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Mini-Reviews in Organic Chemistry

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Review Article

Advances in Chemistry of 2-(Piperazin-1-yl) Quinoline (Part IV)

Author(s): Ghada G. El-Bana* and Moustafa A. Gouda*

Volume 21, Issue 5, 2024

Published on: 19 June, 2023

Page: [542 - 554] Pages: 13

DOI: 10.2174/1570193X20666230509142134

Price: $65

Abstract

This review described the preparation of 2-(piperazin-1-yl) quinoline derivatives from 2- haloquinolines and anilides, which underwent alkylation, arylation, acylation, and reductive amination to form the 2-piprazinoquinolines. 2-(Piperazin-1-yl) quinoline used as building blocks for the synthesis of polyfunctionalized heterocyclic compounds with pharmacological interest.

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[1]
Meldola, R. Coal and What We Get from It: A Romance of Applied Science; Society for Promoting Christian Knowledge: London, UK, 1913.
[2]
Achan, J.; Talisuna, A.O.; Erhart, A.; Yeka, A.; Tibenderana, J.K.; Baliraine, F.N.; Rosenthal, P.J.; D’Alessandro, U. Quinine, an old anti-malarial drug in a modern world: Role in the treatment of malaria. Malar. J., 2011, 10(1), 144.
[http://dx.doi.org/10.1186/1475-2875-10-144] [PMID: 21609473]
[3]
Kirtane, M.V.; Bhandari, A.; Narang, P.; Santani, R. Cinnarizine: A contemporary review. Indian J. Otolaryngol. Head Neck Surg., 2019, 71(S2), 1060-1068.
[http://dx.doi.org/10.1007/s12070-017-1120-7]
[4]
Chen, S.H.; Chao, C.N.; Chen, S.Y.; Lin, H.P.; Huang, H.Y.; Fang, C.Y. Flunarizine, a drug approved for treating migraine and vertigo, exhibits cytotoxicity in GBM cells. Eur. J. Pharmacol., 2021, 892, 173756.
[http://dx.doi.org/10.1016/j.ejphar.2020.173756]
[5]
Hara, H.; Morita, T.; Sukamoto, T.; Cutrer, F. M. Lomerizine (KB‐2796), a new antimigraine drug. CNS Drug Rev., 1995, 1(2), 204-226.
[http://dx.doi.org/10.1111/j.1527-3458.1995.tb00284.x]
[6]
Siragusa, S.; Bistas, K.G.; Saadabadi, A. Fluphenazine. In: StatPearls; StatPearls Publishing: Treasure Island (FL), 2022.
[7]
Davis, R.; Markham, A.; Balfour, J.A. Ciprofloxacin. Drugs, 1996, 51(6), 1019-1074.
[http://dx.doi.org/10.2165/00003495-199651060-00010] [PMID: 8736621]
[8]
Schultz, C. Gatifloxacin ophthalmic solution for treatment of bacterial conjunctivitis: safety, efficacy and patient perspective. Ophthalmol. Eye Dis., 2012, 4, OED.S7383.
[http://dx.doi.org/10.4137/OED.S7383] [PMID: 23650458]
[9]
Lubasch, A.; Erbes, R.; Mauch, H.; Lode, H. Sparfloxacin in the treatment of drug resistant tuberculosis or intolerance of first line therapy. Eur. Respir. J., 2001, 17(4), 641-646.
[http://dx.doi.org/10.1183/09031936.01.17406410] [PMID: 11401058]
[10]
Roussos, N.; Karageorgopoulos, D.E.; Samonis, G.; Falagas, M.E. Clinical significance of the pharmacokinetic and pharmacodynamic characteristics of fosfomycin for the treatment of patients with systemic infections. Int. J. Antimicrob. Agents, 2009, 34(6), 506-515.
[http://dx.doi.org/10.1016/j.ijantimicag.2009.08.013]
[11]
Salem, M.A.; Gouda, M.A.; El-Bana, G.G. Chemistry of 2-(piperazin-1-yl) quinoline-3-carbaldehydes. Mini Rev. Org. Chem., 2022, 19(4), 480-495.
[http://dx.doi.org/10.2174/1570193X18666211001124510]
[12]
Saraf, A.S.; Simonyan, A.V. Synthesis and antiallergic activity in a series of cinnamic acid. Pharm. Chem. J., 1992, 26(7-8), 598-602.
[http://dx.doi.org/10.1007/BF00777140]
[13]
Jaggavarapu, S.R.; Kamalakaran, A.S.; Jalli, V.P.; Gangisetty, S.K.; Ganesh, M.R.; Gaddamanugu, G. Facile eco-friendly synthesis of novel chromeno[4,3-b]pyridine-2,5-diones and evaluation of their antimicrobial and antioxidant properties. J. Chem. Sci., 2014, 126(1), 187-195.
[http://dx.doi.org/10.1007/s12039-013-0565-9]
[14]
Cao, X.H.; Pan, X.; Zhou, P.J.; Zou, J.P.; Asekun, O.T. Manganese(iii)-mediated direct Csp2–H radical trifluoromethylation of coumarins with sodium trifluoromethanesulfinate. Chem. Commun. (Camb.), 2014, 50(25), 3359-3362.
[http://dx.doi.org/10.1039/c3cc49689a] [PMID: 24549088]
[15]
Asagarasu, A.; Matsui, T.; Hayashi, H.; Tamaoki, S.; Yamauchi, Y.; Minato, K.; Sato, M. Discovery of a novel 5-HT(3) antagonist/5-HT(1A) agonist 3-amino-5,6,7,8-tetrahydro-2-{4-[4-(quinolin-2-yl)piperazin-1-yl]butyl}quinazolin-4(3H)-one (TZB-30878) as an orally bioavailable agent for irritable bowel syndrome. J. Med. Chem., 2010, 53(21), 7549-7563.
[http://dx.doi.org/10.1021/jm1002292]
[16]
Deshmukh, M.B.; Chavan, P.B. Synthesis of some new N1-substituted - quinolin-2-(1H)-one derivatives. J. Indian Chem. Soc., 1991, 68(10), 573-574.
[17]
Zhu, C.; Hansen, A.R.; Bateman, T.; Chen, Z.; Holt, T.G.; Hubert, J.A.; Karanam, B.V.; Lee, S.J.; Pan, J.; Qian, S.; Reddy, V.B.G.; Reitman, M.L.; Strack, A.M.; Tong, V.; Weingarth, D.T.; Wolff, M.S.; MacNeil, D.J.; Weber, A.E.; Duffy, J.L.; Edmondson, S.D. Discovery of imidazole carboxamides as potent and selective CCK1R agonists. Bioorg. Med. Chem. Lett., 2008, 18(15), 4393-4396.
[http://dx.doi.org/10.1016/j.bmcl.2008.06.057] [PMID: 18614364]
[18]
Bhunia, S.; Kumar, S.V.; Ma, D. N, N ′-Bisoxalamides enhance the catalytic activity in Cu-catalyzed coupling of (hetero)aryl bromides with anilines and secondary amines. J. Org. Chem., 2017, 82(23), 12603-12612.
[http://dx.doi.org/10.1021/acs.joc.7b02363] [PMID: 29117476]
[19]
Haihong, H.; Zhufang, S.; Hongyihuan, Z.; Jiang, Y.; Ziyun, Q.; Peng, L.; Quan, L.; Suinan, L. Preparation of [4-(nitrogen containing heterocycle)pyrrolidin-2-yl](thiomorpholino)methanone derivatives as DPP-IV inhibitor for the treatment of diabetes China. CN Patent, 105085359 A, 2015.
[20]
Jensen, J.A.; Pedersen, E.B. Phosphorus pentoxide in organic synthesis XXXII: A new synthesis of quipazine and its N -Methyl derivatives. Arch. Pharm. (Weinheim), 1987, 320(10), 1088-1092.
[http://dx.doi.org/10.1002/ardp.198700013]
[21]
Sabnis, R.W.; Rangnekar, D.W.; Sonawane, N.D. 2-aminothiophenes by the gewald reaction. J. Heterocycl. Chem., 1999, 36(2), 333-345.
[http://dx.doi.org/10.1002/jhet.5570360203]
[22]
Kling, A.; Lange, U.E.W.; Mack, H.; Bakker, M.H.M.; Drescher, K.U.; Hornberger, W.; Hutchins, C.W.; Möller, A.; Müller, R.; Schmidt, M.; Unger, L.; Wicke, K.; Schellhaas, K.; Steiner, G. Synthesis and SAR of highly potent dual 5-HT1A and 5-HT1B antagonists as potential antidepressant drugs. Bioorg. Med. Chem. Lett., 2005, 15(24), 5567-5573.
[http://dx.doi.org/10.1016/j.bmcl.2005.04.077] [PMID: 16219465]
[23]
Perrone, R.; Berardi, F.; Colabufo, N.A.; Lacivita, E.; Larizza, C.; Leopoldo, M.; Tortorella, V. Design and synthesis of long-chain arylpiperazines with mixed affinity for serotonin transporter (SERT) and 5-HT1A receptor. J. Pharm. Pharmacol., 2010, 57(10), 1319-1327.
[http://dx.doi.org/10.1211/jpp.57.10.0011] [PMID: 16259761]
[24]
Morelli, E.; Gemma, S.; Budriesi, R.; Campiani, G.; Novellino, E.; Fattorusso, C.; Catalanotti, B.; Coccone, S.S.; Ros, S.; Borrelli, G.; Persico, M.; Fiorini, I.; Nacci, V.; Ioan, P.; Chiarini, A.; Hamon, M.; Cagnotto, A.; Mennini, T.; Fracasso, C.; Colovic, M.; Caccia, S.; Butini, S. Specific targeting of peripheral serotonin 5-HT(3) receptors. Synthesis, biological investigation, and structure-activity relationships. J. Med. Chem., 2009, 52(11), 3548-3562.
[http://dx.doi.org/10.1021/jm900018b] [PMID: 19425598]
[25]
Gomółka, A.; Ciesielska, A.; Wróbel, M.Z.; Chodkowski, A.; Kleps, J.; Dawidowski, M.; Siwek, A.; Wolak, M.; Stachowicz, K.; Sławińska, A.; Nowak, G.; Satała, G.; Bojarski, A.J.; Belka, M.; Ulenberg, S.; Bączek, T.; Skowronek, P.; Turło, J.; Herold, F. Novel 4-aryl-pyrido[1,2-c]pyrimidines with dual SSRI and 5-HT1A activity (Part 5). Eur. J. Med. Chem., 2015, 98, 221-236.
[http://dx.doi.org/10.1016/j.ejmech.2015.05.003] [PMID: 26043160]
[26]
Bertani, B.; Borriello, M.; Bozzoli, A.; Bromidge, S.M.; Granci, E.; Leslie, C.; Serafinowska, H.; Stasi, L.; Vong, A.; Zucchelli, V. Preparation of benzoxazinones as ligands for 5-HT1 receptors and their use in the treatment of CNS disorders, in particular serotonin-related disorders. WO Patent, 2004046124 A1, 2004.
[27]
Krajewski, K.J.; Les, A.; Cybulski, J.; Chilmonczyk, Z.; Bronowska, A.; Szelejewska-Wozniakowska, A. Novel buspirone-like 5-HT receptor ligands. Pol. J. Chem., 2001, 75(1), 71-78.
[http://dx.doi.org/10.1002/chin.200118133]
[28]
Jin, J.; Zhang, K.; Dou, F.; Hao, C.; Zhang, Y.; Cao, X.; Gao, L.; Xiong, J.; Liu, X.; Liu, B.F.; Zhang, G.; Chen, Y. Isoquinolinone derivatives as potent CNS multi-receptor D2/5-HT1A/5-HT2A/5-HT6/5-HT7 agents: Synthesis and pharmacological evaluation. Eur. J. Med. Chem., 2020, 207,, 112709.
[http://dx.doi.org/10.1016/j.ejmech.2020.112709] [PMID: 32877805]
[29]
Cybulski, J.; Chilmonczyk, Z.; Szelejewski, W.; Wojtasiewicz, K.; Wróbel, J.T. An efficient synthesis of buspirone and its analogs. Arch. Pharm. (Weinheim), 1992, 325(5), 313-315.
[http://dx.doi.org/10.1002/ardp.19923250513]
[30]
Lubisch, W.; Dullweber, U.; Starck, D.; Steiner, G.; Bach, A.; Emling, F.; Garcia-Ladona, X.; Teschendorf, H.J.; Wicke, K. WO Patent, 9920616 A1, 1999.
[31]
Bourrain, S.; Hunt, P.A.; Huscroft, I.T.; Kulagowski, J.J.; London, C.; Naylor, E.M.; Raubo, P.A.; Seward, E.M. Preparation of phenyl heterocyclylalkyl sulfones as 5-HT receptor ligands. US Patent, 20040229864 A1,
[32]
Andersen, H.S.; Moller, N.P.H.; Madsen, P. Preparation of acrylic acids as modulators of molecules with phosphotyrosine recognition units. WO Patent, 9739748 A1,
[33]
Komoto, T.; Okada, T.; Sato, S.; Niino, Y.; Oka, T.; Sakamoto, T. New μ-opioid receptor agonists with piperazine moiety. Chem. Pharm. Bull. (Tokyo), 2001, 49(10), 1314-1320.
[http://dx.doi.org/10.1248/cpb.49.1314] [PMID: 11605661]
[34]
Lopchuk, J.M.; Fjelbye, K.; Kawamata, Y.; Malins, L.R.; Pan, C.M.; Gianatassio, R.; Wang, J.; Prieto, L.; Bradow, J.; Brandt, T.A.; Collins, M.R.; Elleraas, J.; Ewanicki, J.; Farrell, W.; Fadeyi, O.O.; Gallego, G.M.; Mousseau, J.J.; Oliver, R.; Sach, N.W.; Smith, J.K.; Spangler, J.E.; Zhu, H.; Zhu, J.; Baran, P.S. Strain-release heteroatom functionalization: Development, scope, and stereospecificity. J. Am. Chem. Soc., 2017, 139(8), 3209-3226.
[http://dx.doi.org/10.1021/jacs.6b13229] [PMID: 28140573]
[35]
Massari, S.; Daelemans, D.; Manfroni, G.; Sabatini, S.; Tabarrini, O.; Pannecouque, C.; Cecchetti, V. Studies on anti-HIV quinolones: New insights on the C-6 position. Bioorg. Med. Chem., 2009, 17(2), 667-674.
[http://dx.doi.org/10.1016/j.bmc.2008.11.056] [PMID: 19091580]
[36]
Massari, S.; Mercorelli, B.; Sancineto, L.; Sabatini, S.; Cecchetti, V.; Gribaudo, G.; Palù, G.; Pannecouque, C.; Loregian, A.; Tabarrini, O. Design, synthesis, and evaluation of WC5 analogues as inhibitors of human cytomegalovirus immediate‐early 2 protein, a promising target for anti‐HCMV treatment. Chem. Med. Chem., 2013, 8(8), 1403-1414.
[http://dx.doi.org/10.1002/cmdc.201300106]
[37]
Carrez, C.; Fassy, F.; Maillet, P.; Thompson, F. Preparation of purine derivatives for use in pharmaceutical compositions for the treatment of cancer. FR Patent, 2880626 A1, 2006.
[38]
Chu-Moyer, M.Y.; Ballinger, W.E.; Beebe, D.A.; Berger, R.; Coutcher, J.B.; Day, W.W.; Li, J.; Mylari, B.L.; Oates, P.J.; Weekly, R.M. Orally-effective, long-acting sorbitol dehydrogenase inhibitors: Synthesis, structure-activity relationships, and in vivo evaluations of novel heterocycle-substituted piperazino-pyrimidines. J. Med. Chem., 2002, 45(2), 511-528.
[http://dx.doi.org/10.1021/jm010440g] [PMID: 11784155]
[39]
Balan, C. Preparation of benzimidazoles as vanilloid receptor ligands. WO Patent, 2004035549 A1, 2004.
[40]
Donalisio, M.; Massari, S.; Argenziano, M.; Manfroni, G.; Cagno, V.; Civra, A.; Sabatini, S.; Cecchetti, V.; Loregian, A.; Cavalli, R.; Lembo, D.; Tabarrini, O. Ethyl 1,8-naphthyridone-3-carboxylates downregulate human papillomavirus-16 E6 and E7 oncogene expression. J. Med. Chem., 2014, 57(13), 5649-5663.
[http://dx.doi.org/10.1021/jm500340h] [PMID: 24905115]
[41]
Dai, M.; He, F.; Jain, R.K.; Karki, R.; Kelleher, J.; Lei, J.; Llamas, L.; Mcewan, M.A.; Miller-Moslin, K.; Perez, L.B. Nitrogen-containing heterocyclic organic compounds as inhibitors of the hedgehog pathway and their preparation and use in the treatment of diseases. WO Patent, 2008110611 A1, 2008.
[42]
Ali, A.; Hunt, J.A.; Kallashi, F.; Kowalchick, J.E.; Kim, D.; Smith, C.J.; Sinclair, P.J.; Sweis, R.F.; Taylor, G.E.; Thompson, C.F. Benzoxa-zole derivatives and related compounds as CETP inhibitors and their preparation, pharmaceutical composition and use for raising HDL and reducing LDL cholesterol and treatment of atherosclerosis. WO Patent, 2007070173 A2, 2007.
[43]
Sidorin, D.N.; Kozyukov, A.V.; Zakharova, V.A.; Porodenko, N.V.; Kryukov, L.N. Piperazinylquinoline amidophosphates: synthesis and study of their action on blocked reverse serotonin uptake. Khim.-Farmat. Zhur., 1992, 26(9-10), 82-83.
[44]
Kubica, K.; Taciak, P.; Czajkowska, A.; Sztokfisz-Ignasiak, A.; Wyrebiak, R.; Podsadni, P.; Mlynarczuk-Bialy, I.; Malejczyk, J.; Mazurek, A. Synthesis and anticancer activity evaluation of some new derivatives of 2-(4-benzoyl-1-piperazinyl)-quinoline and 2-(4-cinnamoyl-1-piperazinyl)-quinoline. Acta Pol. Pharm., 2018, 75(4), 891-901.
[http://dx.doi.org/10.32383/appdr/80098]
[45]
Swanson, D.M.; Dubin, A.E.; Shah, C.; Nasser, N.; Chang, L.; Dax, S.L.; Jetter, M.; Breitenbucher, J.G.; Liu, C.; Mazur, C.; Lord, B.; Gonzales, L.; Hoey, K.; Rizzolio, M.; Bogenstaetter, M.; Codd, E.E.; Lee, D.H.; Zhang, S.P.; Chaplan, S.R.; Carruthers, N.I. Identification and biological evaluation of 4-(3-trifluoromethylpyridin-2-yl)piperazine-1-carboxylic acid (5-trifluoromethylpyridin-2-yl)amide, a high affinity TRPV1 (VR1) vanilloid receptor antagonist. J. Med. Chem., 2005, 48(6), 1857-1872.
[http://dx.doi.org/10.1021/jm0495071] [PMID: 15771431]
[46]
Hurth, K.; Enz, A.; Floersheim, P.; Gentsch, C.; Hoyer, D.; Langenegger, D.; Neumann, P.; Pfäffli, P.; Sorg, D.; Swoboda, R.; Vassout, A.; Troxler, T. SAR of the arylpiperazine moiety of obeline somatostatin sst1 receptor antagonists. Bioorg. Med. Chem. Lett., 2007, 17(14), 3988-3991.
[http://dx.doi.org/10.1016/j.bmcl.2007.04.078] [PMID: 17512199]
[47]
Golubev, V.E.; Trubitsyna, T.K.; Mashkovskii, M.D.; Suvorov, N.N. Synthesis and pharmacological properties of some 1-(2-quinolyl)-4-(indoly-3-alkyl)piperazines. Khim.-Farmat. Zhur., 1981, 15(2), 30-33.
[48]
Ishibuchi, S.; Saruta, K.; Hamada, M.; Matoba, N.; Matsudaira, T.; Seki, M.; Tarao, A.; Honjo, T.; Ogata, S.; Kawata, A. Preparation of imidazolidine-2,4-dione and pyrrolidine-2,5-dione derivatives for suppressing the inductive production of matrix metalloproteinase-9 (MMP-9). WO Patent, 2017007008 A1, 2016.
[49]
Brebion, F.L.; Alvey, L. J.; Amantini, D.; Deprez, P.M.M.J.; Gosmini, R.L.M.; Jary, H.M.; Peixoto, C.; Varin, M.L.C.; De Ceuninck, F.A.; Pop-Botez, I.E. 5-[(Piperazin-1-yl)-3-oxopropyl] imidazolidine-2,4-dione derivatives as ADAMTS inhibitor for the treatment of osteoarthritis and their preparation. WO Patent, 2016102347 A1, 2016.
[50]
Meng, C.Q.; Long, A.; Huber, S.; Gurrala, S.R.; Wilkinson, D.E.; Pacofsky, G. Preparation of O-substituted phenylaminocyclohexanols as anthelmintic compounds. US Patent, 20140142114 A1, 2014.
[51]
Dominguez, C.; Wityak, J.; Prime, M.; Courtney, S.; Yarnold, C.; Brookfield, F.; Marston, R.; MacDonald, D. Heterocyclic derivatives as transglutaminase TG2 inhibitors and their preparation and use for the treatment of diseases. WO Patent, 2011060321 A1, 2011.
[52]
Yao, W.; Zhou, J.; Xu, M.; Zhang, F.; Metcalf, B. Preparation of azaspiroalkane hydroxamides and spirocycloalkane hydroxamides as metalloprotease inhibitors. WO Patent, 2004096139 A2, 2004.
[53]
Chen, Y.; Murray, P.R.D.; Davies, A.T.; Willis, M.C. Direct copper-catalyzed three-component synthesis of sulfonamides. J. Am. Chem. Soc., 2018, 140(28), 8781-8787.
[http://dx.doi.org/10.1021/jacs.8b04532] [PMID: 29965736]
[54]
Bower, J.F.; Kenny, P.W.; Poyser, J.P. Piperazine derivatives, processes for preparing them, pharmaceutical compositions containing them, and their use as antagonists of CC chemokines (CCR2b and CCR5) for the treatment of inflammatory diseases. WO Patent, 2007071952 A1, 2007.
[55]
Di Tu, M.; Shepherd, R.G. Antiatherosclerotic 1-piperazine derivatives. EP94498 A2, 1983.
[56]
Yoshida, T.; Akahoshi, F.; Sakashita, H.; Sonda, S.; Takeuchi, M.; Tanaka, Y.; Nabeno, M.; Kishida, H.; Miyaguchi, I.; Hayashi, Y. Fused bicyclic heteroarylpiperazine-substituted l-prolylthiazolidines as highly potent DPP-4 inhibitors lacking the electrophilic nitrile group. Bioorg. Med. Chem., 2012, 20(16), 5033-5041.
[http://dx.doi.org/10.1016/j.bmc.2012.06.033] [PMID: 22824762]
[57]
Kuduk, S.D.; Chang, R.K. Preparation of heterocyclylmethyl oxoquinolizinecarboxylates as muscarinic M receptor positive allosteric modulators. WO Patent, 2009094279 A1, 2009.
[58]
Liu, Y.; Zhou, E.; Yu, K.; Zhu, J.; Zhang, Y.; Xie, X.; Li, J.; Jiang, H. Discovery of a novel CCR5 antagonist lead compound through fragment assembly. Molecules, 2008, 13(10), 2426-2441.
[http://dx.doi.org/10.3390/molecules13102426] [PMID: 18830165]

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