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Synthesis and antibacterial activity of certain quinoline and quinazoline derivatives containing sulfide and sulfone moieties
Author(s) -
ElZohry Maher F.,
Ahmed Abd ElHamed N.,
Omar Farghaly A.,
AbdAlla Mohamed A.
Publication year - 1992
Publication title -
journal of chemical technology and biotechnology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.64
H-Index - 117
eISSN - 1097-4660
pISSN - 0268-2575
DOI - 10.1002/jctb.280530403
Subject(s) - chemistry , quinoline , quinazoline , hydrogen peroxide , benzene , ethanol , acetic acid , medicinal chemistry , organic chemistry , ethyl chloroacetate , sodium hydroxide , aryl , acetyl chloride , sulfone , chloride , nuclear chemistry , catalysis , alkyl , hydrate
Some aryl and/or heterocyclic mercaptans were allowed to react with 8‐quinolyl chloroacetate (II), 8‐quinolinoxyacetyl chloride (IV) and 3‐(2′‐chloroethyl)‐2‐methyl‐3,4‐dihydroquinazolin‐4‐one (X) in dry benzene and/or sodium hydroxide in absolute ethanol to give corresponding 8‐quinolyl‐α‐mercaptoacetate (V), 8‐quinolinoxythioacetate (VI) and 3‐(2′‐arylmercaptoethyl)‐2‐methyl‐4‐(3H)quinazolin‐4‐ones or 3‐(2′‐heterocyclicmercaptoethyl)‐2‐methyl‐4(3H)‐quinazolin‐4‐ones (XIa‐h). The mercaptans V and XI were subjected to oxidation with hydrogen peroxide/acetic acid mixture (1:2) to afford the corresponding sulfones VII and XII. The structures of the synthesized compounds were elucidated by spectroscopic (IR and 1 H‐NMR) and elemental analyses. Some of these compounds were tested for their antimicrobial activities in comparison with tetracycline as a reference compound.