53821-16-2Relevant articles and documents
Reaction of organozinc halides with aryl isocyanates
Yang, Haoran,Huang, Danfeng,Wang, Ke-Hu,Xu, Changming,Niu, Teng,Hu, Yulai
supporting information, p. 2588 - 2593 (2013/03/28)
Reformatsky reagent, benzylzinc bromide or alkylzinc iodides react with aryl isocyanates directly to give corresponding N-substituted carbamates under mild reaction conditions. However, the reaction of allylzinc bromide or propargylzinc bromide with aryl isocyanates produces the corresponding N-substituted amides. The reactions provide alternative methods for the synthesis of N-substituted carbamates or amides.
Structure-based design, synthesis, and structure-activity relationship studies of HIV-1 protease inhibitors incorporating phenyloxazolidinones
Ali, Akbar,Reddy, G. S. Kiran Kumar,Nalam, Madhavi N. L.,Anjum, Saima Ghafoor,Cao, Hong,Schiffer, Celia A.,Rana, Tariq M.
scheme or table, p. 7699 - 7708 (2010/12/30)
A series of new HIV-1 protease inhibitors with the hydroxyethylamine core and different phenyloxazolidinone P2 ligands were designed and synthesized. Variation of phenyl substitutions at the P2 and P2' moieties significantly affected the binding affinity and antiviral potency of the inhibitors. In general, compounds with 2- and 4-substituted phenyloxazolidinones at P2 exhibited lower binding affinities than 3-substituted analogues. Crystal structure analyses of ligand-enzyme complexes revealed different binding modes for 2- and 3-substituted P2 moieties in the protease S2 binding pocket, which may explain their different binding affinities. Several compounds with 3-substituted P2 moieties demonstrated picomolar binding affinity and low nanomolar antiviral potency against patient-derived viruses from HIV-1 clades A, B, and C, and most retained potency against drug-resistant viruses. Further optimization of these compounds using structure-based design may lead to the development of novel protease inhibitors with improved activity against drug-resistant strains of HIV-1.
Efficient Cs2CO3-promoted solution and solid phase synthesis of carbonates and carbamates in the presence of TBAI
Salvatore, Ralph N,Chu, Feixia,Nagle, Advait S,Kapxhiu, Elona A,Cross, Richard M,Jung, Kyung Woon
, p. 3329 - 3347 (2007/10/03)
Novel solution and solid-phase methods for the synthesis of carbonates and carbamates were developed using cesium bases and TBAI via a three-component coupling. Cesium carbonate not only promoted successful carbonylations of alcohols and carbamations of amines, but also suppressed common side reactions traditionally seen using existing protocols. Various alcohols and amines were examined, using a wide array of alkyl halides, and the results demonstrated this methodology was highly chemoselective. In particular, use of either sterically demanding substrates or amino acid derivatives afforded the corresponding products exclusively, offering a wide variety of applications such as novel protecting groups and peptidomimetic syntheses.
