Synthesis of N-(3,6-dihydro-1(2H)-pyridinyl)benzamides with hyperglycemic-hypoglycemic activity
摘要:
A group of N-(3,6-dihydro-1(2H)-pyridinyl)benzamides 7 were synthesized to determine the effect that the position and physicochemical properties of substituents attached to the heterocyclic ring have on blood glucose levels. 5-Methyl-N-(3,6-dihydro-1(2H)-pyridinyl)benzamide 7b was the most active hyperglycemic agent, elevating blood glucose 124% and 116% at 2 and 4 h, respectively, after a 100 mg/kg po dose. The most active hypoglycemic agent was the 4-acetyl analogue 7o, which was about 50% as active as chlorpropamide, lowering blood glucose 19% at 4 h after a 100 mg/kg po dose. A correlation between blood glucose levels and the partition coefficient P was not observed.
Synthesis and pharmacological evaluation of some N‐[pyridyl(phenyl)carbonylamino]methyl‐1,2,3,6‐tetrahydropyridines
作者:Kinfe K. Redda、Kode Nageswara Rao、S. Heiman、Hailemichael Melles
DOI:10.1002/jps.2600810515
日期:1992.5
Reaction of some picolines 5 with 1-chloro-2,4-dinitrobenzene (6) in acetone furnished methyl-substituted 2,4-dinitrophenylpyridinium chlorides 7. Further reaction with phenyl(pyridyl)carbonyl hydrazides 8 at room temperature furnished isolable 2,4-dinitroanilino derivatives 9, which were then refluxed in a water:dioxane mixture (1:4, v/v) to furnish the methyl-substituted phenyl(pyridyl)carbonyl iminopyridinium