DL 2--2-phenylacetic 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: DL 2--2-phenylacetic acid
• 英文别名: 2--2-phenylacetic acid；2-(N-benzyl-N-tosylamino)-2-phenylacetic acid；2-[Benzyl-(4-methylphenyl)sulfonylamino]-2-phenylacetic acid
• 化学式: C₂₂H₂₁NO₄S
• 分子量: 395.479
• InChiKey: DFENPZJVAUERBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氨基-2-苯基乙酸 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 potassium carbonate 作用下， 以 乙醚 、 乙醇 、 水 、 乙腈 为溶剂， 25.0 ℃ 、137.28 kPa 条件下， 反应 43.5h， 生成 DL 2--2-phenylacetic acid
  参考文献：
  名称：

  Preparation of a 3-phenyl-4(3H)-isoquinolinone and its transformation in 12(11H)-Benzo[c]phenanthridinone derivatives. Crystal structure determinations.

  摘要：

  Trans- and cis-5-(p-toluenesulfonyl)-5,6,13,14-tetrahydro-12(11H)-benzo[c]phenanthridinones have been prepared with excellent yield involving the initial formation of 3-phenyl-2-(p-toluenesulfonyl)-1,2-dihydro-4(3H)-isoquinolinone, as the key intermediate. Spectroscopic studies of the 4(3H)-isoquinolinone and 12(11H)-benzo[c]phenanthridinone derivatives have been developed and their relative configurations have been fully established and confirmed unambiguously by X-ray diffraction analyses.

  DOI：

  10.1016/s0040-4020(01)85708-2

文献信息

• Design, synthesis and collagenase inhibitory activity of some novel phenylglycine derivatives as metalloproteinase inhibitors
  作者：Ankit Ganeshpurkar、Devendra Kumar、Sushil Kumar Singh

  DOI：10.1016/j.ijbiomac.2017.10.008

  日期：2018.2

  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.
• Benzyl 2-[N-benzyl-N-(p-toluenesulfonyl)amino]-2-phenylacetate and its α-amino acid
  作者：M. K. Urtiaga、M. I. Arriortua、D. Badía、E. Domínguez、A. M. González Cameno、X. Solans

  DOI：10.1107/s0108270194002829

  日期：1994.10.15

  The structures of benzyl 2-[N-benzyl-N-(p-toluene-sulfonyl)amino]-2-phenylacetate, C29H27NO4S, (I), and 2-[N-benzyl-N-(p-toluenesulfonyl)amino]-2-phenylacetic acid, C22H21NO4S, (II), have been determined. The geometries of both compounds are similar. The N atoms and the carboxylic C atoms are sp2 hybridized. The N-C(8)-C(9)-O(3) torsion angle in compound (I) [-18.4 (5)-degrees] and the N-C(8)-C(15)-O(4) torsion angle in compound (II) [9.6 (4)-degrees] characterize a synperiplanar conformation for the N atom and the O atom of the C=O group in both compounds studied.
• Preparation of a 3-phenyl-4(3H)-isoquinolinone and its transformation in 12(11H)-Benzo[c]phenanthridinone derivatives. Crystal structure determinations.
  作者：Ana M. González-Cameno、Dolores Badía、Esther Domínguez、M.Karmele Urtiaga、M.Isabel Arriortua、Xavier Solans

  DOI：10.1016/s0040-4020(01)85708-2

  日期：1994.1

  Trans- and cis-5-(p-toluenesulfonyl)-5,6,13,14-tetrahydro-12(11H)-benzo[c]phenanthridinones have been prepared with excellent yield involving the initial formation of 3-phenyl-2-(p-toluenesulfonyl)-1,2-dihydro-4(3H)-isoquinolinone, as the key intermediate. Spectroscopic studies of the 4(3H)-isoquinolinone and 12(11H)-benzo[c]phenanthridinone derivatives have been developed and their relative configurations have been fully established and confirmed unambiguously by X-ray diffraction analyses.