Nitrosation Products of Hexamethylenetetramine

Nitric Oxide Donors: Chemical Activities and Biological Applications

“…243 The nitrosation products of hexamethylenetetramine, 1,3,5-trinitrosoheuahydro-1,3,5-triazine (6) and 3,7-dinitroso-1,3,5,7-tetrazabicyclo[3.3.1]nonane (7), have been shown to form NO at yields of 3.1% or 1.3% in vitro at 37 °C (1 h, pH 7.4), respectively. 244 N-Aryl-N-nitrosamines have higher NO-releasing potentials than N-alkyl-N-nitrosamines, because the resonance effect between the aromatic ring and neighboring nitrogen increases the NO-generating ability. Electron-withdrawing groups on the aromatic ring can weaken the N-NO bond and enhance the NO releasing ability.…”

“…[250][251][252] Inhibition results from the S-nitrosation of the critical cysteine residues in the active sites of the enzymes by the nitrosamines. Compounds 6 and 7 have been found to inhibit thrombus formation in arterioles and venules of rats, 244 while N-nitrosamide 9 exhibited vasodilation and mutagenicity as a result of NO release. 253 N-Aromatic N-nitrosourea 10, which decomposes at ambient temperature without photoirradiation, showed similar NO-generating ability to that of SNAP.…”

“…For example, compounds 2 and 3 release NO in the liver and blood with yields of 1% and 0.01%, respectively . The nitrosation products of hexamethylenetetramine, 1,3,5-trinitrosoheuahydro-1,3,5-triazine ( 6 ) and 3,7-dinitroso-1,3,5,7-tetrazabicyclo[3.3.1]nonane ( 7 ), have been shown to form NO at yields of 3.1% or 1.3% in vitro at 37 °C (1 h, pH 7.4), respectively 13 …”

“…For example, dephostatin and other N -methyl- N -nitrosoanilines ( 1 ) were found to be the inhibitors of protein tyrosine phosphatases, papain, and caspase. − Inhibition results from the S -nitrosation of the critical cysteine residues in the active sites of the enzymes by the nitrosamines. Compounds 6 and 7 have been found to inhibit thrombus formation in arterioles and venules of rats, while N -nitrosamide 9 exhibited vasodilation and mutagenicity as a result of NO release .…”

Facile Assembling of Novel 2,3,6,7,9-pentaazabicyclo- [3.3.1]nona-3,7-diene Derivatives under Microwave and Ultrasound Platforms

“…Triazabicyclo[3.3.1]nonane derivatives such as 2,6,9- and 3,7,9-triazabicyclo[3.3.1]nonanes [24,25,26,27,28] were synthesized from dimerization of α,β-unsaturated carbonyl compounds with alkylamines. Some 1,3,5,7-tetraazabicyclo[3.3.1]nonane derivatives have antithrombotic activities [29]. Although tremendous progress has been achieved in the synthesis of mono-, di-, and tri-azabicyclo[3.3.1]nonanes [1,2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17,18,19,20,21,22,23,24,25,26,27], the synthesis of tetra- and penta-azabicyclo[3.3.1]nonane frameworks has rarely been disclosed in the literature [30,31,32,33].…”