The Open Conference Proceedings Journal

2013, 4 : 38-38
Published online 2013 March 1. DOI: 10.2174/2210289201304010038
Publisher ID: TOPROCJ-4-4-38

Synthesis of New Aminoanthraquinone from 1,4-(Dihydroxy)Anthracene-9,10-Dione

Siti Fadilah Juhan , Siti Mariam Mohd Nor , Mohd Aspollah Sukari , Saripah Salbiah Syed Abdul Aziz , Wong Chee Fah and Hasimah Alimon
Department of chemistry, Faculty of Sciences, Universiti Putra Malaysia 43400 Serdang, Selangor, Malaysia.

ABSTRACT

A new series of aminoanthraquinone were successfully synthesized via two step of reaction. Firstly 1,4-(dihyroxy)anthracene- 9,10-dione was treated with butylamine in the presence of iodobenzene-diacetate to gives 2-(butylamino)-1,4-dihydroxyanthraquinone (1) (90%). In the second step 1 was subjected to reduction, methylation and acylation. Reduction using NaBH4 result 2-(butyamino)anthracene-1,4-dione (2) where as methylation give a mixture of 2-(butyamino)-1-hydroxy-4-methoxyanthracene-9,10-dione (3a) and 2-(butyamino)-1,4-dimethoxyanthracene-9,10-dione (3b) in 2%, 32% and 25% respectively. The acylation produced 2-(butylamino)-9,10-dioxo-9,10-dihydroanthracene-1,4-diyl diacetate (4) in excellent yield. Characterizations of the products were obtained from the analysis by digital melting point equipment, Fourier Transform Infrared Spectroscopy (FT-IR), Direct Injection Mass Spectrometry (DI-MS), Gas Chromatography Mass Spectrometry (GCMS) and also Nuclear Magnetic Resonance (NMR). Compound 4 shows good antimicrobial activities toward methicillinresistant Staphylococcus aureus (MRSA), Pseudomonas aeruginosa, Candida albicans and Escherichia coli with MIC value of 0.1, 0.1, 0.1 and 0.5 mg/mL respectively.

Keywords:

1,4-dihyroxyanthraquinone, Amination, Aminoanthraquinone., antimicrobial activity.