The synthesis of new furo-salicylanilides and their heterocyclic derivatives is described. Twenty-three compounds were screened for their molluscicidal activity against Biomphalaria alexandrina snails, the intermediate host of Schistosoma mansoni. Five of the tested compounds showed no activity, while eighteen compounds showed strong to moderate activity using bayluscide as a reference.
A series of androstane derivatives 2-16 were synthesized from 3β-hydroxyandrostan-17-one derivatives (1a-e). Compounds (1a,b) were treated with ethyl cyanoacetate, cyanoacetamide, or malononitrile and gave the corresponding derivatives 2-7, respectively. Additionally, compounds (1a-e) were condensed with cyanothioacetamide, urea, or guanidine hydrochloride afforded the corresponding derivatives 8-12, which then by Moffat oxidation gave the oxidized derivatives 9, 11 and 13, respectively. Finally, compound (1) condensed with acetyl acetone or ethyl acetoacetate gave cyclohexene derivatives (14a-c) and (15a,b), respectively. Compound 15 was oxidized with a Moffat oxidizing agent and afforded the corresponding oxidized compound 16. The newly synthesized compounds activated the tumor suppressor p53 in cancer cells through inhibition of the p53-specific ubiquitin E3 ligase HDM2.
Oxazine derivatives R 0595Synthesis of Furo-salicylanilides and Their Heterocyclic Derivatives with Anticipated Molluscicidal Activity. -The molluscicidal activity of the new furo-salicylanilides (III) including their derivatives (V), (VI), (VIII) and (IX) is tested against Biomphalaria alexandrina snails, the intermediate host of Schistosoma mansoni. The most efficient compound is (Vb) with an activity comparable to that of bayluscide. Rigidification of the structure decreases the activity, cf. (VI) and (IX). -(HASSAN, G. S.; HEGAZY*, G. H.; SAFWAT, H. M.; Arch. Pharm. (Weinheim, Ger.) 339 (2006) 8, 448-455; Dep. Pharm. Chem., Fac. Pharm., Cairo Univ., Cairo, Egypt; Eng.) -H. Haber 49-164
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.