1,2,3 Triazolesisimportant type of heterocyclic compound successful application in
medicine and as agrochemicals[1]
Number of five
membered nitrogen containing heterocy-cles, have turned out to be potential
chemotherapeutic and pharmacotherapeutic agents. The biological profile of
tria-zoles derivatives is very extensive[2]
symmetrical triazole
moiety are reported to show a broad spectrum of pharmacological activities such
as antibacte-rial, antifungal, antimicrobial, antimycobacte-rial, antioxidant,
analgesic, antipyretic, antican-cer, anticonvulsant and
anti-inflammatoryactivi-ties[3]
Number of five
membered nitrogen containing heterocy-cles, have turned out to be potential
chemotherapeutic and pharmacotherapeutic agents. The biological profile of
tria-zoles derivatives is very extensive. Compounds bearing a symmetrical
triazole moiety are reported to show a broad spectrum of pharmacological
activities such as antibacte-rial, antifungal, antimicrobial,
antimycobacte-rial, antioxidant, analgesic, antipyretic, antican-cer,
anticonvulsant23 and anti-inflammatoryactivi-ties. These observations prompted us to synthesize
N-[5-(substitutedphenyl)-1H-1,2,3-triazol-1-yl]isonicotinamide derivatives and
4-(substituted benzylideneamino)-5- pyridin-4-yl)-4H-1,2,4-triazole-3-thiol
derivatives using isonicotinic acid as starting material by two different
schemes. In the present paper, we describe the synthesis, charac-terization and
antimicrobial as well as anti-inflammatory activities of the synthesized
triazole derivatives. The struc-ture assigned to compounds
was substantiated by
their ana-lytical and other spectral data
Most of the nitrogen-containing molecules are
pharmacologically very active which can be attributed to the fact that
nitrogenous compounds are part and parcel of the biomolecular diversity [1-7].
Amongst the pharmacologically active nitrogenous compounds, a large number of
1,2,3-triazoles and their derivatives attracted considerable attention for the
past few decades due to their chemotherapeutical value. Many 1,2,3-triazoles
including bis-triazoles, are found to be potent antimicrobial analgesic,
anti-inflammatory, local anesthetic anti-convulsant, anti-neoplastic,
anti-malarial, and antiviral agents[4]
Some of them exhibited anti-proliferative, anticancer
activity, and several are used as DNA cleaving agents and potassium channel
activators. Such type of diverse biological functions is also reported with a
variety of bis-triazoles. The ‘click chemistry’ approach has been the most
widely used method for the synthesis of libraries of a large number of
biologically active molecular
frameworks particularly for the regioselective synthesis of
1,2,3-triazoles, which involves the copper(I)- catalyzed cycloaddition reaction
between azides and terminal alkynes (CuAAC). This reaction has been termed as
the ‘cream of the crop’ of ‘click reactions’ and has found application in various
facets of drug discovery as it
enables a modular approach to generate novel
pharmacophores utilizing a collection of reliable chemical
reactions [11,12]. Thus, the development of the copper(I)-catalyzed ‘triazole
click chemistry’ has led to many interesting applications including the
synthesis, medicinal chemistry, molecular biology, and material science. The
bioorthogonality of azide and alkynes [13] has allowed the use of
their [3 + 2] cycloaddition in various
biological applications including target guided synthesis [14]
and activity-based protein profiling [15]. Of particular interest
would be the dimeric heterocyclebased ligands which are designed for specific
target interactions. Various approaches reported for the synthesis of
biologically relevant bis-triazoles include Cu(I)- catalyzed 1,3-dipolar
cycloaddition of monoazides with
diacetylenes or that of monoacetylenes with diazides. For
example, the synthesis of bis-triazoles is reported by the reactions of bis(azidomethyl)benzenes
with several substituted acetylenes [16]. Recently, much attention
has been paid toward the synthesis and pharmacological evaluation of triazoles
and bis-triazoles as potent HIV-1 protease inhibitors [17,18]
and size-specific ligands for mRNA Hairpin loops [19], respectively.
Keeping into consideration the tremendous biological potence of triazoles
and bis-triazoles in general and the antimicrobial activity
in particular, we, in our continuous endeavor toward the synthesis of
pharmacologically active molecules, designed the synthesis of novel
unsymmetrical bis-1,2,3-triazoles and then evaluated them for
antimicrobial activities. The biological results obtained were very interesting
and revealed most of the synthesized
molecules to be potent antimicrobials
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