cyclo(-L-Ser-D-Ser-) | 15996-16-4

• 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: cyclo(-L-Ser-D-Ser-)
• 英文别名: trans-3,6-Bis-hydroxymethyl-piperazin-2,5-dion；3,6-bis-hydroxymethyl-piperazine-2,5-dione；trans-3,6-bis-hydroxymethyl-piperazine-2,5-dione；(3R,6S)-3,6-Bis(hydroxymethyl)piperazine-2,5-dione
• CAS: 15996-16-4
• 化学式: C₆H₁₀N₂O₄
• 分子量: 174.156
• InChiKey: SUWGHSHLNOADHI-ZXZARUISSA-N

物化性质

• 熔点：
  272-273 °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

安全信息

• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  cyclo(-L-Ser-D-Ser-) 、 乙酰氯 在 硫酸 作用下， 以 溶剂黄146 为溶剂， 反应 48.0h， 以35.8%的产率得到trans-3,6-bis<(acetyloxy)methyl>piperazine-2,5-dione
  参考文献：
  名称：

  Synthesis and antimetastatic properties of stereoisomeric tricyclic bis(dioxopiperazines) in the Lewis lung carcinoma model

  摘要：

  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.

  DOI：

  10.1021/jm00147a018
• 作为产物：
  描述：

  DL-丝氨酸甲酯盐酸盐 生成 cyclo(-L-Ser-D-Ser-)
  参考文献：
  名称：

  NAIR, RAGHUNATHAN V.;WITIAK, DONALD T.

  摘要：

  DOI：

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。
• NAIR, RAGHUNATHAN V.;WITIAK, DONALD T.
  作者：NAIR, RAGHUNATHAN V.、WITIAK, DONALD T.

  DOI：——

  日期：——
• WITIAK, D. T.;NAIR, RAGHUNATHAN, V.;SCHMID, F. A., J. MED. CHEM., 1985, 28, N 9, 1228-1234
  作者：WITIAK, D. T.、NAIR, RAGHUNATHAN, V.、SCHMID, F. A.

  DOI：——

  日期：——
• Municio, Anales de la Real Sociedad Espanola de Fisica y Quimica, Serie B: Quimica, 1955, vol. 51, p. 565,570
  作者：Municio

  DOI：——

  日期：——
• US4871736A
  申请人：——

  公开号：US4871736A

  公开（公告）日：1989-10-03