60372-07-8Relevant academic research and scientific papers
Designing new analogs for streamlining the structure of cytotoxic lamellarin natural products
Tangdenpaisal, Kassrin,Worayuthakarn, Rattana,Karnkla, Supatra,Ploypradith, Poonsakdi,Intachote, Pakamas,Sengsai, Suchada,Saimanee, Busakorn,Ruchirawat, Somsak,Chittchang, Montakarn
, p. 925 - 937 (2015/03/31)
Despite the therapeutic potential of marine-derived lamellarin natural products, their preclinical development has been hampered by their lipophilic nature, causing very poor aqueous solubility. In order to develop more drug-like analogs, their structure was streamlined in this study from both the cytotoxic activity and lipophilicity standpoints. First, a modified total synthetic route was successfully devised to construct a library of 59 systematically designed lamellarin analogs, which were then subjected to cytotoxicity and log P determinations. Along with the 25 first-generation lamellarins previously synthesized in our laboratory, the structure-activity and structure-lipophilicity relationships were extensively evaluated. Our results clearly indicated the additional structural requirements around the lamellarin skeleton which, when combined with those reported previously, can provide invaluable guidance for further modifications to increase the aqueous solubility of these compounds.
SYNTHESIS OF 3-O-METHYLATED DERIVATIVES OF CATECHOLAMINES
Kulikov, S. V.,Samartsev, M. A.
, p. 280 - 288 (2007/10/02)
3-O-Methylated catecholamines, used in the radioenzyme method for the analysis of catecholamines in blood, were synthesized. The optimum conditions for the production of both the intermediate and the final products were determined. By the use of tetrabutylammonium bromide in the condensation of nitromethane with O-benzylvanilin it is possible to obtain a high yield of 1-(3-methoxy-4-benzyloxyphenyl)-2-nitroethanol. The latter is easily transformed at a palladium catalyst into methylnoradrenaline by reduction with ammonium formate. The reduction of 1-(3-methoxy-4-benzyloxyphenyl)-2-nitroethylene with hydrogen or its donors at a palladium catalyst takes place significantly more readily in the presence of ferric chloride.
