N⁵-((R)-3-(benzoyllthio)-1-((carboxymethyl)amino)-1-oxopropan-2-yl)-L-glutamine | 51024-68-1

• 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: N⁵-((R)-3-(benzoyllthio)-1-((carboxymethyl)amino)-1-oxopropan-2-yl)-L-glutamine
• 英文别名: S-Benzoylglutathion；γ-L-glutamyl-S-benzoyl-L-cysteinyl-glycine；gamma-L-glutamyl-S-benzoyl-L-cysteinyl-glycine；(2S)-2-amino-5-[[(2R)-3-benzoylsulfanyl-1-(carboxymethylamino)-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
• CAS: 51024-68-1
• 化学式: C₁₇H₂₁N₃O₇S
• 分子量: 411.436
• InChiKey: SYZXWJNOYLEYSJ-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  201
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  苯甲酸 在 potassium hydrogencarbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 26.0h， 生成 N⁵-((R)-3-(benzoyllthio)-1-((carboxymethyl)amino)-1-oxopropan-2-yl)-L-glutamine
  参考文献：
  名称：

  水中 S-酰基和 N-酰基谷胱甘肽与 N-酰基咪唑的实际选择性合成

  摘要：

  我们报道了一种简单而有效的谷胱甘肽酰化反应，用于化学选择性合成 S- 或 N-酰化谷胱甘肽衍生物，在温和条件下并使用水作为溶剂，通过从各自丰富的羧基原位形成酰基咪唑亲电子试剂酸。

  DOI：

  10.1002/ejoc.202400255

文献信息

• Direct Observation of Acyl Nitroso Compounds in Aqueous Solution and the Kinetics of Their Reactions with Amines, Thiols, and Hydroxamic Acids
  作者：Eric Maimon、Ana Lerner、Amram Samuni、Sara Goldstein

  DOI：10.1021/acs.jpca.8b06672

  日期：2018.9.6

  Acyl nitroso compounds or nitrosocarhonyls (RC(O)N═O) are reactive short-lived electrophiles, and their hydrolysis and reactions with nucleophiles produce HNO. Previously, direct detection of acyl nitroso species in nonaqueous media has been provided by time-resolved infrared spectroscopy demonstrating that its half-life is about 1 ms. In the present study hydroxamic acids (RC(O)NHOH) are oxidized

  酰基亚硝基化合物或亚硝基羰基化合物（RC（O）N = O）是反应性短寿命的亲电试剂，它​​们的水解和与亲核试剂的反应会生成HNO。以前，时间分辨红外光谱法可直接检测非水介质中的酰基亚硝基，证明其半衰期约为1毫秒。在本研究中，异羟肟酸（RC（O）NHOH）在缓冲水溶液（pH 5.9-10.2）中被电化学氧化，产生瞬态物质，其特征在于它们在314-330 nm处具有最大吸收。这些瞬态物质通过一级反应分解，主要产生HNO和相应的羧酸，因此归因于RC（O）N = O。RC（O）N = O在水溶液中足够长的半衰期首次允许研究其与各种亲核试剂的反应动力学，这表明亲核反应性遵循硫醇盐>异羟肟酸酯>胺的顺序。CH的金属螯合物3 C（O）NHOH以Cu II > Zn II > Ni II > Co II的功效顺序催化CH 3 C（O）N = O的水解，其中在不存在异羟肟酸酯的情况下，只有Cu II催化水解
• Process for the preparation of glutathione S-acyl derivatives, compounds
  申请人：Boehringer Mannheim Italia S.p.A.

  公开号：US05382679A1

  公开（公告）日：1995-01-17

  A selective and high yield process for S-acylating glutathione, comprising the eaction between glutathione and an acyl chloride or a carboxylic anhydride in trifluoroacetic acid is described.

  本文描述了一种选择性和高产量的S-酰化谷胱甘肽的过程，包括谷胱甘肽与酰氯或羧酸酐在三氟乙酸中反应。
• Selenol esters as specific reagents of the acylation of thiol groups
  作者：Alexandros. Makriyannis、Wolfgang H. H. Guenther、Henry G. Mautner

  DOI：10.1021/ja00806a033

  日期：1973.12
• A PROCESS FOR THE PREPARATION OF GLUTATHIONE S-ACYL DERIVATIVES AND COMPOUNDS OBTAINED FROM SAID PROCESS
  申请人：BOEHRINGER MANNHEIM ITALIA S.P.A.

  公开号：EP0536231B1

  公开（公告）日：1996-10-23
• Methods and Compositions for Treating Psychotic Disorders
  申请人：Sound Pharmaceuticals Incorporated

  公开号：US20170246148A1

  公开（公告）日：2017-08-31

  Disclosed herein are novel drug combinations comprising a glutathione peroxidase (GPx) mimic compound and an antipsychotic agent, pharmaceutical compositions comprising one or more of such combinations, methods of preparing pharmaceutical compositions comprising one or more such combinations, and methods of treatment, prevention, inhibition or amelioration of one or more diseases associated with GPx mediated disorders, psychotic disorders or complications from administering an antipsychotic agent at high dose or long term using such combination or pharmaceutical compositions. Furthermore, a method is disclosed for reducing the anti-psychotic agent's dosages that comprises co-administering a therapeutically effective amount of a glutathione peroxidase mimic compound.