2-phenyl-2-(2,4,6-triisopropylphenylsulfonamido)acetic acid

• 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: 2-phenyl-2-(2,4,6-triisopropylphenylsulfonamido)acetic acid
• 英文别名: 2-Phenyl-2-[[2,4,6-tri(propan-2-yl)phenyl]sulfonylamino]acetic acid；2-phenyl-2-[[2,4,6-tri(propan-2-yl)phenyl]sulfonylamino]acetic acid
• 化学式: C₂₃H₃₁NO₄S
• 分子量: 417.569
• InChiKey: NKPWVIDVLPMJDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  91.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-phenyl-2-(2,4,6-triisopropylphenylsulfonamido)acetic acid 、 氯化苄 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 2-((N-benzyl-(2,4,6-triisopropyl))phenylsulfonamido)-2-phenylacetic acid
  参考文献：
  名称：

  Design, synthesis and collagenase inhibitory activity of some novel phenylglycine derivatives as metalloproteinase inhibitors

  摘要：

  Metalloproteases are a class of proteases having metal ion(s) at their catalytic sites. Bacterial collagenases are involved in human gas gangrene, periodontal diseases, food etc. The Clostridium collagenase occurs in two isoforms COLG and Col_H. The present work is based on the protein structure-based approach for the development of collagenase inhibitors. The sequence analysis and structural alignment of both isoforms showed significant similarity in active site except aspartate switch present in Col_H. The homology model was developed and validated for Col_H peptidase domain with open aspartate switch followed by the docking of designed ligands. Compound 8b showed better interaction due to the presence of the nitro group, The N-benzyl-arylsulfonyl-phenylglycine derivatives were synthesized and characterized by FTIR, H-1 NMR, C-13 NMR and mass spectral analysis. The compounds were evaluated for C. histolyticum collagenase inhibitory activity using gelatin-ninhydrin based assay. Compounds 5b, 3b, 11b, 6b and 8b with IC50 of 24.34 mu M, 29.61 mu M, 28.39 mu M, 31.4 and 32.11 mu M respectively were found to be more active. Further, The Ki of most active compound 5b was found to be 22.02 mu M showing the competitive mode of inhibition of the enzyme. The activity of the derivatives showed correlation with the docking results. (C) 2017 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ijbiomac.2017.10.008
• 作为产物：
  描述：

  2,4,6-三异丙基苯磺酰氯 、 2-氨基-2-苯基乙酸 在 sodium carbonate 、 potassium carbonate 作用下， 以 水 、 丙酮 为溶剂， 生成 2-phenyl-2-(2,4,6-triisopropylphenylsulfonamido)acetic acid
  参考文献：
  名称：

  Design, synthesis and collagenase inhibitory activity of some novel phenylglycine derivatives as metalloproteinase inhibitors

  摘要：

  Metalloproteases are a class of proteases having metal ion(s) at their catalytic sites. Bacterial collagenases are involved in human gas gangrene, periodontal diseases, food etc. The Clostridium collagenase occurs in two isoforms COLG and Col_H. The present work is based on the protein structure-based approach for the development of collagenase inhibitors. The sequence analysis and structural alignment of both isoforms showed significant similarity in active site except aspartate switch present in Col_H. The homology model was developed and validated for Col_H peptidase domain with open aspartate switch followed by the docking of designed ligands. Compound 8b showed better interaction due to the presence of the nitro group, The N-benzyl-arylsulfonyl-phenylglycine derivatives were synthesized and characterized by FTIR, H-1 NMR, C-13 NMR and mass spectral analysis. The compounds were evaluated for C. histolyticum collagenase inhibitory activity using gelatin-ninhydrin based assay. Compounds 5b, 3b, 11b, 6b and 8b with IC50 of 24.34 mu M, 29.61 mu M, 28.39 mu M, 31.4 and 32.11 mu M respectively were found to be more active. Further, The Ki of most active compound 5b was found to be 22.02 mu M showing the competitive mode of inhibition of the enzyme. The activity of the derivatives showed correlation with the docking results. (C) 2017 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ijbiomac.2017.10.008

文献信息

• Sulfonamides as Amine Component in the Petasis-Borono Mannich Reaction: A Concise Synthesis of α-Aryl- and α-Alkenylglycine Derivatives­
  作者：Georg Manolikakes、Andreas Diehl、Omar Ouadoudi、Eleni Andreadou

  DOI：10.1055/s-0037-1610440

  日期：2018.10

  reaction for the first time. A catalyst-free three-component synthesis of α-aryl- and α-alkenylglycine derivatives starting from glyoxylic acid, sulfonamides, and aryl- or alkenylboronic acids is described. This operationally simple method tolerates a broad range of functional groups and enables the generation of a wide array of α-amino acids. Sulfonamides were utilized as amine component in the classic

  摘要 描述了从乙醛酸，磺酰胺和芳基或烯基硼酸开始的无催化剂的三组分合成α-芳基和α-烯基甘氨酸的衍生物。这种操作简单的方法可耐受各种官能团，并能够产生多种α-氨基酸。在经典的Petasis反应中，磺酰胺首次被用作胺成分。 描述了从乙醛酸，磺酰胺和芳基或烯基硼酸开始的无催化剂的三组分合成α-芳基和α-烯基甘氨酸的衍生物。这种操作简单的方法可耐受各种官能团，并能够产生多种α-氨基酸。在经典的Petasis反应中，磺酰胺首次被用作胺成分。