(5aR,10aR)-tetrahydro-3H,5H,8H,10H-bisthiazolo<3,4-a:3',4'-d>pyrazine-5,10-dione | 72744-67-3

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 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: (5aR,10aR)-tetrahydro-3H,5H,8H,10H-bisthiazolo<3,4-a:3',4'-d>pyrazine-5,10-dione
• 英文别名: (5aR,10aR)-tetrahydrodithiazolo[3,4-a:3’,4’-d]pyrazine-5,10(3H,8H)-dione；cyclo[L-Thz-L-Thz]；(5aR)-(5ar,10ac)-tetrahydro-bisthiazolo[3,4-a;3',4'-d]pyrazine-5,10-dione；N,S;N',S'-di-methanediyl-cyclo-(L-cysteinyl->L-cysteinyl)；(5aR,10aR)-Tetrahydrodithiazolo[3,4-a:3',4'-d]pyrazine-5,10(3H,8H)-dione；(3R,9R)-5,11-dithia-1,7-diazatricyclo[7.3.0.03,7]dodecane-2,8-dione
• CAS: 72744-67-3
• 化学式: C₈H₁₀N₂O₂S₂
• 分子量: 230.312
• InChiKey: IBBKEOUUWVDDIT-WDSKDSINSA-N

物化性质

• 熔点：
  166 - 170°C
• 密度：
  1.62
• 溶解度：
  氯仿（微溶）、甲醇（微溶、超声处理）、二氯甲烷

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  91.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5aR,10aR)-tetrahydro-3H,5H,8H,10H-bisthiazolo<3,4-a:3',4'-d>pyrazine-5,10-dione 在 sodium tetrahydroborate 、 四氯化钛 作用下， 以 乙二醇二甲醚 为溶剂， 反应 8.42h， 以39%的产率得到(6R,8aR)-7-methyl-6-(sulfanylmethyl)-thiazolidine[3,4-a]piperazine
  参考文献：
  名称：

  从 L-半胱氨酸及其第一镍配合物开始合成手性多齿配体系统

  摘要：

  从受保护的 L-半胱氨酸出发，可以合成 2, 5-二酮哌嗪 V，用 NaBH4/TiCl4 将其还原生成 (6R,8aR)-7-methyl-6-(sulfanylmethyl)-thiazolidine [3,4- a] 哌嗪，L1H 以及 N，N'-二甲基-（2R，5R）-双（硫烷基甲基）哌嗪，L2H2，它们被分离和表征。L2H2 可以选择性地获得，如果 V 在 DIEA·HCl 存在下被 NaBH4/TiCl4 还原，它代表了一种新型手性配体的前体，因为在去质子化后它提供了两个硫醇基和两个氨基供体功能，用于配位一个金属原子。L1H 和 L2H2 用 NaOMe 去质子化，然后用 NiBr2(dme) 处理，分别导致二聚体配合物 [L1NiBr]2 (1) 和 [L2Ni]2 (2) 的分离。两者都得到了充分的表征，

  DOI：

  10.1002/zaac.201300071
• 作为产物：
  描述：

  N-Boc-(R)-噻唑-4-羧酸 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 N,N'-二异丙基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 (5aR,10aR)-tetrahydro-3H,5H,8H,10H-bisthiazolo<3,4-a:3',4'-d>pyrazine-5,10-dione
  参考文献：
  名称：

  Anti-biofilm and anti-adherence properties of novel cyclic dipeptides against oral pathogens

  摘要：

  Microorganisms embedded in a biofilm are significantly more resistant to antimicrobial agents and the defences of the human immune system, than their planktonic counterpart. Consequently, compounds that can inhibit biofilm formation are of great interest for novel therapeutics. In this study, a screening approach was used to identify novel cyclic dipeptides that have anti-biofilm activity against oral pathogens. Five new active compounds were identified that prevent biofilm formation by the cariogenic bacterium Streptococcus mutans and the pathogenic fungus Candida albicans. These compounds also inhibit the adherence of microorganisms to a hydroxylapatite surface. Further investigations were conducted on these compounds to establish the structure-activity relationship, and it was deduced that the common cleft pattern is required for these molecules to act effectively against biofilms.

  DOI：

  10.1016/j.bmc.2018.11.042

文献信息

• Synthesis and structural study of piperazine-2,5-diones derived from (R)-cysteine
  作者：Asensio González、Svetlana L. Vorob́eva、Ana Linares

  DOI：10.1016/0957-4166(95)00168-o

  日期：1995.6

  Coupling Leuch's anhydrides obtained from (R)-thiazolidine-4-carboxylic acids 1 and 3 with one equivalent of the corresponding ethyl ester derivative of 1 or 3, leads to the formation of chiral piperazine-2,5-diones 2, 4, 5, 6, and 7, on thermal treatment of the intermediate dipeptides. The configuration of the products was established by nOe experiments.

  从（R） -噻唑烷-4-羧酸的耦合而获得Leuch的酸酐1和3与一当量的相应的乙酯衍生物的1或3，导致手性哌嗪-2,5-二酮的形成2，4，5 ，6和7，是关于中间二肽的热处理的。通过nOe实验确定了产品的配置。
• Interfacial supramolecular biomimetic epoxidation catalysed by cyclic dipeptides
  作者：Christopher Bérubé、Xavier Barbeau、Sébastien Cardinal、Pierre-Luc Boudreault、Corinne Bouchard、Nicolas Delcey、Patrick Lagüe、Normand Voyer

  DOI：10.1080/10610278.2016.1236197

  日期：2017.5.4

  We synthesised a library of cis- and trans-cyclic dipeptides and evaluated their efficacy as catalysts in the asymmetric Weitz-Scheffer epoxidation of trans-chalcone. A thorough investigation relying on structure-activity studies and computational studies provided insights into the mechanism of the process. Our results revealed some structural features required for efficient conversion and for introduction of chirality into the product. The cyclic dipeptide acts as a catalyst by templating a supramolecular arrangement at the aqueous-organic interface required for efficient transformations to occur. Among all cyclic dipeptides investigated, cyclo(Leu-Leu) was the most efficient supramolecular catalyst.[GRAPHICS].
• Diketopiperazines from optically active thiazolidine-4-carboxylic acids
  作者：Z. Gy�rgyde�k、Z. Dinya、R. Bogn�r

  DOI：10.1007/bf00473841

  日期：1979.9
• A straightforward synthesis and partial hydrolysis of cysteine-derived 2,5-diketopiperazines
  作者：Daniela Iannotta、Nicola Castellucci、Magda Monari、Claudia Tomasini

  DOI：10.1016/j.tetlet.2010.06.108

  日期：2010.8

  A mild and straightforward preparation of cysteine-derived 2,5-diketopiperazines (DKPs) is reported, by cyclization of (R)-2,2-dimethyltetrahydrothiazole-4-carboxylic acid hydrochloride or of (R)-tetrahydrothiazole-4-carboxylic acid hydrochloride, mediated by HBTU and DIEA. One DKP has been characterized by X-ray analysis, while the other has been hydrolyzed to cyclo-Cys-Cys. The preparation of this latter compound has been previously reported to be troublesome and low yielding. (C) 2010 Elsevier Ltd. All rights reserved.
• DERDDEHAK Z.; DINYA Z.; BOGNAR R., XIMIYA GETEROTSIKL. SOEDIN., 1979, HO 9, 1211-1220
  作者：DERDDEHAK Z.、 DINYA Z.、 BOGNAR R.

  DOI：——

  日期：——