SUZANA (2019) SINTESIS N’-BENZILIDENA-4-HIDROKSIBENZOHIDRAZIDA TERSUBSTITUSI DAN HUBUNGAN STRUKTUR-AKTIVITASNYA SEBAGAI ANTIMIKROBA. Disertasi thesis, UNIVERSITAS AIRLANGGA.

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Abstract

In the present study a series of substituted N’-benzylidene-4-hydroxybenzohydrazides were synthesized and studied for their in vitro antimicrobial potential against Escherichia coli ATCC 8739, Bacillus subtilis ATCC 6633, Candida albicans ATCC 10231 and Trychophyton rubrum. The substituted N’-benzylidene-4-hydroxybenzohydrazide (BHB-substituted) compounds were synthesized synthesized two steps reaction. The first step of acyl nucleophilic substitution reaction produced 4- hydroxybenzohydrazide. The second step of nucleophilic addition - elimination reaction is carried out by reacting 4-hydroxy-benzohydrazide and benzadehyde/derivatives with the yields 50-88%. Identification of BHB-substituted compounds were carried out by UV, IR, 1H-NMR, 13C-NMR and Mass spectroscopies. Analysis of structure-activity relationships showed that the structural changes of N'-benzylidene-4- hydroxybenzohidrazide derivatives can increase antibacterial activity against E. coli ATCC 8739 and B. subtilis ATCC 6633. The compounds BHB-4-Cl and BHB-3,4-Cl2 showed to be most active against E. coli ATCC 8739. Compounds BHB-4-Cl, BHB-3,4- Cl2, BHB-4-Br and BHB-4-N(CH3)2 were pointed to be most active against B. subtilis ATCC 6633. Compound BHB-2,4-Cl2 was pointed to be most active against C.albicans ATCC 10231. And compound BHB-2-OH was pointed to be most active against T.rubrum. The molecular docking study was also performed as a potential ENR inhibitor. The addition of azobenzylidene derivatives to these compounds had influenced the electronic (RS) and lipophilicity (CLog P) properties of compounds, especially in the affinity of the compounds to interact with the ENR inhibitor. Docking studies revealed that steric interaction and hydrogen bonding with amino acid (Asp 1064, Val 1065, Thr 1038, Ala 1066, Glu 1067, Cys 1063 and Ile 1119) of ENR found to be crucial and results are comparable with in vitro antimicrobial activities of synthesized derivatives.

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