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Arch Pharm (Weinheim) ; 345(6): 495-502, 2012 Jun.
Article in English | MEDLINE | ID: mdl-22308019

ABSTRACT

A new class of biologically active 13-membered phosphorus-macroheterocycles (6a-l) were conveniently synthesized from 1,2-bis(salicylidene amino)-phenylene (1), by treating with phosporusoxychloride (3) and followed by reacting with various aromatic thiols and amines (5f-l) in one path, and in another path 1 was directly treated with various phosphorodichloridates (2a-e) in the presence of triethylamine at 0-10°C under N(2) atmosphere in THF. All the title compounds were confirmed by analytical and spectral data (IR, (1) H-, (13) C-, (31) P-NMR, and mass spectra) and screened for anti-oxidant activity. Among these compounds, 6k, 6e, and 6l containing nitro, fluoro, and chloro groups as substituents on the phenyl ring exhibited high anti-oxidant activity with effective inhibitory concentration (IC(50) ) values.


Subject(s)
Free Radical Scavengers/chemical synthesis , Free Radical Scavengers/pharmacology , Organophosphorus Compounds/chemical synthesis , Organophosphorus Compounds/pharmacology , Thiadiazoles/chemical synthesis , Thiadiazoles/pharmacology , Free Radical Scavengers/chemistry , Free Radicals/chemistry , Hydrogen Bonding , Hydroxyl Radical/chemistry , Molecular Conformation , Organophosphorus Compounds/chemistry , Stereoisomerism , Structure-Activity Relationship , Thiadiazoles/chemistry
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