Synthesis and properties of new fused pyrrolo-1,10-phenanthroline type derivatives Scientific paper

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Maria Cristina Al-Matarneh
https://orcid.org/0000-0001-9299-1347
Irina Rosca
Sergiu Shova
https://orcid.org/0000-0002-1222-4373
Ramona Danac
https://orcid.org/0000-0003-4370-5353

Abstract

New fused pyrrolo-phenanthroline type derivatives were synthesized, in two steps, from 1,10-phenanthroline and evaluated for antimicrobial activity and fluorescence properties. Our synthetic approach involved a 3+2 dipolar-cycloaddition of some selected N-substituted 1,10-phenanthrolin-1-ium ylides, (m)ethoxycarbonyl and cyano (1,2-di)substituted acetylenes and alkenes, res­pect­ively. The structures of compounds were supported by analytical and spec­troscopic data. The molecular structures of four selected compounds have also been also determined by monocrystal XRD analyses. All synthesized com­pounds were then evaluated for their potential antimicrobial activity against Staphylo­coccus aureus ATCC25923, Escherichia coli ATCC25922 and Can­dida albicans ATCC10231. Two of the compounds demonstrated significant activity against the above tested strains.

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How to Cite
[1]
M. C. Al-Matarneh, I. Rosca, S. Shova, and R. Danac, “Synthesis and properties of new fused pyrrolo-1,10-phenanthroline type derivatives: Scientific paper”, J. Serb. Chem. Soc., vol. 86, no. 10, pp. 901–915, Sep. 2021.
Section
Organic Chemistry

References

W. Huang, L. Wang, H. Tanaka, T. Ogawa, Eur. J. Inorg. Chem. 10 (2009) 1321 (https://doi.org/10.1002/ejic.200801131)

L. Ming, L. Xiu-Liang, W. Li-Rong, H. Zhi-Qiang, Org. Lett. 15 (2013) 1262 (https://doi.org/10.1021/ol400191b)

E. Szajdzinska-Pietek, M. Pinteala, S. Schlick, Polymer 45 (2004) 4113 (https://doi.org/10.1016/j.polymer.2004.03.101)

L. Leontie, I. Druta, R. Danac, G.I. Rusu, Synth. Met. 155 (2005) 138 (https://doi.org/10.1016/j.synthmet.2005.07.342)

M. Prelipceanu, O. S. Prelipceanu, L. Leontie, R, Danac, Phys. Lett. A368 (2007) 331 (http://dx.doi.org/10.1016/j.physleta.2007.04.013)

G. Accorsi, A. Listorti, K. Yoosaf, N. Armaroli, Chem. Soc. Rev. 38 (2009) 1690 (https://doi.org/10.1039/B806408N)

I. Druta, R. Danac, M. Ungureanu, G. Grosu, G. Drochioiu, Ann. Pharm. Fr. 60 (2002) 348 (https://pubmed.ncbi.nlm.nih.gov/12378146/)

A. Abebe, M. Atlabachew, M. Liyew, E. Ferede, Cogent Chemistry 4 (2018) 1476077 (https://doi.org/10.1080/23312009.2018.1476077)

L. Viganor, O. Howe, P. Mc Carron, M. Mc Cann, M. Devereux, Curr. Top. Med. Chem. 17 (2017) 1280 (https://doi.org/10.2174/1568026616666161003143333)

D. Wesselinova, M. Neykov, N. Kaloyanov,R.Toshkova, G. Dimitrov, Eur. J. Med. Chem. 44 (2009) 2720 (https://doi.org/10.1016/j.ejmech.2009.01.036)

L. Leontie, I. Druta, R. Danac, M. Prelipceanu, G.I. Rusu, Prog. Org. Coat. 54 (2005) 175 (https://doi.org/10.1016/j.porgcoat.2005.06.003)

A. Rotaru, R. Danac, I. Druta, G. Drochioiu, I. Cretescu, Rev. Chim. 56 (2005) 179 (https://revistadechimie.ro/Articles.asp?ID=570)

O. Gunaydin, L. Toppare, Y. Yagci, V. Harabagiu, M. Pinteala, B.C. Simionescu, Polym. Bull. 47(6) (2002) 501 (https://doi.org/10.1007/s002890200014)

E.Maftei, C. V. Maftei, P. G. Jones, M. Freytag, M. H. Franz, G.Kelter, H.-H.Fiebig, M.Tamm, I. Neda, Helv. Chim. Acta 99 (2016) 469 (https://doi.org/10.1002/hlca.201500529)

C. V. Maftei, E. Fodor, P. G. Jones, C. G. Daniliuc, M. H. Franz, G. Kelter, H.-H. Fiebig, M. Tamm, I. Neda, Tetrahedron 72 (2016) 1185 (https://doi.org/10.1016/j.tet.2016.01.011)

L. Leontie, R. Danac, N. Apetroaei, G.I. Rusu, Mater. Chem. Phys. 127 (2011) 471 (https://doi.org/10.1016/j.matchemphys.2011.02.040)

R. Danac, L. Leontie, A. Carlescu, G. I. Rusu, Mater. Chem. Phys. 134 (2012) 1042 (https://doi.org/10.1016/j.matchemphys.2012.03.110)

I. Dhinamkaran, V. Padmini, K. Ganesan, K. Selvarasu, Chemistry Select 2 (2017) 6154 (https://doi.org/10.1002/slct.201700819)

R. Danac, A. Rotaru, G. Drochioiu, I. Druta, J. Heterocycl. Chem. 40 (2003) 283 (https://doi.org/10.1002/jhet.5570400213)

R. Danac, M. Constantinescu, A. Rotaru, A. Vlahovici, I. Cretescu, I. Druta, Rev. Chim. 56 (2005) 85 (https://revistadechimie.ro/Articles.asp?ID=546)

F. Dumitrascu, C. I. Mitan, Tetrahedron Lett. 42 (2001) 8379 (https://doi.org/10.1016/S0040-4039(01)01803-2)

M. Li, X.L. Lv, L. R. Wen, Z.Q. Hu, Chem. Res. Chin. Univ. 29 (2013) 1089 (https://doi.org/10.1007/s40242-013-3224-2)

G. Marandi, N. Hazeri, M. T. Maghsoodlou, S. M. Habibi-Khorassani, N. Akbarzadeh Torbati, F. Rostami Charati, B. W. Skelton, M. Makhad, J. Heterocyclic Chem. 50 (2013) 568 (https://doi.org/10.1002/jhet.1532)

Y. Kitahara, T. Mizuno, A. Kubo, Tetrahedron 60 (2004) 4283 (https://doi.org/10.1016/j.tet.2004.03.057)

R. Heydari, B. Tahamipour, Chin. Chem. Lett. 22 (2011) 1281 (https://doi.org/10.1016/j.cclet.2011.05.035)

C. M. Al-Matarneh, C. Ciobanu, V. Mangalagiu, G. Zbancioc, R. Danac, Rev. Chim. 71 (2020) 287 (https://doi.org/10.37358/RC.20.3.7998)

C. M. Al-Matarneh, M. O. Apostu, I. I. Mangalagiu, R. Danac, Tetrahedron 72 (2016) 4230 (https://doi.org/10.1016/j.tet.2016.05.061)

C. M. Al-Matarneh, C. Ciobanu, M. O. Apostu, I. I. Mangalagiu, R. Danac, C. R. Chim. 21 (2018) 1 (https://doi.org/10.1016/j.crci.2017.11.003)

C. M. Al-Matarneh, D.L. Isac, R. Tigoianu, R. Danac, A. Airinei, J. Lumin. 199 (2018) 6 (https://doi.org/10.1016/j.jlumin.2018.03.005)

C. M. Al-Matarneh, R. Danac, L. Leontie, F. Tudorache, I. Petrila, F. Iacomi, A. Carlescu, G. Nedelcu, I. I. Mangalagiu, Environ. Eng. Manage. J. 14 (2015) 420 (https://doi.org/10.30638/eemj.2015.044)

C. M. Al-Matarneh, S. Shova, I. I. Mangalagiu, R. Danac, J. Enz. Inhib. Med. Chem. 31 (2016) 470 (https://doi.org/10.3109/14756366.2015.1039530)

C. M. Al-Matarneh, M. C. Sardaru, M. O. Apostu, I. Rosca, C. Ciobanu, I. I. Mangalagiu, R. Danac, Studia UBB Chemia LXIV (2019) 67 (https://doi.org/10.24193/subbchem.2019.3.06)

C. M. Al-Matarneh, R. M. Amarandi, A. M. Craciun, I. I. Mangalagiu, G. Zbancioc, R. Danac, Molecules 25 (2020) 527 (https://doi.org/10.3390/molecules25030527)

A. Rotaru, G. Pricope, T. N. Plank, L. Clima, E. L. Ursu, M. Pinteala, J. T. Davis, M. Barboiu, Chem. Comm. 53 (2013) 12668 (https://doi.org/10.1039/C7CC07806D)

M. C. Sardaru, A. M. Craciun, C. M. Al Matarneh, I. A. Sandu, R. M. Amarandi, L. Popovici, C. I. Ciobanu, D. Peptanariu, M. Pinteala, I. I. Mangalagiu, R. Danac, J. Enz. Inhib. Med. Chem. 35 (2020) 1581 (https://doi.org/10.1080/14756366.2020.1801671)

Rigaku Oxford Diffraction, CrysAlisPro software system version 1.171.38.46, Rigaku Corporation, Oxford, 2015

O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard, H. J. Pushmann, Appl. Crystallogr. 42 (2009) 339 (https://doi.org/10.1107/S0021889808042726)

G. M. Sheldrick, Acta Crystallogr., A 71 (2015) 3 (https://doi.org/10.1107/S2053273314026370)

G. M. Sheldrick, Acta Crystaalogr., C 71 (2015) 3 (http://dx.doi.org/10.1107/S2053229614024218)

F. Dumitrascu, C. Draghici, M. R. Caira, L. Barbu, Rev. Chim. 56 (2005) 521 (https://revistadechimie.ro/Articles.asp?ID=649)

F. Dumitrascu, M. R. Caira, C. Draghici, M. T. Caproiu, L. Barbu, Rev. Chim. 60 (2009) 851 (https://revistadechimie.ro/Articles.asp?ID=2338)

N. S. Kozlov, K. N. Gusak, V. A. Serzhanina, L. F. Gladchenko, N. A. Krot, K. Getorotsikl, Chem. Heterocycl. Compd. 23 (1987) 1329 (https://doi.org/10.1007/BF00472258).