271599-72-5Relevant academic research and scientific papers
Design, synthesis and collagenase inhibitory activity of some novel phenylglycine derivatives as metalloproteinase inhibitors
Ganeshpurkar, Ankit,Kumar, Devendra,Singh, Sushil Kumar
, p. 1491 - 1500 (2018)
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 COL_G 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 FT-IR, 1H NMR, 13C 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 μM, 29.61 μM, 28.39 μM, 31.4 and 32.11 μM respectively were found to be more active. Further, The Ki of most active compound 5b was found to be 22.02 μM showing the competitive mode of inhibition of the enzyme. The activity of the derivatives showed correlation with the docking results.
One-step synthesis of racemic α-amino acids from aldehydes, amine components, and gaseous CO2 by the aid of a bismetal reagent
Mita, Tsuyoshi,Higuchi, Yuki,Sato, Yoshihiro
, p. 1123 - 1128 (2013/02/23)
α-Amino acids are essential resources for human life and are highly useful as building blocks for organic synthesis. The core framework of an α-amino acid can be divided into three basic components: an aldehyde, an amine, and carbon dioxide (CO2). We report herein that a one-step synthesis of α-amino acids has been successfully achieved from these three basic and inexpensive chemicals with a single operation, in which the mixture of an aldehyde, a sulfonamide, and gaseous CO2 was heated at 100 °C in the presence of Bu3Sn-SnBu3 and CsF. In this one-pot sequential protocol, two important intermediates (imine and α-amino stannane) are involved and the stannyl anion generated in situ plays a crucial role, particularly for the efficient stannylation of the imine in the presence of proton sources and for promoting retrostannylation of the undesired α-alkoxy stannane owing to its high stability and tolerance of the presence of proton sources. This methodology enabled the synthesis of a wide range of racemic arylglycine derivatives in high yields. Go retro! α-Amino acids are essential resources for human life and are highly useful as building blocks for organic synthesis. The core framework of an α-amino acid is retrosynthesized to an aldehyde, an amine, and carbon dioxide. A one-step synthesis of α-amin Copyright
Hydrolysis of N-(2,2,2-trichloroethyl)arenesulfonamides
Rozentsveig,Levkovskaya,Mirskova,Kashik
, p. 1760 - 1764 (2007/10/03)
The direction of alkaline hydrolysis of N-(2,2,2-trichloro-1-R-ethyl)arenesulfonamides depends on the R substituent in the α-position with respect to the nitrogen atom. Substituents R having an n-donor heteroatom X promote cleavage of the C-N and C-X bonds to release the corresponding sulfonamide. Alkaline hydrolysis of N-(1-aryl-2,2,2-trichloroethyl)arenesulfonamides occurs chemoselectively at the trichloromethyl group. This reaction can be regarded as a preparative route to N-arylsulfonyl-α-arylglycines.
