Two series of naphtho[1,8- ef][1,4]diazepines and pyrrolo[1,2- a]perimidines were prepared starting from 1,8-diaminonaphthalene and hydrazonoyl chlorides. The structures of the products were determined on the basis of their spectral data and elemental analyses. The mechanism of formation of such products was also discussed. The prepared compounds were screened for their antitumor activity against three cell lines, namely, MCF-7, TK-10 and UACC-62, and some derivatives showed promising activity.
References
[1]
Pandya, A.B.; Prajapati, D.G.; Pandya, S.S. Synthesis of novel Naphthalene COX inhibitors for anti-inflammatory activity. J. Appl. Pharm. Sci. 2012, 2, 226–232.
[2]
Mkpenie, V.; Ebong, G.; Obot, I.B.; Abasiekong, B. Evaluation of the effect of azo group on the biological activity of 1-(4-methylphenylazo)-2-naphthol. E-J. Chem. 2008, 5, 431–434, doi:10.1155/2008/438946.
[3]
Strom, M.B.; Haug, B.E.; Rekdal, O.; Skar, M.L.; Stensen, W.; Svendsen, J.S. Important structural features of 15-residue lactoferricin derivatives and methods for improvement of antimicrobial activity. Biochem. Cell Biol. 2002, 80, 65–74, doi:10.1139/o01-236.
[4]
Antonini, I.; Polucci, P.; Magnano, A.; Sparapani, S.; Martelli, S. Rational design, Synthesis, and biological evaluation of bis(pyrimido[5,6,1-de]acridines) and bis(pyrazolo[3,4,5-kl]acridine-5-carboxamides) as new anticancer agents. J. Med. Chem. 2004, 47, 5244–5250, doi:10.1021/jm049706k.
[5]
Akita, M.; Seto, H.; Aoyama, R.; Kimura, J.; Kobayashi, K. Novel rearrangements in the reactions directed toward preparation of spiro-N,N-ketals: Reactions of naphthalene-1,8-diamine with ninhydrin and isatin. Molecules 2012, 17, 13879–13890, doi:10.3390/molecules171213879.
[6]
El-Shaieb, K.M. Condensation of 1-(dicyanomethylene)acenaphthene-2-one with aromatic diamines. J. Chin. Chem. Soc. 2008, 55, 1150–1155.
[7]
Cheeseman, G.W.H.; Eccleshall, S.A. Synthesis of pyrrolo[1,2-a]naphtho[1,8-ef][1,4]diazepines. J. Heterocycl. Chem. 1986, 23, 65–67, doi:10.1002/jhet.5570230113.
[8]
ng？ren, S.H. Transformation of furan-2,3-diones with 1,8-diaminonaphthalene to naphtho-[1,8-ef][1,4]diazepin-2(1H)-ones. Synth. Comm. 2009, 39, 3657–3662, doi:10.1080/00397910902796094.
[9]
Prakash, G.K.S.; Paknia, F.; Narayan, A.; Mathew, T.; Olah, G.A. Synthesis of perimidine and 1,5-benzodiazepine derivatives using tamed Br？nsted acid, BF3–H2O. J. Fluor. Chem. 2013, 152, 99–105, doi:10.1016/j.jfluchem.2013.03.023.
[10]
Luthin, D.R.; Rabinovich, A.K.; Bhumralkar, D.R.; Youngblood, K.L.; Bychowski, R.A.; Dhanoa, D.S.; May, J.M. Synthesis and biological activity of oxo-7H-benzo[e]perimidine-4-carboxylic acid derivatives as potent, nonpeptide corticotropin releasing factor (CRF) receptor antagonists. Bioorg. Med. Chem. Lett. 1999, 9, 765–770, doi:10.1016/S0960-894X(99)00075-X.
Claramunt, R.M.; Dotor, J.; Elguero, J. Structure, Reactivity and synthesis of perimidines derivatives (Dihydroperimidines and perimidinones). Ann. Quim. 1995, 91, 151–183.
[13]
Herbert, J.M.; Woodgate, P.D.; Denny, W.A. Potential antitumor agents. 53. Synthesis, DNA binding properties, and biological activity of perimidines designed as minimal DNA-intercalating agents. J. Med. Chem. 1987, 30, 2081–2086, doi:10.1021/jm00394a025.
[14]
Brana, M.F.; Garrido, M.; Rodriguez, M.; Morcillo, M.J.; Alvarez, Y.; Valladares, Y.; Klebe, G. Synthesis, Structure and cytostatic activity of a series of 2-substituted perimidines. Eur. J. Med. Chem. 1990, 25, 209–215, doi:10.1016/0223-5234(90)90203-F.
[15]
Stefańska, B.; Dzieduszycka, M.; Bontemps-Gracz, M.M.; Borowski, E.; Martelli, S.; Supino, R.; Pratesi, G.; de Cesare, M.A.; Zunino, F.; Ku？nierczyk, H.; et al. 8,11-Dihydroxy-6-[(aminoalkyl)amino]-7H-benzo[e]perimidin-7-ones with activity in multidrug-resistant cell lines: Synthesis and antitumor evaluation. J. Med. Chem. 1999, 42, 3494–3501, doi:10.1021/jm980682p.
[16]
Bu, X.; Deady, L.W.; Finlay, G.J.; Baguley, B.C.; Denny, W.A. Synthesis and cytotoxic activity of 7-Oxo-7H-dibenz[f,ij]isoquinoline and 7-Oxo-7H-benzo[e]perimidine derivatives. J. Med. Chem. 2001, 44, 2004–2014, doi:10.1021/jm010041l.
[17]
Farghaly, T.A.; Mahmoud, H.K. Synthesis of pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidin-5-ones 3 as potential antimicrobial agents. Arch. Pharm. Chem. Life Sci. 2013, 346, 392–402, doi:10.1002/ardp.201200486.
Wan, X.; Lv, X.; He, G.; Yu, A.; Chen, Y. Synthesis of neutral stable polyradicals and their application on photovoltaic devices. Eur. Polym. J. 2011, 47, 1018–1030, doi:10.1016/j.eurpolymj.2011.02.017.
[20]
Bazinet, P.; Yap, G.P.A.; Richeson, D.S. Constructing a stable carbene with a novel topology and electronic framework. J. Am. Chem. Soc. 2003, 125, 13314–13315, doi:10.1021/ja0372661.
[21]
Herbst, W.; Hunger, K. Industrial Organic Pigments, 3rd ed. ed.; Wiley-VCH: Weinheim, Germany, 2004; p. 9.
[22]
Nagao, Y.; Tsuda, K.; Kozawa, K.; Uchida, T. Synthesis and properties of benzimidazole and naphthoimidazole derivatives of perylenedicarboximide. Heterocycles 2001, 54, 757–764, doi:10.3987/COM-00-S(I)64.
[23]
Alfredo, N.V.; Likhatchev, D.; Ramirez, S.B.; Vazquez, J.R.; Valverde, G.C.; Alexandrova, L. Highly effective low temperature route to pyrroloperimidines synthesis and their copolymerization with styrene and methyl methacrylate. Polymer 2008, 49, 3654–3662, doi:10.1016/j.polymer.2008.06.038.
[24]
Mizuguchi, J. Crystal structure and electronic characterization of trans and cis perinone pigments. J. Phys. Chem. B 2004, 108, 8926–8930, doi:10.1021/jp031351d.
[25]
Abdel Hafez, N.A.; Farghaly, T.A.; Al-Omar, M.A.; Abdalla, M.M. Synthesis of bioactive polyheterocyclic ring systems as 5α-reductase inhibitors. Eur. J. Med. Chem. 2010, 45, 4838–4844, doi:10.1016/j.ejmech.2010.07.053.
[26]
Farghaly, T.A.; Gomha, S.M.; Abbas, E.M.; Abdalla, M.M. Hydrazonoyl halides as precursors for new fused heterocycles of 5α-reductase inhibitors. Arch. Pharm. 2012, 345, 117–122, doi:10.1002/ardp.201100212.
[27]
Abdel-Aziz, H.A.; El-Zahabi, H.S.A.; Dawood, K.M. Microwave-assisted synthesis and in-vitro anti-tumor activity of 1,3,4-triaryl-5-N-arylpyrazole-carboxamides. Eur. J. Med. Chem. 2010, 45, 2427–2432, doi:10.1016/j.ejmech.2010.02.026.
[28]
Abdel-Aziz, H.A.; Mekawey, A.A.I.; Dawood, K.M. Convenient synthesis and antimicrobial evaluation of some novel 2-substituted-3-methylbenzofuran derivatives. Eur. J. Med. Chem. 2009, 44, 3637–3644, doi:10.1016/j.ejmech.2009.02.020.
[29]
Dawood, K.M.; Abdel-Gawad, H.; Ellithey, M.; Mohamed, H.A.; Hegazi, B. Synthesis, Anticonvulsant, and anti-inflammatory activities of some new benzofuran-based heterocycles. Arch. Pharm. Chem. Life Sci. 2006, 339, 133–140, doi:10.1002/ardp.200500176.
[30]
Dawood, K.M.; Abdel-Gawad, H.; Ragab, E.A.; Ellithey, M.; Mohamed, H.A. ynthesis, Anticonvulsant, and anti-inflammatory evaluation of some new benzotriazole and benzofuran-based heterocycles. Bioorg. Med. Chem. 2006, 14, 3672–3680, doi:10.1016/j.bmc.2006.01.033.
[31]
Farghaly, T.A.; Abdallah, M.A.; Aziz, A.M.R. Synthesis and antimicrobial activity of some new 1,3,4-thiadiazole derivatives. Molecules 2012, 17, 14625–14636, doi:10.3390/molecules171214625.
[32]
Riyadh, S.M.; Farghaly, T.A.; Abdallah, M.A.; Abdalla, M.M.; Abd El-Aziz, M.R. New pyrazoles incorporating pyrazolylpyrazole moiety: Synthesis, Anti-HCV and antitumor activity. Eur. J. Med. Chem. 2010, 45, 1042–1050, doi:10.1016/j.ejmech.2009.11.050.
Karc？, F.; Sener, N.; Yamac, M.; Sener, I.; Demircal？, A. The synthesis, antimicrobial activity and absorption characteristics of some novel heterocyclic disazo dyes. Dyes Pigments 2009, 80, 47–52, doi:10.1016/j.dyepig.2008.05.001.
[35]
Hamdi, M.; Grech, O.; Sakellariou, R.; Speziale, V. New method of synthesis of 1,5-benzodiazepin-2-ones from 4-hydroxycoumarin. J. Heterocycl. Chem. 1994, 31, 509–511, doi:10.1002/jhet.5570310242.
[36]
Hamdi, N.; Lidrissi, C.; Saoud, M.; Nievas, R.A.; Zarrouk, H. Synthesis of some new biologically active coumarin derivatives. Chem. Heterocycl. Compd. 2006, 42, 320–325, doi:10.1007/s10593-006-0088-0.
[37]
üng？ren, S.H.; Koca, T.; Yilmaz, F. Preparation of perinones via a novel multicomponent synthesis of isoindole scaffold. Tetrahedron 2011, 67, 5409–5414, doi:10.1016/j.tet.2011.05.078.
[38]
Paragamian, V.; Baker, M.B.; Puma, B.M.; Reale, J. A study of the synthesis and some reactions of perimidines. J. Heterocycl. Chem. 1968, 5, 591–597, doi:10.1002/jhet.5570050502.
[39]
Cado, F.; Di-Martino, J.; Jacquault, P.; Bazureau, J.P.; Hamelin, J. Amidine-enediamine tautomerism: Addition of isocyanates to 2-substituted 1H-perimidines. Some syntheses under microwave irradiation. Bull. Soc. Chim. Fr. 1996, 133, 587–595.
[40]
Shawali, A.S.; Zayed, M.M.; Farghaly, T.A. Synthesis and biological activity of new 1H-pyrazolo[3,4-b]quinoxalines (Flavazoles). J. Heterocycl. Chem. 2005, 42, 185–189, doi:10.1002/jhet.5570420202.
[41]
Battin, E.E.; Brumaghim, J.L. Antioxidant activity of sulfur and selenium: A Review of reactive oxygen species scavenging, glutathione peroxidase, and metal binding antioxidant mechanisms. Cell Biochem. Biophys. 2009, 55, 1–23, doi:10.1007/s12013-009-9054-7.
[42]
Davalos, A.; Gomez-Cordoves, C.; Bartolome, B. Extending applicability of the oxygen radical absorbance capacity (ORAC-fluorescein) assay. J. Agric. Food Chem. 2004, 52, 48–54, doi:10.1021/jf0305231.
[43]
Monks, A.; Scudeiro, D.; Skehan, P.; Shoemaker, R.; Paull, K.; Vistica, D.; Hose, C.; Langley, J.; Cronise, P.; Vaigro-Wolff, A.; et al. Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines. J. Natl. Cancer Inst. 1991, 83, 757–766, doi:10.1093/jnci/83.11.757.
