A closer look at N2,6-substituted 1,3,5-triazine-2,4-diamines: Advances in synthesis and biological activities

Polyethylene Glycol as a Green Medium for the Microwave‐Assisted Synthesis of Guanamines

“…The 1,3,5-triazine-2,4-diamine scaffold has found applications for the construction of new bioactive molecules with therapeutic potential targeting various areas. [1] By varying substituents in position 6 of 1,3,5-triazine-2,4-diamines (guanamines), the pharmacological profile of the compounds was tuned from antiparasitic [2] to antiulcer, anti-inflammatory [3] and cardiotonic. [4] Some notable examples include compound 1 (Figure 1) possessing nootropic properties [5] and phosphodiesterase 4 inhibitor Irsogladine [6] approved as a gastric mucosal protectant [7] but also claimed to be effective in models of CNS disorders, such as Parkinson disease.…”

“…The 1,3,5‐triazine‐2,4‐diamine scaffold has found applications for the construction of new bioactive molecules with therapeutic potential targeting various areas [1] . By varying substituents in position 6 of 1,3,5‐triazine‐2,4‐diamines (guanamines), the pharmacological profile of the compounds was tuned from antiparasitic [2] to antiulcer, anti‐inflammatory [3] and cardiotonic [4] .…”

“…mp 264 °C. Possible reaction mechanism for the formation of guanamines 6.Yield 437 mg (86 %), mp 237-239 °C (EtOH) 1. H NMR (300 MHz, DMSO-d 6 ): δ 6.88 (4 H, s, NH 2 ), 7.85 (2 H, d, J = 8.6 Hz, H-3' and H-5'), 8.42 (2 H, d, J = 8.2 Hz, H-2' and H-6').…”

One‐Pot Multicomponent Synthesis of Bis(diamino‐1,3,5‐triazines) under Microwave Irradiation

“…The diamino‐1,3,5‐triazine motif is present in the structure of a mucosal protective agent irsogladine, [1] recently approved antileukemic drug enasidenib, [2,3] and proposed for the breast cancer treatment (Phase II clinical trials) gedatolisib [4] . The diamino‐1,3,5‐triazine scaffold has also been used for the development of diverse bioactive compounds [5] . Inhibitors of the NADPH oxidase 4, [6,7] RAD6 ubiquitin‐conjugating enzyme, [8] Burton's tyrosine kinase, [9] and lysophosphatidic acid transferase β [10] were identified among diamino‐substituted 1,3,5‐triazines.…”

“…[4] The diamino-1,3,5-triazine scaffold has also been used for the development of diverse bioactive compounds. [5] Inhibitors of the NADPH oxidase 4, [6,7] RAD6 ubiquitin-conjugating enzyme, [8] Burton's tyrosine kinase, [9] and lysophosphatidic acid transferase β [10] were identified among diamino-substituted 1,3,5triazines. Compounds with this skeleton have also been found to possess anticancer activity [11][12][13][14][15] and 5-HT 6 -receptor antagonism with procognitive properties.…”