Synthesis and biological evaluation of new imidazo[2,1-b][1,3,4]thiadiazole-benzimidazole derivatives

European Journal of Medicinal Chemistry
Jurupula RamprasadH S Santosh Kumar

Abstract

In this report, we describe the synthesis and biological evaluation of a new series of 2-(imidazo[2,1-b][1,3,4]thiadiazol-5-yl)-1H-benzimidazole derivatives (5a-ac). The molecules were analyzed by (1)H NMR, (13)C NMR, mass spectral and elemental data. The structure of one of the pre-final compounds, 6-(4-methoxyphenyl)-2-(4-methylphenyl)imidazo[2,1-b][1,3,4]thiadiazole-5-carbaldehyde (4d) and that of a target compound, 2-[2-methyl-6-(4-methyl phenyl) imidazo[2,1-b][1,3,4]thiadiazol-5-yl]-1H-benzimidazole (5aa) were confirmed by single crystal XRD studies. All the target compounds were screened for in vitro anti-tuberculosis activity against Mycobacterium tuberculosis H37Rv strain. Seven (5c, 5d, 5l, 5p, 5r, 5z and 5aa) out of twenty nine compounds showed potent anti-tubercular activity with a MIC of 3.125 μg/mL. A p-substituted phenyl group (p-tolyl or p-chlorophenyl) in the imidazo[2,1-b][1,3,4]thiadiazole ring and/or a chloro group in the benzimidazole ring enhance anti-tuberculosis activity whereas a nitro group in the benzimidazole ring reduces the activity. In the antibacterial screening, compounds 5i, 5w and 5ac showed promising activity against the tested bacterial strains. Further, antifungal and antioxidant activities ...Continue Reading

Citations

Jul 28, 2016·European Journal of Medicinal Chemistry·Akanksha Kulshreshtha, Poonam Piplani
Oct 1, 2016·Pharmacological Reports : PR·Rangappa S KeriBhari Mallanna Nagaraja
Jun 10, 2017·Medicinal Research Reviews·Vajinder KumarRahul Jain
May 8, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ismail AlthagafiThoraya A Farghaly
Jan 30, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Daniel InsuastyRodrigo Abonia
Nov 23, 2019·Mini Reviews in Medicinal Chemistry·Mahesh S VasavaHitesh D Patel
May 24, 2016·Archiv der Pharmazie·Olayinka O AjaniIfedolapo O Olanrewaju
Sep 27, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Anamaria CristinaValentin Zaharia
Aug 15, 2019·BMC Chemistry·Sumit TahlanBalasubramanian Narasimhan
Oct 18, 2016·Acta Crystallographica. Section E, Crystallographic Communications·A SowmyaSubhas S Karki

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