Abstract
The synthesis of antimicrobial activity spirocompounds was achieved via the reaction of hydrazonoyl halides 1 with exocyclic 4-arylidene-2-methylimidazolin-5-one 3 in benzene in the presence of triethylamine. Correct elemental analyses and spectral data (IR, 1H NMR, 13C NMR and MS) confirm the structure of the synthesized spirocompounds. All the synthesized compounds were evaluated in vitro for their antimicrobial activity against five gram-positive and two gram-negative bacteria using well diffusion method in Mueller-Hinton agar. Most of them exhibited significant antibacterial activity compared with selected standard drugs.
Highlights
Spirocompounds form a group of generally less investigated compounds
Some new imidazolinone derivatives have been reported as antimicrobial (Desai et al, 2009; Solankee et al, 2004), anticancer (Solankee et al, 2004) and L-DOPA prodrugs in the treatment of Parkinson’s disease (Giorgionia et al, 2010)
Tetrazaspiro[4,4]nona-2,8-dien-6-one derivatives 4a-w were produced via the cycloaddition reaction of nitrilimines 2, generated in situ by the action of triethylamine on hydrazonoyl halides 1a-f in dry benzene at reflux temperature with exocyclic double bond of 4-arylidene-1-aryl-2-methyl-1H-imidazol-5(4H)-one 3a-f (Scheme 1)
Summary
Spirocompounds form a group of generally less investigated compounds. recently growing efforts have been made to synthesize, characterize and investigate the biological activities of these compounds. Many spirocompounds possess very promising biological activities as anticancer agents (Young-Won et al, 2003; Wen-Liang et al, 2007), antibacterial agents (van-der-Sar et al, 2006; Hyeong-Beom et al, 2007), anticonvulsant agents (Jolanta & Krzysztof, 2006; Krzysztof et al, 2008; Jolanta et al, 2006), anti tuberculosis agents (Chande et al, 2005), anti-Alzheimer’s agents (Masakazu et al, 2001), pain-relief agents (Frank et al, 2003; Hans et al, 2006), anti-dermatitis agents (Nakao et al, 2008) and antimicrobial agents (Pawar et al, 2009; Thadhaney et al, 2010) In addition to their medical uses, some spirocompounds have found other uses in the agricultural and industrial fields. The synthesis of new tetrazaspiro[4,4]nona-2,8-dien-6-one derivatives has been achieved
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