title: Synthesis of novel bisindolylmethane Schiff bases and their antibacterial activity.
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 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.
authors.affiliation: Atta-ur-Rahman Institute for Natural Product Discovery, Universiti Teknologi MARA, Puncak Alam Campus 42300, Malaysia.
authors.forename: Syahrul
authors.initials: S
authors.lastname: Imran
authors.affiliation: Atta-ur-Rahman Institute for Natural Product Discovery, Universiti Teknologi MARA, Puncak Alam Campus 42300, Malaysia. taha_hej@yahoo.com.
authors.forename: Muhammad
authors.initials: M
authors.lastname: Taha
authors.affiliation: Atta-ur-Rahman Institute for Natural Product Discovery, Universiti Teknologi MARA, Puncak Alam Campus 42300, Malaysia. norhadiani@puncakalam.uitm.edu.my.
authors.forename: Nor Hadiani
authors.initials: NH
authors.lastname: Ismail
authors.affiliation: Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi-75270, Pakistan.
authors.forename: Khalid Mohammed
authors.initials: KM
authors.lastname: Khan
authors.affiliation: Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Federal Urdu University of Arts, Science and Technology, Karachi-75370, Pakistan.
authors.forename: Farzana
authors.initials: F
authors.lastname: Naz
authors.affiliation: Department of Microbiology, Federal Urdu University of Arts, Sciences and Technology, Gulshan-e-Iqbal Campus, Karachi-75370, Pakistan.
authors.forename: Memona
authors.initials: M
authors.lastname: Hussain
authors.affiliation: Department of Microbiology, Federal Urdu University of Arts, Sciences and Technology, Gulshan-e-Iqbal Campus, Karachi-75370, Pakistan.
authors.forename: Saima
authors.initials: S
authors.lastname: Tauseef
mesh_terms: D000900:Anti-Bacterial Agents / Q000008:administration & dosage* / Q000138:chemical synthesis / Q000737:chemistry; D000935:Antifungal Agents / Q000008:administration & dosage / Q000138:chemical synthesis / Q000737:chemistry; D001547:Benzaldehydes / Q000138:chemical synthesis / Q000737:chemistry; D006090:Gram-Negative Bacteria / Q000187:drug effects*; D006094:Gram-Positive Bacteria / Q000187:drug effects*; D006801:Humans; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D009596:Nitrophenols / Q000138:chemical synthesis / Q000737:chemistry; D012545:Schiff Bases / Q000008:administration & dosage / Q000138:chemical synthesis / Q000737:chemistry*; D014230:Triazoles / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: C512018:1,1-bis(3'-indolyl)methane; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D001547:Benzaldehydes; D007211:Indoles; D009596:Nitrophenols; D012545:Schiff Bases; D014230:Triazoles; C024719:4-nitrophenyl; C030374:indole
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