Synthesis and antibacterial activity of some new hydrazones
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Med Chem Res (2013) 22:2840–2846 DOI 10.1007/s00044-012-0278-5
ORIGINAL RESEARCH
Synthesis and antibacterial activity of some new hydrazones M. Rudrapal • R. Siva Satyanandam • T. Sri Swaroopini • T. Naga Lakshmi • S. Kamar Jaha • S. Zaheera
Received: 4 July 2012 / Accepted: 9 October 2012 / Published online: 30 October 2012 Ó Springer Science+Business Media New York 2012
Abstract New hydrazone derivatives were synthesized by the condensation of some selected heteroaromatic hydrazines with appropriate aromatic ketones at high temperature (100 °C). The structures of the synthesized compounds were established by elemental (CHN) and spectral (IR, 1HNMR, and Mass) analysis. The synthesized compounds were screened for their antibacterial (Bacillus subtilis, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, Salmonella typhi, Proteus mirabilis) activities, which reveal that all the compounds possess activity against all the tested organisms. Keywords Hydrazone Azomethine Heteroaromatic scaffold Antibacterial
Introduction Hydrazones containing an azomethine –NHN=CH– group represent an important class of compounds which possess a wide range of biologic activities (Corey and Enders, 1976). For this reason, hydrazones derived from a diverse group of heteroaromatic scaffolds (Rollas and Ku¨c¸u¨kgu¨zel, 2007) have successfully been incorporated into a number of therapeutically useful drug candidates. For example, isoniazid (isonicotinoyl hydrazone) is a well known and potent antitubercular drug with very high in vivo inhibitory activity against Mycobacterium tuberculosis H37Rv (Sah
M. Rudrapal (&) R. S. Satyanandam T. S. Swaroopini T. N. Lakshmi S. K. Jaha S. Zaheera Aditya Institute of Pharmaceutical Sciences and Research, Surampalem, E. G. Dist. 533 437, Andhra Pradesh, India e-mail: [email protected]
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and Peoples, 1954). In recent days, many newer hydrazone derivatives have also been known to possess antimicrobial (Vicini et al., 2002), anticonvulsant (Dimmock et al., 2000), analgesic, antiinflammatory, antiplatelet (Todeschini et al., 1998), antimalarial (Walcourt et al., 2004), and antitumor activities (Abadi et al., 2003; Imramovsky´ et al., 2007). It is believed that the azomethine (–NHN=CH–) moiety is essential for the bioactivity of hydrazones and/or hydrazone derivatives as reported in various literatures (Rollas and Ku¨c¸u¨kgu¨zel, 2007). A large number of heteroaromatic scaffolds possessing a wide range of biologic including antimicrobial activities have also been investigated (Mariappan et al., 2011; Pattan et al., 2006; Singh et al., 2010). In view of the above-mentioned facts, an assumption has been made to design some newer hydrazone derivatives using such bioactive heteroaromatic scaffolds as the basic structural unit. Some important pharmacophoric scaffolds which include 4-benzylidene-2methyloxazol-5-one, 2-(4-aminophenyl)benzimidazole, 2-amino-4-phenylthiazole, and isonicotinoyl hydrazide were selected for the present study. We reported herein the synthesis and
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