Synthesis and Antimicrobial activity of Bulky molecules comprising Benzothiazole and Sulphonamide moieties
Pritesh R. Patel*, Priyank Patel, Jagath Pillai, Nilesh Darji, Bhagirath Patel
Department of Pharmaceutical Chemistry,
Sat Kaival College of Pharmacy, Sarsa,
Ta & Dist: Anand (Gujarat), India-388365
As part of ongoing studies in developing new antimicrobials, a novel series of 4-acetamido-N-(substituted 1, 3-benzothiazol-2-yl) benzenesulphonamide and N-(substituted 1, 3-benzothiazol-2-yl)-4-(substituted aryl diazenyl) benzenesulphonamide were synthesized in order to determine their antibacterial and antifungal activity. The synthesized compounds were tested in vitro against two Gram-positive bacteria like Staphylococcus aureus, Bacillus subtilis; two Gram-negative bacteria like Escherichia coli, Pseudomonas aeruginosaand one fungal strain Candida albicans in comparison with standard drugs. Microbiological results showed that the synthesized compounds possessed a broad spectrum of antibacterial and antifungal activity against the tested microorganisms. The compounds with a 6-chloro (SK5b), 7-chloro-6-fluoro(SK5d) and 6-nitro (SK5e) on 2-amino benzothiazole ring possessing azo linkage showed better antimicrobial activity; almost similar or less to that of standard drugs thus they could be promising candidates for novel drugs. The novel heterocyclic derivatives were characterized by Physical characterization (Melting point, TLC) and different Spectroscopy techniques (IR, 1H NMR and Mass spectroscopy).
Reference Id: PHARMATUTOR-ART-1331
The major drawback of current treatment of infectious diseases are challenging due to resistance to antimicrobial agents and their side effects. Limited numbers of antimicrobials are available to treat infections caused by fungi and mycobacteria. Chemotherapy for cancer treatment, immunosuppressive drugs for treatment of autoimmune diseases and organ transplant recipients, and infections (such as AIDS) that alter the effectiveness of the host immune system render individuals at high risk for fungal infections and certain mycobacterial infections. Numbers of new infectious diseases have been discovered. So, there is an urgent need to develop novel drugs molecule, with fewer side effects, broad spectrum activity, better stability and drugs with shorter lengths for the treatment of infectious disease. Microbial infection indirectly invites another disease due to low immunity power during infectious conditions. In the global market there are many antimicrobial agents but they all have some or more drawbacks, so to remove these drawbacks it is necessary to develop new antimicrobial agents. Rationale behind this work is to develop a molecule having good anti-microbial activity.
Based on review of Literature Benzothiazole, Sulphonamide and Azo moieties show significant antibacterial and antifungal activity. Based on review of literature 2-amino Benzothiazole at 4, 5 & 6th position substitution to improve biological activities. Literature survey reveals that electron withdrawing or donating groups amend the liphophilicity of the test compounds, which in turn alters permeability across the bacterial cell membrane.1 From research article Bhusari K. et al., concluded that Benzothiazole moiety attached to sulphonamide to improve antibacterial and antifungal properties.2 From research article Chaudhari M. et al., reported that synthesize and screen the antibacterial activity of some new Benzothiazole derivatives containing azo group in their structure.3According to research article MKPENIE V. et al., reported that azo compound of naphthalene and use it to investigate its inhibitory effect on the biological activities of bacterial strains. The presence of azo group contributed more than 60% of the antibacterial activities exhibited by azo-2-naphthol on all the bacteria tested.4So, based on these important concepts to develop novel bulky molecules comprising Benzothiazole, Sulphonamide, Azo group as potent antibacterial and antifungal agents.
MATERIAL AND METHODS
All the Chemicals and Solvents were obtained from E-Merck, India (AR grade) and were used further purification. The melting point of the synthesized compounds were determined in open capillary using VEEGO MELTING POINT APPARATUS model VMP-D and recorded in Celsius without correction. Purity of the compound was verified by precoated TLC plates (E- Merck Kieselgel 60 F254). The Infrared spectra for the synthesized compounds were recorded using SHIMADZU-FTIR 8400S spectrometer using KBr as a back ground. 1H NMR spectra of the synthesized compounds were taken using BRUKER Advance-II 400 NMR spectrometer using Tetramethyl silane as an internal standard. 1H NMR spectra were recorded with DMSO as a solvent & the chemical shift data were expressed as delta values related to TMS. Mass spectra of the synthesized compounds were taken using 2010EV LCMS SHIMADZU instrument at 70 eV.
Figure 1: Route of synthesis
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