882690-75-7Relevant academic research and scientific papers
Synthesis of new thiazole-2, -4, and -5-yl-(amino)methylphosphonates and phosphinates: Unprecedented cleavage of thiazole-2 derivatives under acidic conditions
Olszewski, Tomasz Krzysztof,Boduszek, Bogdan
experimental part, p. 8661 - 8666 (2011/01/04)
An efficient and reliable synthesis of new thiazole-(amino) methylphosphonic, phosphinic acids, and phosphine oxides is reported. The synthetic protocol is based on nucleophilic addition of phosphorous species to thiazole derived imines. Unexpectedly, it was discovered that heating of thiazole-2-yl-(amino)methylphosphonates and phosphinates with aqueous HCl leads to their decomposition resulting in a rupture of the C-P bond, rejecting of the phosphorus containing fragment and formation of the corresponding secondary N-(thiazole-2-yl-methyl)-alkylamines. Two alternative mechanisms for this cleavage are postulated.
Synthesis of thiazole aminophosphine oxides, aminophosphonic and aminophosphinic acids and Cu(II) binding abilities of thiazole aminophosphonic acids
Olszewski, Tomasz K.,Boduszek, Bogdan,Sobek, Sylwia,Koz?owski, Henryk
, p. 2183 - 2189 (2007/10/03)
A series of new aminophosphine oxides, aminophosphonic and aminophosphinic acids derived from thiazole was synthesized by addition of phosphine oxides or silylated phosphorus esters to the corresponding thiazole aldimines. The thiazole aldimines were obta
Second-generation peptidomimetic inhibitors of protein farnesyltransferase demonstrating improved cellular potency and significant in vivo efficacy
O'Connor, Stephen J.,Barr, Kenneth J.,Wang, Le,Sorensen, Bryan K.,Tasker, Andrew S.,Sham, Hing,Shi-Chung, Ng,Cohen, Jerome,Devine, Edward,Cherian, Sajeev,Saeed, Badr,Zhang, Haichao,Jang Yun, Lee,Warner, Robert,Tahir, Stephen,Kovar, Peter,Ewing, Patricia,Alder, Jeffrey,Mitten, Michael,Leal, Juan,Marsh, Kennan,Bauch, Joy,Hoffman, Daniel J.,Sebti, Said M.,Rosenberg, Saul H.
, p. 3701 - 3710 (2007/10/03)
The synthesis and evaluation of analogues of previously reported farnesyltransferase inhibitors, pyridyl benzyl ether 3 and pyridylbenzylamine 4, are described. Substitution of 3 at the 5-position of the core awl ring resulted in inhibitors of equator less potency against the enzyme and decreased efficacy in a cellular assay against Ras processing by the enzyme. Substitution of 4 at the benzyl nitrogen yielded 26, which showed improved efficacy and potency and yet presented a poor pharmacokinetic profile. Further modification afforded 30, which demonstrated a dramatically improved pharmacokinetic profile. Compounds 26 and 29 demonstrated significant in vivo efficacy in nude mice inoculated with MiaPaCa-2, a human pancreatic tumor- derived cell line.
