Synthesis
of new series of N-3-[-{2-(substituted phenyl-4-
oxo-5-(substituted
benzylidene)-1,3-thiazolidine}-carbamyl]-
propyl-2-aminothiazole
and their biological importance
PUSHKAL SAMADHIYA*,
RITU SHARMA, SANTOSH K SRIVASTAVA and
SAVITRI D
SRIVASTAVA
Synthetic Organic
Chemistry Laboratory, Department of Chemistry, Dr. H S Gour University (A
Central
University), Sagar,
India 470 003
e-mail:
pushkalsamadhiya@rediffmail.com
MS received 4
December 2010; revised 7 May 2011; accepted 11 May 2011
Abstract.
Synthesis of new series of N-3-[-{2-(substituted
phenyl-4-oxo-5-(substituted benzylidene)-1,3-
thiazolidine}-carbamyl]-propyl-2-aminothiazole,
5(a–s) have been developed. The cycloaddition reaction of
thioglycolic acid
with N-{3-(substituted benzylidine-carbamyl)-propyl}-2-aminothiazole, 3(a–s)
in the presence
of anhydrous ZnCl2
afforded new heterocyclic compounds N1-3-[-{2-(substituted
phenyl-4-oxo-1,3-
thiazolidine}-carbamyl]-propyl-2-aminothiazole
4(a–s). The latter product on treatment with several selected
substituted
aromatic aldehydes in the presence of C2H5ONa undergoes
Knoevenagel reaction to yield 5(a–s).
The structure of
compounds 1, 2, 3(a–s), 4(a–s) and 5(a–s) were
confirmed by IR, 1H NMR, 13C NMR, FAB
mass and chemical
analysis. All final compounds were screened for their antimicrobial activity
against some
selected bacteria
and fungi and antituberculosis study against M. tuberculosis, gave
acceptable activity.
Graphical
Abstract. A
new series of N-3-[-{2-(substituted phenyl-4-oxo-5-(substituted
benzylidene)-1,3-thiazolidine}-carbamyl]-propyl-2-aminothiazole,
5(a–s) have
been synthesized from
2-aminothiazole. The structures of compounds were
confirmed by spectroscopic and
chemical methods. All the compounds were
screened for their antimicrobial and
antituberculosis activities.
Keywords. Synthesis; aminothiazole; thiazolidinone; antimicrobial;
antitubercular.