(2R)-2-benzyl-2-methoxycarbonyl-1-(2-nitrobenzenesulfonyl)-aziridine | 923578-97-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R)-2-benzyl-2-methoxycarbonyl-1-(2-nitrobenzenesulfonyl)-aziridine
• 英文别名: methyl (2R)-2-benzyl-1-(2-nitrophenyl)sulfonylaziridine-2-carboxylate
• CAS: 923578-97-6
• 化学式: C₁₇H₁₆N₂O₆S
• 分子量: 376.39
• InChiKey: CNCDXCYGHFRXOG-QNSVNVJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R)-2-benzyl-2-methoxycarbonyl-1-(2-nitrobenzenesulfonyl)-aziridine 在 氢氟酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 33.0h， 生成 N-[(R)-3-Benzyl-1-((S)-2-hydroxy-1-methyl-ethyl)-2-oxo-azetidin-3-yl]-2-nitro-benzenesulfonamide
  参考文献：
  名称：

  Synthesis of β-Lactam Scaffolds for Ditopic Peptidomimetics

  摘要：

  Ring opening of alpha-substituted-alpha-methoxycarbonyl-N-nosylaziridines provides a practical access to enantiopure alpha,alpha'-disubstituted beta-lactam scaffolds, novel types of ditopic reverse turn surrogates. The procedure is general, short, and high yielding and starts from handy alpha-substituted serinates and alpha-amino acid derivatives.

  DOI：

  10.1021/ol0626241
• 作为产物：
  描述：

  (2S,4R)-4-benzyl-2-(tert-butyl)-3-formyl-4-methoxycarbonyl-1,3-oxazolidine 在 盐酸 、 potassium hydrogencarbonate 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 23.0h， 生成 (2R)-2-benzyl-2-methoxycarbonyl-1-(2-nitrobenzenesulfonyl)-aziridine
  参考文献：
  名称：

  Synthesis of β-Lactam Scaffolds for Ditopic Peptidomimetics

  摘要：

  Ring opening of alpha-substituted-alpha-methoxycarbonyl-N-nosylaziridines provides a practical access to enantiopure alpha,alpha'-disubstituted beta-lactam scaffolds, novel types of ditopic reverse turn surrogates. The procedure is general, short, and high yielding and starts from handy alpha-substituted serinates and alpha-amino acid derivatives.

  DOI：

  10.1021/ol0626241

文献信息

• Design, synthesis and evaluation of β-lactam antigenic peptide hybrids; unusual opening of the β-lactam ring in acidic media
  作者：Marion Tarbe、Itxaso Azcune、Eva Balentová、John J. Miles、Emily E. Edwards、Kim M. Miles、Priscilla Do、Brian M. Baker、Andrew K. Sewell、Jesus M. Aizpurua、Céline Douat-Casassus、Stéphane Quideau

  DOI：10.1039/c003877f

  日期：——

  β-Lactam peptides were envisioned as conformational constraints in antigenic peptides (APs). Three different β-lactam tripeptides of varying flexibility were prepared in solution and incorporated in place of the central part of the altered melanoma associated antigenic peptide Leu27-Melan-A26–35 using solid phase synthesis techniques. Upon TFA cleavage from the solid support, an unexpected opening of the β-lactam ring occurred with conservation of the amide bond. After adaptation of the solid phase synthesis strategy, β-lactam peptides were successfully obtained and both opened and closed forms were evaluated for their capacity to bind to the antigen-presenting class-I MHC HLA-A2 protein system. None of the closed β-lactam peptides bound to HLA-A2, but their opened variants were shown to be moderate to good HLA-A2 ligands, one of them being even capable of stimulating a Melan-A-specific T cell line.

  设想β-内酰胺肽在抗原肽(APs)中作为构象约束。通过溶液制备了三种不同灵活性的β-内酰胺三肽，并采用固相合成技术将其取代改变的黑色素瘤相关抗原肽Leu27-Melan-A26-35的中心部分。在TFA从固相支持物切割后，发生了意外的β-内酰胺环打开，同时保留了酰胺键。在固相合成策略的适应之后，成功获得了β-内酰胺肽，并且评估了它们的打开和关闭形式与抗原呈递I类MHC HLA-A2蛋白系统的结合能力。没有任何封闭的β-内酰胺肽与HLA-A2结合，但它们的打开变体显示出从中等到良好的HLA-A2配体能力，其中一个甚至能够刺激Melan-A特异性T细胞系。
• BETA-LACTAMIC RGD CYCLOPEPTIDES CONTAINING GAMMA TURNS
  申请人：UNIVERSIDAD DEL PAIS VASCO-EUSKAL HERRIKO UNIBERSITATEA

  公开号：EP1864995A1

  公开（公告）日：2007-12-12

  A compound of the formula (I):         cyclo[Arg-Gly-Asp-(beta-Lactam)]     (I) containing at least one γ turn where (beta-Lactam)- is a fragment of 3-amino-1-(2-carbonylmethyl)-azetidin-2-one of the formula (II) where R1, R2, R3, R4 , R5 and R6 are selected independently from the group formed by hydrogen, unsubstituted or substituted alkyl, unsubstituted or substituted aryl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted arylalkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted heterocycloalkyl, -COR7, -C(0)OR7, -CO)NR7R8 -C=NR7 -CN, -OR7, - _ OC(O)7, -S(O)t-R7 , -NR7R8, -NR7C(O)R9, -NO2, -N=CR7R8 or halogen; where two of them can be bridged to form a cyclic substituent; their enantiomers, diastereomers or their pharmaceutically acceptable salts. These compounds selectively inhibit certain integrins and are useful for the treatment of diseases such as cancer, metastasis of cancerous solid tumors, thrombosis, restenosis following percutaneous transluminal coronary angioplasty (PTCA), rheumatoid arthritis or osteoporosis. They are also useful in systems of diagnostic and analysis.

  式 (I) 的化合物： 环[Arg-Gly-Asp-（β-内酰胺）] (I) 含有至少一个 γ 转折，其中（β-内酰胺）- 是式 (II) 的 3-氨基-1-（2-羰基甲基）-氮杂环丁-2-酮的片段 其中 R1、R2、R3、R4、R5 和 R6 分别独立地选自氢、未取代或取代的烷基、未取代或取代的芳基、未取代或取代的环烷基、未取代或取代的烯基未取代或取代的芳烷基、未取代或取代的杂环烷基、未取代或取代的杂环烷基、-COR7、-C(0)OR7、-CO)NR7R8 -C=NR7 -CN、-OR7、- _OC(O)7、-S(O)t-R7、-NR7R8、-NR7C(O)R9、-NO2、-N=CR7R8 或卤素；它们的对映体、非对映体或它们的药学上可接受的盐。 这些化合物选择性地抑制某些整合素，可用于治疗癌症、癌症实体瘤转移、血栓形成、经皮腔内冠状动脉成形术（PTCA）后再狭窄、类风湿性关节炎或骨质疏松症等疾病。它们在诊断和分析系统中也很有用。
• Stereomodulating effect of remote groups on the NADH-mimetic reduction of alkyl aroylformates with 1,4-dihydronicotinamide-β-lactam amides
  作者：Jesus M. Aizpurua、Claudio Palomo、Raluca M. Fratila、Pablo Ferrón、José I. Miranda

  DOI：10.1016/j.tet.2010.02.085

  日期：2010.4

  Conformationally restricted NADH peptidomimetics 4a-e, characterized by the presence of a (1,4-dihydronicotinamide)-(beta-lactam) moiety, have been synthesized and used to study the Mg2+ cation-promoted asymmetric reduction of alkyl aroylformates in acetonitrile. Increasing the bulkiness of peripheral substituents at the nitrogen atom of the beta-lactam ring, at the 1,4-dihydronicotinamide moiety, or at the aroylformate ester group, was found to cause weak but clearly detectable variations of the enantiomeric excess of the reaction. A rational for these observations was consistent with a chelated NADH/Mg2+/ArCOCO2R3 ternary complex model, according to DFT calculations computed at a B3LYP/631G(sic) theory level. (C) 2010 Elsevier Ltd. All tights reserved.
• Synthesis of β-Lactam Scaffolds for Ditopic Peptidomimetics
  作者：Claudio Palomo、Jesus M. Aizpurua、Eva Balentová、Azucena Jimenez、Joseba Oyarbide、Raluca M. Fratila、José Ignacio Miranda

  DOI：10.1021/ol0626241

  日期：2007.1.1

  Ring opening of alpha-substituted-alpha-methoxycarbonyl-N-nosylaziridines provides a practical access to enantiopure alpha,alpha'-disubstituted beta-lactam scaffolds, novel types of ditopic reverse turn surrogates. The procedure is general, short, and high yielding and starts from handy alpha-substituted serinates and alpha-amino acid derivatives.