Abstract
Molecules containing triazolopyrimidine core showed diverse biological activities, including anti-Alzheimer's, anti-diabetes, anti-cancer, anti-microbial, anti-tuberculosis, anti-viral, anti-malarial, anti-inflammatory, anti-parkinsonism, and anti-glaucoma activities. Triazolopyrimidines have 8 isomeric structures, including the most stable 1,2,4-triazolo[1,5- a] pyrimidine ones. Triazolopyrimidines were obtained by using various chemical reactions, including a) 1,2,4-triazole nucleus annulation to pyrimidine, b) pyrimidines annulation to 1,2,4-triazole structure, c) 1,2,4-triazolo[l,5-a] pyrimidines rearrangement, and d) pyrimidotetrazine rearrangement. This review discusses synthetic methods, recent pharmacological actions and drug delivery perspectives of triazolopyrimidines.
Keywords: Alzheimer's, triazolopyrimidine, pharmacological actions, biology, drug delivery, tetrazines.
[http://dx.doi.org/10.1006/phrs.2001.0864]
[http://dx.doi.org/10.1002/cbf.1126]
[http://dx.doi.org/10.1016/j.bmc.2009.02.010]
[http://dx.doi.org/10.2174/1389557517666171101112850]
[http://dx.doi.org/10.1016/j.bioorg.2019.102919]
[http://dx.doi.org/10.1007/s00044-020-02609-1]
[http://dx.doi.org/10.1016/j.bmc.2019.06.004]
[http://dx.doi.org/10.1016/j.ejmech.2017.04.064]
[http://dx.doi.org/10.1016/j.ejmech.2016.04.053]
[http://dx.doi.org/10.1016/j.ejmech.2015.01.042]
[http://dx.doi.org/10.1016/j.ejmech.2016.02.032]
[http://dx.doi.org/10.1016/j.bmcl.2013.11.074]
[http://dx.doi.org/10.1016/j.steroids.2012.03.002]
[http://dx.doi.org/10.1016/j.tetlet.2008.07.134]
[http://dx.doi.org/10.1007/s10593-013-1369-z]
[http://dx.doi.org/10.1016/j.ultsonch.2013.12.007]
[http://dx.doi.org/10.3390/molecules17021860]
[http://dx.doi.org/10.1007/s11164-020-04226-4]
[http://dx.doi.org/10.1007/s11030-015-9604-4]
[http://dx.doi.org/10.1002/slct.201802221]
[http://dx.doi.org/10.4155/fmc-2018-0285]
[http://dx.doi.org/10.1021/jm00041a016]
[http://dx.doi.org/10.1007/s00044-016-1733-5]
[http://dx.doi.org/10.1515/znb-1983-1223]
[http://dx.doi.org/10.1016/j.ejmech.2009.10.007]
[http://dx.doi.org/10.4314/bcse.v32i3.10]
[http://dx.doi.org/10.1016/j.arabjc.2013.11.025]
[http://dx.doi.org/10.1016/j.ejmech.2019.111843]
[http://dx.doi.org/10.1021/jm060717i]
[http://dx.doi.org/10.1158/0008-5472.CAN-07-1420]
[http://dx.doi.org/10.1016/j.bioorg.2019.103307]
[http://dx.doi.org/10.1016/j.bmc.2017.05.030]
[http://dx.doi.org/10.1002/cbdv.200800168]
[http://dx.doi.org/10.1016/S0006-8993(02)02898-6]
[http://dx.doi.org/10.1016/j.bmc.2009.03.018]
[http://dx.doi.org/10.1021/jm8014537]
[http://dx.doi.org/10.1021/jm0494321]
[http://dx.doi.org/10.1002/ptr.6211]
[http://dx.doi.org/10.1186/s13065-019-0560-4]
[http://dx.doi.org/10.1007/s11164-020-04285-7]
[http://dx.doi.org/10.1016/j.jnutbio.2009.01.009]
[http://dx.doi.org/10.1007/s10534-005-3689-7]
[http://dx.doi.org/10.2337/diab.29.8.665]
[http://dx.doi.org/10.1016/j.jinorgbio.2020.111235]
[http://dx.doi.org/10.1016/j.bbalip.2014.07.008]
[http://dx.doi.org/10.1016/j.ejmech.2009.07.013]
[http://dx.doi.org/10.3390/molecules25215133]
[http://dx.doi.org/10.1086/595011]
[http://dx.doi.org/10.1093/jac/dky019]
[http://dx.doi.org/10.5155/eurjchem.3.4.455-460.683]
[http://dx.doi.org/10.3390/molecules27030765]
[http://dx.doi.org/10.1007/s11030-020-10043-z]
[http://dx.doi.org/10.1021/np100648q]
[http://dx.doi.org/10.1021/acs.jnatprod.6b00057]
[http://dx.doi.org/10.1101/cshperspect.a017863]
[http://dx.doi.org/10.1016/j.bmcl.2014.02.054]
[http://dx.doi.org/10.1128/JVI.78.17.9144-9153.2004]
[http://dx.doi.org/10.1007/978-3-662-06099-5_4]
[http://dx.doi.org/10.1021/acs.jmedchem.5b00012]
[http://dx.doi.org/10.1016/j.ejmech.2020.112944]
[http://dx.doi.org/10.1016/j.ejmech.2021.113494]
[http://dx.doi.org/10.1128/JVI.75.5.2246-2252.2001]
[http://dx.doi.org/10.3389/fmicb.2019.00002]
[http://dx.doi.org/10.1111/cbdd.13760]
[http://dx.doi.org/10.2174/138955705774933310]
[http://dx.doi.org/10.1021/op4002356]
[http://dx.doi.org/10.1016/j.ijantimicag.2020.106054]
[http://dx.doi.org/10.1073/pnas.2003138117]
[http://dx.doi.org/10.1126/science.abc1560]
[http://dx.doi.org/10.3390/molecules27030801]
[http://dx.doi.org/10.1016/j.bmcl.2008.11.101]
[http://dx.doi.org/10.1016/S0968-0896(03)00429-2]
[http://dx.doi.org/10.1016/j.bioorg.2021.104841]
[http://dx.doi.org/10.2174/187152610791163336]
[http://dx.doi.org/10.1016/j.ejmech.2019.01.047]
[http://dx.doi.org/10.1126/scitranslmed.aaa6645]
[http://dx.doi.org/10.3390/molecules17078285]
[http://dx.doi.org/10.1021/jm801343r]
[http://dx.doi.org/10.1016/j.ejmech.2020.112941]
[http://dx.doi.org/10.1016/j.ejmech.2021.113227]
[http://dx.doi.org/10.1021/acs.jcim.5b00680]
[http://dx.doi.org/10.1016/0753-3322(89)90109-1]
[http://dx.doi.org/10.1111/ene.13439]
[http://dx.doi.org/10.2174/1570159X13666150716165726]
[http://dx.doi.org/10.1002/slct.201702599]
[http://dx.doi.org/10.3390/md19040201]
[http://dx.doi.org/10.3389/fncel.2018.00338]
[http://dx.doi.org/10.3390/ijms221910794]
[http://dx.doi.org/10.1021/jm5005623]
[http://dx.doi.org/10.1021/acs.jmedchem.0c01605]
[http://dx.doi.org/10.2165/00023210-200519120-00002]
[http://dx.doi.org/10.1016/j.eclinm.2021.100988]
[http://dx.doi.org/10.1016/j.brainres.2016.08.016]
[http://dx.doi.org/10.1007/s00702-010-0433-4]
[http://dx.doi.org/10.1038/oncsis.2015.10]
[http://dx.doi.org/10.1016/j.bmcl.2017.06.038]
[http://dx.doi.org/10.3390/cancers13112584]
[http://dx.doi.org/10.1186/s12943-021-01355-1]
[http://dx.doi.org/10.1016/j.arabjc.2013.04.002]
[http://dx.doi.org/10.1080/13543776.2019.1648433]
[http://dx.doi.org/10.2174/1568026617666170104145640]
[http://dx.doi.org/10.1016/j.bmcl.2018.05.010]
[http://dx.doi.org/10.3390/pharmaceutics14061191]
[http://dx.doi.org/10.1016/j.ejmech.2021.113449]
[http://dx.doi.org/10.1016/j.bioorg.2022.105687]
[http://dx.doi.org/10.3389/fonc.2022.820696]
[http://dx.doi.org/10.1016/j.drudis.2019.12.001]
[http://dx.doi.org/10.1016/j.bmcl.2005.11.048]
[http://dx.doi.org/10.3390/cancers11111786]
[http://dx.doi.org/10.3389/fphar.2022.842376]
[http://dx.doi.org/10.1002/ardp.201700137]
[http://dx.doi.org/10.1016/j.ejmech.2020.113108]
[http://dx.doi.org/10.1021/acs.jmedchem.9b00274]
[http://dx.doi.org/10.1016/j.bmcl.2018.11.044]
[http://dx.doi.org/10.1007/s11302-008-9100-8]
[http://dx.doi.org/10.1212/01.WNL.0000095205.33940.99]
[http://dx.doi.org/10.3390/molecules27072366]
[http://dx.doi.org/10.1016/S0301-0082(99)00011-8]
[http://dx.doi.org/10.1016/j.bmcl.2004.07.048]
[http://dx.doi.org/10.1021/acsmedchemlett.1c00599]
[http://dx.doi.org/10.1007/978-94-007-7359-2_17]
[http://dx.doi.org/10.1111/j.1748-1716.1951.tb00833.x]
[http://dx.doi.org/10.1001/archopht.1959.04220010082009]
[http://dx.doi.org/10.1016/j.neuroscience.2006.11.016]
[http://dx.doi.org/10.3390/molecules27010064]
[http://dx.doi.org/10.3897/rrpharmacology.8.77854]
[http://dx.doi.org/10.1080/10406638.2020.1750042]
[http://dx.doi.org/10.1134/S1070428021120204]
[http://dx.doi.org/10.1111/j.1365-2125.1996.tb00006.x]
[http://dx.doi.org/10.1016/j.ijpharm.2006.06.023]
[http://dx.doi.org/10.1155/2017/4925495]
[http://dx.doi.org/10.3109/10717544.2014.948643]
[http://dx.doi.org/10.1186/s12951-020-00766-4]
[http://dx.doi.org/10.1186/s40591-016-0048-8]
[http://dx.doi.org/10.1186/1556-276X-9-343]
[http://dx.doi.org/10.1080/10717544.2018.1474967]
[http://dx.doi.org/10.1016/j.apsb.2013.10.001]
[http://dx.doi.org/10.1002/app.40696]
[http://dx.doi.org/10.1177/0885328210363504]
[http://dx.doi.org/10.3390/ma15051934]
[http://dx.doi.org/10.1016/j.nanoso.2019.100367]