(2S)-1-(2-nitrophenyl)sulfonylpyrrolidine-2-carboxamide | 739365-94-7

• 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: (2S)-1-(2-nitrophenyl)sulfonylpyrrolidine-2-carboxamide
• CAS: 739365-94-7
• 化学式: C₁₁H₁₃N₃O₅S
• 分子量: 299.307
• InChiKey: XCRSHZVMOZVGFY-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.23
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  123.61
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S)-1-(2-nitrophenyl)sulfonylpyrrolidine-2-carboxamide 在 吡啶 、 咪唑 、 盐酸 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三乙胺 、 三氟乙酸 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 乙醚 为溶剂， 生成 (S)-1-((S)-2-Amino-2-cyclohexyl-acetyl)-pyrrolidine-2-carbonitrile
  参考文献：
  名称：

  2-cyanopyrrolidides as potent, stable inhibitors of dipeptidyl peptidase IV

  摘要：

  A novel series of stable, potent inhibitors of dipeptidyl peptidase IV has been developed. A number of dipeptide analogues, incorporating a 2-cyanopyrrolidide, were found to have K-i values of less than 5 nM versus human DP-IV and half-lives of >48h in aqueous solution (pH 7.4). (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00190-4
• 作为产物：
  描述：

  邻硝基苯磺酰氯 、 L-脯氨酸 在 ammonium hydroxide 、 sodium hydroxide 、 聚碳化二亚胺 、 ONSu 作用下， 生成 (2S)-1-(2-nitrophenyl)sulfonylpyrrolidine-2-carboxamide
  参考文献：
  名称：

  2-cyanopyrrolidides as potent, stable inhibitors of dipeptidyl peptidase IV

  摘要：

  A novel series of stable, potent inhibitors of dipeptidyl peptidase IV has been developed. A number of dipeptide analogues, incorporating a 2-cyanopyrrolidide, were found to have K-i values of less than 5 nM versus human DP-IV and half-lives of >48h in aqueous solution (pH 7.4). (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00190-4

文献信息

• Organophosphorus and Nitro-Substituted Sulfonate Esters of 1-Hydroxy-7-azabenzotriazole as Highly Efficient Fast-Acting Peptide Coupling Reagents
  作者：Louis A. Carpino、Jusong Xia、Chongwu Zhang、Ayman El-Faham

  DOI：10.1021/jo0300183

  日期：2004.1.1

  with HOAt are excellent coupling reagents for peptide synthesis which are generally superior to their uronium/guanidinium analogues and HOBt- or HODhbt-derived phosphate ester counterparts in minimizing loss of configuration during segment coupling. The phosphinyl analogues are more shelf-stable than the phosphoryl systems. The new reagents have been tested in segment couplings leading to two tripeptides

  有机磷酸酯9，10，14，和15经由的二乙基-和二苯基磷酰氯，二（反应制备ö甲苯基）氧膦基氯，2,8-二dimethylphenoxaphosphinyl酰氯与加入HOAt是用于肽合成的优良的偶合剂，其一般优于它们的铀/胍类似物和HOBt或HODhbt衍生的磷酸酯对应物，可最大程度地减少链段偶联过程中构型的损失。膦酰基类似物比磷酰基体系更稳定。新的试剂已在分段偶联了测试引向两个三肽（20，21）和六肽22。还显示了ACP十肽的固相组装的出色效用。用衍生自HOAt的2-和4-硝基-和2,4-二硝基苯基磺酰基酯获得了相似的结果。
• 2-cyanopyrrolidides as potent, stable inhibitors of dipeptidyl peptidase IV
  作者：Doreen M. Ashworth、Butrus Atrash、Graham R. Baker、Andrew J. Baxter、Paul D. Jenkins、D.Michael Jones、Michael Szelke

  DOI：10.1016/0960-894x(96)00190-4

  日期：1996.5

  A novel series of stable, potent inhibitors of dipeptidyl peptidase IV has been developed. A number of dipeptide analogues, incorporating a 2-cyanopyrrolidide, were found to have K-i values of less than 5 nM versus human DP-IV and half-lives of >48h in aqueous solution (pH 7.4). (C) 1996 Elsevier Science Ltd