摘要
不同尾部与众所周知的碳酸酐酶(CA)药效团的连接导致了几种新的CA抑制剂(CAI)的开发。 这种“尾巴”的一个非常好的例子是碳水化合物,它代表了广泛的化学型,从而导致大量新的CAI。 在过去几年中,已经制备了几种含有不同支架的C-肉桂酰基糖苷并作为碳酸酐酶抑制剂进行了研究,表明它们中的一些是非常有效和选择性的CAI。 本文将回顾这些Cglycosides的合成和生物活性的最新发展。
关键词: 碳水化合物,酶抑制,抗肿瘤,结核,杂环,CAI,碳酸酐酶。
[1]
Supuran, C.T. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat. Rev. Drug Discov., 2008, 7(2), 168-181.
[http://dx.doi.org/10.1038/nrd2467] [PMID: 18167490]
[http://dx.doi.org/10.1038/nrd2467] [PMID: 18167490]
[2]
Supuran, C.T. Carbonic anhydrase inhibitors and activators for novel therapeutic applications. Future Med. Chem., 2011, 3(9), 1165-1180.
[http://dx.doi.org/10.4155/fmc.11.69] [PMID: 21806379]
[http://dx.doi.org/10.4155/fmc.11.69] [PMID: 21806379]
[3]
(a)Capasso, C.; Supuran, C.T. Inhibition of bacterial carbonic anhydrases as a novel approach to escape drug resistance. Curr. Top. Med. Chem., 2017, 17(11), 1237-1248.
[http://dx.doi.org/10.2174/1568026617666170104101058] [PMID: 28049405]
(b)Capasso, C.; Supuran, C.T. Bacterial, fungal and protozoan carbonic anhydrases as drug targets. Expert Opin. Ther. Targets, 2015, 19(12), 1689-1704.
[http://dx.doi.org/10.1517/14728222.2015.1067685] [PMID: 26235676]
(c)Capasso, C.; Supuran, C.T. Anti-infective carbonic anhydrase inhibitors: a patent and literature review. Expert Opin. Ther. Pat., 2013, 23(6), 693-704.
[http://dx.doi.org/10.1517/13543776.2013.778245] [PMID: 23488877]
[http://dx.doi.org/10.2174/1568026617666170104101058] [PMID: 28049405]
(b)Capasso, C.; Supuran, C.T. Bacterial, fungal and protozoan carbonic anhydrases as drug targets. Expert Opin. Ther. Targets, 2015, 19(12), 1689-1704.
[http://dx.doi.org/10.1517/14728222.2015.1067685] [PMID: 26235676]
(c)Capasso, C.; Supuran, C.T. Anti-infective carbonic anhydrase inhibitors: a patent and literature review. Expert Opin. Ther. Pat., 2013, 23(6), 693-704.
[http://dx.doi.org/10.1517/13543776.2013.778245] [PMID: 23488877]
[4]
Winum, J.Y.; Poulsen, S.A.; Supuran, C.T. Therapeutic applications of glycosidic carbonic anhydrase inhibitors. Med. Res. Rev., 2009, 29(3), 419-435.
[http://dx.doi.org/10.1002/med.20141] [PMID: 19058143]
[http://dx.doi.org/10.1002/med.20141] [PMID: 19058143]
[5]
Ernst, B.; Magnani, J.L. From carbohydrate leads to glycomimetic drugs. Nat. Rev. Drug Discov., 2009, 8(8), 661-677.
[http://dx.doi.org/10.1038/nrd2852] [PMID: 19629075]
[http://dx.doi.org/10.1038/nrd2852] [PMID: 19629075]
[6]
(a)Liao, H.; Ma, J.; Yao, H.; Liu, X.W. Recent progress of C-glycosylation methods in the total synthesis of natural products and pharmaceuticals. Org. Biomol. Chem., 2018, 16(11), 1791-1806.
[http://dx.doi.org/10.1039/C8OB00032H] [PMID: 29464265]
(b)Sadraei, S.I.; Reynolds, M.R.; Trant, J.F. The synthesis and biological characterization of acetal-free mimics of the tumor-associated carbohydrate antigens. Adv. Carbohydr. Chem. Biochem., 2017, 74, 137-237.
[http://dx.doi.org/10.1016/bs.accb.2017.10.003] [PMID: 29173726]
(c)Yang, Y.; Yu, B. Recent Advances in the chemical synthesis of C-glycosides. Chem. Rev., 2017, 117(19), 12281-12356.
[http://dx.doi.org/10.1021/acs.chemrev.7b00234] [PMID: 28915018]
(d)Koester, D.C.; Holkenbrink, A.; Werz, D.B. Recent advances in the synthesis of carbohydrate mimetics. Synthesis, 2010, 19, 3217-3242.
[http://dx.doi.org/10.1039/C8OB00032H] [PMID: 29464265]
(b)Sadraei, S.I.; Reynolds, M.R.; Trant, J.F. The synthesis and biological characterization of acetal-free mimics of the tumor-associated carbohydrate antigens. Adv. Carbohydr. Chem. Biochem., 2017, 74, 137-237.
[http://dx.doi.org/10.1016/bs.accb.2017.10.003] [PMID: 29173726]
(c)Yang, Y.; Yu, B. Recent Advances in the chemical synthesis of C-glycosides. Chem. Rev., 2017, 117(19), 12281-12356.
[http://dx.doi.org/10.1021/acs.chemrev.7b00234] [PMID: 28915018]
(d)Koester, D.C.; Holkenbrink, A.; Werz, D.B. Recent advances in the synthesis of carbohydrate mimetics. Synthesis, 2010, 19, 3217-3242.
[7]
Sattin, S.; Bernardi, A. Design and synthesis of glycomimetics. Carbohydr. Chem., 2016, 41, 1-25.
[8]
Asensio, J.L.; Cañada, F.J.; Cheng, X.; Khan, N.; Mootoo, D.R.; Jiménez-Barbero, J. Conformational differences between O- and C-glycosides: the α-O-man-(1-->1)-β-Gal/α-C-Man-(1-->1)-β-Gal case-a decisive demonstration of the importance of the exo-anomeric effect on the conformation of glycosides. Chemistry, 2000, 6(6), 1035-1041.
[http://dx.doi.org/10.1002/(SICI)1521-3765(20000317)6:6<1035:AID-CHEM1035>3.0.CO;2-G] [PMID: 10785824]
[http://dx.doi.org/10.1002/(SICI)1521-3765(20000317)6:6<1035:AID-CHEM1035>3.0.CO;2-G] [PMID: 10785824]
[9]
Bisht, S.S.; Pandey, J.; Sharma, A.; Tripathi, R.P. Aldol reaction of β-C-glycosylic ketones: synthesis of C-(E)-cinnamoyl glycosylic compounds as precursors for new biologically active C-glycosides. Carbohydr. Res., 2008, 343(9), 1399-1406.
[http://dx.doi.org/10.1016/j.carres.2008.04.021] [PMID: 18474364]
[http://dx.doi.org/10.1016/j.carres.2008.04.021] [PMID: 18474364]
[10]
Roy, P.; Dhara, D.; Parida, P.K.; Kar, R.K.; Bhunia, A.; Jana, K.; Sinha Babu, S.P.; Misra, A.K. C-cinnamoyl glycosides as a new class of anti-filarial agents. Eur. J. Med. Chem., 2016, 114, 308-317.
[http://dx.doi.org/10.1016/j.ejmech.2016.03.001] [PMID: 27015610]
[http://dx.doi.org/10.1016/j.ejmech.2016.03.001] [PMID: 27015610]
[11]
Mugunthan, G.; Ramakrishna, K.; Sriram, D.; Yogeeswari, P.; Ravindranathan Kartha, K.P. Synthesis and screening of (E)-1-(β-D-galactopyranosyl)-4-(aryl)but-3-ene-2-one against Mycobacterium tuberculosis. Bioorg. Med. Chem. Lett., 2011, 21(13), 3947-3950.
[http://dx.doi.org/10.1016/j.bmcl.2011.05.037] [PMID: 21641797]
[http://dx.doi.org/10.1016/j.bmcl.2011.05.037] [PMID: 21641797]
[12]
(a)Bragnier, N.; Scherrmann, M.C. One-step synthesis of β-C-glycosidic ketones in aqueous media: the case of 2-acetamido sugars. Synthesis, 2005, 5, 814-818.
(b)Wang, J.; Li, Q.; Ge, Z.; Li, R. A versatile and convenient route to ketone C-pyranosides and ketone C-furanosides from unprotected sugars. Tetrahedron, 2012, 68(4), 1315-1320.
[http://dx.doi.org/10.1016/j.tet.2011.11.029]
(b)Wang, J.; Li, Q.; Ge, Z.; Li, R. A versatile and convenient route to ketone C-pyranosides and ketone C-furanosides from unprotected sugars. Tetrahedron, 2012, 68(4), 1315-1320.
[http://dx.doi.org/10.1016/j.tet.2011.11.029]
[13]
Bisht, S.S.; Pandey, J.; Sharma, A.; Tripathi, R.P. Aldol reaction of β-C-glycosylic ketones: synthesis of C-(E)-cinnamoyl glycosylic compounds as precursors for new biologically active C-glycosides. Carbohydr. Res., 2008, 343(9), 1399-1406.
[http://dx.doi.org/10.1016/j.carres.2008.04.021] [PMID: 18474364]
[http://dx.doi.org/10.1016/j.carres.2008.04.021] [PMID: 18474364]
[14]
Supuran, C.T. Carbonic anhydrase inhibitors. Bioorg. Med. Chem. Lett., 2010, 20(12), 3467-3474.
[http://dx.doi.org/10.1016/j.bmcl.2010.05.009] [PMID: 20529676]
[http://dx.doi.org/10.1016/j.bmcl.2010.05.009] [PMID: 20529676]
[15]
(a)Maresca, A.; Temperini, C.; Vu, H.; Pham, N.B.; Poulsen, S.A.; Scozzafava, A.; Quinn, R.J.; Supuran, C.T. Non-zinc mediated inhibition of carbonic anhydrases: coumarins are a new class of suicide inhibitors. J. Am. Chem. Soc., 2009, 131(8), 3057-3062.
[http://dx.doi.org/10.1021/ja809683v] [PMID: 19206230]
(b)Maresca, A.; Temperini, C.; Pochet, L.; Masereel, B.; Scozzafava, A.; Supuran, C.T. Deciphering the mechanism of carbonic anhydrase inhibition with coumarins and thiocoumarins. J. Med. Chem., 2010, 53(1), 335-344.
[http://dx.doi.org/10.1021/jm901287j] [PMID: 19911821]
(c)Temperini, C.; Innocenti, A.; Scozzafava, A.; Parkkila, S.; Supuran, C.T. The coumarin-binding site in carbonic anhydrase accommodates structurally diverse inhibitors: the antiepileptic lacosamide as an example and lead molecule for novel classes of carbonic anhydrase inhibitors. J. Med. Chem., 2010, 53(2), 850-854.
[http://dx.doi.org/10.1021/jm901524f] [PMID: 20028100]
(d)Maresca, A.; Supuran, C.T. Coumarins incorporating hydroxy- and chloro-moieties selectively inhibit the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII over the cytosolic ones I and II. Bioorg. Med. Chem. Lett., 2010, 20(15), 4511-4514.
[http://dx.doi.org/10.1016/j.bmcl.2010.06.040] [PMID: 20580555]
[http://dx.doi.org/10.1021/ja809683v] [PMID: 19206230]
(b)Maresca, A.; Temperini, C.; Pochet, L.; Masereel, B.; Scozzafava, A.; Supuran, C.T. Deciphering the mechanism of carbonic anhydrase inhibition with coumarins and thiocoumarins. J. Med. Chem., 2010, 53(1), 335-344.
[http://dx.doi.org/10.1021/jm901287j] [PMID: 19911821]
(c)Temperini, C.; Innocenti, A.; Scozzafava, A.; Parkkila, S.; Supuran, C.T. The coumarin-binding site in carbonic anhydrase accommodates structurally diverse inhibitors: the antiepileptic lacosamide as an example and lead molecule for novel classes of carbonic anhydrase inhibitors. J. Med. Chem., 2010, 53(2), 850-854.
[http://dx.doi.org/10.1021/jm901524f] [PMID: 20028100]
(d)Maresca, A.; Supuran, C.T. Coumarins incorporating hydroxy- and chloro-moieties selectively inhibit the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII over the cytosolic ones I and II. Bioorg. Med. Chem. Lett., 2010, 20(15), 4511-4514.
[http://dx.doi.org/10.1016/j.bmcl.2010.06.040] [PMID: 20580555]
[16]
Carta, F.; Temperini, C.; Innocenti, A.; Scozzafava, A.; Kaila, K.; Supuran, C.T. Polyamines inhibit carbonic anhydrases by anchoring to the zinc-coordinated water molecule. J. Med. Chem., 2010, 53(15), 5511-5522.
[http://dx.doi.org/10.1021/jm1003667] [PMID: 20590092]
[http://dx.doi.org/10.1021/jm1003667] [PMID: 20590092]
[17]
(a)Innocenti, A.; Vullo, D.; Scozzafava, A.; Supuran, C.T. Carbonic anhydrase inhibitors: interactions of phenols with the 12 catalytically active mammalian isoforms (CA I-XIV). Bioorg. Med. Chem. Lett., 2008, 18(5), 1583-1587.
[http://dx.doi.org/10.1016/j.bmcl.2008.01.077] [PMID: 18242985]
(b)Innocenti, A.; Hilvo, M.; Scozzafava, A.; Parkkila, S.; Supuran, C.T. Carbonic anhydrase inhibitors: Inhibition of the new membrane-associated isoform XV with phenols. Bioorg. Med. Chem. Lett., 2008, 18(12), 3593-3596.
[http://dx.doi.org/10.1016/j.bmcl.2008.04.077] [PMID: 18501600]
(c)Innocenti, A.; Vullo, D.; Scozzafava, A.; Supuran, C.T. Carbonic anhydrase inhibitors: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg. Med. Chem., 2008, 16(15), 7424-7428.
[http://dx.doi.org/10.1016/j.bmc.2008.06.013] [PMID: 18579385]
(d)Bayram, E.; Senturk, M.; Kufrevioglu, O.I.; Supuran, C.T. In vitro inhibition of salicylic acid derivatives on human cytosolic carbonic anhydrase isozymes I and II. Bioorg. Med. Chem., 2008, 16(20), 9101-9105.
[http://dx.doi.org/10.1016/j.bmc.2008.09.028] [PMID: 18819808]
(e)Oztürk Sarikaya, S.B.; Topal, F.; Sentürk, M.; Gülçin, I.; Supuran, C.T. In vitro inhibition of α-carbonic anhydrase isozymes by some phenolic compounds. Bioorg. Med. Chem. Lett., 2011, 21(14), 4259-4262.
[http://dx.doi.org/10.1016/j.bmcl.2011.05.071] [PMID: 21669522]
[http://dx.doi.org/10.1016/j.bmcl.2008.01.077] [PMID: 18242985]
(b)Innocenti, A.; Hilvo, M.; Scozzafava, A.; Parkkila, S.; Supuran, C.T. Carbonic anhydrase inhibitors: Inhibition of the new membrane-associated isoform XV with phenols. Bioorg. Med. Chem. Lett., 2008, 18(12), 3593-3596.
[http://dx.doi.org/10.1016/j.bmcl.2008.04.077] [PMID: 18501600]
(c)Innocenti, A.; Vullo, D.; Scozzafava, A.; Supuran, C.T. Carbonic anhydrase inhibitors: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg. Med. Chem., 2008, 16(15), 7424-7428.
[http://dx.doi.org/10.1016/j.bmc.2008.06.013] [PMID: 18579385]
(d)Bayram, E.; Senturk, M.; Kufrevioglu, O.I.; Supuran, C.T. In vitro inhibition of salicylic acid derivatives on human cytosolic carbonic anhydrase isozymes I and II. Bioorg. Med. Chem., 2008, 16(20), 9101-9105.
[http://dx.doi.org/10.1016/j.bmc.2008.09.028] [PMID: 18819808]
(e)Oztürk Sarikaya, S.B.; Topal, F.; Sentürk, M.; Gülçin, I.; Supuran, C.T. In vitro inhibition of α-carbonic anhydrase isozymes by some phenolic compounds. Bioorg. Med. Chem. Lett., 2011, 21(14), 4259-4262.
[http://dx.doi.org/10.1016/j.bmcl.2011.05.071] [PMID: 21669522]
[18]
Riafrecha, L.E.; Rodríguez, O.M.; Vullo, D.; Supuran, C.T.; Colinas, P.A. Synthesis of C-cinnamoyl glycosides and their inhibitory activity against mammalian carbonic anhydrases. Bioorg. Med. Chem., 2013, 21(6), 1489-1494.
[http://dx.doi.org/10.1016/j.bmc.2012.09.002] [PMID: 23010455]
[http://dx.doi.org/10.1016/j.bmc.2012.09.002] [PMID: 23010455]
[19]
Buchieri, M.V.; Riafrecha, L.E.; Rodríguez, O.M.; Vullo, D.; Morbidoni, H.R.; Supuran, C.T.; Colinas, P.A. Inhibition of the β-carbonic anhydrases from mycobacterium tuberculosis with C-cinnamoyl glycosides: identification of the first inhibitor with anti-mycobacterial activity. Bioorg. Med. Chem. Lett., 2013, 23(3), 740-743.
[http://dx.doi.org/10.1016/j.bmcl.2012.11.085] [PMID: 23265903]
[http://dx.doi.org/10.1016/j.bmcl.2012.11.085] [PMID: 23265903]
[20]
Durdagi, S.; Şentürk, M.; Ekinci, D.; Balaydın, H.T.; Göksu, S.; Küfrevioğlu, Ö.İ.; Innocenti, A.; Scozzafava, A.; Supuran, C.T. Kinetic and docking studies of phenol-based inhibitors of carbonic anhydrase isoforms I, II, IX and XII evidence a new binding mode within the enzyme active site. Bioorg. Med. Chem., 2011, 19(4), 1381-1389.
[http://dx.doi.org/10.1016/j.bmc.2011.01.016] [PMID: 21282059]
[http://dx.doi.org/10.1016/j.bmc.2011.01.016] [PMID: 21282059]
[21]
Riafrecha, L.E.; Rodríguez, O.M.; Vullo, D.; Supuran, C.T.; Colinas, P.A. Attachment of carbohydrates to methoxyaryl moieties leads to highly selective inhibitors of the cancer associated carbonic anhydrase isoforms IX and XII. Bioorg. Med. Chem., 2014, 22(19), 5308-5314.
[http://dx.doi.org/10.1016/j.bmc.2014.07.052] [PMID: 25156300]
[http://dx.doi.org/10.1016/j.bmc.2014.07.052] [PMID: 25156300]
[22]
Alterio, V.; Di Fiore, A.; D’Ambrosio, K.; Supuran, C.T.; De Simone, G. Multiple binding modes of inhibitors to carbonic anhydrases: how to design specific drugs targeting 15 different isoforms? Chem. Rev., 2012, 112(8), 4421-4468.
[http://dx.doi.org/10.1021/cr200176r] [PMID: 22607219]
[http://dx.doi.org/10.1021/cr200176r] [PMID: 22607219]
[23]
Riafrecha, L.E.; Vullo, D.; Ouahrani-Bettache, S.; Köhler, S.; Dumy, P.; Winum, J.Y.; Supuran, C.T.; Colinas, P.A. Inhibition of β-carbonic anhydrases from Brucella suis with C-cinnamoyl glycosides incorporating the phenol moiety. J. Enzyme Inhib. Med. Chem., 2015, 30(6), 1017-1020.
[http://dx.doi.org/10.3109/14756366.2014.986120] [PMID: 25676329]
[http://dx.doi.org/10.3109/14756366.2014.986120] [PMID: 25676329]
[24]
Riafrecha, L.E.; Bua, S.; Supuran, C.T.; Colinas, P.A. Improving the carbonic anhydrase inhibition profile of the sulfamoylphenyl pharmacophore by attachment of carbohydrate moieties. Bioorg. Chem., 2018, 76, 61-66.
[http://dx.doi.org/10.1016/j.bioorg.2017.10.020] [PMID: 29136525]
[http://dx.doi.org/10.1016/j.bioorg.2017.10.020] [PMID: 29136525]
[25]
Llantén, H.; Barata-Vallejo, S.; Postigo, A.; Colinas, P.A. Synthesis of C-glycosylmethyl isoxazoles via aerobic oxidation of ketoximes catalyzed by TEMPO. Tetrahedron Lett., 2017, 58(15), 1507-1511.
[http://dx.doi.org/10.1016/j.tetlet.2017.03.005]
[http://dx.doi.org/10.1016/j.tetlet.2017.03.005]