Synthesis of aroyl isothiocyanate derivatives of biological interest

Abstract

Isothiocyanate plays an important role in the biosynthesis of hypothiocyanite by a lactoperoxidase. The complete absence of isothiocyanate or deficiency of isothiocyanate in human body cause of damaging human host defense system. Isothiocyanate is a potent competitive inhibitor to the thyroid symporter. It is also a versatile synthon which can be readily transferred to other functional groups. Therefore, synthesis of isothiocyanate derivative is an important research area at this age. Keeping view in mind, a facile synthetic route for the synthesis of isothiocyanate derivatives (2-6) is developed using available chemical reagents. The very simple and general procedure is the stirring of equimolar mixture of triethylammoniumphenolate and benzoyl isothiocyanate in DMF at room temperature for 8-13 hours. The products were characterized by the chemical methods and spectroscopic evidences such as IR and1H NMR. Moderate yield was obtained. Antibacterial screening showed not so significant activity against Gram-positive and Gram- negative bacteria.

X= -H, -NO2, -OH, -OCH3, -N(CH3)2

Synthesis of Aroyl Isothiocyanate Derivatives: Serial no Starting material Product M.P.(°C) %Yield

1.

151-153

43

2.

161-164

40

3.

171-173

38

Serial no Starting material Product M.P.(°C) %Yield

4.

155-159

48

5.

175-179

41