title: Synthesis, spectroscopic characterization, crystal structure, DNA interaction study and invitro biological screenings of 4-(5-chloro-2-hydroxyphenylamino)-4-oxobut-2-enoic acid.
abstract: The titled compound, 4-(5-chloro-2-hydroxyphenylamino)-4-oxobut-2-enoic acid was synthesized and characterized by various techniques like elemental analyses, FT-IR, NMR ((1)H, and (13)C) and single crystal X-ray structural analysis. The appearance of the OH peak of the carboxylic acid in the FT-IR and NMR spectra conform the formation of the compound. A good agreement was found between the calculated values of C, H, N and found values in elemental analysis that show the purity of the compound. Protons H2 and H3 are in cis conformation with each other as conformed both from (1)H NMR as well as from single crystal X-ray analysis. The molecular structure of the title compound, C₁₀H₁₀NO₃Cl, is stabilized by short intramolecular OH---O hydrogen bonds within the molecule. In the crystal structure, intermolecular NH---O hydrogen bonds link molecules into zigzag chains resulting in a dendrimer like structure. The title compound was screened for biological activities like interaction with DNA, cytotoxicity, antitumor and antioxidant activities. DNA interaction study reveals that the binding mode of interaction of the compound with SS-DNA is intercalative as it results in hypochromism along with significant red shift of 5 nm. It was also found to be effective antioxidant of 2,2-diphenyl-1-picrylhydrazyl radical (DPPH) and show almost comparable antioxidant activity to that of the standard and known antioxidant, ascorbic acid, at higher concentration. The antitumor activity data of the compound shows that it can be used as potent antitumor agent.
authors.affiliation: Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan. Electronic address: m.siraj09@yahoo.com.
authors.forename: Muhammad
authors.initials: M
authors.lastname: Sirajuddin
authors.affiliation: Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan.
authors.lastname: Nooruddin
authors.affiliation: Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan. Electronic address: drsa54@yahoo.com.
authors.forename: Saqib
authors.initials: S
authors.lastname: Ali
authors.affiliation: Department of Chemistry, Loughborough University, Leicestershire LE11 3TU, UK.
authors.forename: Vickie
authors.initials: V
authors.lastname: McKee
authors.affiliation: Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan; Department of Chemistry, University of Science and Technology, Bannu, Pakistan.
authors.forename: Shahan Zeb
authors.initials: SZ
authors.lastname: Khan
authors.affiliation: Centralized Research Laboratory (CRL), University of Peshawar, K.P.K., Pakistan.
authors.forename: Khan
authors.initials: K
authors.lastname: Malook
mesh_terms: D000814:Aniline Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000494:pharmacology*; D000975:Antioxidants / Q000737:chemistry / Q000494:pharmacology*; D001156:Artemia / Q000187:drug effects; D002087:Butyrates / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D060326:Chemistry Techniques, Synthetic; D018360:Crystallography, X-Ray; D004247:DNA / Q000737:chemistry; D050091:Dendrimers; D004353:Drug Evaluation, Preclinical / Q000379:methods; D004354:Drug Screening Assays, Antitumor / Q000379:methods; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D011198:Solanum tuberosum; D013056:Spectrophotometry, Ultraviolet; D017550:Spectroscopy, Fourier Transform Infrared
chemical_list: C000601650:4-(5-chloro-2-hydroxyphenylamino)-4-oxobut-2-enoic acid; D000814:Aniline Compounds; D000970:Antineoplastic Agents; D000975:Antioxidants; D002087:Butyrates; D050091:Dendrimers; D004247:DNA
keywords: Antioxidant activity; Antitumor activity; Crystal structure; Cytotoxicity; DNA interaction