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Expert Opinion on Therapeutic Patents Volume 11, 2001 - Issue 2
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Review

Quinoline antimalarials

Timothy J Egan Department of Chemistry, University of Cape Town, Private Bag, Rondebosch 7701, South Africa. [email protected]
Pages 185-209 | Published online: 25 Feb 2005

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Mohammad M. Al-Sanea, Ahmed Elkamhawy, Sora Paik, Silvia Bua, So Ha Lee, Mohamed A. Abdelgawad, Eun Joo Roh, Wagdy M. Eldehna & Claudiu T. Supuran. (2019) Synthesis and biological evaluation of novel 3-(quinolin-4-ylamino)benzenesulfonamides as carbonic anhydrase isoforms I and II inhibitors. Journal of Enzyme Inhibition and Medicinal Chemistry 34:1, pages 1457-1464.
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Christoph Boss, Olivier Corminboeuf, Corinna Grisostomi & Thomas Weller. (2006) Inhibitors of aspartic proteases – potential antimalarial agents. Expert Opinion on Therapeutic Patents 16:3, pages 295-317.
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Sabine Willems & Daniel Merk. (2022) Medicinal Chemistry and Chemical Biology of Nurr1 Modulators: An Emerging Strategy in Neurodegeneration. Journal of Medicinal Chemistry 65:14, pages 9548-9563.
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Bianca Seitz, Thomas Schneider, Nikola Majstorovic, Maximilian Fleischmann & Gerhard Maas. (2021) Reactions of 1-Trifluoromethylprop-2-yne 1-Iminium Salts with Nitroanilines: Synthesis of 4-Trifluoromethylnitroquinolines and 1,2,3-Trisubstituted 5-Trifluoromethylpyrroles. Synthesis 54:08, pages 2057-2069.
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Mohammad Abid, Shailja Singh, Timothy J. Egan & Mukesh C. Joshi. (2022) Structural-activity Relationship of Metallo-aminoquines as Next Generation Antimalarials. Current Topics in Medicinal Chemistry 22:6, pages 436-472.
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Nguyen Huu Dinh, Trinh Thi Huan & Le Thi Hoa. (2022) Synthesis and NMR Spectroscopic Characteristics of Novel Polysubstituted Quinolines Incorporating Furoxan Moiety. HETEROCYCLES 104:2, pages 365.
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Inder Kumar, Ankita Thakur, Manisha & Upendra Sharma. (2021) α-Oxygenation of N -aryl/alkyl heterocyclic compounds via ruthenium photocatalysis . Reaction Chemistry & Engineering 6:11, pages 2087-2091.
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Mohd. Suhail. (2021) The Target Determination and the Mechanism of Action of Chiral-Antimalarial Drugs: A Docking Approach. Journal of Computational Biophysics and Chemistry 20:05, pages 501-516.
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Fostino R.B. Bokosi, Richard M. Beteck, Mziyanda Mbaba, Thanduxolo E. Mtshare, Dustin Laming, Heinrich C. Hoppe & Setshaba D. Khanye. (2021) Design, synthesis and biological evaluation of mono- and bisquinoline methanamine derivatives as potential antiplasmodial agents. Bioorganic & Medicinal Chemistry Letters 38, pages 127855.
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Pedro N. Batalha, Luana S.M. Forezi, Carolina G.S. Lima, Fernanda P. Pauli, Fernanda C.S. Boechat, Maria Cecília B.V. de Souza, Anna C. Cunha, Vitor F. Ferreira & Fernando de C. da Silva. (2021) Drug repurposing for the treatment of COVID-19: Pharmacological aspects and synthetic approaches. Bioorganic Chemistry 106, pages 104488.
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Mziyanda Mbaba, Taryn M. Golding & Gregory S. Smith. (2020) Recent Advances in the Biological Investigation of Organometallic Platinum-Group Metal (Ir, Ru, Rh, Os, Pd, Pt) Complexes as Antimalarial Agents. Molecules 25:22, pages 5276.
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Benedito Santos, Daniel Gonzaga, Fernando da Silva, Vitor Ferreira & Celia Garcia. (2020) Plasmodium falciparum Knockout for the GPCR-Like PfSR25 Receptor Displays Greater Susceptibility to 1,2,3-Triazole Compounds That Block Malaria Parasite Development. Biomolecules 10:8, pages 1197.
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Sarah Louise Rawe & Claire McDonnell. 2020. Antimalarial Agents. Antimalarial Agents 65 98 .
Chandraprakash Kumarasamy, Amsaveni Sundarasamy, Sankaran Mathan, Uvarani Chokkalingam, Ata Athar, Mohan Palathurai Subramaniam & Suresh Thangaraj. (2019) An Yb(OTf) 3 ‐catalyzed, convergent synthesis of new pyranyl‐ and chromenyl‐substituted quinolines through an eco‐friendly approach . Journal of Heterocyclic Chemistry 56:11, pages 2986-2992.
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Tameryn Stringer, Lubbe Wiesner & Gregory S. Smith. (2019) Ferroquine-derived polyamines that target resistant Plasmodium falciparum. European Journal of Medicinal Chemistry 179, pages 78-83.
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Tameryn Stringer, Maria Alejandra Silva Quintero, Lubbe Wiesner, Gregory S. Smith & Ebbe Nordlander. (2019) Evaluation of PTA-derived ruthenium(II) and iridium(III) quinoline complexes against chloroquine-sensitive and resistant strains of the Plasmodium falciparum malaria parasite. Journal of Inorganic Biochemistry 191, pages 164-173.
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Nadia Baartzes, Tameryn Stringer & Gregory S. Smith. 2019. Advances in Bioorganometallic Chemistry. Advances in Bioorganometallic Chemistry 193 213 .
Hardeep Kaur, Marta Machado, Carmen de Kock, Peter Smith, Kelly Chibale, Miguel Prudêncio & Kamaljit Singh. (2015) Primaquine–pyrimidine hybrids: Synthesis and dual-stage antiplasmodial activity. European Journal of Medicinal Chemistry 101, pages 266-273.
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Gordana Tasic, Veselin Maslak, Suren Husinec, Nina Todorovic & Vladimir Savic. (2015) Study of the intramolecular Heck reaction: synthesis of the bicyclic core of corialstonidine. Tetrahedron Letters 56:19, pages 2529-2532.
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Nicolas Chopin, Maurice Médebielle & Guillaume Pilet. (2013) 8-Aminoquinoline and 2-aminopyridine trifluoromethyl-derived enaminone ligands and their Co(II), Ni(II) and Zn(II) metal complexes: Structural arrangements due to F⋯H interactions. Journal of Fluorine Chemistry 155, pages 89-96.
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Warren A. Andayi, Timothy J. Egan, Jiri Gut, Philip J. Rosenthal & Kelly Chibale. (2013) Synthesis, Antiplasmodial Activity, and β-Hematin Inhibition of Hydroxypyridone–Chloroquine Hybrids. ACS Medicinal Chemistry Letters 4:7, pages 642-646.
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Samkele Nsumiwa, David Kuter, Sergio Wittlin, Kelly Chibale & Timothy J. Egan. (2013) Structure–activity relationships for ferriprotoporphyrin IX association and β-hematin inhibition by 4-aminoquinolines using experimental and ab initio methods. Bioorganic & Medicinal Chemistry 21:13, pages 3738-3748.
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Paloma F. Salas, Christoph Herrmann & Chris Orvig. (2013) Metalloantimalarials. Chemical Reviews 113:5, pages 3450-3492.
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Paloma F. Salas, Christoph Herrmann, Jacqueline F. Cawthray, Corinna Nimphius, Alexander Kenkel, Jessie Chen, Carmen de Kock, Peter J. Smith, Brian O. Patrick, Michael J. Adam & Chris Orvig. (2013) Structural Characteristics of Chloroquine-Bridged Ferrocenophane Analogues of Ferroquine May Obviate Malaria Drug-Resistance Mechanisms. Journal of Medicinal Chemistry 56:4, pages 1596-1613.
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Bryan T. Mott, Ken Chih-Chien Cheng, Rajarshi Guha, Valerie P. Kommer, David L. Williams, Jon J. Vermeire, Michael Cappello, David J. Maloney, Ganesha Rai, Ajit Jadhav, Anton Simeonov, James Inglese, Gary H. Posner & Craig J. Thomas. (2012) A furoxan–amodiaquine hybrid as a potential therapeutic for three parasitic diseases. MedChemComm 3:12, pages 1505.
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Lotta Glans, Dale Taylor, Carmen de Kock, Peter J. Smith, Matti Haukka, John R. Moss & Ebbe Nordlander. (2011) Synthesis, characterization and antimalarial activity of new chromium arene–quinoline half sandwich complexes. Journal of Inorganic Biochemistry 105:7, pages 985-990.
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Vincent K. Zishiri, Roger Hunter, Peter J. Smith, Dale Taylor, Robert Summers, Kiaran Kirk, Rowena E. Martin & Timothy J. Egan. (2011) A series of structurally simple chloroquine chemosensitizing dibemethin derivatives that inhibit chloroquine transport by PfCRT. European Journal of Medicinal Chemistry 46:5, pages 1729-1742.
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Paul M. O’Neill, Victoria E. Barton, Stephen A. Ward & James Chadwick. 2012. Treatment and Prevention of Malaria. Treatment and Prevention of Malaria 19 44 .
Agata Semeniuk, Justyna Kalinowska-Tluscik, Wojciech Nitek & Barbara J. Oleksyn. (2008) Intermolecular Interactions in Crystalline Hydroxychloroquine Sulfate in Comparison with Those in Selected Antimalarial Drugs. Journal of Chemical Crystallography 38:5, pages 333-338.
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Agata Semeniuk, Agnieszka Niedospial, Justyna Kalinowska-Tluscik, Wojciech Nitek & Barbara J. Oleksyn. (2008) Molecular geometry of antimalarial amodiaquine in different crystalline environments. Journal of Molecular Structure 875:1-3, pages 32-41.
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Margaret A.L. Blackie, Paul Beagley, Simon L. Croft, Howard Kendrick, John R. Moss & Kelly Chibale. (2007) Metallocene-based antimalarials: An exploration into the influence of the ferrocenyl moiety on in vitro antimalarial activity in chloroquine-sensitive and chloroquine-resistant strains of Plasmodium falciparum. Bioorganic & Medicinal Chemistry 15:20, pages 6510-6516.
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Thomas Hänscheid, Timothy J Egan & Martin P Grobusch. (2007) Haemozoin: from melatonin pigment to drug target, diagnostic tool, and immune modulator. The Lancet Infectious Diseases 7:10, pages 675-685.
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César Portela, Carlos M. M. Afonso, Madalena M. M. Pinto, Dinora Lopes, Fátima Nogueira & Virgílio do Rosário. (2007) Synthesis and Antimalarial Properties of New Chloro‐9 H ‐xanthones with an Aminoalkyl Side Chain . Chemistry & Biodiversity 4:7, pages 1508-1519.
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Iwona Tesarowicz, Barbara J. Oleksyn & Wojciech Nitek. (2006) Crystal and molecular structures of trichloro‐cobalt(II) complexes of epiquinine, epiquinidine, and epidihydrocinchonine. Chirality 19:2, pages 152-161.
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Giovanni W. Amarante, Mario Benassi, Adão A. Sabino, Pierre M. Esteves, Fernando Coelho & Marcos N. Eberlin. (2006) Formation of substituted N-oxide hydroxyquinolines from o-nitrophenyl Baylis–Hillman adduct: a new key intermediate intercepted by ESI-(+)-MS(/MS) monitoring. Tetrahedron Letters 47:47, pages 8427-8431.
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Jiří Zima, Anca-Iulia Stoica, Alice Zítová & Jiří Barek. (2006) Voltammetric Determination of Selected Aminoquinolines Using Carbon Paste Electrode. Electroanalysis 18:2, pages 158-162.
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Timothy J. Egan & Kanyile K. Ncokazi. (2005) Quinoline antimalarials decrease the rate of β-hematin formation. Journal of Inorganic Biochemistry 99:7, pages 1532-1539.
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Adina Ryckebusch, Marie-Ange Debreu-Fontaine, Elisabeth Mouray, Philippe Grellier, Christian Sergheraert & Patricia Melnyk. (2005) Synthesis and antimalarial evaluation of new N1-(7-chloro-4-quinolyl)-1,4-bis(3-aminopropyl)piperazine derivatives. Bioorganic & Medicinal Chemistry Letters 15:2, pages 297-302.
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Derek B. Lowe, Steven Magnuson, Ning Qi, Ann-Marie Campbell, James Cook, Zhenqiu Hong, Ming Wang, Mareli Rodriguez, Furahi Achebe, Harold Kluender, Wai C. Wong, William H. Bullock, Arthur I. Salhanick, Terri Witman-Jones, Mary E. Bowling, Christine Keiper & Kevin B. Clairmont. (2004) In vitro SAR of (5-(2H)-isoxazolonyl) ureas, potent inhibitors of hormone-sensitive lipase. Bioorganic & Medicinal Chemistry Letters 14:12, pages 3155-3159.
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César Portela, Carlos M.M. Afonso, Madalena M.M. Pinto & Maria João Ramos. (2004) Definition of an electronic profile of compounds with inhibitory activity against hematin aggregation in malaria parasite. Bioorganic & Medicinal Chemistry 12:12, pages 3313-3321.
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Timothy J. Egan & Kanyile K. Ncokazi. (2004) Effects of solvent composition and ionic strength on the interaction of quinoline antimalarials with ferriprotoporphyrin IX. Journal of Inorganic Biochemistry 98:1, pages 144-152.
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Mei‐Lin Go. (2003) Novel antiplasmodial agents. Medicinal Research Reviews 23:4, pages 456-487.
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Paul Beagley, Margaret A. L. Blackie, Kelly Chibale, Cailean Clarkson, Reinout Meijboom, John R. Moss, Peter J. Smith & Hong Su. (2003) Synthesis and antiplasmodial activity in vitro of new ferrocene–chloroquine analogues. Dalton Trans.:15, pages 3046-3051.
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Helder M Marques & Kenneth L Brown. (2002) Molecular mechanics and molecular dynamics simulations of porphyrins, metalloporphyrins, heme proteins and cobalt corrinoids. Coordination Chemistry Reviews 225:1-2, pages 123-158.
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Paul Beagley, Margaret A. L. Blackie, Kelly Chibale, Cailean Clarkson, John R. Moss & Peter J. Smith. (2002) Synthesis and antimalarial activity in vitro of new ruthenocene–chloroquine analogues. J. Chem. Soc., Dalton Trans.:23, pages 4426-4433.
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