Pyrano[2,3-e]isoindol-2-ones, new angelicin heteroanalogues

Synthesis of the new ring system 6,8-dihydro-5H-pyrrolo[3,4-h]quinazoline

“…Supplementary data ( Table 2 containing the GI 50 of 8o against 59 tested human tumor cell lines and spectroscopic and analytical data for 8c-o) associated with this article can be found, in the online version, at doi: 10 …”

“…8 In addition pyrrolo[3,2-f]quinazolines of type 5 are effective for neoplastic diseases as inhibitors of the dihydrofolate reductase (DHFR). 9 We have recently studied the synthesis of isoindole-based ring systems such as the pyrano[2,3-e]isoindol-2-one 10 amino)methylene]cyclohexane-1,3-dione 9 which was reacted with phenylglycine to give the enaminoacid 10. Cyclization of this latter in acetic anhydride and triethylamine gave the expected dihydroisoindole 11.…”

“…12 Tetrahydroisoindole-4-ones 12b,c were conveniently prepared as described before. 10 Ketones 12a-c were functionalized on the nitrogen atom in THF or DMF using NaH as the base and an alkylating agent such as MeI, BnCl, ClBnpMe, or ClBnpOMe to give the corresponding N-substituted derivatives 13d-o (60-98%).…”

Synthesis of isoindolo[1,4]benzoxazinone and isoindolo[1,5]benzoxazepine: two new ring systems of pharmaceutical interest

“…They have been identified as novel microtubule-targeting agents that possess the ability to potently to induce cell cycle arrest and apoptosis against solid tumors and hematological malignancies. 9 In the course of our research on polycyclic nitrogen systems, we have synthesized several ring systems bearing pyrrole, 10e20 indole, 21e27 indazole, 28,29 and isoindole, 30 moieties with antitumor activity.…”

Synthesis of substituted isoindolo[2,1-a]quinoxalin-6-yl–amino and 6-imino-5-yl thiourea derivatives

“…Quinoxalinylethylpyridylthioureas (QXPTs) of type 1 and 2 ( Figure 2) represent another class of NNRTIs; many compounds showed a potent activity against both HIV-1 wild-type RT and various HIV-1 mutants HIV-1 RT. 16 Considering the good experience reached in the course of our researches on polycyclic nitrogen systems, bearing pyrrole, [17][18][19][20][21][22][23][24] indole, [25][26][27][28][29][30][31][32][33][34][35] isoindole 36-38 and indazole …”