有显著提升。该反应已被用于制备多种喹唑啉生物碱中存在的吡嗪并[2,1-b]喹唑啉-3,6-二酮系统的衍生物。它还可以应用于合成含有抗多药耐药天然产物N-乙酰基阿德米宁的完整六环体系化合物，以及其他包含circumdatin E的五环框架的化合物。微波辅助反应在应用于双乳酰亚胺醚时也比热反应更为高效，得到了对应的五环吡嗪并[2,1-b:5,4-b′]双喹唑啉-8,16-二酮，产率极佳。
• Synthesis of Neoechinulin A and Derivatives
  作者：Susumu Kobayashi、Kouji Kuramochi、Toshiaki Aoki、Atsuo Nakazaki、Shinji Kamisuki、Masahiro Takeno、Kensuke Ohnishi、Kuniaki Kimoto、Nobuo Watanabe、Takashi Kamakura、Takao Arai、Fumio Sugawara

  DOI：10.1055/s-0028-1083634

  日期：2008.12

  Neoechinulin A isolated from Eurotium rubrum showed cytoprotection activity against peroxynitrite generated from SIN-1 [3-(4-morpholinyl)sydnonimine hydrochloride] in PC12 cells. As we are interested in this biological activity, we synthesized neoechinulin A and its derivatives. In this article, we fully report the isolation of natural neoechinulin A and B, a total synthesis of (-)-neoechinulin A, and determination of the absolute configuration of natural neoechinulin A. In addition, we describe herein syntheses of neoechinulin A derivatives, including a biotinylated neoechinulin A derivative, which will be useful for identification of the binding proteins of neoechinulin A.

  来自红酵母菌的Neoechinulin A对PC12细胞中由SIN-1[3-(4-吗啉基)西东胺盐酸盐]产生的过氧亚硝酸盐具有细胞保护活性。由于我们对这种生物活性感兴趣，因此合成了Neoechinulin A及其衍生物。本文中，我们详细报道了天然Neoechinulin A和B的分离、(-)-Neoechinulin A的全合成以及天然Neoechinulin A绝对构型的确定。此外，本文还描述了Neoechinulin A衍生物的合成，包括生物素化的Neoechinulin A衍生物，这将有助于鉴定Neoechinulin A的结合蛋白。
• Stereoselective Synthesis of 2,4-Diamino Acids by Asymmetric Hydrogenation
  作者：Nam Gyu Park、Sannamu Lee、Hiroshi Maeda、Haruhiko Aoyagi、Tetsuo Kato

  DOI：10.1246/bcsj.62.2315

  日期：1989.7

  A stereoselective synthesis of unusual basic amino acids, ornithine, 2,4-diaminopentanoic acid, and 2,4-diamino-6-methylheptanoic acid, was achieved by the hydrogenation of cyclic α,β-dehydro dipeptides obtained by the condensation of cyclo(–Gly–l(or d)-aminoacyl–) and protected linear or chiral amino aldehydes. The degree of chiral induction greatly depended on the bulkiness of the side chains of α,β-dehydro amino acids. The Rf values on paper chromatography of (2S,4S or 2R,4S)-diaminopentanoic acid prepared by the present method were different from the reported values of a compound which had been obtained from metabolic products of Clostridium sticklandii and estimated to be 2,4-diaminopentanoic acid.

  通过环状α,β-脱水二肽与保护的线性或手性氨基酸醛的缩合反应制得的环状α,β-脱水二肽，经氢化反应成功实现了不寻常的基本氨基酸——鸟氨酸、2,4-二氨基戊酸和2,4-二氨基-6-甲基庚酸的选择性立体合成。手性诱导的程度很大程度上取决于α,β-脱水氨基酸侧链的体积。本方法制备的(2S,4S或2R,4S)-二氨基戊酸在纸层析上的Rf值与从梭状芽孢杆菌Sticklandii代谢产物中获得的并推测为2,4-二氨基戊酸的化合物所报道的Rf值不同。
• Comparative study of synthetic approaches to 1-arylmethylenepyrazino[2,1-b]quinazoline-3,6-diones
  作者：Pilar Cledera、Carmen Avendaño、J.Carlos Menéndez

  DOI：10.1016/s0040-4020(98)00744-3

  日期：1998.10

  4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-diones (2) was studied. Four synthetic methods were compared, namely direct condensation with the product of the reaction between anthranilic acid and thionyl chloride, transformation into monothioiminoethers or monoiminoethers followed by reaction with anthranilic acid derivatives, and monoacylation with o-azidobenzoyl chloride followed by intramolecular aza-Wittig reaction

  研究了3-芳基亚甲基哌嗪-2，5-二酮（1）向1-芳基亚甲基-2，4-二氢-1 H-吡嗪并[ 2，1 - b ]喹唑啉-3，6-二酮（2）的转化。比较了四种合成方法，即直接与邻氨基苯甲酸和亚硫酰氯之间的反应产物缩合，转化为单硫亚氨基醚或单亚氨基醚，然后与邻氨基苯甲酸衍生物反应，与邻叠氮基苯甲酰氯单酰化，然后进行分子内aza-Wittig反应。通过后一种方法可获得最佳结果。
• Bioinspired Synthesis of the Furopyrazine Alkaloid Hyrtioseragamine A
  作者：Shi-Wei Kim、Paul A. Hume、Jonathan Sperry

  DOI：10.1021/acs.joc.1c00174

  日期：2021.3.19

  A biosynthetic hypothesis proposed herein was used to guide the total synthesis of the marine-derived alkaloid hyrtioseragamine A. In the key biomimetic step, an enedione underwent acid-mediated isomerization–cyclodehydration to form the rare furopyrazine core of the natural product. The spectroscopic data for the synthetic sample is in full agreement with that described in the isolation report.

  本文提出的生物合成假说被用来指导海洋生物碱羟丝氨酸胺A的全合成。在关键的仿生步骤中，烯二酮经历了酸介导的异构化-环脱水反应，形成了天然产物中稀有的呋喃吡嗪核。合成样品的光谱数据与隔离报告中描述的数据完全一致。