New carbodithioate derivatives: synthesis, characterization, and in vitro antibacterial, antifungal, antitubercular, and
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Med Chem Res (2013) 22:4700–4707 DOI 10.1007/s00044-013-0472-0
ORIGINAL RESEARCH
New carbodithioate derivatives: synthesis, characterization, and in vitro antibacterial, antifungal, antitubercular, and antimalarial activity Tarunkumar Nanjibhai Akhaja • Jignesh Priyakant Raval
Received: 16 July 2012 / Accepted: 6 January 2013 / Published online: 19 January 2013 Ó Springer Science+Business Media New York 2013
Abstract A series of structurally new, 2-(5-substituted2,3-dioxoindolin-1-yl)ethyl/propyl 4-(3,4-dichlorophenyl) piperazine-1-carbodithioate derivatives 5a–j were designed and synthesized by conventional technique as well as ultrasound irradiation. All the new compounds were characterized by spectral and elemental analyses. Furthermore, they were evaluated for their in vitro antibacterial, antifungal, antitubercular, and antimalarial activities. The results indicated that some of the synthesized compounds posses promising antimicrobial activity against some grampositive and gram-negative bacteria. Compounds 5b, 5d, and 5e displayed the highest inhibition (99 %) in the range of 3.10–6.25 lg/ml against Mycobacterium tuberculosis H37 Rv, while compounds 5b–g displayed promising antimalarial activity in the range of 0.043–0.092 lg/mL against Plasmodium falciparum 3D7. Thus, these molecules can provide prospective leads in chemotherapy against tuberculosis and malaria. Keywords Isatin 2,3-Dioxoindoline Carbodithioate Ultrasound Antitubercular Antimalarial activities
T. N. Akhaja (&) J. P. Raval Department of Pharmaceutical Chemistry, Ashok & Rita Patel Institute of Integrated Study and Research in Biotechnology and Allied Sciences (ARIBAS), New Vallabh Vidyanagar 388121, Gujarat, India e-mail: [email protected] J. P. Raval e-mail: [email protected]
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Introduction Sulfur-containing heterocycles are undoubtedly one of the most important targets in organic as well as medicinal chemistry. They are not only widely distributed in natural products but also found to be useful as pharmaceutical agents. Structurally, dithiocarbamates (DTC) (Thorn and Ludwig, 1962) are examples of such heterocyclic system which is found to have interesting chemistry and wide utility. They have received considerable interest because they are ubiquitously found in a variety of biologically active compounds (Erian and Sherif, 1999; Wood and Gardner, 1941; Bowden and Chana, 1990; Beji et al., 1999; Goel et al., 2002). They are proved to be important for its applications in pesticides, fungicides, vulcanization of rubber (Marinovich et al., 2001; Weissmahr et al., 1998; Len et al., 1996; Bergendorff and Hansson, 2002; Halimehjani et al., 2010), as linkers in solid-phase organic synthesis (Morf et al., 2006; Mcclain and Hsieh, 2004; Dunn, 1989), radical precursors (Crich and Quintero, 1989; Zard, 1997; Barton, 1992), ionic liquids (Zhang et al., 2005), and quantam dots (Wang et al., 2008). Besides antibacterial (Ates et al., 1995; Gu¨nay et al., 1999; Farghaly et al., 1999; Xu et al., 2002; Ozkirimli et al., 2005) and antifu
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