Cancer is a disease that kills the world and it is estimated that in 2030 the incidence of this disease in the world reach 21.4 million new cases with 13.2 million deaths. Due to the resistance, non-selectivity and high cytotoxicity, many of the current drugs produce side effects such as bone marrow depression, sterility, risk of non-lymphocytic leukemia, among others. Thus it is necessary to the development of new anticancer drugs that have less harmful effects. Thus, six new compounds were synthesized, four acridínicos derivative, a derivative of bis (cloroetila) and palladium (II) complex acridínico, whose acronyms, respectively (Acri)2N, AcriPro, ACDMA, ACBr2MAN, (Most)2N and ACDMAPd. All these compounds derived from Schiff base had satisfactory yields and characterized by NMR techniques (1H, 13C, COSY, J solved) spectroscopy in the infrared, mass spectrometry and elemental analysis. The strains used human tumor cells were HT-29 (human colon cancer), MCF-7 (human breast cancer), Hep-2 (human larynx carcinoma), NCI-H292 (carcinoma human pulmonary mucoepidermoid) and HL -60 (acute promyelocytic leukemia) and derivatives AcriPro, ACDMA, (Most)2N and ACDMAPd showed the best results of IC50 for the HL-60 cells. / Conselho Nacional de Desenvolvimento Científico e Tecnológico / O câncer é uma das doenças que mais mata no mundo e estima-se que em 2030 a incidência no mundo desta doença alcance 21,4 milhões de novos casos com 13,2 milhões de mortes. Devido à resistência, a não seletividade e a alta citotoxicidade, grande parte dos fármacos atuais produzem efeitos indesejáveis tais como: depressão na medula óssea, esterilidade, risco de leucemia não linfocítica, entre outros. Desta forma faz-se necessário o desenvolvimento de novos fármacos antitumorais que possuam menos efeitos agressivos. Assim, foram sintetizados seis novos compostos, sendo quatro derivados acridínicos, um derivado bis(cloroetila) e um complexo de paládio(II) acridínico, que tem como acrônimos, respectivamente, (Acri)2N, AcriPro, ACDMA, ACBr2MAN, (Most)2N e ACDMAPd. Todos esses compostos derivados de base de Schiff tiveram rendimentos satisfatórios e foram caracterizados pelas técnicas de RMN (1H, 13C, COSY, J resolvido), espectroscopia na região do infravermelho, espectrometria de massas e Análise Elementar. As linhagens de células tumorais humanas utilizadas foram HT-29 (câncer de cólon humano), MCF-7 (câncer de mama humano), HEp-2 (carcinoma de laringe humana), NCI-H292 (carcinoma mucoepidermoide de pulmão humano) e HL-60 (leucemia promielocitica aguda) e os derivados AcriPro, ACDMA, ACDMAPd e (Most)2N apresentaram os melhores resultados de CI50 para a células HL-60.

Les précurseurs de ligands base de Schiff électro-donneurs et électro-accepteurs R-ONOH₂ sont préparés par réaction de monocondensation entre les β-dicétones appropriées et respectivement le 1,2- et le 1,2-4-nitro-aminophénol. Ils existent exclusivement sous leurs formes tautomériques céto-énamine en solution et à l'état solide. Dans les complexes correspondants de NiII et de CuII, le métal adopte une géométrie plan carré et est coordiné par les atomes d'azote et d'oxygène du ligand dianionique tridentate et par l'azote du coligand pyridine. L'hyperpolarisabilité quadratique, déterminée par la technique DHL est très élevée. La substitution de la pyridine par la 4,4'-bipyridine conduit systématiquement aux complexes dimériques correspondants. Un composé similaire comportant l'espaceur bis(4-pyridyle)acétylène est formé après réaction de couplage croisé de Sonogashira. Cette même réaction de couplage croisé entre les blocs de construction électrodonneurs et électro-accepteur permettent de préparer le système «push-pull» D-π-A désiré. Les réponses ONL du second ordre des complexes contenant le ligand électro-actif methylène-pyrane peuvent être modulées par bi- (R = An) et tétra- (R = Fc) oxydation réversible avec formation/rupture d'une liaison C-C, constituant ainsi un nouvel exemple de commutateur ONL-2 réversible. / Electron donating and electron withdrawing ligand precursors R-ONOH₂ were prepared by monocondensation reaction of the appropriate β-diketones and 1,2- and 1,2-4-nitro-aminophenol, respectively. They do exclusively exist as their enaminone tautomeric form both in solid-state and in solution phase. In their corresponding Schiff base complexes of NiII and CuII, the central metal is tetracoordinated in a square-planar environment. The coordination sphere is formed by the nitrogen and oxygen atoms of the dianionic tridentate ligand and the fourth coordination site is occupied by the nitrogen atom of the pyridine co-ligand. The derivative exhibited a high quadratic hyperpolarizability (β1.91) determined by the HLS technique. Substitution of 4,4’-bipyridine for pyridine invariably leads to the formation of the respective dimers [(R-ONO)MII(4,4’-bipy)MII(ONO-R)]. A similar compound having the bis(4-pyridyle)acetylene as spacer was formed upon cross-coupling Sonogashira reaction with ethynylpyridine chlorhydrate. The same cross-coupling reaction carried out between the electron releasing and electron withdrawing building blocks, respectively, allowed the preparation of the expected «push-pull» D-π-A system. The second-order NLO responses of compounds bearing a redox active methylenepyran ligand can be modulated upon reversible bi- (R = An) and tetra- (R = Fc) oxydation involving C-C bond formation/breaking reactions, thus forming a new class of NLO molecular switches.