cyclo-cys-cys | 76392-90-0

• 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-cys-cys
• 英文别名: cyclo-L-cysteine-L-cysteine；(R)-cis-3,6-bis-mercaptomethyl-piperazine-2,5-dione；(R)-cis-3,6-Bis-mercaptomethyl-piperazin-2,5-dion；(3R,6R)-3,6-bis(sulfanylmethyl)piperazine-2,5-dione
• CAS: 76392-90-0
• 化学式: C₆H₁₀N₂O₂S₂
• 分子量: 206.29
• InChiKey: WGNVDMWTBDMWQI-IMJSIDKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 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：
  60.2
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-甲基咪唑 、 锌 、 cyclo-cys-cys 以 neat (no solvent) 为溶剂， 以67%的产率得到
  参考文献：
  名称：

  Zinc complexation of cyclic dipeptides containing cysteine and/or histidine

  摘要：

  The cyclic dipeptides c-HisHis, c-GlyCys, c-HisCys and c-CysCys were prepared in an analytically pure form. Potentiometric titrations in the presence of zinc nitrate showed that they all form a species of composition ZnL in solution, which in case of c-CysCys is dimeric. Except for c-CysCys they also form the complex ZnL2, which in case of c-GlyCys is polymeric. Contrary to the expectation the preorganization of the peptide donors does not enhance the complex stabilities in comparison to those of the non-cyclic peptides. Preparative reactions have yielded the compounds Zn(c-HisHiS)Cl-2, Zn(c-GlyCys)(2), Zn(c-GlyCys)(2). neocuproin, Zn-2(c-HisCys)(3)I, and Zn(c-CysCys)(N-methylimidazole)(2). (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0020-1693(01)00561-8
• 作为产物：
  描述：

  (5aR,10aR)-tetrahydro-3H,5H,8H,10H-bisthiazolo<3,4-a:3',4'-d>pyrazine-5,10-dione 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以88%的产率得到cyclo-cys-cys
  参考文献：
  名称：

  A straightforward synthesis and partial hydrolysis of cysteine-derived 2,5-diketopiperazines

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2010.06.108

文献信息

• Synthesis of Polycysteine
  作者：Shumpei Sakakibara、Hisaya Tani

  DOI：10.1246/bcsj.29.85

  日期：1956.1

  S-thiophenyl-L-cysteine was described. S-thiophenyl-L-cysteine was prepared from benzenesulfenyl chloride and L-cysteine hydrochloride in absolute alcohol and its chemical properties were studied. This amino acid was polymerized by the N-carboxy anhydride method in ethyl thioglycolate containing an active sulfhydryl group, and it was confirmed by the studies of infrared spectra of these substances that the resultant

  描述了通过 S-噻吩-L-半胱氨酸合成多半胱氨酸。以苯磺酰氯和L-半胱氨酸盐酸盐为原料，在无水酒精中制备了S-噻吩-L-半胱氨酸，并对其化学性质进行了研究。该氨基酸在含有活性巯基的巯基乙醇酸乙酯中通过 N-羧基酸酐法聚合，并通过这些物质的红外光谱研究证实，所得聚合物是被二酮哌嗪污染的聚半胱氨酸。通过用巯基乙酸和甲醇处理该聚合物来分离纯聚半胱氨酸。制备了苯甲酰衍生物和S-噻吩基-L-半胱氨酸的乙酯盐酸盐。
• Greenstein, Journal of Biological Chemistry, 1937, vol. 118, p. 327
  作者：Greenstein

  DOI：——

  日期：——
• Cysteine Prodrugs
  申请人：Lawton Daniel

  公开号：US20160081987A1

  公开（公告）日：2016-03-24

  Novel cysteine prodrugs and their use in the treatment of diseases and/or conditions, including but not limited to diseases and/or conditions of the Central Nervous System (CNS), including but not limited to schizophrenia, drug craving, drug addiction, bipolar disorder, anxiety, depression, Parkinson's disease, Alzheimer's disease, cognitive dysfunction, multiple sclerosis, Amyotrophic lateral sclerosis (ALS), ischemic stroke, HIV dementia, and Huntington's disease.
• US9457014B2
  申请人：——

  公开号：US9457014B2

  公开（公告）日：2016-10-04
• [EN] CYSTEINE PRODRUGS<br/>[FR] PRO-MÉDICAMENTS CYSTÉINES
  申请人：PROMENTIS PHARM INC

  公开号：WO2013016727A1

  公开（公告）日：2013-01-31

  Novel cysteine prodrugs and their use in the treatment of diseases and/or conditions, including but not limited to diseases and/or conditions of the Central Nervous System (CNS), including but not limited to schizophrenia, drug craving, drug addiction, bipolar disorder, anxiety, depression, Parkinson's disease, Alzheimer's disease, cognitive dysfunction, multiple sclerosis, Amyotrophic lateral sclerosis (ALS), ischemic stroke, HIV dementia, and Huntington's disease.