(3S,6S)-3,6-二(羟基甲基)-2,5-哌嗪二酮 | 23409-30-5

• 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
• 中文名称: (3S,6S)-3,6-二(羟基甲基)-2,5-哌嗪二酮
• 英文名称: cyclo(-L-Ser-L-Ser-)
• 英文别名: cyclo(Ser-Ser)；(3S,6S)-3,6-bis(hydroxymethyl)piperazine-2,5-dione
• CAS: 23409-30-5
• 化学式: C₆H₁₀N₂O₄
• 分子量: 174.156
• InChiKey: SUWGHSHLNOADHI-IMJSIDKUSA-N

物化性质

• 熔点：
  >260 °C
• 沸点：
  675.0±40.0 °C(Predicted)
• 密度：
  1.353±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  98.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,6S)-3,6-二(羟基甲基)-2,5-哌嗪二酮 生成 丝氨酰-丝氨酸
  参考文献：
  名称：

  Reactions of 3,6-bis(aminoxymethyl)-2,5-piperazinedione with acid and alkali. Kinetic study

  摘要：

  DOI：

  10.1021/jo01274a047
• 作为产物：
  描述：

  L-丝氨酸 以 乙二醇 为溶剂， 反应 24.0h， 以83%的产率得到(3S,6S)-3,6-二(羟基甲基)-2,5-哌嗪二酮
  参考文献：
  名称：

  一种含环状酰胺结构的生物基环氧树脂前驱体及其制备方法和应用

  摘要：

  本发明公开了一种含环状酰胺结构的生物基环氧树脂前驱体，还公开了所述含环状酰胺结构的生物基环氧树脂前驱体的制备方法和应用，包括：将天然氨基酸单体经过简单的缩合反应得到生物基多官能团单体，再将得到的生物基多官能团单体进行环氧化反应，制得所述含环状酰胺结构的生物基环氧树脂前驱体并将其固化后应用于制备生物基热固性环氧树脂。本发明制备流程简单，操作方法简便，可控制性好，易于实施，适用于大规模工业化生产；得到热固性环氧树脂具备优异的热学性能和力学性能，具有替代现有石油基环氧树脂的可能性。

  公开号：

  CN109384775A

文献信息

• Facile Synthesis of Cyclic Dipeptides and Detection of Racemization
  作者：Toshihisa Ueda、Morinobu Saito、Tetsuo Kato、Nobuo Izumiya

  DOI：10.1246/bcsj.56.568

  日期：1983.2

  Several cyclic dipeptides were synthesized by refluxing methanolic solution of dipeptide methyl esters in high yield and purity. Cyclic dipeptides prepared by the Fischer method, the Nitecki method, and the present methanol-reflux method were compared with respect to yield and optical purity. The methanol-reflux method usually gave good results. High-performance liquid chromatography was effectively applied to detect racemization.

  通过回流二肽甲酯的甲醇溶液，合成了几个高产率和高纯度的环状二肽。通过Fischer法、Nitecki法和当前的甲醇回流法准备的环状二肽，在产率和光学纯度方面进行了比较。甲醇回流法通常能得到良好的结果。高效液相色谱法有效地应用于检测外消旋化。
• DINUCLEOTIDE COMPOUNDS FOR HCV INFECTION
  申请人：IDENIX PHARMACEUTICALS, INC.

  公开号：US20140112886A1

  公开（公告）日：2014-04-24

  Provided herein are compounds, compositions and methods for the treatment of Flaviviridae infections, including HCV infections. In certain embodiments, compounds and compositions of nucleoside derivatives are disclosed, which can be administered either alone or in combination with other anti-viral agents. In certain embodiments, the compounds comprise two 2′-methyl nucleotides linked according to Formula I: N 1 -L-N 2 (I) or a pharmaceutically acceptable salt, ester, solvate, stereoisomer, isomeric form, tautomeric form or polymorphic form thereof; wherein N 1 , L and N 2 are as described herein.

  本文提供了用于治疗黄病毒科感染，包括HCV感染的化合物、组合物和方法。在某些实施方式中，披露了核苷类衍生物的化合物和组合物，可以单独或与其他抗病毒药物联合给药。在某些实施方式中，所述化合物包括根据以下式I连接的两个2'-甲基核苷酸：N1-L-N2(I)或其药学上可接受的盐、酯、溶剂合物、立体异构体、同分异构体、互变异构体或其多形形式；其中N1、L和N2如本文所述。
• Nucleophilic reactivity of amines with an α-formylglycyl enol-tosylate fragment
  作者：Sitaram Bhavaraju、Michael A. McGregor、William Rosen

  DOI：10.1016/j.tetlet.2007.09.018

  日期：2007.10

  while a 3°-amine, DABCO, exclusively yields a bis-3,6-ylidenepiperazine-2,5-dione product. These competitive reaction pathways with amine electron donors are shown to arise mechanistically via the same intermediate, or its tautomers, with an H-bond assisted nucleophilic substitution process being operative in the former case and an elimination reaction pathway in the latter instance.

  所述Ë的烯醇甲苯磺酸小号1°-3-苄基-6-甲酰基哌嗪-2,5-二酮进行反应-和2° -胺，得到其相应的3小号苄基6 Ê -endiamine产品，同时一个3° -胺，DABCO，仅产生双-3,6-亚苄基哌嗪-2,5-二酮产物。这些与胺电子给体的竞争性反应途径被证明是通过相同的中间体或其互变异构体机械产生的，在前一种情况下，H键辅助的亲核取代过程起作用，而在后一种情况下，则是消除反应途径。
• Protein Backbone Modification by Novel C.alpha.-C Side-Chain Scission
  作者：Darshan Ranganathan、Narendra K. Vaish、Kavita Shah

  DOI：10.1021/ja00094a008

  日期：1994.7

  alpha-Ketoamide (-NH-CO-CO-) units in intact peptides are generated from Ser/Thr residues via Ru(VIII)catalyzed C-alpha-C side-chain scission. Facets associated with this novel cu-carbon modification have been probed with 75 peptides chosen to represent every possible peptide environment. The reactions were carried out at room temperature with in situ generated Ru(VIII) in biphasic (CH3CN/CCl4/pH 3 phosphate buffer, 1:1:2 v/v) medium. Whereas Ser/Thr residues placed at the C-terminal end in peptides undergo N-C bond scission leading to des-Ser/Thr peptide amides-thus acting as Gly equivalents in simulating the alpha-amidating action of pituitary enzymes-those located at the N-terminal or nonterminal or even at the C-terminal position (protected as amide) were found to undergo oxidative C-C bond scission (involving C-alpha and C side-chain bond), resulting in the generation of alpha-ketoamide (-NH-CO-CO-) units in the intact peptide backbone. The difference in the products arising from C-alpha-C side-chain scission of Ser/Thr esters and amides is rationalized on the basis of a common mechanism involving either oxaloesters [Pep-NH-CO-COX; X = OMe] or oxalamides [X = NH2 or NH-Pep] arising from the oxidation of initially formed carbinolamide intermediates [Pep-NH-CH(OH)-COX],wherein, while the former are shown to undergo hydrolysis to terminal amides [Pep-NH2], the oxalamides are found to be stable to hydrolysis. Ancillary noteworthy findings are those of peptide bond scission when contiguous Ser-Ser/Thr-Thr residues are present and the oxidative cleavage at C-terminal Tyr/Trp sites generating des amides. The oxidative methodology presented here is mild, simple, and practical and proceeds with chiral retention. The insensitivity of a large number of amino acid residues, such as Gly, Ala, Leu, Asn, Gln, Asp, Glu, Pro, Arg, Phe, Lys, Val, and Aib, and N-protecting groups, such as Boc, Z, and Bz, toward Ru(VIII) under the experimental conditions should make this methodology practical and useful. Sulfur-containing amino acids Cys and Met get oxidized to sulfones in the products.
• Synthesis and antimetastatic properties of stereoisomeric tricyclic bis(dioxopiperazines) in the Lewis lung carcinoma model
  作者：Donald T. Witiak、Raghunathan V. Nair、Franz A. Schmid

  DOI：10.1021/jm00147a018

  日期：1985.9

  Synthesis of trans- and cis-tetrahydrodipyrazino[1,2-a:1',2'-d] pyrazine-1,3,7,9(2H,4H,8H,10H)-tetrone analogues 10 and 11 belonging to the bis(dioxopiperazine) class of antitumor agents and their bis(morpholinomethyl) derivatives 12 and 13 are described with use of 2,5-dimethylpyrazine as the starting material. Synthetic studies utilizing 3,6-disubstituted 2,5-dioxopiperazine precursors are included. Evaluation of 10-13 in the Lewis Lung carcinoma model indicated the bis(morpholinomethyl) analogue cis-13 to be antimetastatic, whereas the trans isomer 12 was toxic at a similar dose effecting a decrease in the life span of treated mice. The parent bis(dioxopiperazines) 10 and 11 were ineffective as antitumor or antimetastatic drugs.