Synthesis of Novel Bisindolylmethane Schiff bases and Their Antibacterial Activity

Molecules

Syahrul Imran²  Muhammad Taha²  Nor Hadiani Ismail²  Khalid Mohammed Khan³  Farzana Naz¹  Memona Hussain⁴ 

[1] Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Federal Urdu University of Arts, Science and Technology, Karachi-75370, Pakistan;Atta-ur-Rahman Institute for Natural Product Discovery, Universiti Teknologi MARA, Puncak Alam Campus 42300, Malaysia;H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi-75270, Pakistan;Department of Microbiology, Federal Urdu University of Arts, Sciences and Technology, Gulshan-e-Iqbal Campus, Karachi-75370, Pakistan

关键词: indole;    bisindolylmethane;    bisindole Schiff base;    antibacterial;    sodium borohydride;    nickel acetate;   

DOI  :  10.3390/molecules190811722

来源: mdpi

【 摘 要 】

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 3–26 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.

【 授权许可】

CC BY   
© 2014 by the authors; licensee MDPI, Basel, Switzerland.