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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Review Article

A Review on Diverse Biological Activity of Heterocyclic Nucleus Pyrazine and its Derivatives: A Key for the Researchers

Author(s): Shilpi Pathak*, Neetu Agrawal and Sonam Gaur

Volume 21, Issue 4, 2024

Published on: 09 October, 2023

Page: [351 - 361] Pages: 11

DOI: 10.2174/0115701786273932230927062616

Price: $65

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Abstract

Pyrazine belongs to the 1, 4-diazines family, which is a significant class of heterocyclic compounds. Various pyrazine derivatives have been produced and successfully confirmed as medicines with various pharmacological activities like anti-inflammatory, antitubercular, anticancer, antibacterial, and neurological activity, with some of them becoming clinically utilized pharmaceuticals globally. This review includes a survey on pyrazine derivatives possessing different pharmacological activities. The class of pyrazine-based potential medications has grown rapidly in terms of both the absolute quantity of studied compounds and the range of various biological activities. Additionally, there is a lot of potential for this scaffold, which medicinal chemists ought to investigate for the creation of novel potential drug candidates.

Keywords: Pyrazine, heterocyclic compound, biological activities, chemistry, pharmacophores, mycobacterium.

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[1]
Choudhary, D.; Garg, S.; Kaur, M.; Sohal, H.S.; Malhi, D.S.; Kaur, L.; Verma, M.; Sharma, A.; Mutreja, V. Polycycl. Aromat. Compd., 2023, 43(5), 4512-4578.
[http://dx.doi.org/10.1080/10406638.2022.2092873]
[2]
Tambat, N.; Mulani, S.K.; Ahmad, A.; Shaikh, S.B.; Ahmed, K. Russ. J. Bioorganic Chem., 2022, 48(5), 865-895.
[http://dx.doi.org/10.1134/S1068162022050259]
[3]
Ong, K.T.; Liu, Z.Q.; Tay, M.G. Borneo J. Resour, 2017, 7(2), 60-75.
[http://dx.doi.org/10.33736/bjrst.591.2017]
[4]
Dolezal, M.; Zitko, J. Expert Opin. Ther. Pat., 2015, 25(1), 33-47.
[http://dx.doi.org/10.1517/13543776.2014.982533] [PMID: 25523365]
[5]
Dhok, S.S.; Bhandarkar, S.E. Int. J. Res. Pharm. Chem., 2015, 5, 312-316.
[6]
Hou, W.; Dai, W.; Huang, H.; Liu, S.L.; Liu, J.; Huang, L.J.; Huang, X.H.; Zeng, J.L.; Gan, Z.W.; Zhang, Z.Y.; Lan, J.X. Eur. J. Med. Chem., 2023, 258, 115544.
[http://dx.doi.org/10.1016/j.ejmech.2023.115544] [PMID: 37300915]
[7]
Huigens, R.W., III; Brummel, B.R.; Tenneti, S.; Garrison, A.T.; Xiao, T. Molecules, 2022, 27(3), 1112.
[http://dx.doi.org/10.3390/molecules27031112] [PMID: 35164376]
[8]
Müller, R.; Rappert, S. Appl. Microbiol. Biotechnol., 2010, 85(5), 1315-1320.
[http://dx.doi.org/10.1007/s00253-009-2362-4] [PMID: 19957079]
[9]
Maga, J.A. Food Rev. Int., 1992, 8(4), 479-558.
[http://dx.doi.org/10.1080/87559129209540951]
[10]
Fedotov, V.V.; Valieva, M.I.; Taniya, O.S.; Aminov, S.V.; Kharitonov, M.A.; Novikov, A.S.; Kopchuk, D.S.; Slepukhin, P.A.; Zyryanov, G.V.; Ulomsky, E.N.; Rusinov, V.L.; Charushin, V.N. Molecules, 2022, 27(22), 8029.
[http://dx.doi.org/10.3390/molecules27228029] [PMID: 36432130]
[11]
Taniya, O.S.; Fedotov, V.V.; Novikov, A.S.; Sadieva, L.K.; Krinochkin, A.P.; Kovalev, I.S.; Kopchuk, D.S.; Zyryanov, G.V.; Liu, Y.; Ulomsky, E.N.; Rusinov, V.L.; Charushin, V.N. Dyes Pigments, 2022, 204, 110405.
[http://dx.doi.org/10.1016/j.dyepig.2022.110405]
[12]
Dubovtsev, A.Y.; Zvereva, V.V.; Shcherbakov, N.V.; Dar’in, D.V.; Novikov, A.S.; Kukushkin, V.Y. Org. Biomol. Chem., 2021, 19(20), 4577-4584.
[http://dx.doi.org/10.1039/D1OB00513H] [PMID: 33954321]
[13]
Lystsova, E.A.; Novikov, A.S.; Dmitriev, M.V.; Maslivets, A.N.; Khramtsova, E.E. Molecules, 2023, 28(14), 5495.
[http://dx.doi.org/10.3390/molecules28145495] [PMID: 37513367]
[14]
Sheina, E.S.; Shestakova, T.S.; Deev, S.L.; Khalymbadzha, I.A.; Slepukhin, P.A.; Eltsov, O.S.; Novikov, A.S.; Shevyrin, V.A.; Charushin, V.N.; Chupakhin, O.N. Chem. Asian J., 2023, 18(5), e202201306.
[http://dx.doi.org/10.1002/asia.202201306] [PMID: 36662627]
[15]
Burianova, V.K.; Bolotin, D.S.; Novikov, A.S.; Kolesnikov, I.E.; Suslonov, V.V.; Zhdanov, A.P.; Zhizhin, K.Y.; Kuznetsov, N.T. Inorg. Chim. Acta, 2018, 482, 838-845.
[http://dx.doi.org/10.1016/j.ica.2018.07.038]
[16]
Buslov, I.V.; Novikov, A.S.; Khrustalev, V.N.; Grudova, M.V.; Kubasov, A.S.; Matsulevich, Z.V.; Borisov, A.V.; Lukiyanova, J.M.; Grishina, M.M.; Kirichuk, A.A.; Serebryanskaya, T.V.; Kritchenkov, A.S.; Tskhovrebov, A.G. Symmetry, 2021, 13(12), 2350.
[http://dx.doi.org/10.3390/sym13122350]
[17]
Khrustalev, V.N.; Grishina, M.M.; Matsulevich, Z.V.; Lukiyanova, J.M.; Borisova, G.N.; Osmanov, V.K.; Novikov, A.S.; Kirichuk, A.A.; Borisov, A.V.; Solari, E.; Tskhovrebov, A.G. Dalton Trans., 2021, 50(31), 10689-10691.
[http://dx.doi.org/10.1039/D1DT01322J] [PMID: 34165455]
[18]
Starnovskaya, E.S.; Kopchuk, D.S.; Khasanov, A.F.; Taniya, O.S.; Nikonov, I.L.; Valieva, M.I.; Pavlyuk, D.E.; Novikov, A.S.; Zyryanov, G.V.; Chupakhin, O.N. Molecules, 2022, 27(20), 6879.
[http://dx.doi.org/10.3390/molecules27206879] [PMID: 36296472]
[19]
Demyanov, Y.V.; Sadykov, E.H.; Rakhmanova, M.I.; Novikov, A.S.; Bagryanskaya, I.Y.; Artem’ev, A.V. Molecules, 2022, 27(18), 6059.
[http://dx.doi.org/10.3390/molecules27186059] [PMID: 36144790]
[20]
Mardaleishvili, I.R.; Vologzhanina, A.V.; Novikov, A.S.; Shienok, A.I. J. Struct. Chem., 2022, 63, 626-633.
[http://dx.doi.org/10.1134/S002247662204014X]
[21]
Bonde, C.G.; Gaikwad, N.J. Bioorg. Med. Chem., 2004, 12(9), 2151-2161.
[http://dx.doi.org/10.1016/j.bmc.2004.02.024] [PMID: 15080915]
[22]
Gür, M. Şener, N.; Muğlu, H.; Çavuş, M.S.; Özkan, O.E.; Kandemirli, F.; Şener, İ. J. Mol. Struct., 2017, 1139, 111-118.
[http://dx.doi.org/10.1016/j.molstruc.2017.03.019]
[23]
Zaki, R.M.; Kamal El-Dean, A.M.; Radwan, S.M. Abd ul-Malik. M.A. J. Chin. Chem. Soc., 2020, 67(4), 658-673.
[http://dx.doi.org/10.1002/jccs.201900056]
[24]
abrahim, T.; Mohammed, M.N. J. Phys. Conf. Ser., 2019, 1294(5), 052074.
[http://dx.doi.org/10.1088/1742-6596/1294/5/052074]
[25]
El-emary, T.I. J. Chin. Chem. Soc., 2006, 53, 391-401.
[26]
Bo, Y.X.; Xiang, R.; Xu, Y.; Hao, S.Y.; Wang, X.R.; Chen, S.W. Bioorg. Med. Chem., 2020, 28(5), 115351.
[http://dx.doi.org/10.1016/j.bmc.2020.115351] [PMID: 32035750]
[27]
Kékesi, L. Sipos, A.; Németh, G.; Pató, J.; Breza, N.; Baska, F.; Őrfi, L.; Kéri, G. Bioorg. Med. Chem. Lett., 2013, 23(22), 6152-6155.
[http://dx.doi.org/10.1016/j.bmcl.2013.09.005] [PMID: 24095095]
[28]
Argyros, O.; Lougiakis, N.; Kouvari, E.; Papafotika, A.; Raptopoulou, C.P.; Psycharis, V.; Christoforidis, S.; Pouli, N.; Marakos, P.; Tamvakopoulos, C. Eur. J. Med. Chem., 2017, 126, 954-968.
[http://dx.doi.org/10.1016/j.ejmech.2016.12.025] [PMID: 28006668]
[29]
Chtita, S.; Ghamali, M.; Larif, M.; Adad, A. Int. J. Innov. Res. Sci. Eng. Technol., 2013, 2, 7951-7962.
[30]
Racané, L. Kraljević Pavelić S.; Ratkaj, I.; Stepanić V.; Pavelić K.; Tralić-Kulenović V.; Karminski-Zamola. G. Eur. J. Med. Chem., 2012, 55, 108-116.
[http://dx.doi.org/10.1016/j.ejmech.2012.07.005] [PMID: 22841279]
[31]
Tantawy, E.S.; Amer, A.M.; Mohamed, E.K.; Abd Alla, M.M.; Nafie, M.S. J. Mol. Struct., 2020, 1210, 128013-128021.
[http://dx.doi.org/10.1016/j.molstruc.2020.128013]
[32]
Singh, I.; Luxami, V.; Paul, K. Eur. J. Med. Chem., 2019, 180, 546-561.
[http://dx.doi.org/10.1016/j.ejmech.2019.07.042] [PMID: 31344614]
[33]
Temple, C., Jr; Wheeler, G.P.; Elliott, R.D.; Rose, J.D.; Kussner, C.L.; Comber, R.N.; Montgomery, J.A. J. Med. Chem., 1982, 25(9), 1045-1050.
[http://dx.doi.org/10.1021/jm00351a008] [PMID: 7131483]
[34]
Uygun, M.T.; Amudi, K. Turaçlı İ.D.; Menges, N. Mol. Divers., 2022, 26(1), 113-124.
[http://dx.doi.org/10.1007/s11030-020-10161-8] [PMID: 33387184]
[35]
Wang, S.; Yuan, X.; Qian, H.; Li, N.; Wang, J. Int. J. Mol. Sci., 2020, 21(5), 1665.
[http://dx.doi.org/10.3390/ijms21051665] [PMID: 32121303]
[36]
Xu, S.; Sun, C.; Chen, C.; Zheng, P.; Zhou, Y.; Zhou, H.; Zhu, W. Molecules, 2017, 22(2), 310.
[http://dx.doi.org/10.3390/molecules22020310] [PMID: 28218676]
[37]
Zheng, P.; Zhang, J.; Ma, H.; Yuan, X.; Chen, P.; Zhou, J.; Zhang, H. Bioorg. Med. Chem., 2019, 27(7), 1391-1404.
[http://dx.doi.org/10.1016/j.bmc.2019.02.045] [PMID: 30824168]
[38]
Zorina, A.D.; Nikiforova, N.S.; Zarubaev, V.V.; Marchenko, S.A.; Selivanov, S.I.; Starova, G.L.; Mehtiev, A.R.; Rodionov, E.I.; Rodionova, A.A.; Trifonov, R.E. Mendeleev Commun., 2019, 29(5), 500-502.
[http://dx.doi.org/10.1016/j.mencom.2019.09.007]
[39]
Zhao, L.; Yang, Y.; Guo, Y.; Yang, L.; Zhang, J.; Zhou, J.; Zhang, H. Bioorg. Med. Chem., 2017, 25(8), 2482-2490.
[http://dx.doi.org/10.1016/j.bmc.2017.03.008] [PMID: 28314513]
[40]
Zhang, H.; Wang, Y.; Zhu, P.; Liu, J.; Xu, S.; Yao, H.; Jiang, J.; Ye, W.; Wu, X.; Xu, J. Eur. J. Med. Chem., 2015, 97, 235-244.
[http://dx.doi.org/10.1016/j.ejmech.2015.04.057] [PMID: 25984840]
[41]
Abu-Hashem, A.A.; El-Shazly, M. Med. Chem., 2018, 14(4), 356-371.
[http://dx.doi.org/10.2174/1573406414666180112110947] [PMID: 29332598]
[42]
Maccoss, M.; Meurer, L.C.; Hoogsteen, K.; Springer, J.P.; Koo, G.; Peterson, L.B.; Tolman, R.L.; Emini, E. J. Heterocycl. Chem., 1993, 30(5), 1213-1220.
[http://dx.doi.org/10.1002/jhet.5570300508]
[43]
Zhang, Y.B.; Wang, X.L.; Liu, W.; Yang, Y.S.; Tang, J.F.; Zhu, H.L. Bioorg. Med. Chem., 2012, 20(21), 6356-6365.
[http://dx.doi.org/10.1016/j.bmc.2012.08.059] [PMID: 23018096]
[44]
Das, R.; Shilakari, G.; Asthana, A. J. Pharm. Sci. Res., 2015, 7, 806-811.
[45]
Chitre, T.S.; Asgaonkar, K.D.; Miniyar, P.B.; Dharme, A.B.; Arkile, M.A.; Yeware, A.; Sarkar, D.; Khedkar, V.M.; Jha, P.C. Bioorg. Med. Chem. Lett., 2016, 26(9), 2224-2228.
[http://dx.doi.org/10.1016/j.bmcl.2016.03.055] [PMID: 27017114]
[46]
Kucerova-Chlupacova, M.; Kunes, J.; Buchta, V.; Vejsova, M.; Opletalova, V. Molecules, 2015, 20(1), 1104-1117.
[http://dx.doi.org/10.3390/molecules20011104] [PMID: 25587786]
[47]
Kolli, M.K.; Padi, K.R.; Singh, N.; Tatipamula, V.B. Der Pharma Chem., 2018, 10, 153-158.
[48]
Abdel-Aziz, M.; Abdel-Rahman, H.M. Eur. J. Med. Chem., 2010, 45(8), 3384-3388.
[http://dx.doi.org/10.1016/j.ejmech.2010.04.025] [PMID: 20488590]
[49]
Dolezal, M.; Miletin, M.; Kunes, J.; Kralova, K.; Control, D.; Chemistry, O. Molecules, 2002, 7(3), 363-373.
[http://dx.doi.org/10.3390/70300363]
[50]
Gangarapu, N.R.; Ranganatham, A.; Reddy, E.K.; Yellappa, S.; Chandrasekhar, K.B. Arch. Pharm., 2020, 353(7), 1900368.
[http://dx.doi.org/10.1002/ardp.201900368] [PMID: 32399980]
[51]
Semelkova, L.; Konecna, K.; Paterova, P.; Kubicek, V.; Kunes, J.; Novakova, L.; Marek, J.; Naesens, L.; Pesko, M.; Kralova, K.; Dolezal, M.; Zitko, J. Molecules, 2015, 20(5), 8687-8711.
[http://dx.doi.org/10.3390/molecules20058687] [PMID: 26007174]
[52]
Hassan, N.W.; Saudi, M.N.; Abdel-Ghany, Y.S.; Ismail, A.; Elzahhar, P.A.; Sriram, D.; Nassra, R.; Abdel-Aziz, M.M.; El-Hawash, S.A. Bioorg. Chem., 2020, 96, 103610.
[http://dx.doi.org/10.1016/j.bioorg.2020.103610] [PMID: 32028062]
[53]
Reddyrajula, R.; Dalimba, U. Bioorg. Med. Chem. Lett., 2020, 30(2), 126846.
[http://dx.doi.org/10.1016/j.bmcl.2019.126846] [PMID: 31839540]
[54]
Al-Tamimi, A.M.S.; Mary, Y.S.; Miniyar, P.B.; Al-Wahaibi, L.H.; El-Emam, A.A. Armaković S.; Armaković. S.J. J. Mol. Struct., 2018, 1164, 459-469.
[http://dx.doi.org/10.1016/j.molstruc.2018.03.085]
[55]
Janssens, T.K.S.; Tyc, O.; Besselink, H.; de Boer, W.; Garbeva, P. FEMS Microbiol. Lett., 2019, 366(3), 1-10.
[http://dx.doi.org/10.1093/femsle/fnz023] [PMID: 30698709]
[56]
Kuo, G.H.; Prouty, C.; Wang, A.; Emanuel, S.; DeAngelis, A.; Zhang, Y.; Song, F.; Beall, L.; Connolly, P.J.; Karnachi, P.; Chen, X.; Gruninger, R.H.; Sechler, J.; Fuentes-Pesquera, A.; Middleton, S.A.; Jolliffe, L.; Murray, W.V. J. Med. Chem., 2005, 48(15), 4892-4909.
[http://dx.doi.org/10.1021/jm058205b] [PMID: 16033269]
[57]
Cugola, A.; Donati, D.; Guarneri, M.; Micheli, F.; Missio, A.; Pecunioso, A.; Reggiani, A.; Tarzia, G.; Zanirato, V. Bioorg. Med. Chem. Lett., 1996, 6(22), 2749-2754.
[http://dx.doi.org/10.1016/S0960-894X(96)00492-1]
[58]
Ma, T.; Zou, F.; Pusch, S.; Yang, L.; Zhu, Q.; Xu, Y.; Gu, Y.; von Deimling, A.; Zha, X. Bioorg. Med. Chem., 2017, 25(24), 6379-6387.
[http://dx.doi.org/10.1016/j.bmc.2017.10.009] [PMID: 29089260]
[59]
Richter, H.G.F.; Adams, D.R.; Benardeau, A.; Bickerdike, M.J.; Bentley, J.M.; Blench, T.J.; Cliffe, I.A.; Dourish, C.; Hebeisen, P.; Kennett, G.A.; Knight, A.R.; Malcolm, C.S.; Mattei, P.; Misra, A.; Mizrahi, J.; Monck, N.J.T.; Plancher, J.M.; Roever, S.; Roffey, J.R.A.; Taylor, S.; Vickers, S.P. Bioorg. Med. Chem. Lett., 2006, 16(5), 1207-1211.
[http://dx.doi.org/10.1016/j.bmcl.2005.11.083] [PMID: 16361098]
[60]
Tardy, S.; Orsato, A.; Mologni, L.; Bisson, W.H.; Donadoni, C.; Gambacorti-Passerini, C.; Scapozza, L.; Gueyrard, D.; Goekjian, P.G. Bioorg. Med. Chem., 2014, 22(4), 1303-1312.
[http://dx.doi.org/10.1016/j.bmc.2014.01.007] [PMID: 24468632]

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