Benzo[c]phenanthrene derivatives: Synthesis, optical properties and cytotoxic activity
DOI:
https://doi.org/10.24297/jac.v12i9.6706Keywords:
Benzo[c]phenanthrene, Ketone, Heck coupling, Photocyclization,Amines, Cytotoxic activity.Abstract
A new benzo[c]phenanthrene ketone has been synthesized through Heck coupling and oxidative photocyclization. The optical properties of the target tetracyclic system were also investigated by UV-visible absorption and photoluminescence spectroscopy and an emission in the visible region was observed. The tetracyclic ketone has been reacted with primary amines in the presence of Lewis acid followed by NaBH4 reduction to provide new polyaromatic secondary amines in good yields and purity. All the synthesized new compounds were identified and characterized through a combination of nuclear magnetic resonance spectroscopy and mass spectrometric methods. The cytotoxic activity of all pure benzo[c]phenanthrene derivatives has been evaluated against Hep-2 cell line using (MTT) coloriÂmetric assay.
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References
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[29] Huang P. Q., Wang Y., Xiao K. J., Huang Y. H.,A general method for the direct transformation of common tertiary amides into ketones and amines by addition of Grignard reagents,Tetrahedron71 (2015) 4248.[30] Wu B., Gao X., Chen M. W., Zhou Y. G.,Direct amination of 2-(1-tosylalkyl)phenols with aqueous ammonia: a metal-free synthesis of primary amines,Tetrahedron Lett.56 (2015) 1135.
[31] Liew S. K., He Z., St Denis J. D., Yudin A. K.,Stereocontrolled synthesis of 1,2- and 1,3-diamine building blocks from aziridine aldehyde dimmers,J. Org. Chem.78 (2013) 11637.
[32] Gomez-Bengoa E., Jimenez J., Lapuerta I., Mielgo A., Oiarbide M., Otazo I., Velilla I., Vera S., Palomo C.,Combined α,α-dialkylprolinol ether/Brønsted acid promotes Mannich reactions of aldehydes with unactivated imines. An entry to anti-configured propargylic amino alcohols,Chem. Sci.3 (2012) 2949.
[33] Izumiseki A., Yoshida K., Yanagisawa A.,Catalytic asymmetric three-component mannich-type reaction of alkenyl trichloroacetates,Org. Lett.11 (2009) 5310.
[34] Parmar D., Sugiono E., Raja S., Rueping M.,Complete field guide to asymmetric BINOL-phosphate derived Brønsted Acid and metal catalysis: History and classification by mode of activation; Brønsted acidity, hydrogen bonding, ion pairing, and metal phosphates,Chem. Rev.114 (2014) 9047.
[35] Wang D. –S., Chen Q. –A., Li W., Yu C. –B., Zhou Y. –G., Zhang X.,Pd-Catalyzed asymmetric hydrogenation of unprotected indoles activated by Brønsted acids,J. Am. Chem. Soc.132 (2010) 8909.
[36] Hou G., Gosselin F., Li W., McWilliams J. C., Sun Y., Weisel M., O’Shea P. D., Chen C. –Y., Davies I. W., Zhang X.,Enantioselective Hydrogenation of N-H Imines,J. Am. Chem. Soc.131 (2009) 9882.
[37] Kuehne M. E.,The applications of enamines to a new synthesis of b-ketonitriles,J. Am. Chem. Soc.81 (1959) 5400.
[38] Taguchi K., Westheimer F. H.,Catalysis by molecular sieves in the preparation of ketimines and enamines,J. Org. Chem.36 (1971) 1570.
[39] Jaworska M., Åaczkowski K. Z., WeÅ‚niak M., Welke M., Wojtczak A.,Imines derived from (1S, 2R)-norephedrine as catalysts in the enantioselective addition of diethylzinc to aldehydes,Applied Catalysis A: General357 (2009) 150.
[40] Billman J. H., Tai K. M. J.,Reduction of Schiff bases. II. Benzhydrylamines and structurally related compounds,J. Org. Chem.23 (1958) 535.
[41] Bolton R., Dank T. N., PaulJ. M.,Preparation and reduction of some camphor imines,Tetrahedron Lett.35 (1994) 3411.
[42] Emerson W. S.,Organic Reactions,Wiley, New York 4, 1948, 174.
[43] Hutchins R. O.,Natale N.,Cyanoborohydride. Utility and applications in organic synthesis. A review,Org. Prep. Proced. lnt.11 (1979) 201.
[44] Whitesell J. K., in Comprehensive Organic Synthesis,Trost B. M., Fleming, I.Ed. Pergamon Press, Oxford 6, 1991, 724and 8 25.
[45] (a) GribbleG. W., in Reductions in Organic Synthesis, ACS Symposium Series641, Abdel-Majid, A. F. Ed. American Chemical Society, Washington, DC, 1996, 167; (b) Abdel-Majid, A. F. ibid, 201.
[46] Abirami M., Gopiesh Khanna V., Kannabiran K.,Antibacterial activity of marine Streptomyces SP. isolated from Andaman & Nicobar Islands, Int J Pharm. Bio. Sci.4 (2013) 280.
[47] Chen J. J., Hung H. C., Sung P. J., Chen I. S., Kuo W. L.,Aporphine alkaloids and cytotoxic lignans from the roots of Illigeraluzonensis, Phytochemistry72 (2011) 523.
[48] Yazdiniapour Z., Ghanadian M., Zolfaghari B., Lanzotti V.,6(17)-Epoxylathyranediterpenes from Euphorbia sogdiana Popov with cytotoxic activity,Fitoterapia108 (2016) 87. [49] Hu J., Song Y., Mao X., Wang Z. J., Zhao Q. J.,Limonoids isolated from Toonasinensis and their radical scavenging, anti-inflammatory and cytotoxic activities,Journal of Functional Foods20 (2016) 1. [50] Huang L. H., Li Y., Xu H. D., Zheng Y. F.,Liu H. M.,Synthesis and biological evaluation of novel C6-cyclo secondary amine substituted purine steroid-nucleosides analogues,Steroids85 (2014) 13. [51] Akbaş H.,Okumuş A.,Kılıç Z.,Hökelek T.,Süzen Y.,Koç L. Y.,Açık L.,Çelik Z. B.,Phosphorus-nitrogencompounds part 27.Syntheses,structuralcharacterizations, antimicrobial and cytotoxic activities, and DNA interactions of new phosphazenes bearing secondary amino and pendant (4-fluorobenzyl)spiro groups,European Journal of Medicinal Chemistry70 (2013) 294.
[2] Harvey R. G., Polycyclic Aromatic Hydrocarbons; Chemistry and Carcinogenicity Cambridge University Press: Cambridge, UK 1991 Chapter 3.
[3] Stevenson J. L., Von Haam E.,Carcinogenicity of benz[a]anthracene and benzo[c]phenanthrene derivatives, Am. Ind. Hyg. Assoc. J.26 (1965) 475.
[4] AlouiF.,El AbedR.,MarinettiA.,Ben Hassine B.,Synthesis and characterization of new hexahelicene derivatives,Tetrahedron Lett.48 (2007) 2017.
[5] AlouiF.,MoussaS.,Ben Hassine B.,Synthesis and characterization of a new hexacyclichelicene,Tetrahedron Lett.53 (2012) 3216.
[6] Lefebvre Q., Jentsch M., Rueping M.,Continuous flow photocyclization of stilbenes-scalable synthesis of functionalized phenanthrenes and helicenes,Beilstein J. Org. Chem.9 (2013) 1883.
[7] Karikomi M., Yamada M., Ogawa Y., Houjou H., Seki K., Hiratani K., Haga K., Uyehara T.,Novel synthesis of a unique helical quinone derivative by coupling reaction of 2-hydroxybenzo[c]phenanthrene,Tetrahedron Lett.46 (2005) 5867.
[8] Pataki J., DiRaddo P., Harvey R. G.,An efficient synthesis of the highly tumorigenic anti-diol epoxide derivative of benzo[c]phenanthrene,J. Org. Chem.54 (1989) 840. [9] Thirunarayanan G.,Vanangamudi G.,Synthesis, spectral studies, antimicrobial and insect antifeedant activities of some substituted styryl 4′-fluorophenyl ketones,Arabian Journal of Chemistry7 (2014) 1055.
[10] Marquise N., Chevallier F., Nassar E., Frédérich M., Ledoux A., Halauko Y. S., Ivashkevich O. A., Matulis V. E., Roisnel T.,Dorcet V., Mongin F.,Substituted Azafluorenones: Access from dihalogenodiaryl ketones by Palladium-catalyzed auto-tandem processes and evaluation of their antibacterial, antifungal, antimalarial and antiproliferative activities,Tetrahedron72 (2016) 825.
[11] Karpaviciene I., Valiuliene G., Raskevicius V., Lebedyte I., Brukstus A., Kairys V., Navakauskiene R., Cikotiene I.,Synthesis and antiproliferative activity of α-branched α,β-unsaturated ketones in human hematological and solid cancer cell lines,European Journal of Medicinal Chemistry98 (2015) 30. [12] Ning X., Guo Y., Ma X., Zhu R., Tian C., Wang X., Mac Z., Zhang Z., Liu J.,Synthesis and neuroprotective effect of E-3,4-dihydroxy styrylaralkyl ketones derivatives against oxidative stress and inflammation,Bioorganic & Medicinal Chemistry Letters23 (2013) 3700. [13] Ben Hassine B., Gorsane M., Pecher J., Martin R. H.,Diastereoselective NaBH4 reductions of (dl) α-keto esters,Bull. SOC. Chim. Belg.94 (1985) 597.
[14] Schiff H.,A new range of organic bases,Ann. Chem.131 (1864) 118.
[15] Moffett R. B., Rabjohn N.,Editor, Organic Synthesis; John Wiley &Sons, Inc., New York4, 1963, 605.
[16] Johansson A.,Methods for the asymmetric preparation of amines,Contemporary Organic Synthesis2 (1995) 393. [17] Duthaler R. O.,Recent developments in the stereoselective synthesis of α-aminoacids,Tetrahedron50 (1994) 1539.
[18] Juaristi E.,Enantioselective synthesis of beta-amino acids. Wiley-VCH Publishers, New York, 1997, 45.
[19] Clifton J. E., Collins I., Hallett P., Hartley D., Lunts L. H. C., Wicks P. D.,Arylethanolamines derived from salicylamide with .alpha.- and .beta.-adrenoceptor blocking activities. Preparation of labetalol, its enantiomers and related salicylamides,J. Med. Chem.25 (1982) 670.
[20] Betti M.,β-naphtholphenylaminomethane,Org. Synth.1 (1941) 381.
[21] Cardellicchio C., Ciccarella G., Naso F., Schingaro E., Scordari F.,The Betti base: absolute configuration and routes to a family of related chiral nonracemic bases,Tetrahedron: Asymmetry9 (1998) 3667.
[22] Semakin A. N., Agababyan D. P., Kim S., Lee S., Yu Sukhorukov A., Fedina K. G., Oh J., Ioffe S. L.,Oximinoalkylamines as ligands for Cu-assisted azide-acetylene cycloaddition,Tetrahedron Lett.56 (2015) 6335.
[23] KlugeT., Bette M., Vetter C., Schmidt J., Steinborn D.,Synthesis and characterization of diacetyl platinum(II) complexes with two primary and secondary amine ligands,Journal of Organometallic Chemistry715 (2012) 93.
[24] Bálint E., Tripolszky A., Jablonkai E., Karaghiosoff K., Czugler M., Mucsi Z., Kollár L., Pongrácz P., Keglevich G.,Synthesis and use of α-aminophosphine oxides and N,N-bis(phosphinoylmethyl)amines-A study on the related ring platinum complexes,Journal of Organometallic Chemistry801 (2016) 111.
[25] Kumar V., Upadhyay N., Manhas A.,Designing, syntheses, characterization, computational study and biological activities of silver-phenothiazine metal complex,Journal of Molecular Structure1099(2015) 135.
[26] Backvall J. E., Bjorkman E. E., Bystrom S. E.,Palladium-promoted asymetricoxyamination of alkenes application to the synthesis of optically active aryloxypropanolamines,Tetrahedron Lett.23 (1982) 943.
[27] Zhang G., Ji X., Yu H., Yang L., Jiao P., Huang H.,Palladium-catalyzed hydroaminocarbonylation of alkenes with amines promoted by weak acid,Tetrahedron Lett.57 (2016) 383. [28] Cottineau F., Maigrot N., Mazaleyrat J. P.,Reductive cleavage of axially disymmetric tertiary amines and quaternary ammonium salts by lithium aluminium hydride. Synthesis of new 1,1′-binaphthyl substituted amines,Tetrahedron Lett.26 (1985) 421.
[29] Huang P. Q., Wang Y., Xiao K. J., Huang Y. H.,A general method for the direct transformation of common tertiary amides into ketones and amines by addition of Grignard reagents,Tetrahedron71 (2015) 4248.[30] Wu B., Gao X., Chen M. W., Zhou Y. G.,Direct amination of 2-(1-tosylalkyl)phenols with aqueous ammonia: a metal-free synthesis of primary amines,Tetrahedron Lett.56 (2015) 1135.
[31] Liew S. K., He Z., St Denis J. D., Yudin A. K.,Stereocontrolled synthesis of 1,2- and 1,3-diamine building blocks from aziridine aldehyde dimmers,J. Org. Chem.78 (2013) 11637.
[32] Gomez-Bengoa E., Jimenez J., Lapuerta I., Mielgo A., Oiarbide M., Otazo I., Velilla I., Vera S., Palomo C.,Combined α,α-dialkylprolinol ether/Brønsted acid promotes Mannich reactions of aldehydes with unactivated imines. An entry to anti-configured propargylic amino alcohols,Chem. Sci.3 (2012) 2949.
[33] Izumiseki A., Yoshida K., Yanagisawa A.,Catalytic asymmetric three-component mannich-type reaction of alkenyl trichloroacetates,Org. Lett.11 (2009) 5310.
[34] Parmar D., Sugiono E., Raja S., Rueping M.,Complete field guide to asymmetric BINOL-phosphate derived Brønsted Acid and metal catalysis: History and classification by mode of activation; Brønsted acidity, hydrogen bonding, ion pairing, and metal phosphates,Chem. Rev.114 (2014) 9047.
[35] Wang D. –S., Chen Q. –A., Li W., Yu C. –B., Zhou Y. –G., Zhang X.,Pd-Catalyzed asymmetric hydrogenation of unprotected indoles activated by Brønsted acids,J. Am. Chem. Soc.132 (2010) 8909.
[36] Hou G., Gosselin F., Li W., McWilliams J. C., Sun Y., Weisel M., O’Shea P. D., Chen C. –Y., Davies I. W., Zhang X.,Enantioselective Hydrogenation of N-H Imines,J. Am. Chem. Soc.131 (2009) 9882.
[37] Kuehne M. E.,The applications of enamines to a new synthesis of b-ketonitriles,J. Am. Chem. Soc.81 (1959) 5400.
[38] Taguchi K., Westheimer F. H.,Catalysis by molecular sieves in the preparation of ketimines and enamines,J. Org. Chem.36 (1971) 1570.
[39] Jaworska M., Åaczkowski K. Z., WeÅ‚niak M., Welke M., Wojtczak A.,Imines derived from (1S, 2R)-norephedrine as catalysts in the enantioselective addition of diethylzinc to aldehydes,Applied Catalysis A: General357 (2009) 150.
[40] Billman J. H., Tai K. M. J.,Reduction of Schiff bases. II. Benzhydrylamines and structurally related compounds,J. Org. Chem.23 (1958) 535.
[41] Bolton R., Dank T. N., PaulJ. M.,Preparation and reduction of some camphor imines,Tetrahedron Lett.35 (1994) 3411.
[42] Emerson W. S.,Organic Reactions,Wiley, New York 4, 1948, 174.
[43] Hutchins R. O.,Natale N.,Cyanoborohydride. Utility and applications in organic synthesis. A review,Org. Prep. Proced. lnt.11 (1979) 201.
[44] Whitesell J. K., in Comprehensive Organic Synthesis,Trost B. M., Fleming, I.Ed. Pergamon Press, Oxford 6, 1991, 724and 8 25.
[45] (a) GribbleG. W., in Reductions in Organic Synthesis, ACS Symposium Series641, Abdel-Majid, A. F. Ed. American Chemical Society, Washington, DC, 1996, 167; (b) Abdel-Majid, A. F. ibid, 201.
[46] Abirami M., Gopiesh Khanna V., Kannabiran K.,Antibacterial activity of marine Streptomyces SP. isolated from Andaman & Nicobar Islands, Int J Pharm. Bio. Sci.4 (2013) 280.
[47] Chen J. J., Hung H. C., Sung P. J., Chen I. S., Kuo W. L.,Aporphine alkaloids and cytotoxic lignans from the roots of Illigeraluzonensis, Phytochemistry72 (2011) 523.
[48] Yazdiniapour Z., Ghanadian M., Zolfaghari B., Lanzotti V.,6(17)-Epoxylathyranediterpenes from Euphorbia sogdiana Popov with cytotoxic activity,Fitoterapia108 (2016) 87. [49] Hu J., Song Y., Mao X., Wang Z. J., Zhao Q. J.,Limonoids isolated from Toonasinensis and their radical scavenging, anti-inflammatory and cytotoxic activities,Journal of Functional Foods20 (2016) 1. [50] Huang L. H., Li Y., Xu H. D., Zheng Y. F.,Liu H. M.,Synthesis and biological evaluation of novel C6-cyclo secondary amine substituted purine steroid-nucleosides analogues,Steroids85 (2014) 13. [51] Akbaş H.,Okumuş A.,Kılıç Z.,Hökelek T.,Süzen Y.,Koç L. Y.,Açık L.,Çelik Z. B.,Phosphorus-nitrogencompounds part 27.Syntheses,structuralcharacterizations, antimicrobial and cytotoxic activities, and DNA interactions of new phosphazenes bearing secondary amino and pendant (4-fluorobenzyl)spiro groups,European Journal of Medicinal Chemistry70 (2013) 294.
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2016-04-24
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Guédouar, H., Aloui, F., & Ben hassine, B. (2016). Benzo[c]phenanthrene derivatives: Synthesis, optical properties and cytotoxic activity. JOURNAL OF ADVANCES IN CHEMISTRY, 12(9), 4404–4412. https://doi.org/10.24297/jac.v12i9.6706
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