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Molecules 2014, 19(8), 11722-11740;

Synthesis of Novel Bisindolylmethane Schiff bases and Their Antibacterial Activity

Atta-ur-Rahman Institute for Natural Product Discovery, Universiti Teknologi MARA, Puncak Alam Campus 42300, Malaysia
Faculty of Applied Science, Universiti Teknologi MARA, Shah Alam 40450, Selangor D.E., Malaysia
Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi-75270, Pakistan
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Federal Urdu University of Arts, Science and Technology, Karachi-75370, Pakistan
Department of Microbiology, Federal Urdu University of Arts, Sciences and Technology, Gulshan-e-Iqbal Campus, Karachi-75370, Pakistan
Authors to whom correspondence should be addressed.
Received: 2 July 2014 / Revised: 23 July 2014 / Accepted: 1 August 2014 / Published: 6 August 2014
(This article belongs to the Section Medicinal Chemistry)
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In an effort to develop new antibacterial drugs, some novel bisindolylmethane derivatives containing Schiff base moieties were prepared and screened for their antibacterial activity. The synthesis of the bisindolylmethane Schiff base derivatives 326 was carried out in three steps. First, the nitro group of 3,3'-((4-nitrophenyl)-methylene)bis(1H-indole) (1) was reduced to give the amino substituted bisindolylmethane 2 without affecting the unsaturation of the bisindolylmethane moiety using nickel boride in situ generated. Reduction of compound 1 using various catalysts showed that combination of sodium borohydride and nickel acetate provides the highest yield for compound 2. Bisindolylmethane Schiff base derivatives were synthesized by coupling various benzaldehydes with amino substituted bisindolylmethane 2. All synthesized compounds were characterized by various spectroscopic methods. The bisindolylmethane Schiff base derivatives were evaluated against selected Gram-positive and Gram-negative bacterial strains. Derivatives having halogen and nitro substituent display weak to moderate antibacterial activity against Salmonella typhi, S. paratyphi A and S. paratyphi B. View Full-Text
Keywords: indole; bisindolylmethane; bisindole Schiff base; antibacterial; sodium borohydride; nickel acetate indole; bisindolylmethane; bisindole Schiff base; antibacterial; sodium borohydride; nickel acetate

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This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Imran, S.; Taha, M.; Ismail, N.H.; Khan, K.M.; Naz, F.; Hussain, M.; Tauseef, S. Synthesis of Novel Bisindolylmethane Schiff bases and Their Antibacterial Activity. Molecules 2014, 19, 11722-11740.

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