Synthesis, Characterization And Biological Evaluation Of Naphthalene - And Coumarin-Based Chalcones

• Main Author: Lim , Sumithda Yeong Hui
• Format: Thesis
• Language: English
• Published: 2016
• Subjects: QC1 Physics (General)
• Online Access: http://eprints.usm.my/31375/1/SUMITHDA_LIM_YEONG_HUI_24.pdf; http://eprints.usm.my/31375/

Kajian ini dimulakan dengan sintesis dan pencirian dua siri utama bahan pemula: pengalkilan naftaldehid (2-8) dan pengasetilan kumarin tertukar ganti (9-11). Bahan pemula yang diperoleh dikenalpasti melalui kaedah spektroskopi seperti inframerah transformasi Fourier (FTIR), resonans magnet nukleus (NMR) dan mikroanalisis CHN. Analisa pembelauan sinar-X hablur tunggal (XRD) juga dijalankan dengan hablur bagi sebatian 3, 34, dan 41 menghablur dalam sistem kristal triklinik. Lima siri kalkon kemudiannya disintesis melalui kaedah kondensasi Claisen-Schmidt dengan tiga siri diterbitkan daripada kumarin asetil tertukar ganti (12-33) dan dua siri yang lain diterbitkan daripada asetofenon tertukar ganti (34-46). Semua kalkon yang disintesis telah dicirikan dengan analisa unsur (CHN), spektroskopi FTIR , 1H-NMR, 13C-NMR, DEPT 135, 1H-1H COSY, 1H-13C HMQC dan 1H-13C HMBC. Kalkon 23, 28, 34, dan 41 telah dipilih untuk analisis kristolografi. This study was started by the synthesis and characterization of two main series of starting materials: alkylation of naphthaldehydes (2-8) and acetylation of substituted coumarins (9-11). The starting materials thus obtained were elucidated by the spectroscopic methods such as fourier transform infrared (FTIR), nuclear magnetic resonance (NMR) and CHN microanalyses. Single crystal X-ray diffraction (XRD) analyses have also been carried out wherein the crystals of compound 3, 34 and 41 crystallized in a triclinic crystal system. Five novel series of chalcones were subsequently synthesized by means of Claisen-Schmidt condensation wherein three series were derived from substituted acetyl coumarins (12-33) and the remaining two series was derived from substituted acetophenones (34-46). All the synthesized chalcones were characterized by elemental analysis (CHN), FTIR, 1H-NMR, 13C-NMR, DEPT 135, 1H-1H COSY, 1H-13C HMQC and 1H-13C HMBC spectroscopy. Selected chalcones, 23, 28, 34, and 41 were selected for crystallography analysis.