Synthesis, Fungicidal Activity, and 3D-QSAR of Pyridazinone-Substituted 1,3,4-Oxadiazoles and 1,3,4-Thiadiazoles

Abstract

A series of novel 5-[1-aryl-1,4-dihydro-6-methylpyridazin-4-one-3-yl] -2-arylamino-1,3,4-oxadiazoles, fungicidally active, were synthesized based on bioisosterism and tested in vivo against wheat leaf rust, Puccinia recondita. These compounds were shown to be fungicidally active, and their activity was influenced by the nature of the substituents. By using the three-dimensional quantitative structure-activity relationships (3D-QSAR) method of comparative molecular field analysis (CoMFA), we have studied the structure and activity relationship of the compounds containing both pyridazinone-substituted 1,3,4-thiadiazoles and pyridazinone-substituted 1,3,4-oxadiazoles. The 3D-QSAR modes gave good correlation between the variations on percent inhibition and the steric-electrostatic properties. The results are consistent with a common mode of action for the pyridazinone-substituted 1,3,4-thiadiazoles and the pyridazinone-substituted 1,3,4-oxadiazoles, which further confirms that the 1,3,4-oxadiazole ring is a bioisosteric analogue of the 1,3,4-thiadiazole ring. These offer important structural insights into designing highly active compounds prior to their synthesis.

Silver Nanoparticles Effect on Antimicrobial and Antifungal Activity of New Heterocycles

“…[21][22][23] Pyridazines including mono-and bicyclic derivatives have attracted much attention due to their potential biological activities. 24 The recent advances in combinatorial chemistry and high throughput screening have confirmed the tremendous importance of heterocycles as templates in the search for novel pharmacologically useful low molecular weight compounds.…”

Synthesis and Evaluation of Antiangiogenic and Anticancer Properties of Novel Oxadiazole Analogues

“…Condensation of one mole of compound 5 with two moles of 6a-d in the presence of potassium carbonate and DMF afforded compounds 7a-d (scheme-1). Besides, compound 1 on treatment with compound 3 in the presence of 2,6 lutidine, O-(benzotriazol-1-yl)-N,N,N0,N0-tetramethyluronium tetrafluoroborate (TBTU) and dichloromethane (DCM) afforded N,N(4.4'-dinitro)dibenzoyl hydrazide (8). Compound 8 on treatment with phosphorous pentoxide yield 2,5(4,4'-dinitro)diphenyl 1,3,4-oxadiazole (9).…”

“…Five member nitrogen containing heterocycles with oxygen atom are an important class of compounds in medicinal chemistry. Oxadiazole derivatives have attracted much attention among five-membered oxygen containing heterocycles because of their biological and pharmacological properties like antibacterial [4][5][6] , antimicrobial 7 , fungicidal 8 , anti-inflammatory 9 , antipsychotic 10 , anticonvulsant 11 , antidepressant 12 and anticancer 13 . In the light of the above discussion we have investigated the effects of oxadiazoles related compounds on a panel of cell-lines.…”

Separation of palmitic acid from over used oil for production of heterogeneous organic derivatives of potential biological activities

“…The structure elucidation of all synthesized compounds is based on the elemental analysis and spectral data (IR, 1 H NMR, 13 C NMR and MS). antifungal [12][13][14], antioxidant [15] and antidepressant [16 ].…”