title: Synthesis and structure-activity relationships of heterocyclic compounds containing a trimethoxyarene function.
abstract: Pyrazole-, isoxazole-, and pyrazolone-containing systems were prepared from 3,4-dihydro-5,6,7-trimethoxy-1(2H)-naphthalenone, 3,4-dihydro-6,7,8-trimethoxy-1(2H)-naphthalenone, and 3,4-dihydro-6,7,8-trimethoxy-1(2H)-phenanthrone. Primarily, the pyrazoles displayed inhibition of growth in the microbial screens and in tissue culture. Correlation of the heteroatom distances between the oxygen atoms of two methoxy groups and a nitrogen atom in the pyrazole function with the percent plating efficiency on KB cell growth suggests increased inhibition as the (OA-N)/(OB-N) ratio deviates from one. No trend was observed in relating the OA-N-OB angle and activity for the examples studied.
mesh_terms: D001412:Bacillus subtilis / Q000254:growth & development; D002478:Cells, Cultured; D003864:Depression, Chemical; D006801:Humans; D007555:Isoxazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D008738:Methyl Ethers / Q000138:chemical synthesis / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D009281:Naphthalenes / Q000138:chemical synthesis / Q000494:pharmacology; D010080:Oxazoles / Q000138:chemical synthesis*; D010616:Phenanthrenes / Q000138:chemical synthesis / Q000494:pharmacology; D011551:Pseudomonas fluorescens / Q000254:growth & development; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: D007555:Isoxazoles; D008738:Methyl Ethers; D009281:Naphthalenes; D010080:Oxazoles; D010616:Phenanthrenes; D011720:Pyrazoles