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Combination Of Bioactive Moieties With Different Heteroatom(s): Application Of The Suzuki Cross‐coupling Reaction

Rahul V Patel, Jigar K. Patel, Premlata Kumari, Kishor H. Chikhalia
Published 2012 · Chemistry

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Two series of thiophene/benzothiophene-linked quinolinyl oxadiazoles condensed to the substituted N-benzothiazolyl acetamides have been synthesized via the Suzuki cross-coupling reaction. The ester derivative of 6-bromo-substituted quinoline was reacted via the Suzuki cross-coupling reaction with commercially available (benzo)thiophen-2-ylboronic acid at optimized temperature in 1,2-dimethoxy ethane and water in the presence of potassium carbonate and palladium tetrakis. The resulting derivatives were then hydrazinolized using 99% hydrazine hydrate followed by cyclization using carbon disulfide in ethanolic KOH to furnish the corresponding oxadiazoles, which were then condensed with various substituted 2-chloro-N-benzothiazolyl acetamides to produce the final scaffolds involving a unique combination of four heterocycles to be examined for their antimicrobial activity against two Gram-positive bacteria (Staphylococcus aureus and Bacillus cereus), three Gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa, and Klebsiella pneumoniae), and two fungal species (Aspergillus niger and Candida albicans). The investigation of biological screening data revealed that the majority of the compounds tested have demonstrated excellent activity (minimum inhibitory concentrations; 6.25–50 µg/mL) against most of the microorganisms as compared with the standard and hence they warrant more consideration as prospective antimicrobial agents. New products (9a–10i) were characterized by physicochemical, elemental, and spectral (IR, 1H NMR, and 13C NMR) data. © 2012 Wiley Periodicals, Inc. Heteroatom Chem 23:399–410, 2012; View this article online at DOI 10.1002/hc.21027
This paper references
Synthesis and antifungal activity of novel sulfoxide derivatives containing trimethoxyphenyl substituted 1,3,4-thiadiazole and 1,3,4-oxadiazole moiety.
F. Liu (2008)
Novel 5-(2-hydroxyphenyl)-3-substituted-2,3-dihydro-1,3,4-oxadiazole-2-thione derivatives: promising anticancer agents.
Ahmed S. Aboraia (2006)
Bacteria on the rampage
J. Davies (1996)
Molecular properties prediction, synthesis and antimicrobial activity of some newer oxadiazole derivatives.
M. A. Bakht (2010)
In vitro antitumor and antiviral activities of new benzothiazole and 1,3,4-oxadiazole-2-thione derivatives
Tashfeen Akhtar (2008)
N-{[(6-substituted-1,3-benzothiazole-2-yl)amino]carbonothioyl}-2/4-substituted benzamides: synthesis and pharmacological evaluation.
A. Rana (2008)
Synthesis of carbon-11 labeled fluorinated 2-arylbenzothiazoles as novel potential PET cancer imaging agents.
M. Wang (2006)
Synthesis and biological property of some novel 1,3,4-oxadiazoles.
G. C. Ramaprasad (2010)
Past, present, and future of antimicrobial agents.
R. Moellering (1995)
Oxadiazole mannich bases: synthesis and antimycobacterial activity.
M. Ali (2007)
Palladium-Catalyzed Suzuki-Type Self-Coupling of Arylboronic Acids. A Mechanistic Study
M. Moreno-Mañas (1996)
Synthesis and preliminary evaluation of some substituted coumarins as anticonvulsant agents.
K. M. Amin (2008)
The Palladium-Catalyzed Cross-Coupling Reaction of Phenylboronic Acid with Haloarenes in the Presence of Bases
N. Miyaura (1981)
Synthesis, characterisation and biological activity of novel 4-thiazolidinones, 1,3,4-oxadiazoles and some related compounds.
S. G. Kuecuekguezel (2002)
Synthesis and antifungal activities of 5-(3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4-thiadiazole and 5-(3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4-oxadiazole derivatives.
C. Chen. (2007)
Benzo[b]thiophenes, Part I: Synthesis and Antimicrobial Activity of Benzo[b]thienyl‐1,3,4‐oxadiazole, ‐1,2,4‐triazoline, and ‐thiazoline Derivatives
Omaima M. Aboulwafa (1992)
Glycopeptide antibiotic resistance.
Jeff Pootoolal (2002)
Synthesis and pharmacological evaluation of 2-substituted benzo[b]thiophenes as anti-inflammatory and analgesic agents.
Issa M. I. Fakhr (2009)
Novel antibacterial agents for the treatment of gram positive infections
A. Pearson (2003)
Synthesis and antimicrobial study of novel heterocyclic compounds from hydroxybenzophenones.
S. Khanum (2005)
Synthesis and Antimicrobial Activity ofSome New Thioether Derivatives of Quinoxaline
D. P. Singh (2011)
Synthesis, characterization and biological activities of some new benzo[b]thiophene derivatives.
Arun M. Isloor (2010)
Transmission of substituent effects in heterocyclic systems by carbon-13 nuclear magnetic resonance. Benzothiazoles
S. N. Sawhney (1979)
Synthesis of some 2-[(benzazole-2-yl)thioacetylamino]thiazole derivatives and their antimicrobial activity and toxicity.
G. Turan‐Zitouni (2004)
Antimycobacterial activity of new 3-substituted 5-(pyridin-4-yl)-3H-1,3,4-oxadiazol-2-one and 2-thione derivatives. Preliminary molecular modeling investigations.
M. G. Mamolo (2005)
Combating resistance in a challenging, changing environment.
F. Goldstein (2007)
Design and synthesis of 1,3-biarylsulfanyl derivatives as new anti-breast cancer agents.
Atul Kumar (2011)
Clinical-Use-Associated Decrease in Susceptibility of Vancomycin-Resistant Enterococcus faecium to Linezolid: a Comparison with Quinupristin-Dalfopristin
I. Raad (2004)
Synthesis, characterization and antimicrobial activity of some disubstituted 1,3,4-oxadiazoles carrying 2-(aryloxymethyl)phenyl moiety.
C. S. Naveena (2010)
Design, synthesis and biological evaluation of 1,3,4-oxadiazole derivatives.
K. K. Jha (2010)

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