BENZIMIDAZOLE HYBRIDE MOLECULES A.U. Berdiev., I.S. Ortikov., B.Zh. Elmuradov S.Yu. Yunusov Institute of the Chemistry of Plant Substances Academy of sciences of the Republic of Uzbekistan st. Mirzo-Ulugbek, 77, 100170 Tashkent Thieno[2,3-d]pyrimidines (TPs) derived molecules have been reported to possess
multiple biological activities, including inhibitory activity against the interaction
between DNA repair proteins Rev7 and Rev3L, HCVreplication, the transcription factor
Nrf2 and kinases. Therefore, the construction of the TP backbone has drawn attention in
the organic synthesis community.
Currently, the best reported synthesis of TPs requires stoichiometric catalysts and
multiple steps, including a Knoevenagel condensation, followed by a Gewald reaction,
and heat-promoted cyclization.In subsequently experiments, the reaction of the obtained
TPs with phosphorus oxychloride (POCl
3
) in the presence of tertiary amines (TEA)
replaced the oxygen of the carbonyl group in the position 4
th
with a chlorine atom. Their
susceptibility to nucleophilic substitution reactions suggests that they are one of the
most important synthons for modern organic synthesis.
Literature survey revealed that incorporation of different groups in TP heterocyclic
ring enhanced antibacterial and antifungal activity. Encouraged by the diverse
biological activities of novel TP derivatives, it was decided to prepare a new series of
derivatives of TP core. In the present work 5,6-polymethylene-4-chloro TPs
(3a-c) were
reacted with relevant heterocyclic amine in absolute ethanol to form 4-heteryl TPs
(4a- c) , which were synthesized by nucleophilic substitution of different multisubstituted 4-
chloro TPs with benzimidazole to get target compounds. The synthesis of respective
compounds was achieved by a systematic approach is outlined in the follow:
Structure of all synthesized compounds was confirmed by IR,
1
H and
13
C NMR
spectroscopy. Further these compounds are subject for biological activity.
