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Molecules 2014, 19(8), 11722-11740; doi:10.3390/molecules190811722

Synthesis of Novel Bisindolylmethane Schiff bases and Their Antibacterial Activity

1
Atta-ur-Rahman Institute for Natural Product Discovery, Universiti Teknologi MARA, Puncak Alam Campus 42300, Malaysia
2
Faculty of Applied Science, Universiti Teknologi MARA, Shah Alam 40450, Selangor D.E., Malaysia
3
Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi-75270, Pakistan
4
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Federal Urdu University of Arts, Science and Technology, Karachi-75370, Pakistan
5
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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Abstract

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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MDPI and ACS Style

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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