Synthesis and Antifungal Activity of Novel Benzimidazol-2-ylcyanoketone Oxime Ethers Containing Morpholine Moiety

Abstract

A series of benzimidazol-2-ylcyanoketone oxime ethers containing morpholine moiety (4a～4h) were synthesized from 2-benzimidazolyl acetonitrile, sodium nitrite, chloroacetyl morpholine and haloalkane/benzyl chloride via sequential reactions of oximation, substitution and etherification. The structures of the target compounds were elucidated by IR, NMR, MS, and elemental analysis. All the target compounds were tested for in vitro antifungal activities against Botrytis cinerea and Sclerotinia sclerotiorum by the mycelium growth rate test, and the results indicated that some compounds displayed higher antifungal activity as compared to carbendazim, among which the compounds containing 4-fluorobenzyl or 4-chlorobenzyl moiety (4e, 4f) have excellent activity.

Pharmacological and Toxicological Screening of Novel Benzimidazole-Morpholine Derivatives as Dual-Acting Inhibitors

“…Furthermore, the benzimidazole ring is a structural bioisostere of some of the nucleobases existing in natural nucleotides, which can interact easily with the biopolymers in living systems [ 9 ]; this feature is often accepted as the responsible for its biological importance, either alone or as incorporated into different templates. It has been reported to show many pharmacological activities including antimicrobial, MAO or cyclooxygenase (COX) inhibitory, or anticholinesterase [ 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 ]. Besides, albendazole, mebendazole and tiabendazole are some examples of antimicrobial agents that carry the benzimidazole ring ( Figure 2 ).…”