A series of sulpha/substituted derivatives of phenyl azo-1,2-diazole have been synthesized and tested as an anti-inflammatory and anti-bacterial activity in mature albino rats hind paw by taking Diclofenac sodium as standard. N¹-(4-hydroxy benzoyl)-3-methyl-5-phenyl-4(N-4-chlorophenylazo)-1,2-diazole is synthesized by a two-step process. In the first step, synthesis of N¹-4-chlorophenyl hydrazono-1-methyl-3-phenyl propane-1,3-dione by the reciprocal action of 1-methyl-5-phenylpropane-1,3-dione and diazonium salt solution of phenyl-chloride interacts with 4-hydroxybenzoic acid hydrazide to form the final compound. These diazoles, the heterocyclic compounds which contained electron withdrawing groups, were screened for analgesic activity by acetic acid induced writing method, and for anti-inflammatory activity carried on carrageenan-induced paw edema. The synthesized substituted Chlorophenylazo-1,2-diazole nucleus exhibited significant anti-bacterial, anti-cancer, anti-inflammatory activity, muscle relaxing and moderate activity in anti-proliferative studies.