Synthesis and application of some new S-(substituted)thio- and thienoquinoline derivatives as antimicrobial agents

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Title:Synthesis and application of some new S-(substituted)thio- and thienoquinoline derivatives as antimicrobial agents
Creators:
Awad, Ibrahim M. A.
Abdel-Rahman, Abdu E.
Bakhite, Etify A.
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 56, 8, pp. 1749-1760

Abstract

Ethyl (4-aryl-3-cyano-5,6,7,8-tetrahydro-2-quinolinylthio) acetate (<i>IIa, IIb</i>) were prepared and reacted with hydrazine hydrate to give hydrazines <i>IIIa, IIIb</i> which underwent cyclization into thienoquinoline derivatives <i>IVa, IVb</i>. Reaction of <i>IIIa, IIIb</i> with phenyl isocyanate yielded semicarbazides <i>Va, Vb</i>. Similarly, <i>IIIa, IIIb</i> and <i>IVb</i> were interacted with methyl/phenyl isothiocyanates affording the corresponding thiosemicarbazide derivatives <i>VIa - VId</i> and <i>XIVa, XIVb</i> respectively. On the other hand, condensation of <i>IIIb</i> with acetylacetone gave the pyrazole <i>VII</i> treatment with ethoxide furnished <i>VIII</i>. Also, <i>IIIa, IIIb</i> and <i>IVa, IVb</i> reacted with aromatic aldehydes to afford hydrazones <i>IXa - IXf</i> and <i>XIa - XIf</i> respectively. Cyclodehydration of <i>IXd - IXf</i> with thioglycolic acid furnished 4-thiazolidinone derivatives <i>Xa - Xc</i>. Moreover, <i>IVb</i> was reacted with formic acid/acetic anhydride to give <i>XII</i> and <i>XIII</i>. Diazotization of <i>IVb</i> gave azide <i>XV</i> which underwent Curtius rearrangement into <i>XVI</i>. The structures of all newly synthesized compounds were confirmed by elemental analyses and spectral data. Also, the most of these compounds were tested in vitro for their antimicrobial activities against some Gram-positive and Gram-negative bacteria.

Title:Synthesis and application of some new S-(substituted)thio- and thienoquinoline derivatives as antimicrobial agents
Creators:
Awad, Ibrahim M. A.
Abdel-Rahman, Abdu E.
Bakhite, Etify A.
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:56
Number:8
Page Range:pp. 1749-1760
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19911749UNSPECIFIED
ID Code:5102
Item Type:Article
Deposited On:22 Feb 2010 11:30
Last Modified:22 Feb 2010 10:30

Citation

Awad, Ibrahim M. A.; Abdel-Rahman, Abdu E.; Bakhite, Etify A. (1991) Synthesis and application of some new S-(substituted)thio- and thienoquinoline derivatives as antimicrobial agents. Collection of Czechoslovak Chemical Communications, 56 (8). pp. 1749-1760. ISSN 0010-0765

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