N,N'-sulfonyl bis-L-alanine dimethyl ester | 323178-08-1

• 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: N,N'-sulfonyl bis-L-alanine dimethyl ester
• 英文别名: methyl (2S)-2-[[(2S)-1-methoxy-1-oxopropan-2-yl]sulfamoylamino]propanoate
• CAS: 323178-08-1
• 化学式: C₈H₁₆N₂O₆S
• 分子量: 268.291
• InChiKey: MWEAVUQELVYREJ-WDSKDSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N,N'-sulfonyl bis-L-alanine dimethyl ester 在 Grubbs catalyst first generation 、 potassium carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 15.5h， 生成 2,2'-(2S,2'S)-[(2,3,6,7-tetrahydro-1,2,7-thiadiazepine-1,1-dioxido-2,7-diyl)]bis-propionic acid dimethyl ester
  参考文献：
  名称：

  环硫酰胺拟肽的封闭环复分解策略

  摘要：

  讨论了合成许多受约束的磺酰胺的闭环复分解（RCM）策略。该方法利用了磺酰胺和磺酰基氨基甲酸酯的内在化学性质来生成对称和不对称的环状磺酰胺。揭示了两种策略，一种集中在烯丙基化磺酰胺9a - e的RCM反应上，以高产率生成C 2-对称环状磺酰胺4a - e。第二种RCM策略是利用已知的氨基磺酸磺酰基酯15制备不对称的环状磺酰胺16和6分两个四个步骤。总体而言，所描述的路线适用于代表新的拟肽支架的多种受约束的二肽磺酰胺的合成。

  DOI：

  10.1016/s0040-4020(00)00885-1
• 作为产物：
  描述：

  L-丙氨酸甲酯盐酸盐 在 磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以31%的产率得到N,N'-sulfonyl bis-L-alanine dimethyl ester
  参考文献：
  名称：

  环硫酰胺拟肽的封闭环复分解策略

  摘要：

  讨论了合成许多受约束的磺酰胺的闭环复分解（RCM）策略。该方法利用了磺酰胺和磺酰基氨基甲酸酯的内在化学性质来生成对称和不对称的环状磺酰胺。揭示了两种策略，一种集中在烯丙基化磺酰胺9a - e的RCM反应上，以高产率生成C 2-对称环状磺酰胺4a - e。第二种RCM策略是利用已知的氨基磺酸磺酰基酯15制备不对称的环状磺酰胺16和6分两个四个步骤。总体而言，所描述的路线适用于代表新的拟肽支架的多种受约束的二肽磺酰胺的合成。

  DOI：

  10.1016/s0040-4020(00)00885-1

文献信息

• Cyclosulfamides as Constraint Dipeptides: The Synthesis and Structure of Chiral Substituted 1,2,5-Thiadiazolidine 1,1-Dioxides: Evaluation of the Toxicity
  作者：Amel Bendjeddou、Houria Djebbar、Malika Berredjem、Z'Hour Hattab、Zine Regainia、Nour-Eddine Aouf

  DOI：10.1080/10426500500327014

  日期：2006.7.1

  A general synthesis for the preparation of chiral N-N′ substituted 1,2,5-thiadiazolidine 1,1-dioxides has been developed beginning with proteogenic amino acid, sulfuryl chloride, and dibromoethane. The selected chemistry and spectral properties of these compounds are examined. Overall, routes described are applicable to the synthesis of a variety of constrained dipeptidal sulfamides representing novel

  从蛋白质氨基酸、磺酰氯和二溴乙烷开始，已经开发了用于制备手性 NN' 取代的 1,2,5-噻二唑烷 1,1-二氧化物的一般合成方法。检查这些化合物的选定化学和光谱特性。总体而言，所描述的路线适用于代表新型拟肽支架的各种受限二肽磺酰胺的合成。
• Amino acid-derived, 7-membered cyclic sulfamides and methods of synthesizing the same
  申请人：University of Kansas

  公开号：US06359129B1

  公开（公告）日：2002-03-19

  New sulfamide compounds and methods of forming those compounds are provided. The inventive methods comprise subjecting a template opened-ring sulfamide compound to a ring-closing metathesis reaction in the presence of a Grubbs catalyst to yield a heterocyclic sulfamide. Advantageously, the template structures can be provided with a wide array of functional groups (e.g., substituted and unsubstituted amino acid side chains, peptides) chosen to provide particular properties to the compound. The preferred heterocyclic sulfamides are represented by a formula selected from the group consisting of

  提供了新的磺胺化合物和形成这些化合物的方法。创新的方法包括将一个模板开环磺胺化合物置于格氏催化剂存在下进行环闭合芳构反应，以产生一个杂环磺胺化合物。优点是，模板结构可以配有各种功能基团（例如，取代和未取代的氨基酸侧链、肽），以赋予化合物特定的性质。优选的杂环磺胺化合物由以下组成的公式代表：
• Synthesis and Anticonvulsant Activity of Amino Acid-Derived Sulfamides
  作者：Luciana Gavernet、Juan E. Elvira、Gisela A. Samaja、Valentina Pastore、Mariana Sella Cravero、Andrea Enrique、Guillermina Estiu、Luis E. Bruno-Blanch

  DOI：10.1021/jm800764p

  日期：2009.3.26

  Sulfamides are promising functions for the design of new antiepileptic drugs (Bioorg. Med. Chem. 2007, 15, 1556-1567; 5604-5614). Following previous research in this line, a set of amino acid-derived sulfamides has been designed, synthesized, and tested as new anticonvulsant compounds. The experimental data confirmed the ability of some of the structures to suppress the convulsions originated by the electrical seizure (MES test) at low doses (100 mg/kg).
• Inhibition pattern of sulfamide-related compounds in binding to carbonic anhydrase isoforms I, II, VII, XII and XIV
  作者：Luciana Gavernet、José L. Gonzalez Funes、Pablo H. Palestro、Luis E. Bruno Blanch、Guillermina L. Estiu、Alfonso Maresca、Ivana Barrios、Claudiu T. Supuran

  DOI：10.1016/j.bmc.2012.10.048

  日期：2013.3

  A set of sulfamides and sulfamates were synthesized and tested against several isoforms of carbonic anhydrase: CA I, CA II, CA VII, CA XII and CA XIV. The biological assays showed a broad range of inhibitory activity, and interesting results were found for several compounds in terms of activity (K-i < 1 mu m) and selectivity: some aromatic sulfamides are active against CA I, CA II and/or CA VII; while they are less active in CA XII and CA XIV. On the other hand, bulky sulfamides are selective to CA VII. To understand the origin of the different inhibitory activity against each isozyme we used molecular modeling techniques such as docking and molecular dynamic simulations. (C) 2012 Elsevier Ltd. All rights reserved.
• Ring-Closing Metathesis Strategies to Cyclic Sulfamide Peptidomimetics
  作者：Joseph M Dougherty、Donald A Probst、Randall E Robinson、Joel D Moore、Thomas A Klein、Kelley A Snelgrove、Paul R Hanson

  DOI：10.1016/s0040-4020(00)00885-1

  日期：2000.12

  sulfamides and sulfonyl carbamates to generate both symmetric and unsymmetric cyclic sulfamides. Two strategies are revealed, one centers on the RCM reaction of allylated sulfamides 9a–e to generate the C2-symmetric cyclic sulfamides 4a–e in high yields. A second RCM strategy utilizes the known sulfonyl carbamate 15 to prepare unsymmetric cyclic sulfamides 16 and 6 in two four-step sequences. Overall

  讨论了合成许多受约束的磺酰胺的闭环复分解（RCM）策略。该方法利用了磺酰胺和磺酰基氨基甲酸酯的内在化学性质来生成对称和不对称的环状磺酰胺。揭示了两种策略，一种集中在烯丙基化磺酰胺9a - e的RCM反应上，以高产率生成C 2-对称环状磺酰胺4a - e。第二种RCM策略是利用已知的氨基磺酸磺酰基酯15制备不对称的环状磺酰胺16和6分两个四个步骤。总体而言，所描述的路线适用于代表新的拟肽支架的多种受约束的二肽磺酰胺的合成。