51640-62-1Relevant academic research and scientific papers
Diphenylacetylene-linked peptide strands induce bidirectional β-sheet formation
Lingard, Hannah,Han, Jeongmin T.,Thompson, Amber L.,Leung, Ivanhoe K. H.,Scott, Richard T. W.,Thompson, Sam,Hamilton, Andrew D.
supporting information, p. 3650 - 3653 (2014/04/17)
In the search for synthetic mimics of protein secondary structures relevant to the mediation of protein-protein interactions, we have synthesized a series of tetrasubstituted diphenylacetylenes that display β-sheet structures in two directions. Extensive
4-Substituted 5-nitroisoquinolin-1-ones from intramolecular Pd-catalysed reaction of N-(2-alkenyl)-2-halo-3-nitrobenzamides
Dhami, Archana,Mahon, Mary F.,Lloyd, Matthew D.,Threadgill, Michael D.
experimental part, p. 4751 - 4765 (2009/10/23)
4-Methyl- and 4-benzyl-5-aminoisoquinolin-1-ones are close analogues of the water-soluble PARP-1 inhibitor 5-AIQ. Their synthesis was approached through Pd-catalysed cyclisations of N-(2-alkenyl)-2-iodo-3-nitrobenzamides. Reaction of N,N-diallyl-2-iodo-3-nitrobenzamide with Pd(PPh3)4 gave a mixture of 2-allyl-4-methyl-5-nitroisoquinolin-1-one and 2-allyl-4-methylene-5-nitro-3,4-dihydroisoquinolin-1-one. N-Benzhydryl-N-cinnamyl-2-iodo-3-nitrobenzamide similarly gave 2-benzhydryl-4-benzyl-5-nitroisoquinolin-1-one and 2-benzhydryl-4-benzylidene-5-nitro-3,4-dihydroisoquinolin-1-one. The isomeric products are not interconvertible. A deuterium-labelling study indicated that the isomers were formed by different pathways: a π-allyl-Pd route and the classical Heck route. The corresponding secondary amides N-allyl-2-iodo-3-nitrobenzamide and N-((substituted)-cinnamyl)-2-iodo-3-nitrobenzamide gave good yields of the required 4-methyl- and 4-((substituted)-benzyl)-5-nitroisoquinolin-1-ones, respectively, under optimised conditions (Pd(PPh3)4, Et3N, Bu4NCl, 150 °C, rapid heating). Hydrogenation of the nitro groups gave 4-methyl- and 4-benzyl-5-aminoisoquinolin-1-ones, which were potent inhibitors of PARP-1 activity.
A New Synthesis of 2,2'-Disubstituted Unsymmetrical Biphenyls Based on the Intramolecular Ullmann Coupling Reaction Utilising Salicyl Alcohol as a Template
Takahashi, Masami,Ogiku, Tsuyosi,Okamura, Kimio,Da-te, Tadamasa,Ohmizu, Hiroshi,et al.
, p. 1473 - 1480 (2007/10/02)
A synthesis of 2,2'-disubstituted unsymmetrical biphenyls was examined by using the template-directed intramolecular Ullmann coupling reaction as a key step.The Ullmann coupling reaction of the diesters 1-5 showed that the most suitable ring size for the intramolecular Ullmann coupling reaction is an eleven-membered ring.On the basis of these results, salicyl alcohol was selected as a template.Acylations of salicyl alcohol by two different aroyl chlorides proceeded regioselectively in a one-pot procedure to afford the diesters 18 in good yields.The intramolecular Ullmann coupling reaction of 18 by the dropwise-addition method gave the cyclisation products 19 in high yields.Hydrogenolysis of 19 proceeded regioselectively to afford the unsymmetrical biphenyls 21 in quantitative yields, while the regioselective cleavage of the ester bonds of 19 by nucleophilic substitution reactions gave the corresponding 2,2'-disubstituted unsymmetrical biphenyls 22 and 24 in good yields.
Assymetric Synthesis of Axially Chiral, Unsymmetrical Diphenic Acids via Intramolecular Ullmann Coupling Reaction
Miyano, Sotaro,Fukushima, Hiroshi,Handa, Shigeru,Ito, Hiromitsu,Hashimoto, Harukichi
, p. 3249 - 3254 (2007/10/02)
A partical route to unsymmetrical diphenic acids is described.Successive esterification of ethylene glycol with two different 2-halobenzoyl chlorides gave the corresponding mixed diester, which was treated with copper powder in bolding DMF under dilution conditions.Silica-gel column chromatography allowed ready separation of the intramolecularly coupled cyclic diester (30-60 percent yield) from other by-products accompanying the Ullmann reaction, and alkaline hydrolysis gave unsymmetrical diphenic acid.Axially chiral, unsymmetrical diphenic acids of more than 99 percent enantiomeric excess were obtained from the reaction of mixed diesters prepared from (R)-1,1'-bi-2-naphthol.
