Abstract
1,4-dihydropyridine is a versatile class of compounds with multiple biological activities, thus holding significant pharmacological potential. Recent studies have provided evidence concerning the anticancer, antimicrobial, and anti-inflammatory properties of 1,4-dihydropyridines, as well as their potential in Alzheimer’s disease treatment. Therefore, this class of compounds is a promising candidate in studies of drug development and drug discovery. The major derivatives of 1,4-dihydropyridine can be synthesized through one-pot synthesis in many different ways, varying the solvents, catalysts, and experimental conditions. Due to the compound’s remarkable potential and ease of production, in this review we aimed to present the biological activities and synthesis methodologies of the main 1,4-dihydropyridine derivatives reported by scientific literature over the past decade.
Graphical Abstract
[http://dx.doi.org/10.1016/j.ejmech.2017.03.025] [PMID: 28342939]
[http://dx.doi.org/10.3390/molecules16098041] [PMID: 21931285]
[http://dx.doi.org/10.2174/1573406414666180418143048] [PMID: 29669502]
[http://dx.doi.org/10.1134/S1070363217030264]
[http://dx.doi.org/10.1016/j.bioorg.2020.104582] [PMID: 33450547]
[http://dx.doi.org/10.1016/j.actatropica.2020.105768] [PMID: 33245907]
[http://dx.doi.org/10.1007/s00044-015-1367-z]
[http://dx.doi.org/10.1016/j.ejmech.2015.03.018] [PMID: 25817770]
[http://dx.doi.org/10.3390/ijms21207652] [PMID: 33081112]
[http://dx.doi.org/10.3390/molecules25061329] [PMID: 32183349]
[http://dx.doi.org/10.1016/j.ejmech.2013.12.001] [PMID: 24384550]
[http://dx.doi.org/10.1007/s00044-012-0156-1]
[http://dx.doi.org/10.1007/s00044-011-9680-7]
[http://dx.doi.org/10.1016/j.bmc.2010.03.038] [PMID: 20382537]
[http://dx.doi.org/10.21203/rs.3.rs-611018/v1]
[http://dx.doi.org/10.1007/BF03245875]
[http://dx.doi.org/10.1016/j.bioorg.2021.105054] [PMID: 34146919]
[http://dx.doi.org/10.2298/JSC200818064G]
[http://dx.doi.org/10.1016/j.bioorg.2019.103047] [PMID: 31234130]
[http://dx.doi.org/10.1134/S1068162021020163]
[http://dx.doi.org/10.1111/cbdd.12973] [PMID: 28294548]
[http://dx.doi.org/10.1007/s11164-018-3541-7]
[http://dx.doi.org/10.1002/jhet.3921]
[http://dx.doi.org/10.1016/j.cclet.2011.07.009]
[http://dx.doi.org/10.1002/cbdv.201900577] [PMID: 31823465]
[http://dx.doi.org/10.1007/s00044-010-9321-6]
[http://dx.doi.org/10.1080/10406638.2018.1533875]
[http://dx.doi.org/10.1007/s00044-011-9698-x]
[http://dx.doi.org/10.1016/j.ejmech.2014.01.059] [PMID: 24534541]
[http://dx.doi.org/10.1007/s10600-011-9982-5]
[http://dx.doi.org/10.1016/j.bmcl.2012.03.030] [PMID: 22464458]
[http://dx.doi.org/10.1080/14756366.2020.1740695] [PMID: 32183576]
[http://dx.doi.org/10.1007/BF03246554]
[http://dx.doi.org/10.1002/jhet.2925]
[http://dx.doi.org/10.1016/j.ejmech.2018.02.005] [PMID: 29665527]
[http://dx.doi.org/10.1016/j.molstruc.2020.128325]
[http://dx.doi.org/10.1002/jhet.2547]
[PMID: 26600848]
[http://dx.doi.org/10.1016/j.bioorg.2021.105377] [PMID: 34670329]
[http://dx.doi.org/10.1007/s00044-017-2088-2]
[http://dx.doi.org/10.4172/pharmaceutical-sciences.1000294]
[http://dx.doi.org/10.1007/s00706-013-1145-x]
[http://dx.doi.org/10.3109/14756366.2011.599029] [PMID: 21846203]
[http://dx.doi.org/10.1016/j.bmc.2013.07.014] [PMID: 23910989]
[http://dx.doi.org/10.1016/j.jscs.2020.10.001]
[http://dx.doi.org/10.1016/j.compbiomed.2020.104117] [PMID: 33217661]
[http://dx.doi.org/10.1371/journal.pone.0160842] [PMID: 27508497]
[http://dx.doi.org/10.1007/s10600-011-9873-9]
[http://dx.doi.org/10.5185/amlett.2017.1495]
[http://dx.doi.org/10.1016/j.matchemphys.2016.12.039]
[http://dx.doi.org/10.1016/j.bioorg.2020.104274] [PMID: 33339080]
[http://dx.doi.org/10.1007/s00706-020-02549-x]
[http://dx.doi.org/10.1016/j.taap.2018.10.025] [PMID: 30391378]
[http://dx.doi.org/10.2147/DDDT.S119995] [PMID: 28243063]
[http://dx.doi.org/10.1080/14756366.2021.1944126] [PMID: 34210212]
[http://dx.doi.org/10.1007/s11030-021-10281-9] [PMID: 34671894]
[http://dx.doi.org/10.1080/10406638.2021.2021254]
[http://dx.doi.org/10.4103/1735-5362.293515] [PMID: 33312215]
[http://dx.doi.org/10.1007/s11164-017-3087-0]
[http://dx.doi.org/10.3987/COM-16-13451]
[http://dx.doi.org/10.3390/ph14100987] [PMID: 34681211]
[http://dx.doi.org/10.1107/S2056989018014251] [PMID: 30443384]
[http://dx.doi.org/10.1002/masy.202100056]
[http://dx.doi.org/10.1016/j.cattod.2021.07.006]
[http://dx.doi.org/10.1016/j.molstruc.2020.129430]
[http://dx.doi.org/10.1016/j.crgsc.2021.100108]
[http://dx.doi.org/10.1016/j.mtcomm.2021.102791]
[http://dx.doi.org/10.1016/j.cdc.2021.100688]
[http://dx.doi.org/10.1039/D1RA01256H] [PMID: 35479678]
[http://dx.doi.org/10.1007/s40097-020-00361-x]
[http://dx.doi.org/10.1016/j.poly.2019.114340]
[http://dx.doi.org/10.1007/s11696-018-0666-5]
[http://dx.doi.org/10.1016/j.tetlet.2018.10.010]
[http://dx.doi.org/10.17576/mjas-2017-2101-02]
[http://dx.doi.org/10.1016/j.tetlet.2017.02.038]
[http://dx.doi.org/10.1007/s00706-016-1657-2]
[http://dx.doi.org/10.1002/hlca.201500265]
[http://dx.doi.org/10.1002/hlca.201500009]
[http://dx.doi.org/10.1016/j.ultsonch.2014.05.026] [PMID: 24974005]
[http://dx.doi.org/10.1016/j.tetlet.2012.10.106]
[http://dx.doi.org/10.1039/c3ra40706c]
[http://dx.doi.org/10.1039/c2nj40060j]
[http://dx.doi.org/10.1002/hlca.201000354]
[http://dx.doi.org/10.1055/s-0030-1258462]
[http://dx.doi.org/10.2174/1385272820666160805112208]
[http://dx.doi.org/10.1016/j.tetlet.2010.06.041]
[http://dx.doi.org/10.1039/C7RA11974G] [PMID: 35542621]
[http://dx.doi.org/10.3998/ark.5550190.p009.445]
[http://dx.doi.org/10.5012/bkcs.2012.33.4.1170]
[http://dx.doi.org/10.1080/00397911.2013.831903]
[http://dx.doi.org/10.1107/S2056989020004065] [PMID: 32280509]
[http://dx.doi.org/10.1007/s11164-019-03942-w]
[http://dx.doi.org/10.1080/00397911.2017.1304556]
[http://dx.doi.org/10.1002/chem.201000837] [PMID: 20922717]
[http://dx.doi.org/10.1039/C6RA17990H]
[http://dx.doi.org/10.1039/C6RA13848A]
[http://dx.doi.org/10.2174/2213337206666190701130253]
[http://dx.doi.org/10.1016/j.diamond.2019.107661]
[http://dx.doi.org/10.1002/cphc.201000463] [PMID: 21254318]
[http://dx.doi.org/10.1166/jnn.2016.12432] [PMID: 27427743]
[http://dx.doi.org/10.1039/C6RA01002D]
[http://dx.doi.org/10.1016/j.eurpolymj.2010.09.014]
[http://dx.doi.org/10.1246/cl.150503]
[http://dx.doi.org/10.1039/C5NJ02098K]
[http://dx.doi.org/10.1080/00397911.2015.1109127]
[http://dx.doi.org/10.2174/1570178613666160104232735]
[http://dx.doi.org/10.1039/C4RA12219D]
[http://dx.doi.org/10.1039/C7NJ03281A]
[http://dx.doi.org/10.1039/C4RA13045F]
[http://dx.doi.org/10.3390/app2020368]
[http://dx.doi.org/10.3390/molecules17055339] [PMID: 22565483]
[http://dx.doi.org/10.1016/j.polymer.2013.04.055]
[http://dx.doi.org/10.1107/S2056989015014966] [PMID: 26396906]
[http://dx.doi.org/10.1039/c3ra23484c]
[http://dx.doi.org/10.1021/acsomega.9b02755] [PMID: 31858048]
[http://dx.doi.org/10.1002/slct.201600719]
[http://dx.doi.org/10.1186/s13065-019-0545-3] [PMID: 31384788]
[http://dx.doi.org/10.1515/hc-2020-0005]
[http://dx.doi.org/10.1080/10406638.2020.1764988]
[http://dx.doi.org/10.1080/10406638.2018.1481115]
[http://dx.doi.org/10.1007/s10562-019-02845-0]
[http://dx.doi.org/10.1080/10406638.2020.1768411]
[http://dx.doi.org/10.1007/s11164-013-1284-z]
[http://dx.doi.org/10.1002/jccs.201800411]
[http://dx.doi.org/10.1039/C6RA25709G]
[http://dx.doi.org/10.1016/j.jtusci.2014.03.003]
[http://dx.doi.org/10.1007/s11164-016-2814-2]
[http://dx.doi.org/10.1016/j.molstruc.2020.128326]
[http://dx.doi.org/10.1080/10406638.2019.1616305]
[http://dx.doi.org/10.1002/jhet.692]
[http://dx.doi.org/10.1515/hc-2012-0053]
[http://dx.doi.org/10.1016/j.catcom.2014.11.015]
[http://dx.doi.org/10.5267/j.ccl.2019.8.001]
[http://dx.doi.org/10.1155/2013/850254]
[http://dx.doi.org/10.1007/s11164-015-2001-x]
[http://dx.doi.org/10.1080/10406638.2019.1678184]
[http://dx.doi.org/10.1080/15533174.2011.609221]
[http://dx.doi.org/10.1080/10406638.2016.1207687]
[http://dx.doi.org/10.1080/00397911.2013.838791]
[http://dx.doi.org/10.1002/aoc.5026]
[PMID: 24250444]
[http://dx.doi.org/10.1016/j.arabjc.2014.10.026]
[http://dx.doi.org/10.1080/10406638.2019.1567560]
[http://dx.doi.org/10.1155/2013/930787] [PMID: 24501587]
[http://dx.doi.org/10.1039/c3ra44058c]
[http://dx.doi.org/10.1155/2012/214231]
[http://dx.doi.org/10.1002/slct.201700265]
[http://dx.doi.org/10.1039/C5OB02655E] [PMID: 26837413]
[http://dx.doi.org/10.1002/jhet.508]
[http://dx.doi.org/10.1080/00397910902987792]
[http://dx.doi.org/10.1016/j.jscs.2011.10.005]
[http://dx.doi.org/10.1007/s13738-017-1156-3]
[http://dx.doi.org/10.1021/acssuschemeng.5b00900]
[http://dx.doi.org/10.1007/s12039-013-0431-9]
[http://dx.doi.org/10.1016/j.crci.2014.07.010]
[http://dx.doi.org/10.1007/s10562-014-1202-z]
[http://dx.doi.org/10.2478/s11696-010-0070-2]
[http://dx.doi.org/10.1007/s00706-014-1206-9]
[http://dx.doi.org/10.1016/j.bmcl.2014.06.047] [PMID: 25042338]
[http://dx.doi.org/10.1039/C5RA19595K]
[http://dx.doi.org/10.1016/j.tetlet.2016.03.089]
[http://dx.doi.org/10.4067/S0717-97072012000400017]
[http://dx.doi.org/10.1016/j.jtice.2017.10.013]
[http://dx.doi.org/10.17159/0379-4350/2015/v68a3]
[http://dx.doi.org/10.1016/j.molliq.2018.04.125]
[http://dx.doi.org/10.1016/j.cplett.2019.136784]
[http://dx.doi.org/10.1016/j.molcata.2013.11.010]
[http://dx.doi.org/10.1002/aoc.3943]
[http://dx.doi.org/10.1016/j.solidstatesciences.2019.03.020]
[http://dx.doi.org/10.1002/aoc.3999]
[http://dx.doi.org/10.1002/slct.201802505]
[http://dx.doi.org/10.1016/j.molstruc.2019.127011]
[http://dx.doi.org/10.1007/s13738-018-1526-5]
[http://dx.doi.org/10.1080/00304948.2019.1600132]
[http://dx.doi.org/10.1002/aoc.4370]
[http://dx.doi.org/10.1007/s11164-017-3002-8]
[http://dx.doi.org/10.1016/j.jcis.2017.07.010] [PMID: 28715862]
[http://dx.doi.org/10.1039/C7RA10758G]
[http://dx.doi.org/10.1007/s11164-016-2559-y]
[http://dx.doi.org/10.1007/s11030-020-10109-y] [PMID: 32507980]
[http://dx.doi.org/10.1007/s11164-020-04158-z]
[http://dx.doi.org/10.1007/s10562-019-02986-2]
[http://dx.doi.org/10.1007/s11030-019-09949-0] [PMID: 30955149]
[http://dx.doi.org/10.1007/s10876-019-01739-w]
[http://dx.doi.org/10.1016/j.carbpol.2018.12.069] [PMID: 30658798]
[http://dx.doi.org/10.1002/aoc.4636]
[http://dx.doi.org/10.1007/s13738-018-1417-9]
[http://dx.doi.org/10.1002/aoc.4245]
[http://dx.doi.org/10.1016/j.ijbiomac.2017.11.050] [PMID: 29137997]
[http://dx.doi.org/10.1002/aoc.3974]
[http://dx.doi.org/10.1007/s10562-017-2159-5]
[http://dx.doi.org/10.1007/s00706-016-1906-4]
[http://dx.doi.org/10.1080/15533174.2015.1004419]
[http://dx.doi.org/10.1039/C6RA19776K]
[http://dx.doi.org/10.1039/C6RA16459E]
[http://dx.doi.org/10.1039/C4NJ01588F]
[http://dx.doi.org/10.2174/1570178612666150724235806]
[http://dx.doi.org/10.1002/jhet.2070]
[http://dx.doi.org/10.1039/C4RA12673D]
[http://dx.doi.org/10.1007/s00706-012-0742-4]
[http://dx.doi.org/10.1016/j.tetlet.2011.07.031]
[http://dx.doi.org/10.1080/17518253.2010.482065]
[http://dx.doi.org/10.1007/s13369-010-0010-z]
[http://dx.doi.org/10.1016/j.jfluchem.2009.10.009]
[http://dx.doi.org/10.1002/jhet.793]
[http://dx.doi.org/10.1016/j.cclet.2014.03.037]
[http://dx.doi.org/10.1016/S1872-2067(14)60087-5]
[http://dx.doi.org/10.1016/j.jscs.2014.01.009]
[http://dx.doi.org/10.1002/aoc.5822]
[http://dx.doi.org/10.1007/s11164-019-04049-y]
[http://dx.doi.org/10.1007/s11164-019-03802-7]
[http://dx.doi.org/10.1002/aoc.4368]
[http://dx.doi.org/10.1002/aoc.4151]
[http://dx.doi.org/10.1039/C7NJ03562D]
[http://dx.doi.org/10.1002/aoc.3815]
[http://dx.doi.org/10.1002/aoc.3845]
[http://dx.doi.org/10.1039/C7NJ00063D]
[http://dx.doi.org/10.1007/s13738-022-02505-y]
[http://dx.doi.org/10.1007/s13738-021-02420-8]
[http://dx.doi.org/10.21203/rs.3.rs-462994/v1]
[http://dx.doi.org/10.1080/10406638.2021.1991393]
[http://dx.doi.org/10.1038/s41598-022-05411-8] [PMID: 35087116]
[http://dx.doi.org/10.1007/s11144-021-02072-y]
[http://dx.doi.org/10.1039/D1RA07381H] [PMID: 35425328]
[http://dx.doi.org/10.1038/s41598-021-97360-x] [PMID: 34611176]
[http://dx.doi.org/10.1007/s11164-020-04322-5]
[http://dx.doi.org/10.1038/s41598-020-80884-z] [PMID: 33504833]
[http://dx.doi.org/10.1002/jhet.4242]
[http://dx.doi.org/10.3390/ecsoc-25-11717]
[http://dx.doi.org/10.1080/10406638.2019.1614639]
[http://dx.doi.org/10.1007/s10562-021-03734-1]
[http://dx.doi.org/10.1080/10406638.2021.1884100]
[http://dx.doi.org/10.1016/j.poly.2021.115102]
[http://dx.doi.org/10.4067/S0717-97072021000205136]
[http://dx.doi.org/10.1039/D0NJ05687A]
[http://dx.doi.org/10.1007/s11172-015-0835-4]
[http://dx.doi.org/10.1016/j.crci.2011.12.001]
[http://dx.doi.org/10.1016/j.ultsonch.2009.11.003] [PMID: 20006532]
[http://dx.doi.org/10.1016/j.jscs.2013.10.001]
[http://dx.doi.org/10.5560/znb.2013-2323]
[http://dx.doi.org/10.29356/jmcs.v58i2.173]
[http://dx.doi.org/10.1016/j.ejmech.2018.03.069] [PMID: 29609122]
[http://dx.doi.org/10.1007/BF03246091]
[http://dx.doi.org/10.1002/slct.201801476]
[http://dx.doi.org/10.1080/00397911.2010.550704]
[http://dx.doi.org/10.1002/ardp.201800307] [PMID: 31012156]
[http://dx.doi.org/10.1080/00397911.2010.517610]
[http://dx.doi.org/10.1007/s10812-017-0478-3]
[http://dx.doi.org/10.1016/j.tetlet.2012.10.065]
[http://dx.doi.org/10.1134/S1070428010050234]
[http://dx.doi.org/10.1134/S1070428010080038]
[http://dx.doi.org/10.1016/j.tet.2014.02.067]
[http://dx.doi.org/10.1016/j.matpr.2017.06.437]
[http://dx.doi.org/10.1039/C4CC03079F] [PMID: 25046767]
[http://dx.doi.org/10.1002/ejoc.201900880]
[http://dx.doi.org/10.1016/j.tet.2015.07.058]
[http://dx.doi.org/10.1016/j.dyepig.2019.107616]
[http://dx.doi.org/10.1002/cjoc.201090211]
[http://dx.doi.org/10.1021/acs.joc.9b03307] [PMID: 32070098]
[http://dx.doi.org/10.1134/S1070428016030155]