Abstract
The biological and medicinal chemistry of the oxocarbon acids 2,3- dihydroxycycloprop-2-en-1-one (deltic acid), 3,4-dihydroxycyclobut-3-ene-1,2-dione (squaric acid), 4,5-dihydroxy-4-cyclopentene-1,2,3-trione (croconic acid), 5,6-dihydroxycyclohex- 5-ene-1,2,3,4-tetrone (rhodizonic acid) and their derivatives is reviewed and their key chemical properties and reactions are discussed. Applications of these compounds as potential bioisosteres in biological and medicinal chemistry are examined. Reviewed areas include cell imaging, bioconjugation reactions, antiviral, antibacterial, anticancer, enzyme inhibition, and receptor pharmacology.
[http://dx.doi.org/10.1039/c0cs00200c] [PMID: 21399835]
[http://dx.doi.org/10.1021/acs.bioconjchem.0c00356] [PMID: 32786372]
[http://dx.doi.org/10.1002/chem.201704388] [PMID: 29119615]
[http://dx.doi.org/10.1021/jm1013693] [PMID: 21413808]
[http://dx.doi.org/10.1021/acs.chemrev.0c00416] [PMID: 32930577]
[http://dx.doi.org/10.1021/acs.jmedchem.5b01963] [PMID: 26967507]
[http://dx.doi.org/10.1002/ejoc.201600137] [PMID: 27790071]
[http://dx.doi.org/10.1016/j.chempr.2019.02.027]
[http://dx.doi.org/10.1016/j.bmcl.2016.11.058] [PMID: 27913181]
[http://dx.doi.org/10.1002/ijch.198000088]
[http://dx.doi.org/10.1021/cr00014a004]
[http://dx.doi.org/10.1021/ja00834a047]
[http://dx.doi.org/10.1021/ja00428a043]
[http://dx.doi.org/10.1016/S0040-4039(01)83530-9]
[http://dx.doi.org/10.1021/ar00089a004]
[http://dx.doi.org/10.1021/ja01016a064]
[http://dx.doi.org/10.1016/S0040-4039(01)84565-2]
[http://dx.doi.org/10.1021/ja01073a067]
[http://dx.doi.org/10.1021/jo00925a009]
[http://dx.doi.org/10.1021/ja00965a033]
[http://dx.doi.org/10.1021/ja00807a033]
[http://dx.doi.org/10.1016/j.bmcl.2003.10.058] [PMID: 14698165]
[http://dx.doi.org/10.1021/jo00094a055]
[http://dx.doi.org/10.1021/ja00257a081]
[http://dx.doi.org/10.1107/S0021889873008770]
[http://dx.doi.org/10.1016/S0040-4039(00)00084-8]
[http://dx.doi.org/10.1021/jo991267n] [PMID: 10813951]
[http://dx.doi.org/10.1002/qua.22453]
[http://dx.doi.org/10.1021/jo301575c] [PMID: 22954314]
[http://dx.doi.org/10.1016/S0040-4039(01)96160-X]
[http://dx.doi.org/10.1021/acs.orglett.7b02383] [PMID: 28862452]
[http://dx.doi.org/10.1021/jacs.7b03010] [PMID: 28478678]
[http://dx.doi.org/10.1021/ar400019p] [PMID: 23551251]
[http://dx.doi.org/10.1039/C7CS00159B] [PMID: 28379234]
[http://dx.doi.org/10.2174/0929867325666180309113222] [PMID: 29521206]
[http://dx.doi.org/10.1021/acs.joc.7b02083] [PMID: 28832145]
[http://dx.doi.org/10.1039/c39800000223]
[http://dx.doi.org/10.1055/s-0033-1338516]
[http://dx.doi.org/10.1039/C4SC02402H] [PMID: 26504512]
[http://dx.doi.org/10.1039/C5RA05254H]
[http://dx.doi.org/10.1002/anie.201605214] [PMID: 27578602]
[http://dx.doi.org/10.3390/polym9030079]
[http://dx.doi.org/10.1002/cber.19811140225]
[http://dx.doi.org/10.1002/1099-0690(200301)2003:1<151:AID-EJOC151>3.0.CO;2-7]
[http://dx.doi.org/10.1021/ja01522a083]
[http://dx.doi.org/10.5059/yukigoseikyokaishi.53.330]
[http://dx.doi.org/10.1039/c3cs60153f] [PMID: 23873344]
[http://dx.doi.org/10.1016/j.ejmech.2020.112872] [PMID: 33035923]
[http://dx.doi.org/10.1039/c3cc44039g] [PMID: 23884200]
[http://dx.doi.org/10.1002/anie.196608881]
[http://dx.doi.org/10.1080/00397919708006826]
[http://dx.doi.org/10.1002/cber.19911240539]
[http://dx.doi.org/10.1002/jlac.197319730411]
[http://dx.doi.org/10.1039/c3ra41369a]
[http://dx.doi.org/10.1039/C5RA05383H]
[http://dx.doi.org/10.1021/ja00722a044]
[http://dx.doi.org/10.1021/jo00246a016]
[http://dx.doi.org/10.1021/jo00246a017]
[http://dx.doi.org/10.1021/jo00306a012]
[http://dx.doi.org/10.1016/S0040-4039(00)73543-X]
[http://dx.doi.org/10.1007/s00214-002-0373-7]
[http://dx.doi.org/10.1039/j29680000435]
[http://dx.doi.org/10.1016/S0009-2614(01)01229-5]
[http://dx.doi.org/10.1016/j.theochem.2004.01.024]
[http://dx.doi.org/10.1107/S0108768101014963] [PMID: 11717486]
[http://dx.doi.org/10.1080/713738914]
[http://dx.doi.org/10.1002/smll.201600284] [PMID: 27062376]
[http://dx.doi.org/10.1002/smll.202201275] [PMID: 35585681]
[http://dx.doi.org/10.1002/chem.201702841] [PMID: 28768048]
[http://dx.doi.org/10.1002/tcr.201600140] [PMID: 28266131]
[http://dx.doi.org/10.1002/chem.201801052] [PMID: 29570872]
[http://dx.doi.org/10.1021/acs.joc.8b01847] [PMID: 30277392]
[http://dx.doi.org/10.1039/D2OB00633B] [PMID: 35521781]
[http://dx.doi.org/10.1021/acs.biomac.7b01614] [PMID: 29528623]
[http://dx.doi.org/10.1021/acsami.1c24114] [PMID: 35403421]
[http://dx.doi.org/10.1021/acs.langmuir.1c02080] [PMID: 34806889]
[http://dx.doi.org/10.3390/ijms22073329] [PMID: 33805101]
[http://dx.doi.org/10.1002/marc.202200318] [PMID: 35687083]
[http://dx.doi.org/10.1016/j.bmc.2022.116855] [PMID: 35640378]
[http://dx.doi.org/10.1039/c3cc47894g] [PMID: 24402188]
[http://dx.doi.org/10.1002/ejoc.201700218]
[http://dx.doi.org/10.1021/acs.jmedchem.0c00617] [PMID: 32787096]
[http://dx.doi.org/10.1002/anie.202117330] [PMID: 35150468]
[http://dx.doi.org/10.1039/B707734C]
[http://dx.doi.org/10.1021/ol062691v] [PMID: 17192100]
[http://dx.doi.org/10.1039/c3dt52215f] [PMID: 24113779]
[http://dx.doi.org/10.1016/j.biomaterials.2013.10.039] [PMID: 24169004]
[http://dx.doi.org/10.1562/0031-8655(2002)076<0672:SDFPTS>2.0.CO;2] [PMID: 12511049]
[http://dx.doi.org/10.1016/j.crci.2015.05.012]
[http://dx.doi.org/10.1039/b911064j] [PMID: 19841772]
[http://dx.doi.org/10.3762/bjoc.11.274] [PMID: 26734100]
[http://dx.doi.org/10.1021/ja042404n] [PMID: 15755140]
[http://dx.doi.org/10.1021/acs.orglett.0c01922] [PMID: 32663029]
[http://dx.doi.org/10.1038/s42004-021-00456-8] [PMID: 35474961]
[http://dx.doi.org/10.1021/acs.analchem.0c01226] [PMID: 32429660]
[http://dx.doi.org/10.1039/C7CC09241E] [PMID: 29250617]
[http://dx.doi.org/10.1021/jo100104g] [PMID: 20486682]
[http://dx.doi.org/10.1039/C8CP02576B] [PMID: 29978159]
[http://dx.doi.org/10.1039/C7CC08706C] [PMID: 29354832]
[http://dx.doi.org/10.1002/cplu.202100275] [PMID: 34351081]
[http://dx.doi.org/10.1039/D0CC04090H] [PMID: 32812561]
[http://dx.doi.org/10.1039/D0DT04273K] [PMID: 33635308]
[http://dx.doi.org/10.1039/C5RA24521D]
[http://dx.doi.org/10.4155/fmc-2018-0595] [PMID: 31280669]
[http://dx.doi.org/10.1021/bc00009a003] [PMID: 1932213]
[http://dx.doi.org/10.1002/cbic.201600699] [PMID: 28182850]
[http://dx.doi.org/10.1016/j.carres.2017.10.012] [PMID: 29247910]
[http://dx.doi.org/10.1021/jo962300y] [PMID: 11671646]
[http://dx.doi.org/10.1002/anie.201906737] [PMID: 31328344]
[http://dx.doi.org/10.1016/j.ejmech.2017.03.058] [PMID: 28411454]
[http://dx.doi.org/10.1039/C7OB00448F] [PMID: 28294277]
[http://dx.doi.org/10.1039/C6CC05961A] [PMID: 27711378]
[http://dx.doi.org/10.1371/journal.pntd.0003881] [PMID: 26154421]
[http://dx.doi.org/10.3390/biom5031671] [PMID: 26213980]
[http://dx.doi.org/10.1002/anie.201406843] [PMID: 25318465]
[http://dx.doi.org/10.1021/bm300103u] [PMID: 22376203]
[http://dx.doi.org/10.1002/chem.201200182] [PMID: 23135990]
[http://dx.doi.org/10.1021/acsabm.1c00177] [PMID: 35006854]
[http://dx.doi.org/10.1016/j.bmcl.2004.06.072] [PMID: 15324908]
[http://dx.doi.org/10.1002/cmdc.201900559] [PMID: 32057189]
[PMID: 35003886]
[http://dx.doi.org/10.1128/aac.01659-21] [PMID: 34843390]
[PMID: 35809349]
[http://dx.doi.org/10.1016/j.bmc.2011.10.018] [PMID: 22071522]
[http://dx.doi.org/10.1038/nature09099] [PMID: 20485428]
[http://dx.doi.org/10.1039/c2md20011b]
[http://dx.doi.org/10.1016/j.ejmech.2013.08.037] [PMID: 24077527]
[http://dx.doi.org/10.1016/j.bmc.2016.03.005] [PMID: 26968650]
[http://dx.doi.org/10.3390/molecules26164739] [PMID: 34443327]
[http://dx.doi.org/10.1016/j.exppara.2016.07.013] [PMID: 27480054]
[http://dx.doi.org/10.1021/jm4017015] [PMID: 24410674]
[http://dx.doi.org/10.3390/ma13235505] [PMID: 33276688]
[http://dx.doi.org/10.1039/c004165c] [PMID: 20532300]
[http://dx.doi.org/10.1039/C7MO00006E] [PMID: 29725679]
[http://dx.doi.org/10.1016/j.bmc.2019.01.033] [PMID: 30728107]
[http://dx.doi.org/10.1093/nass/1.1.121] [PMID: 12836294]
[http://dx.doi.org/10.1021/ja027131f] [PMID: 12392419]
[http://dx.doi.org/10.1016/j.ejmech.2016.08.047] [PMID: 27592390]
[http://dx.doi.org/10.1002/ejoc.200300682]
[http://dx.doi.org/10.1002/ejoc.200500520]
[http://dx.doi.org/10.1016/j.bmc.2021.116369] [PMID: 34482229]
[http://dx.doi.org/10.1039/C6CC04089F] [PMID: 27377058]
[http://dx.doi.org/10.1016/j.tetlet.2004.11.044]
[http://dx.doi.org/10.1055/s-2005-872109]
[http://dx.doi.org/10.1021/jo00110a060]
[http://dx.doi.org/10.1021/acs.orglett.5b01268] [PMID: 26035233]
[http://dx.doi.org/10.1002/chem.201803930] [PMID: 30242922]
[http://dx.doi.org/10.1016/j.bmc.2013.02.032] [PMID: 23490157]
[http://dx.doi.org/10.1016/j.tetlet.2007.08.103]
[http://dx.doi.org/10.1002/anie.200602790] [PMID: 17001726]
[http://dx.doi.org/10.1002/cmdc.201200157] [PMID: 22777958]
[http://dx.doi.org/10.1016/j.bmcl.2012.10.009] [PMID: 23103095]
[http://dx.doi.org/10.1021/acschembio.8b00250] [PMID: 29897729]
[http://dx.doi.org/10.1016/j.bbagrm.2014.12.007] [PMID: 25497381]
[http://dx.doi.org/10.1021/jm400793v] [PMID: 24261904]
[http://dx.doi.org/10.1016/j.ejmech.2022.114501] [PMID: 35716517]
[http://dx.doi.org/10.1016/j.ejmech.2021.113838] [PMID: 34571173]
[http://dx.doi.org/10.1016/j.ejmech.2013.04.046] [PMID: 23708012]
[http://dx.doi.org/10.1039/C5MD00515A]
[PMID: 16573260]
[http://dx.doi.org/10.1016/j.clindermatol.2014.12.001] [PMID: 25889130]
[http://dx.doi.org/10.1016/j.cell.2022.04.025]
[http://dx.doi.org/10.1126/science.179.4080.1324] [PMID: 17835939]
[http://dx.doi.org/10.1080/10408390601062021] [PMID: 18274964]
[http://dx.doi.org/10.1016/0006-2952(82)90240-4] [PMID: 7059356]
[http://dx.doi.org/10.1042/bj2330719] [PMID: 3707519]
[http://dx.doi.org/10.1021/jo950451f] [PMID: 11667082]
[http://dx.doi.org/10.1016/j.bmcl.2013.04.088] [PMID: 23726343]
[http://dx.doi.org/10.1111/bph.13727] [PMID: 28127755]
[http://dx.doi.org/10.1021/jm00103a010] [PMID: 1361582]
[http://dx.doi.org/10.1021/jm970504g] [PMID: 9457246]
[http://dx.doi.org/10.1358/dof.2002.027.07.685790]
[http://dx.doi.org/10.1021/jm00022a007] [PMID: 7473569]
[http://dx.doi.org/10.1016/j.bmcl.2007.09.039] [PMID: 17910915]
[http://dx.doi.org/10.1007/s00726-002-0402-9] [PMID: 12707812]
[http://dx.doi.org/10.1016/j.bmcl.2008.06.038] [PMID: 18585912]
[http://dx.doi.org/10.1016/S0960-894X(02)00075-6] [PMID: 11909715]
[http://dx.doi.org/10.1021/jm00151a007] [PMID: 3941412]
[http://dx.doi.org/10.1111/j.1365-2036.1989.tb00217.x] [PMID: 2577694]
[http://dx.doi.org/10.1111/j.1365-2036.1989.tb00248.x] [PMID: 2577500]
[PMID: 1979811]
[http://dx.doi.org/10.1248/bpb1978.14.285] [PMID: 1686058]
[http://dx.doi.org/10.1254/jjp.57.13] [PMID: 1686920]
[http://dx.doi.org/10.1016/0014-2999(95)00512-9] [PMID: 8788415]
[http://dx.doi.org/10.1016/0960-894X(96)00313-7]
[http://dx.doi.org/10.1016/S0006-2952(97)00416-4] [PMID: 9448737]
[http://dx.doi.org/10.1097/MOH.0000000000000476] [PMID: 30407218]
[http://dx.doi.org/10.3389/fimmu.2012.00263] [PMID: 22936934]
[http://dx.doi.org/10.21037/tcr.2016.10.06]
[http://dx.doi.org/10.1016/j.bmcl.2006.04.082] [PMID: 16697193]
[http://dx.doi.org/10.1124/jpet.106.118927] [PMID: 17496166]
[http://dx.doi.org/10.1016/j.bmcl.2009.01.033] [PMID: 19196511]
[http://dx.doi.org/10.1039/C8RA01806E] [PMID: 35541503]
[http://dx.doi.org/10.1016/j.bmcl.2006.12.067] [PMID: 17236763]
[http://dx.doi.org/10.2174/156802610791561246] [PMID: 20536426]
[http://dx.doi.org/10.1021/acs.oprd.5b00072]
[http://dx.doi.org/10.1016/j.bmcl.2009.08.014] [PMID: 19713110]
[http://dx.doi.org/10.1016/j.bmcl.2005.06.077] [PMID: 16054360]
[http://dx.doi.org/10.1016/j.bmcl.2019.08.006] [PMID: 31416666]
[http://dx.doi.org/10.1001/jamadermatol.2017.0725] [PMID: 28538997]
[http://dx.doi.org/10.1002/iid3.241] [PMID: 30756512]
[http://dx.doi.org/10.1016/j.jaad.2020.04.021] [PMID: 32289388]
[http://dx.doi.org/10.1016/S0140-6736(06)69157-5] [PMID: 16890836]
[http://dx.doi.org/10.1371/journal.pone.0178293] [PMID: 28542584]
[PMID: 30165415]
[http://dx.doi.org/10.1086/521624] [PMID: 17955436]
[http://dx.doi.org/10.2165/11633630-000000000-00000] [PMID: 22686620]
[http://dx.doi.org/10.1111/pde.12387] [PMID: 25040421]
[http://dx.doi.org/10.1111/dth.14726] [PMID: 33377267]
[http://dx.doi.org/10.1021/acs.jmedchem.2c00227] [PMID: 35612311]
[http://dx.doi.org/10.1128/AAC.00445-19] [PMID: 31358590]
[http://dx.doi.org/10.1016/S1473-3099(20)30770-2] [PMID: 33587897]
[PMID: 25678771]
[http://dx.doi.org/10.1016/j.jgar.2021.02.017] [PMID: 33684606]
[http://dx.doi.org/10.2174/1568026621666210913122346] [PMID: 34517802]
[http://dx.doi.org/10.1021/acs.jmedchem.6b01358] [PMID: 28075132]
[http://dx.doi.org/10.1016/j.ejmech.2020.112538] [PMID: 32927218]
[http://dx.doi.org/10.1039/b610745a] [PMID: 17047870]
[http://dx.doi.org/10.3762/bjoc.6.90] [PMID: 20978621]
[http://dx.doi.org/10.1002/cbic.201000774] [PMID: 21472956]
[http://dx.doi.org/10.1128/JB.01103-12] [PMID: 22843845]
[http://dx.doi.org/10.1021/acs.jmedchem.5b00050] [PMID: 25798859]
[http://dx.doi.org/10.3389/fcell.2020.576946] [PMID: 33117804]
[http://dx.doi.org/10.1038/sj.onc.1210610] [PMID: 17694083]
[http://dx.doi.org/10.1016/j.bmcl.2006.06.090] [PMID: 16870438]
[http://dx.doi.org/10.1016/j.bmcl.2018.06.029] [PMID: 30122227]
[http://dx.doi.org/10.1074/jbc.M113.490706] [PMID: 23897821]
[http://dx.doi.org/10.1021/acs.jmedchem.7b01457] [PMID: 29251920]
[http://dx.doi.org/10.1124/dmd.113.056176] [PMID: 24492893]
[http://dx.doi.org/10.1016/j.bcp.2021.114677] [PMID: 34265280]
[http://dx.doi.org/10.1200/JCO.2000.18.5.1135] [PMID: 10694567]
[http://dx.doi.org/10.1021/jo0517848] [PMID: 16356002]
[http://dx.doi.org/10.1111/iep.12344] [PMID: 32219922]
[http://dx.doi.org/10.1172/JCI115742] [PMID: 1569188]
[http://dx.doi.org/10.1042/BJ20151072] [PMID: 26657033]
[http://dx.doi.org/10.1016/j.bcp.2019.02.034] [PMID: 30826327]
[http://dx.doi.org/10.1016/j.bmcl.2008.08.116] [PMID: 19932024]
[http://dx.doi.org/10.1021/cr040478b] [PMID: 16464006]
[http://dx.doi.org/10.1186/s41021-016-0037-9] [PMID: 27350828]
[http://dx.doi.org/10.1074/jbc.M112.367243] [PMID: 22692201]
[http://dx.doi.org/10.1016/j.dnarep.2020.102941] [PMID: 32866775]
[http://dx.doi.org/10.1093/nar/gkv1256] [PMID: 26582912]
[http://dx.doi.org/10.1002/slct.201803375] [PMID: 31414040]
[http://dx.doi.org/10.1080/13543776.2019.1629419] [PMID: 31172829]
[http://dx.doi.org/10.3390/metabo8010019] [PMID: 29495652]
[http://dx.doi.org/10.1080/17460441.2020.1743676] [PMID: 32208982]
[http://dx.doi.org/10.3390/ijms23147685] [PMID: 35887037]
[http://dx.doi.org/10.1016/j.bmc.2009.03.041] [PMID: 19364658]
[http://dx.doi.org/10.1074/jbc.C200418200] [PMID: 12171911]
[http://dx.doi.org/10.1002/cbic.201402714] [PMID: 25940742]
[http://dx.doi.org/10.1021/jm3010338] [PMID: 23088608]
[http://dx.doi.org/10.1021/jo9614147]
[http://dx.doi.org/10.1021/jo035546t] [PMID: 15049622]
[http://dx.doi.org/10.1007/BF00702841]
[http://dx.doi.org/10.2174/1570179412666150710182456]
[http://dx.doi.org/10.1016/S0040-4039(00)86831-8]
[http://dx.doi.org/10.1002/1521-3765(20020415)8:8<1804:AID-CHEM1804>3.0.CO;2-C] [PMID: 11933108]
[http://dx.doi.org/10.1002/1521-3773(20010504)40:9<1779:AID-ANIE17790>3.0.CO;2-6] [PMID: 11353510]
[http://dx.doi.org/10.1107/S0108270195011887]
[http://dx.doi.org/10.1039/b100020i]
[http://dx.doi.org/10.1039/B312545A] [PMID: 14765252]
[http://dx.doi.org/10.1016/j.comptc.2011.06.024]
[http://dx.doi.org/10.1021/j100528a010]
[http://dx.doi.org/10.1021/j100588a009]
[http://dx.doi.org/10.1039/C6CE00308G]
[http://dx.doi.org/10.1039/b104386m] [PMID: 12240385]
[http://dx.doi.org/10.1039/B810216N] [PMID: 19122914]
[http://dx.doi.org/10.1039/B610408H] [PMID: 17136251]
[http://dx.doi.org/10.1063/1.4813500] [PMID: 23901998]
[http://dx.doi.org/10.1080/00150193.2017.1282758]
[http://dx.doi.org/10.1002/adfm.201705463]
[http://dx.doi.org/10.1021/nl500026j] [PMID: 24548267]
[http://dx.doi.org/10.1016/j.jpowsour.2013.10.131]
[http://dx.doi.org/10.3109/14756369309040767]
[http://dx.doi.org/10.1080/03086647608078939]
[http://dx.doi.org/10.1039/C7OB00441A] [PMID: 28272644]
[http://dx.doi.org/10.1039/C4SC01629G] [PMID: 26146535]
[http://dx.doi.org/10.1002/anie.201207535] [PMID: 23283851]
[http://dx.doi.org/10.1039/b926164h] [PMID: 20820462]
[http://dx.doi.org/10.1021/acsami.8b06664] [PMID: 30221925]
[http://dx.doi.org/10.1016/S0040-4020(01)82926-4]
[http://dx.doi.org/10.1002/jlac.19626570118]
[http://dx.doi.org/10.1016/j.dyepig.2007.10.006]
[http://dx.doi.org/10.1039/C7CC05196D] [PMID: 28828431]
[http://dx.doi.org/10.1016/j.biomaterials.2016.04.041] [PMID: 27177219]
[http://dx.doi.org/10.1093/annonc/mdl104] [PMID: 16740598]
[http://dx.doi.org/10.1016/j.biomaterials.2017.03.009] [PMID: 28324863]
[http://dx.doi.org/10.1021/acsanm.8b00195] [PMID: 30506043]
[http://dx.doi.org/10.1039/C5CC08317F] [PMID: 26502996]
[http://dx.doi.org/10.1139/v91-079]
[http://dx.doi.org/10.1002/kin.550260105]
[http://dx.doi.org/10.1016/j.tiv.2006.01.009] [PMID: 16504460]
[http://dx.doi.org/10.1021/ja304199x] [PMID: 22881120]
[http://dx.doi.org/10.1021/acs.chemmater.5b01717]
[http://dx.doi.org/10.1021/ja0021417] [PMID: 11457287]
[http://dx.doi.org/10.1039/C8CC06317F] [PMID: 30246824]
[http://dx.doi.org/10.1021/acsnano.7b09177] [PMID: 29617114]
[http://dx.doi.org/10.1016/0026-265X(72)90038-0]
[http://dx.doi.org/10.1002/1521-3749(200211)628:11<2259:AID-ZAAC2259>3.0.CO;2-C]
[http://dx.doi.org/10.1002/anie.200460278] [PMID: 15340955]
[PMID: 13723839]
[PMID: 13750246]
[PMID: 5585302]
[http://dx.doi.org/10.1254/jjp.18.312] [PMID: 5304400]
[http://dx.doi.org/10.1016/0302-4598(80)87009-7]
[http://dx.doi.org/10.1016/0891-5849(95)02179-5] [PMID: 8721612]
[http://dx.doi.org/10.1272/jnms1923.37.310] [PMID: 5478470]
[http://dx.doi.org/10.1016/0014-5793(79)80539-6] [PMID: 499526]
[http://dx.doi.org/10.1039/B107317F]
[http://dx.doi.org/10.1021/j100507a006]
[PMID: 24061240]
[http://dx.doi.org/10.1002/chem.201303190] [PMID: 24123324]
[http://dx.doi.org/10.1002/1521-3765(20020118)8:2<433:AID-CHEM433>3.0.CO;2-T] [PMID: 11843155]
[http://dx.doi.org/10.1107/S160053680400529X]
[http://dx.doi.org/10.1016/0166-1280(95)04279-F]
[http://dx.doi.org/10.1016/0022-2860(71)87065-5]
[http://dx.doi.org/10.1016/j.tet.2010.09.064]
[PMID: 5616568]