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TRUCTURE OF ORGANIC COMPOUNDS

Synthesis, Characterization, and Crystal Structure of Sulfonamide Chalcone: (E)-4-MethoxyN-(4-(3-(3,4,5-trimethoxyphenyl)acryloyl)phenyl)benzenesulfonamide1 T. Kobkeatthawina, S. Chantraprommaa, *, C. S. Chidan Kumarb, c, and H.-K. Funb, d a Department

of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Prince of Songkla University, Songkhla 90110, Thailand b X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM Penang, Malaysia c Department of Engineering Chemistry, Alva’s Institute of Engineering & Technology, Visvesvaraya Technological University, Mijar, Moodbidri 574225, Karnataka, India dDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia *e-mail: [email protected] Received January 13, 2015

Abstract—The title sulfonamide chalcone derivative was synthesized by condensation reaction of N-(4acetylphenyl)-4-methoxybenzenesulfonamide and 3,4,5-trimethoxybenzaldehyde in basic solution. The structure was determined using FT-IR, 1H-NMR and UV-Vis spectroscopy. The crystal structure was characterized by single crystal X-ray structure analysis: triclinic system, sp. gr. P1, Z = 2; a = 7.9273(5), b = 9.3159(6), c = 18.0174(12) Å, α = 94.6420(18)°, β = 93.0310(17)°, γ = 114.9200(15)°. In crystal packing, the molecules are linked by N–H···O hydrogen bonds into chains along the [100] direction. The crystal is further stabilized by weak C–H···O and C–H···π interactions. DOI: 10.1134/S1063774515070135

INTRODUCTION Sulfonamides are antibiotics commonly used to treat infectious diseases. Their development led to a medical revelation in drug treatments. The structure of sulfonamides containing an –SO2NH– group can be found in many pharmacologically active compounds: recent reports have described anticancer [1] and antibacterial [2] activities. Chalcone derivatives are frequently used in medicinal chemistry as they are key intermediates for synthesis of compounds with numerous biological activities. The two combined pharmacophores involving sulfonamides and chalcones, or sulfonamide chalcones, have been shown to exhibit interestingly synergistic effect in biological activity; sulfonamide chalcones have been reported to display various biological activities such as antityrosinase [3], antimalarial [4], anti-inflammatory [5], antiα-glucosidase [6] and antitumor [7]. Herein, we report the synthesis, characterization and crystal structure of a new sulfonamide chal1 The article is published in the original.

cone derivative (E)-4-methoxy-N-(4-(3-(3,4,5-trimethoxyphenyl)acryloyl)phenyl)-benzenesulfonamide. In addition our anti-tyrosinase assay showed that this compound exhibited anti-tyrosinase activity with 48.14% inhibition. EXPERIMENTAL Reagents and techniques. All reagents and solvents for synthesis and analysis were commercially available and used as received without further purification. Methanol (MeOH) and pyridine were purchased from Merck, sodium hydroxide (NaOH) was purch