N,N'-(二硫代二乙烯)二乙酰胺 | 638-44-8

• 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: N,N'-(二硫代二乙烯)二乙酰胺
• 英文名称: N,N'-(dithiodiethylene)bisacetamide
• 英文别名: N,N'-diacetylcystamine；2-Acetamidoaethyl-disulfid；2-Acetamidoethyl disulfide；N-[2-(2-acetamidoethyldisulfanyl)ethyl]acetamide
• CAS: 638-44-8
• 化学式: C₈H₁₆N₂O₂S₂
• 分子量: 236.359
• InChiKey: KIBCSYBEMXURBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  N,N'-(二硫代二乙烯)二乙酰胺 在 磷酸二乙酯钠盐 作用下， 以 四氢呋喃 为溶剂， 反应 144.0h， 生成 bis(2-acetylaminoethyl) sulfide
  参考文献：
  名称：

  Phosphonic Acids. VII. The Reaction of Sodium Diethyl Phosphonate with Organic Disulfides

  摘要：

  DOI：

  10.1021/ja00894a019
• 作为产物：
  描述：

  2-Acetamidoaethyl-N,N-dimethyl-trithiopercarbamat 以 1,4-二氧六环 为溶剂， 生成 N,N'-(二硫代二乙烯)二乙酰胺
  参考文献：
  名称：

  Organic disulfides and related substances. XXV. Thiocarbamoyl and imidocarbamoyl disulfides

  摘要：

  DOI：

  10.1021/jo01274a037
• 作为试剂：
  描述：

  DL-半胱氨酸 在 N,N'-(二硫代二乙烯)二乙酰胺 作用下， 生成 DL-胱氨酸
  参考文献：
  名称：

  Rate constants and equilibrium constants for thiol-disulfide interchange reactions involving oxidized glutathione

  摘要：

  DOI：

  10.1021/ja00526a042

文献信息

• Step-Economic Synthesis of Biomimetic β-Ketopolyene Thioesters and Demonstration of Their Usefulness in Enzymatic Biosynthesis Studies
  作者：Johannes Wunderlich、Theresa Roß、Marius Schröder、Frank Hahn

  DOI：10.1021/acs.orglett.0c01348

  日期：2020.7.2

  by limited access to appropriate substrate surrogates. We present a step-economic synthetic access to biomimetic β-ketopolyene thioesters that is based on an Ir-catalyzed reductive Horner–Wadsworth–Emmons olefination. New β-ketotriene and pentaenethioates of pantetheine and N-acetylcysteamine were exemplarily synthesized via short and concise routes. The usefulness of these compounds was demonstrated

  多烯硫酯中间体的生物合成工艺研究由于难以获得合适的底物替代物而变得复杂。我们提出了一种仿生的β-酮多烯硫酯的逐步经济合成方法，该方法基于Ir催化的还原性Horner-Wadsworth-Emmons烯烃化反应。示例性地通过简短的途径合成泛酸的新的β-酮三烯和戊烯硫醚以及N-乙酰基半胱胺。这些化合物的有用性在体外测定中得到了证明，该酮还原酶结构域来自Mycolactone生物合成的MycKRB。
• Oxidative Formation of Disulfide Bonds by a Chemiluminescent 1,2-Dioxetane under Mild Conditions
  作者：Caroline S. Sauer、Johannes Köckenberger、Markus R. Heinrich

  DOI：10.1021/acs.joc.0c00569

  日期：2020.7.17

  The oxidation of alkyl thiols to disulfides has been achieved under mild conditions using a chemiluminescent 1,2-dioxetane as a stoichiometric oxidant. Besides the mild and biocompatible reaction conditions, this approach offers the possibility to monitor the presence of thiols through oxidation and chemiluminescence of the remaining dioxetane.

  使用化学发光的1,2-二氧杂环丁烷作为化学计量的氧化剂，在温和的条件下已将烷基硫醇氧化为二硫化物。除了温和且生物相容的反应条件外，该方法还可以通过剩余二氧杂环丁烷的氧化和化学发光监测硫醇的存在。
• Characterization of the promiscuous <i>N</i>-acyl CoA transferase, LgoC, in legonoxamine biosynthesis
  作者：Fleurdeliz Maglangit、Saad Alrashdi、Justine Renault、Laurent Trembleau、Catherine Victoria、Ming Him Tong、Shan Wang、Kwaku Kyeremeh、Hai Deng

  DOI：10.1039/d0ob00320d

  日期：——

  More than 500 siderophores are known to date, but only three were identified to be aryl-containing hydroxamate siderophores, legonoxamines A and B from Streptomyces sp. MA37, and aryl ferrioxamine 2 from Micrococcus luteus KLE1011.

  迄今已知超过500种铁载体，但只有三种被确认为含芳基羟酰胺的铁载体，分别是来自Streptomyces sp. MA37的legonoxamines A和B，以及来自Micrococcus luteus KLE1011的芳基铁螯合物2。
• Lipophilic analogs of sparsomycin as strong inhibitors of protein synthesis and tumor growth: a structure-activity relationship study
  作者：Leon A. G. M. Van den Broek、Ester Lazaro、Zbigniew Zylicz、Paul J. Fennis、Frank A. N. Missler、Peter Lelieveld、Marina Garzotto、D. J. Theo Wagener、Juan P. G. Ballesta、Harry C. J. Ottenheijm

  DOI：10.1021/jm00128a051

  日期：1989.8

  Fourteen derivatives of sparsomycin (1) were synthesized. Six of them were prepared following a novel synthetic route starting from the L-amino acid alanine. Some physicochemical properties, viz. lipophilicity and water solubility, of selected derivatives were measured. The biological activity was tested in vitro in cell-free protein synthesis inhibition assays, in bacterial and tumor cell growth inhibition

  合成了十四个Sparsomycin（1）的衍生物。从L-氨基酸丙氨酸开始，按照新颖的合成路线制备了其中的六个。一些理化性质，即。测量了所选衍生物的亲脂性和水溶性。在无细胞蛋白质合成抑制试验，细菌和肿瘤细胞生长抑制试验以及小鼠L1210白血病体内模型中体外测试了生物学活性。同样对于选定的药物，确定了小鼠的急性毒性。在蛋白质合成抑制系统中使用了来自真核生物和原核生物的核糖体。观察到亲脂性参数之间存在线性关系。发现小鼠中的水溶性和药物毒性与亲脂性呈线性关系。所有研究的衍生物都比1具有更高的亲脂性。脱羟基斯帕霉素类似物（30-33）表现出一种有趣的现象：疏水性增加，同时水溶性大大增加。我们发现，由于用较大的烷硫基取代了1的SMe基团，药物的疏水性增加导致药物的生物活性增加。但是，不仅疏水性，而且取代基的形状和大小也很重要。在同源系列1-9-10-11-12、21-22-23-24和30-31-32
• Synthesis of Reversible Shell Crosslinked Nanostructures
  申请人：McCormick Charles L.

  公开号：US20080234391A1

  公开（公告）日：2008-09-25

  In one aspect, the present invention is directed to a thermally responsive AB diblock copolymer prepared by RAFT polymerization wherein the diblock copolymer comprises poly(N-(3-aminopropyl)methacrylamide hydrochloride)-block-(N-isopropylacrylamide). Nanostructures of the thermally responsive diblock copolymer are formed by molecularly dissolving the diblock copolymer in aqueous solution at room temperature; and increasing the solution temperature to form nanostructures, for example vesicles or micelles. The first RAFT polymerization of an unprotected amino acid based monomer directly in water is also disclosed. The present invention also provides a method of forming shell cross-linked vesicles by adding a RAFT synthesized anionic homopolymer to a solution of the thermally responsive diblock copolymer. A method of forming interpolyelectrolyte complexed micelles or vesicles is also disclosed, the method comprising preparing by sequential aqueous RAFT polymerization a block copolymer comprised of N,N,-dimethyl acrylamide (DMA), N-acryloyl alanine (AAL) and N-isopropyl acrylamide (NIPAM); dissolving the block copolymers into aqueous solution; raising the solution temperature above the lower critical solution temperature of the NIPAM block; allowing the micelle solution to equilibrate; adjusting the pH of the solution to about 5; adding a cationic polymer to the solution; and stirring the solution. The reaction is readily reversed by the addition of a salt solution. In another aspect of the invention a reversible shell cross-linked micelle of a triblock copolymer cross-linked with cystamine is disclosed where a cleaving agent can be added to cleave the micelles. The reaction can be reversed with the addition of tris(2-carboxyethyl)phosphine or dithiothreitol.

  在一个方面，本发明涉及一种通过RAFT聚合制备的热响应性AB二嵌段共聚物，其中该二嵌段共聚物包括聚(N-(3-氨丙基)甲基丙烯酰胺盐酸盐)-嵌段-(N-异丙基丙烯酰胺)。通过在室温下将二嵌段共聚物分子溶解在水溶液中，并提高溶液温度形成纳米结构，例如囊泡或胶束。还公开了在水中直接进行的未保护氨基酸基单体的第一次RAFT聚合。本发明还提供了一种通过向热响应性二嵌段共聚物溶液中添加RAFT合成的阴离子均聚物来形成壳交联囊泡的方法。还公开了一种形成互聚电解质复合胶束或囊泡的方法，该方法包括通过顺序水相RAFT聚合制备由N,N-二甲基丙烯酰胺(DMA)、N-丙烯酰基丙氨酸(AAL)和N-异丙基丙烯酰胺(NIPAM)组成的嵌段共聚物；将嵌段共聚物溶解于水溶液中；将溶液温度升至NIPAM块的临界溶液温度以上；使胶束溶液达到平衡；将溶液pH值调整到约5；向溶液中加入阳离子聚合物；并搅拌溶液。通过添加盐溶液可以轻松地逆转反应。在发明的另一个方面，公开了一种可逆的通过半胱氨酸交联的三嵌段共聚物的壳交联胶束，其中可以添加裂解剂来裂解胶束。通过添加三(2-羧乙基)磷或二硫代己醇可以逆转反应。