100619-46-3Relevant 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.
THE INTERMOLECULAR BENZYNE CYCLOADDITION (IBC) APPROACH TO 7-SUBSTITUTED APORPHINOIDS.MECHANISTIC CONSIDERATIONS
Atanes, N.,Castedo, L.,Cobas, A.,Guitian, E.,Saa, C.,Saa, J. M.
, p. 7947 - 7956 (2007/10/02)
7-Alkyl-substituted aporphinoids were obtained in moderate yield through the reaction of N-protected 1-ethylidene-1,2,3,4-tetrahydroisoquinolines with benzyne. 7-Alkoxy and 7-chloro derivatives were also prepared by this route, though in lower yield.Mecha
