Synthesis and antiproliferative mechanism of action of pyrrolo[3′,2′:6,7] cyclohepta[1,2-d]pyrimidin-2-amines as singlet oxygen photosensitizers

European Journal of Medicinal Chemistry

Volumn 123, Issue , 2016, Pages 447-461

  Spanò, Virginia ^a   Frasson, Ilaria ^b   Giallombardo, Daniele ^a   Doria, Filippo ^c   Parrino, Barbara ^a   Carbone, Anna ^a   Montalbano, Alessandra ^a   Nadai, Matteo ^b   Diana, Patrizia ^a   Cirrincione, Girolamo ^a   Freccero, Mauro ^c   Richter, Sara N ^b   Barraja, Paola ^a  

^a UNIVERSITY OF PALERMO   (Italy)

^b UNIVERSITY OF PADOVA   (Italy)

^c UNIVERSITY OF PAVIA   (Italy)

Author keywords

Antiproliferative activity; Photodynamic therapy; Photosensitizing agents; Pyrrolo 3 ,2 :6,7 cyclohepta 1,2 d pyrimidin 2 amines; Reactive oxygen species

Indexed keywords

10 (4 METHOXYBENZYL) 2 (PHENYLAMINO) 5,6,7,10 TETRAHYDROPYRROLO[3',2':6,7]CYCLOHEPTA[1,2 D]PYRIMIDINE 9 CARBOXAMIDE; 10 BENZYL 2 (PHENYLAMINO) 5,6,7,10 TETRAHYDROPYRROLO[3',2':6,7]CYCLOHEPTA[1,2 D]PYRIMIDINE 9 CARBOXAMIDE; 10 METHYL 2 (PHENYLAMINO) 5,6,7,10 TETRAHYDROPYRROLO[3',2':6,7]CYCLOHEPTA[1,2 D]PYRIMIDINE 9 CARBOXAMIDE; 2 (CYCLOHEXYLAMINO) 10 (4 METHOXYBENZYL) 5,6,7,10 TETRAHYDROPYRROLO[3',2':6,7]CYCLOHEPTA[1,2 D]PYRIMIDINE 9 CARBOXAMIDE; 2 (CYCLOHEXYLAMINO) 10 BENZYL 5,6,7,10 TETRAHYDROPYRROLO[3',2':6,7]CYCLOHEPTA[1,2 D]PYRIMIDINE 9 CARBOXAMIDE; 2 (CYCLOHEXYLAMINO) 10 METHYL 5,6,7,10 TETRAHYDROPYRROLO[3',2':6,7]CYCLOHEPTA[1,2 D]PYRIMIDINE 9 CARBOXAMIDE; 2 AMINO 10 (4 METHOXYBENZYL) 5,6,7,10 TETRAHYDROPYRROLO[3',2':6,7]CYCLOHEPTA[1,2 D]PYRIMIDINE 9 CARBOXAMIDE; 2 AMINO 10 (4 METHOXYBENZYL) 5,6,7,10 TETRAHYDROPYRROLO[3',2':6,7]CYCLOHEPTA[1,2 D]PYRIMIDINE 9 CARBOXYLATE; 2 AMINO 10 BENZYL 5,6,7,10 TETRAHYDROPYRROLO[3',2':6,7]CYCLOHEPTA[1,2 D]PYRIMIDINE 9 CARBOXAMIDE; 2 AMINO 10 BENZYL 5,6,7,10 TETRAHYDROPYRROLO[3',2':6,7]CYCLOHEPTA[1,2 D]PYRIMIDINE 9 CARBOXYLATE; 2 AMINO 10 METHYL 5,6,7,10 TETRAHYDROPYRROLO[3',2':6,7]CYCLOHEPTA[1,2 D]PYRIMIDINE 9 CARBOXAMIDE; 2 AMINO 10 METHYL 5,6,7,10 TETRAHYDROPYRROLO[3',2':6,7]CYCLOHEPTA[1,2 D]PYRIMIDINE 9 CARBOXYLATE; ACETYLCYSTEINE; ETHYL 10 (4 METHOXYBENZYL) 2 (PHENYLAMINO) 5,6,7,10 TETRAHYDROPYRROLO[3',2':6,7]CYCLOHEPTA[1,2 D]PYRIMIDINE 9 CARBOXYLATE; ETHYL 10 BENZYL 2 (PHENYLAMINO) 5,6,7,10 TETRAHYDROPYRROLO[3',2':6,7]CYCLOHEPTA[1,2 D]PYRIMIDINE 9 CARBOXYLATE; ETHYL 10 METHYL 2 (PHENYLAMINO) 5,6,7,10 TETRAHYDROPYRROLO[3',2':6,7]CYCLOHEPTA[1,2 D]PYRIMIDINE 9 CARBOXYLATE; ETHYL 2 (CYCLOHEXYLAMINO) 10 (4 METHOXYBENZYL) 5,6,7,10 TETRAHYDROPYRROLO[3',2':6,7]CYCLOHEPTA[1,2 D]PYRIMIDINE 9 CARBOXYLATE; ETHYL 2 (CYCLOHEXYLAMINO) 10 BENZYL 5,6,7,10 TETRAHYDROPYRROLO[3',2':6,7]CYCLOHEPTA[1,2 D]PYRIMIDINE 9 CARBOXYLATE; ETHYL 2 (CYCLOHEXYLAMINO) 10 METHYL 5,6,7,10 TETRAHYDROPYRROLO[3',2':6,7]CYCLOHEPTA[1,2 D]PYRIMIDINE 9 CARBOXYLATE; ETHYL 2 AMINO 10 (4 METHOXYBENZYL) 5,6,7,10 TETRAHYDROPYRROLO[3',2':6,7]CYCLOHEPTA[1,2 D]PYRIMIDINE 9 CARBOXYLATE; ETHYL 2 AMINO 10 BENZYL 5,6,7,10 TETRAHYDROPYRROLO[3',2':6,7]CYCLOHEPTA[1,2 D]PYRIMIDINE 9 CARBOXYLATE; ETHYL 2 AMINO 10 METHYL 5,6,7,10 TETRAHYDROPYRROLO[3',2':6,7]CYCLOHEPTA[1,2 D]PYRIMIDINE 9 CARBOXYLATE; PHOTOSENSITIZING AGENT; PROPIONIC ACID DERIVATIVE; PYRROLE DERIVATIVE; PYRROLO[3',2':6,7]CYCLOHEPTA[1,2 D]PYRIMIDIN 2 AMINE DERIVATIVE; REACTIVE OXYGEN METABOLITE; SINGLET OXYGEN; UNCLASSIFIED DRUG; AMINE; ANTINEOPLASTIC AGENT;

ANTIPROLIFERATIVE ACTIVITY; APOPTOSIS; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CELL DAMAGE; CELL DEATH; CELL POPULATION; CONFOCAL MICROSCOPY; CONTROLLED STUDY; CYTOTOXIC CONCENTRATION; CYTOTOXICITY; DRUG SYNTHESIS; EC50; FEMALE; HELA CELL LINE; HT 29 CELL LINE; HUMAN; HUMAN CELL; IN VITRO STUDY; LYSOSOME; MCF 7 CELL LINE; MITOCHONDRIAL MEMBRANE POTENTIAL; MITOCHONDRION; MITOCHONDRION SWELLING; OXIDATIVE STRESS; PHOTOCYTOTOXICITY; PHOTOLYSIS; PHOTOOXIDATION; PHOTOSENSITIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; SELECTIVITY INDEX; SPECTROPHOTOMETRY; STRUCTURE ACTIVITY RELATION; CELL PROLIFERATION; CHEMISTRY; DRUG DESIGN; DRUG EFFECTS; KINETICS; METABOLISM; RADIATION RESPONSE; SYNTHESIS; TUMOR CELL LINE;

AMINES; ANTINEOPLASTIC AGENTS; CELL DEATH; CELL LINE, TUMOR; CELL PROLIFERATION; CHEMISTRY TECHNIQUES, SYNTHETIC; DRUG DESIGN; HUMANS; KINETICS; PHOTOLYSIS; PHOTOSENSITIZING AGENTS; SINGLET OXYGEN;

EID: 84979944506     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2016.07.051     Document Type: Article

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