Synthesis and pharmacological evaluation of N-[4-(t-amino)-2- butynyloxy] phthalimides

Abstract

A series of aminoacetylenicoxyphthalimide namely N-[4-(t-amino)-2-butynyloxy] phthalimides were synthesized from the reaction of N-hydroxyphthalimide with propargyl bromide in sodium ethoxide to generate N-(2-butynyloxy)phthalimide. The desired compounds were prepared through Mannich reaction of N-(2-butynyloxy)phthalimide with formaldehyde, appropriate amine in peroxide-free dioxin and cuprous chloride as catalyst. The N-[4-(t-amino)-2-butynyloxy] phthalimides were investigated for their rectal temperature, motor activity and palpebral pitosis effects in comparison with harmaline, all compounds showed similar activity to harmaline, however compound 4 was more potent than harmaline.

Evolution and development of potent monobactam sulfonate candidate IMBZ18g as a dual inhibitor against MDR Gram-negative bacteria producing ESBLs

“…The hydroxylamine 14 was produced successively by condensation of 11 and chloroacetyl chloride, nucleophilic substitution of 12 with N -hydroxyphthalimide, and hydrazinolysis of 13 in 81%–88% yields. Series 17 was easily prepared through Gabreil reaction and hydrazinolysis starting from 15 12 , 13 . Alternatively, series 20 was prepared via esterification of 18 in the presence of 1,8-diazabicyclo [5.4.0]undec-7-ene (DBU), and ammonolysis of 19 with O -(diphenylphosphinyl) hydroxylamine in the presence of sodium tert -butoxide or sodium hydrogen 7 in good yields ( Scheme 1 B–D).…”