2,2'-Phthaloyl-,2,2'-isophthaloyl-, and 2,2'-terephthaloylbis[1,1,1-trimethylhydrazinium] dihydroxide, bis(inner salts): synthesis, partition coefficients, toxicity and effect on ganglionic transmission.
2,2'-Phthaloyl-, 2,2'-isophthaloyl, and 2,2'-terephthaloyl-boff++[1,1,1-trimethylhydrazinium] dihydroxide, bis(inner salts) 7, 8, and 9 and their hydrazide and hydrazinium diiodide precursors were synthesized and tested for toxicity and their ability to block sympathetic ganglionic transmission. Only the 2,2'-phthaloyl and isophthaloylhydrazinium diiodides 4 and 5 produced weak inhibition of nerve transmission (35% at 2.15 X 10(-3) M). The inner salts were appreciably less toxic than the hydrazinium diiodides in brine shrimp testing. The log P (log10, chloroform pH 7 buffer system) values of all compounds were determined and those of the inner salts and hydrazinium diiodides were in the range of -3.03 to -3.60.
Cates
L A
LA
Li
V S
VS
Basrur
J P
JP
Alkadhi
K A
KA
D000818:Animals; D055598:Chemical Phenomena; D002621:Chemistry; D033364:Decapoda; D005730:Ganglionic Blockers / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D006834:Hydrazines / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D066298:In Vitro Techniques; D010795:Phthalic Acids / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D051381:Rats; D012995:Solubility; D009435:Synaptic Transmission / Q000187:drug effects*
D005730:Ganglionic Blockers; D006834:Hydrazines; D010795:Phthalic Acids; C049461:2,2'-phthaloyl bis(trimethylhydrazinium); C049460:2,2'-isophthaloyl bis(trimethylhydrazinium); C049462:2,2'-terephthaloyl bis(trimethylhydrazinium)