Progressive Insights into the Pharmacological Importance of Isoquinoline Derivatives in Modern Therapeutics
-
Harris J, Pope WJ. Isoquinoline and the isoquinoline-reds. J Chem Soc 1922;121:1029-1033.
-
Pozharskii AF, Soldatenkov AT, Katritzky AR. Heterocycles in life and society: an introduction to heterocyclic chemistry, biochemistry and applications. John Wiley & Sons; 2011.
-
Katritzky AR, Pozharskii AF, Soldatenkov A. Heterocycles in Life and Society: An Introduction to Heterocyclic Chemistry, Biochemistry and Applications. John Wiley & Sons; 2011.
-
Khan F, Qidwai T, Shukla RK, Gupta V. Alkaloids Derived from Tyrosine: Modified Benzyltetrahydroisoquinoline Alkaloids. Nat Prod 2013;8(3):405-460.
-
Gilchrist TL. Heterocyclic chemistry. Addison Wesley Longman, UK; 1997.
-
O'Neil, Maryadele J. The Merck Index. Whitehouse Station; 2001.
-
Quinoline. Encyclopedia Britannica. 1911;11(22): 758-759.
-
Ram VJ, Sethi A, Nath M, Pratap R. The Chemistry of Heterocycles: Nomenclature and Chemistry of Three to Five Membered Heterocycles. Elsevier; 2019.
-
Braude EA, Nachod FC. Determination of organic structures by physical methods. Elsevier; 2013.
-
Jie JL. Name Reactions: A Collection of Detailed Mechanisms and Synthetic Applications. Springer Science Ltd.; 2014.
-
Wang Y, Patil P, Kurpiewska K, Kalinowska-Tluscik J, Do?mling A. Diverse Isoquinoline Scaffolds by Ugi/Pomeranz–Fritsch and Ugi/Schlittler–Mu?ller Reactions. Org Lett 2019;21(10):3533-3537.
-
Marella A, Tanwar OP, Saha R, Ali MR, Srivastava S, Akhter M, Shaquiquzzaman M, Alam MM. Quinoline: A versatile heterocyclic. Saudi Pharm J 2013;21(1):1-2.
-
Pandeya SN, Tyagi A. Synthetic approaches for quinoline and isoquinoline. ChemInform 2012;43(3):5361-5365.
-
Lass?Flörl C. The changing face of epidemiology of invasive fungal disease in Europe. Mycoses 2009;52(3):197-205.
-
Palomino JC, Martin A. Drug Resistance Mechanisms in Mycobacterium tuberculosis. Antibiotics 2014,3(3):317-340.
-
Kakhkia S, Shahosseinia S, Zarghi A. Pyrrolo[2,1-a] Isoquinoline-Based Derivatives as New Cytotoxic Agents, Iranian J Pharm Res 2016;15(4):743-751.
-
Heravi M, Nazari N. Bischler-Napieralski reaction in total synthesis of isoquinoline-based natural products. An old reaction, a new application. Curr Org Chem 2015;19(24):2358-2408.
-
Pashev AS, Burdzhiev NT, Stanoeva ER. Synthetic Approaches toward the Benzo [a] quinolizidine System. A Review. Org Prep Proced Int 2016;48(6):425-467.
-
Awuah E, Capretta A. Strategies and synthetic methods directed toward the preparation of libraries of substituted isoquinolines. J Org Chem 2010;75(16):5627-5634.
-
Zheng B, Trieu TH, Li FL, Zhu XL, He YG, Fan QQ, Shi XX. Copper-Catalyzed Benign and Efficient Oxidation of Tetrahydroisoquinolines and Dihydroisoquinolines Using Air as a Clean Oxidant. ACS Omega 2018;3(7):8243-8252.
-
Pfaller MA, Diekema DJ. Epidemiology of invasive candidiasis: a persistent public health problem. Clin Microbiol Rev 2007;20(1):133-163.
-
Negri M, Martins M, Henriques M, Svidzinski TI, Azeredo J, Oliveira R. Examination of potential virulence factors of Candida tropicalis clinical isolates from hospitalized patients. Mycopathologia 2010;169(3):175-182.
-
Baron S. Alphaviruses (Togaviridae) and Flaviviruses (Flaviviridae)--Medical Microbiology. University of Texas Medical Branch at Galveston; 1996.
-
Borg-von ZM, Kunz L, Ruchel R, Reichard U, Weig M, Gross U. Epidemiology and antifungal susceptibilities of Candida spp. to six antifungal agents. Antimicrob Chemother 2007;60:424–428.
-
Siwek A, Stefa?ska J, Dzitko K, Ruszczak A. Antifungal effect of 4-arylthiosemicarbazides against Candida species. Search for molecular basis of antifungal activity of thiosemicarbazide derivatives. J Mol Model 2012;18(9):4159-4170.
-
Surikova OV, Zachinyaeva AV, Mikhailovskii AG, Zachinyaev YV. Synthesis of 2, 2-dimethyl-1, 2-dihydrobenzo [f]-isoquinolines displaying antifungal activity. Chem Heterocycl Compd 2011;46(12):1471-1475.
-
Cantrell CL, Dayan FE, Duke SO. Natural products as sources for new pesticides. J Nat Prod 2012;75(6):1231-1242.
-
Walton JN. Brain's Diseases of the Nervous System. Oxford: Oxford University Press; 1977.
-
Abe K, Saitoh T, Horiguchi Y, Utsunomiya I, Taguchi K. Synthesis and Neurotoxicity of Tetrahydroisoquinoline Derivatives for Studying Parkinson’s Disease. Biol Pharm Bull 2005;28(8):1355-1362.
-
Ishiwata K, Koyanagi Y, Abe K, Kawamura K, Taguchi K, Saitoh T, Toda J, Senda M, Sano T. Evaluation of neurotoxicity of TIQ and MPTP and of parkinsonism?preventing effect of 1?MeTIQ by in vivo measurement of pre?synaptic dopamine transporters and post?synaptic dopamine D2 receptors in the mouse striatum. J Neurochem 2001;79(4):868-876.
-
Nagatsu T. Isoquinoline neurotoxins in the brain and Parkinson's disease. Neurosci Res 1997;29(2):99-111.
-
Bembenek ME, Abell CW, Chrisey LA, Rozwadowska MD, Gessner W, Brossi A. Inhibition of monoamine oxidases A and B by simple isoquinoline alkaloids: racemic and optically active 1, 2, 3, 4-tetrahydro-, 3, 4-dihydro-, and fully aromatic isoquinolines. J Med Chem 1990;33(1):147-152.
-
Antkiewicz-Michaluk L, W?sik A, Michaluk J. 1-Methyl-1,2,3,4-tetrahydroisoquinoline, an endogenous amine with the unexpected mechanism of action: new vistas of therapeutic application. Neurotox Res 2013;25(1):1-12.
-
Storch A, Ott S, Hwang YI, Ortmann R, Hein A, Frenzel S, et al. Selective dopaminergic neurotoxicity of isoquinoline derivatives related to Parkinson’s disease: studies using heterologous expression systems of the dopamine transporter. Biochem Pharmacol 2002;63(5):909-920.
-
Smith I. Mycobacterium tuberculosis pathogenesis and molecular determinants of virulence. Clin Microbiol Rev 2003;16(3):463-496.
-
Andersen P. TB vaccines: progress and problems. Trends Immunol 2001;22:160-168.
-
Barnes DS. Historical perspectives on the aetiology of tuberculosis. Microb Infect 2000;2(4):431-440.
-
Brosch R, Gordon SV, Marmiesse M, Brodin P, Buchrieser C, Eiglmeier K, Garnier T, Gutierrez C, Hewinson G, Kremer K, Parsons LM. A new evolutionary scenario for the Mycobacterium tuberculosis complex. Proc Natl Acad Sci 2002;99:3684-3689.
-
Dookie N, Rambaran S, Padayatchi N, Mahomed S, Naidoo K. Evolution of drug resistance in Mycobacterium tuberculosis: a review on the molecular determinants of resistance and implications for personalized care. J Antimicrob Chemother 2018;73(5):1138-1151.
-
Smets RJ, Torfs E, Lemière F, Cos P, Cappoen D, Tehrani KA. Synthesis and antitubercular activity of 1-and 3-substituted benzo [g] isoquinoline-5, 10-diones. Org Biomol Chem 2019;17(11):2923-2939.
-
Jain S, Chandra V, Jain PK, Pathak K, Pathak D, Vaidya A. Comprehensive review on current developments of quinoline-based anticancer agent. Arabian J Chem 2019;12(8):4920-4946.
-
Liu MC, Lin TS, Penketh P, Sartorelli AC. Synthesis and antitumor activity of 4-and 5-substituted derivatives of isoquinoline-1-carboxaldehyde thiosemicarbazone. J Med Chem 1995;38(21):4234-4243.
-
Liu MC, Lin TS, Sartorelli AC Chemical and biological properties of cytotoxic alpha-(N)-heterocyclic carboxaldehyde thiosemicarbazones. Prog Med Chem 1995;32:1-35.
-
Wang X, Zhang H, Chen X. Drug resistance and combating drug resistance in cancer. Cancer Drug Resist 2019;2:141-160.
-
Janecka A, Wyr?bska A, Gach K, Fichna J, Janecki T. Natural and synthetic α-methylenelactones and α-methylenelactams with anticancer potential. Drug Discov Today 2012;17(11-12):561-572.
-
Yang X, Yang S, Chai H, Yang Z, Lee RJ, Liao W, et al. A novel isoquinoline derivative anticancer agent and its targeted delivery to tumour cells using transferrin-conjugated liposomes. PLoS One 2015;10(8):e0136649.
-
Yan Y, En D, Zhuang Z, Guo Y, Liao WW. Synthesis of densely functionalized α-methylene γ-butyrolactones via an organocatalytic one-pot allylic-alkylation–cyclization reaction. Tetrahedron Lett 2014;55(2):479-482.
-
Bollini M, Casal JJ, Alvarez DE, Boiani L, González M, Cerecetto H, et al. New potent imidazoisoquinolinone derivatives as anti-Trypanosoma cruzi agents: biological evaluation and structure–activity relationships. Bioorg Med Chem 2009;17(4):1437-1444.
-
Liao WL, Li SQ, Wang J, Zhang ZY, Yang ZW, Xu D, et al. An efficient and facile method for the synthesis of benzimidazoisoquinoline derivatives via a multicomponent reaction. ACS Comb Sci 2016;18(1):65-69.
-
Bailly C. Anticancer Properties of Lamellarins. Mar Drugs 2015;13(3):1105–1123.
-
Kakhki S, Shahosseini S, Zarghi A. Design and synthesis of pyrrolo [2, 1-a] isoquinoline-based derivatives as new cytotoxic agents. Iranian J Pharm Res 2016;15(4):743.
-
Facompré M, Tardy C, Bal-Mahieu C, Colson P, Perez C, Manzanares I, et al. A novel potent inhibitor of topoisomerase I. Cancer Res 2003;63(21):7392-7399.
-
Jiang M, Huang O, Zhang X, Xie Z, Shen A, Liu H, et al. Curcumin induces cell death and restores tamoxifen sensitivity in the antiestrogen-resistant breast cancer cell lines MCF-7/LCC2 and MCF-7/LCC9. Molecules 2007;18:701-720.
-
Yue W, Wang JP, Li Y, Fan P, Liu G, Zhang N, Conaway M, Wang H, Korach KS, Bocchinfuso W, Santen R. Effects of estrogen on breast cancer development: Role of estrogen receptor-independent mechanisms. Int J Cancer 2010;127(8):1748-1757.
-
Kakhki S, Shahosseini S, Zarghi A. Design, synthesis and cytotoxicity evaluation of new 2-aryl-5, 6-dihydropyrrolo[2, 1-a]isoquinoline derivatives as topoisomerase inhibitors. Iran J Pharm Res 2014,13:71-77.
-
Kingman S. Glaucoma is the second leading cause of blindness globally. Bull World Health Org. 2004;82:887-888.
-
Feng Y, Lograsso PV, Defert O. Rho kinase (ROCK) inhibitors and their therapeutic potential. J Med Chem 2016;59(2):269–300.
-
Oliveira RG, Guerra FS, Mermelstein CD, Fernandes PD, Bastos IT, Costa FN, et al. Synthesis and pharmacological evaluation of novel isoquinoline N-sulphonylhydrazones designed as ROCK inhibitors. J Enzyme Inhib Med Chem 2018;33(1):1181-1193.
-
Tanna AP, Johnson M. Rho-kinase inhibitors as a novel treatment for glaucoma and ocular hypertension. Ophthalmology 2018;125(11):1741-1756.
-
Wang SK, Chang RT. An emerging treatment option for glaucoma: Rho kinase inhibitors. Clin Ophthalmol 2014;8:883-890.
-
Mérour JY, Buron F, Plé K, Bonnet P, Routier S. The azaindole framework in the design of kinase inhibitors. Molecules. 2014;19(12):19935-19979.
-
Angeli A, Chiaramonte N, Manetti D, Romanelli MN, Supuran CT. Investigation of piperazines as human carbonic anhydrase I, II, IV and VII activators. J Enzyme Inhib Med Chem 2018;33(1):303-308.
-
Lane CA, Hardy J, Schott JM. Alzheimer's disease. Eur J Neurol 2018;25:59–70.
-
Rajmohan R, Reddy PH. Amyloid-beta and phosphorylated tau accumulations cause abnormalities at synapses of Alzheimer’s disease neurons. J Alzheimer's Dis 2017;57(4):975-999.
-
Nordberg A, Ballard C, Bullock R, Darreh-Shori T, Somogyi M. A review of butyrylcholinesterase as a therapeutic target in the treatment of Alzheimer’s disease. Prim Care Companion CNS Disord 2013;15(2):PCC.12r01412.
-
Anand R, Gill KD, Mahdi AA. Therapeutics of Alzheimer’s disease: Past, present and future. Neuropharmacology 2014;76:27–50.
-
Ehret MJ, Chamberlin KW. Current practices in the treatment of Alzheimer disease: Where is the evidence after the phase III Trials. Clin Ther 2015;37:1604-1616.
-
Lleo A. Current therapeutic option for Alzheimer’s disease. Curr Genom 2007;8:550-558.
-
Kumar S. Dual inhibition of acetylcholinesterase and butyrylcholinesterase enzymes by allicin. Indian J Pharmacol 2015;47(4):444-446.
-
Lane RM, Potkin SG, Enz A. Targeting acetylcholinesterase and butyrylcholinesterase in dementia. Int J Neuropsychopharmacol 2006;9:101-124.
-
Giacobini E. Cholinesterase inhibitors: new roles and therapeutic alternatives. Pharmacol Res 2004;50:433-440.
-
Bedard J, May S, Heurex L, Stamminger T, Chan L. Antiviral properties of a series of 1,6-naphthyridine and 7,8-dihydro isoquinoline derivatives exhibiting potent activity against human cytomegalovirus. Antimicrob Agent Chemother 2000;44:929-937.
-
Chan L, Jin H, Stefanac T, Lavallée JF, Falardeau G, Wang W, Bédard J, et al. Discovery of 1, 6-naphthyridines as a novel class of potent and selective human cytomegalovirus inhibitors. J Med Chem 1999;42(16):3023-3025.
-
Chan L, Jin H, Stefanac T, Wang W, Lavallée JF, Bédard J, et al. Isoquinoline-6-carboxamides as potent and selective anti-human cytomegalovirus (HCMV) inhibitors. Bioorg Med Chem Lett. 1999;9(17):2583-6.
-
Galán A, Moreno L, Párraga J, Serrano Á, Sanz MJ, Cortes D, et al. Novel isoquinoline derivatives as antimicrobial agents. Bioorg Med Chem 2013;21(11):3221-3230.
-
Galán A, Moreno L, Párraga J, Serrano Á, Sanz MJ, Cortes D, Cabedo N. Novel isoquinoline derivatives as antimicrobial agents. Bioorg Med Chem 2013;21(11):3221-3230.
-
Sloop JC. Advances in the Preparation of Fluorinated Isoquinolines: A Decade of Progress. J Chem 2017;2017.
-
Nord C, Levenfors JJ, Bjerketorp J, Sahlberg C, Guss B, Öberg B, Broberg A. Antibacterial Isoquinoline Alkaloids from the Fungus Penicillium Spathulatum Em19. Molecules 2019;24(24):4616.
-
Srivastava A, Talaue M, Liu S, Degen D, Ebright RY, Sineva E, et al. New target for inhibition of bacterial RNA polymerase:‘switch region’. Curr Opin Microbiol 2011;14(5):532-543.
-
Seuring T, Archangelidi O, Suhrcke M. The economic cost of type 2 diabetes: a global systematic review. Pharmacoeconomics 2015;33:811-831.
-
Lee YS, Kim WS, Kim KH, Yoon MJ, Cho HJ, Shen Y, et al. Berberine, a natural plant product, activates AMP-activated protein kinase with beneficial metabolic effects in diabetic and insulin-resistant states. Diabetes 2006;55:2256-2264.
-
Zhang H, Wei J, Xue R, Wu JD, Zhao W, Wang ZZ, et al. Berberine lowers blood glucose in type 2 diabetes mellitus patients through increasing insulin receptor expression. Metabolomics 2010;59:285-292.
-
Yin J, Gao Z, Liu D, Liu Z, Ye J. Berberine improves glucose metabolism through induction of glycolysis. Am J Physiol Endocrinol Metab 2008;294:E148-E156.
-
Xu M, Xiao Y, Yin J, Hou W, Yu X, Shen L, et al. Berberine promotes glucose consumption independently of AMP-activated protein kinase activation. PLoS One 2014;9(7):e103702.
-
Ren G, Wang YX, Li YH, Song DQ, Kong WJ, Jiang JD. Structure-activity relationship of berberine derivatives for their glucose-lowering activities. Int J Clin Exp Med 2017;10(3):5054-5060.
-
Cheng Z, Chen AF, Wu F, Sheng L, Zhang HK, Gu M, et al. 8, 8-Dimethyldihydroberberine with improved bioavailability and oral efficacy on obese and diabetic mouse models. Bioorg Med Chem 2010;18(16):5915-5924.
-
Muñoz GD, Dudley GB. Synthesis of 1, 2, 3, 4-tetrahydroquinolines including angustureine and congeneric alkaloids. A review. Org Prep Proced Int 2015;47(3):179-206.
-
Jacquemond-Collet I, Hannedouche S, Fabre N, Fourasté I, Moulis C. Two tetrahydroquinoline alkaloids from Galipea officinalis. Phytochemistry 1999;51(8):1167-1169.
-
Pan WH, Xu XY, Shi N, Tsang SW, Zhang HJ. Antimalarial activity of plant metabolites. Int J Mol Sci 2018;19(5):1382.
-
Anthony MP, Burrows JN, Duparc S, Moehrle J, Wells TN. The global pipeline of new medicines for the control and elimination of malaria. Malaria J 2012;11(1):316.
-
Schlitzer M. Antimalarial drugs–what is in use and what is in the pipeline. Archiv der Pharm 2008;341(3):149-163.