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Review Article

果糖-1,6-双磷酸酶抑制剂：近期（2000-2017年）进展和结构-活性关系研究的回顾

卷 26, 期 29, 2019

页: [5542 - 5563] 页: 22

弟呕挨: 10.2174/0929867325666180831133734

价格: $65

摘要

糖尿病，通常称为糖尿病，是全球第八大死亡原因。 截至2015年，估计全世界约有4.15亿人患有糖尿病，其中2型糖尿病是最常见的，约占所有患病率上升的诊断病例的90-95％。 1，6-二磷酸果糖酶是最近发现的治疗这种慢性疾病的重要治疗靶标之一。 在此重点综述中，我们重点介绍了自2000年以来发现和开发的不同果糖1,6-双磷酸酶抑制剂的最新进展和结构-活性关系研究。

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« Previous Next »
[1]
WHO report on diabetes. Available at: http://www.who.int/diabetes/action_online/basics/en [Access date: September 24, 2019].
[2]
Danaei, G.; Finucane, M.M.; Lu, Y.; Singh, G.M.; Cowan, M.J.; Paciorek, C.J.; Lin, J.K.; Farzadfar, F.; Khang, Y.H.; Stevens, G.A.; Rao, M.; Ali, M.K.; Riley, L.M.; Robinson, C.A.; Ezzati, M. National, regional, and global trends in fasting plasma glucose and diabetes prevalence since 1980: systematic analysis of health examination surveys and epidemiological studies with 370 country-years and 2·7 million participants. Lancet, 2011, 378(9785), 31-40.
[http://dx.doi.org/10.1016/S0140-6736(11)60679-X] [PMID: 21705069]
[3]
WHO report on top 10 causes of mortality. Available at: http://www.who.int/mediacentre/factsheets/fs310/en/ [Access date: June , 2018].
[4]
Engelgau, M.M.; Narayan, K.M.V.; Herman, W.H. Screening for type 2 diabetes. Diabetes Care, 2000, 23(10), 1563-1580.
[http://dx.doi.org/10.2337/diacare.23.10.1563] [PMID: 11023153]
[5]
Pilkis, S.J.; Granner, D.K. Molecular physiology of the regulation of hepatic gluconeogenesis and glycolysis. Annu. Rev. Physiol., 1992, 54, 885-909.
[http://dx.doi.org/10.1146/annurev.ph.54.030192.004321] [PMID: 1562196]
[6]
Kaur, R.; Dahiya, L.; Kumar, M. Fructose-1,6-bisphosphatase inhibitors: a new valid approach for management of type 2 diabetes mellitus. Eur. J. Med. Chem., 2017, 141, 473-505.
[http://dx.doi.org/10.1016/j.ejmech.2017.09.029] [PMID: 29055870]
[7]
Dang, Q.; Van Poelje, P.D.; Erion, M.D. The discovery and development of MB07803, a second-generation fructose- 1,6-bisphosphatase inhibitor with im-proved pharmacokinetic properties, as a potential treatment of type 2 diabetes in: New therapeutic strategies for type 2 diabetes: small molecule approaches. In: The Royal Society of Chemistry; 11306-323., 2012; pp. 306-322.
[8]
Barciszewski, J.; Wisniewski, J.; Kolodziejczyk, R.; Jaskolski, M.; Rakus, D.; Dzugaj, A. T-to-R switch of muscle fructose-1,6-bisphosphatase involves fundamental changes of secondary and quaternary structure. Acta Crystallogr. D Struct. Biol., 2016, 72(Pt 4), 536-550.
[http://dx.doi.org/10.1107/S2059798316001765] [PMID: 27050133]
[9]
Van Schaftingen, E.; Jett, M.F.; Hue, L.; Hers, H.G. Control of liver 6-phosphofructokinase by fructose 2,6-bisphosphate and other effectors. Proc. Natl. Acad. Sci. USA, 1981, 78(6), 3483-3486.
[http://dx.doi.org/10.1073/pnas.78.6.3483] [PMID: 6455662]
[10]
Pilkis, S.J.; El-Maghrabi, M.R.; Pilkis, J.; Claus, T. Inhibition of fructose-1,6-bisphosphatase by fructose 2,6-bisphosphate. J. Biol. Chem., 1981, 256(8), 3619-3622.
[PMID: 6260770]
[11]
Pilkis, S.J.; el-Maghrabi, M.R.; Claus, T.H. Hormonal regulation of hepatic gluconeogenesis and glycolysis. Annu. Rev. Biochem., 1988, 57, 755-783.
[http://dx.doi.org/10.1146/annurev.bi.57.070188.003543] [PMID: 3052289]
[12]
Taketa, K.; Pogell, B.M. Allosteric inhibition of rat liver fructose 1,6-diphosphatase by adenosine 5′-monophosphate. J. Biol. Chem., 1965, 240, 651-662.
[PMID: 14275118]
[13]
Ke, H.M.; Liang, J-Y.; Zhang, Y.P.; Lipscomb, W.N. Conformational transition of fructose-1,6-bisphosphatase: structure comparison between the AMP complex (T form) and the fructose 6-phosphate complex (R form). Biochemistry, 1991, 30(18), 4412-4420.
[http://dx.doi.org/10.1021/bi00232a007] [PMID: 1850623]
[14]
Zhang, Y.; Liang, J-Y.; Huang, S.; Lipscomb, W.N. Toward a mechanism for the allosteric transition of pig kidney fructose-1,6-bisphosphatase. J. Mol. Biol., 1994, 244(5), 609-624.
[http://dx.doi.org/10.1006/jmbi.1994.1755] [PMID: 7990142]
[15]
Dang, Q.; Kasibhatla, S. R.; Reddy, K. R.; Erion, M. D.; Reddy, M. R.; Agarwal, A. Preparation of heteroaromatic phosphonates as fructose 1,6-bisphosphatase inhibitors. PCT Pat., WO 2000014095 A1 March 16, 2000.
[16]
Erion, M. D.; Vanpoelje, P. A. A combination of fructose- 1,6-bisphosphatase (FBPase) inhibitors and insulin sensitizers for the treatment of diabetes. PCT Pat., 2000. WO 2000038666 A2 20000706.
[17]
Bookser, B. C.; Dang, Q.; Reddy, K. R. Preparation of arylheterocycle phosphates as antidiabetics and aryl fructose-1,6-bisphosphatase inhibitors. Int. Patent Appl., WO2001066553, 2000.
[18]
Dang, Q.; Kasibhatla, S.R.; Reddy, K.R.; Erion, M.D.; Reddy, M.R.; Agarwal, A. Preparation of heteroaromatic phosphonates as fructose 1,6-bisphosphatase inhibitors. U.S. Patent US 6489476 B1, December 03, 2002.
[19]
Bauer, P.H.; Wright, S.W.; Schnur, R.C. Preparation of 4- phenylaminoquinazoline derivatives as fructose 1,6- bisphosphatase inhibitors. U.S. Patent US 20030144308 A1, July 31, 2007.
[20]
Yoshida, T.; Okuno, A. Fructose 1,6-bisphosphatase inhibitors as preventives for the onset of diabetes. PCT Patent WO 2004009118 A1, January 29, 2004.
[21]
Erion, M.D.; Van Poelje, P.D. Preparation of 2-(5- phosphono)furanyl substituted heteroar-omatic compounds as fructose-1,6- bisphosphatase (FBPase) inhibitors for use in combination with insulin sensitizers for the treatment of diabetes. US Patent, US 6756360 B1, June 29, 2004.
[22]
Yoshida, T.; Okuno, A. fructose 1,6-bisphosphatase (FBPase) inhibitor preventative agents for diabetes mellitus and related Conditions. US Patent, US 20050187194 A1, August 25, 2005.
[23]
Dang, Q.; Kopcho, J.J.; Hecker, S.J.; Ugarkar, B.G. Preparation of thiazole compounds as fructose 1,6- bisphosphatase inhibitors. PCT Patent, WO 2006023515 A2, March 2, 2006.
[24]
Carniato, D.; Arbellot, A.; Moinet, G.; Audet, A.; Botton, G. Preparation of imidazolylmethylbenzoates as fructose- 1,6-bisphosphatase inhibitors. Eur. Pat., EP 1752450 A1, February 14, 2007.
[25]
Gubler, M.; Haap, W.; Hebeisen, P.; Kitas, E.A.; Kuhn, B.; Minder, R.E.; Schott, B.; Wessel, H.P. Preparation of sulfonylureido thiazoles as fructose-1,6-bisphosphatase (FBPase) inhibitors for the treatment of diabetes. PCT Patent, WO 2007137962 A1, December 06, 2007.
[26]
Reddy, R. K.; Erion, M. D.; Dang, Q. Preparation of azabenzimidazole derivatives as prodrug inhibitors of fructose 1,6-bisphosphatase. PCT Patent, WO 2008019309 A, February 14, 2008.
[27]
Botton, G.; Leriche, C.; Arbellot, A.; Audet, A.; Gleitz, J. Preparation of 1H-benzimidazol-5-yl-3,6-dihydro-2H-1,3,4- thiadiazin-2-one derivatives as inhibitors of fructose-1,6- bisphosphatase, and their pharmaceutical compositions for treating diseases associated with insulin resistance syndrome especially diabetes. PCT Patent, WO 2009062576 A2, May 22, 2009.
[28]
Haap, W.; Hebeisen, P.; Kitas, E.A.; Kuhn, B.; Mohr, P.; Wessel, H.P. Preparation of pyridine compounds as fructose- 1,6-bisphosphatase inhibitors for use in treating diseases such as diabetes. PCT Patent, WO 2009068468 A2, June 04, 2009.
[29]
Hebeisen, P.; Kitas, E.A.; Minder, R.E.; Mohr, P.; Wessel, H.P. Preparation of aminothiazole derivatives as fructose- 1,6-bisphosphatase inhibitors for treating diseases such as diabetes. PCT Patent, WO 2009068467 A1, June 04, 2009.
[30]
Kantrowitz, E.R.; Heng, S. Dibenzofuran derivatives as fructose 1,6-biphosphatase inhibitors and their preparation and use in mono and combina-tion therapy of type 2 diabetes. PCT Patent, WO 2010091185 A2. August 12, 2010.
[31]
Li, J.; Tang, J.; Li, J.; He, H.; Gao, L.; Yang, F.; Yang, L.; Yusupu, A. Preparation of 2,5-diaryl-1,3,4-oxadiazole compounds for treating type II diabetes. China Patent, CN 102924399 A, February 13, 2013.
[32]
Wan, J.; Han, X.; Chen, H.; Zhu, H.; Feng, L.; Ren, Y.; Chi, B. Application of nitrostyrene derivatives for inhibiting fruc-tose-1,6-bisphosphatase. China Pat., CN 104146989 A, November 19, 2014.
[33]
Heng, S.; Harris, K.M.; Kantrowitz, E.R. Designing inhibitors against fructose 1,6-bisphosphatase: exploring natural products for novel inhibitor scaffolds. Eur. J. Med. Chem., 2010, 45(4), 1478-1484.
[http://dx.doi.org/10.1016/j.ejmech.2009.12.055] [PMID: 20116906]
[34]
Soberón, M.; Lopez, O.; Miranda, J.; Tabche, M.L.; Morera, C. Genetic evidence for 5-aminoimidazole-4-carboxamide ribonucleotide (AICAR) as a negative effector of cytochrome terminal oxidase cbb3 production in Rhizobium etli. Mol. Gen. Genet., 1997, 254(6), 665-673.
[http://dx.doi.org/10.1007/s004380050464] [PMID: 9202382]
[35]
Dougherty, M.J.; Boyd, J.M.; Downs, D.M. Inhibition of fructose-1,6-bisphosphatase by aminoimidazole carboxamide ribotide prevents growth of Salmonella enterica purH mutants on glycerol. J. Biol. Chem., 2006, 281(45), 33892-33899.
[http://dx.doi.org/10.1074/jbc.M604429200] [PMID: 16987812]
[36]
Wright, S.W.; Hageman, D.L.; McClure, L.D.; Carlo, A.A.; Treadway, J.L.; Mathiowetz, A.M.; Withka, J.M.; Bauer, P.H. Allosteric inhibition of fructose-1,6-bisphosphatase by anilinoquinazolines. Bioorg. Med. Chem. Lett., 2001, 11(1), 17-21.
[http://dx.doi.org/10.1016/S0960-894X(00)00586-2] [PMID: 11140724]
[37]
Wright, S.W.; Carlo, A.A.; Danley, D.E.; Hageman, D.L.; Karam, G.A.; Mansour, M.N.; McClure, L.D.; Pandit, J.; Schulte, G.K.; Treadway, J.L.; Wang, I.K.; Bauer, P.H. 3-(2-carboxyethyl)-4,6-dichloro-1H-indole-2-carboxylic acid: an allosteric inhibitor of fructose-1,6-bisphosphatase at the AMP site. Bioorg. Med. Chem. Lett., 2003, 13(12), 2055-2058.
[http://dx.doi.org/10.1016/S0960-894X(03)00310-X] [PMID: 12781194]
[38]
von Geldern, T.W.; Lai, C.; Gum, R.J.; Daly, M.; Sun, C.; Fry, E.H.; Abad-Zapatero, C. Benzoxazole benzenesulfonamides are novel allosteric inhibitors of fructose-1,6-bisphosphatase with a distinct binding mode. Bioorg. Med. Chem. Lett., 2006, 16(7), 1811-1815.
[http://dx.doi.org/10.1016/j.bmcl.2006.01.015] [PMID: 16442285]
[39]
Zhu, D.W.; Xu, G.J.; Rehse, P.H.; Shi, R.; Zhao, F.K.; Lin, S.X. Crystallization and preliminary crystallographic data of fructose-1,6-bisphosphatase from human muscle. Acta Crystallogr. D Biol. Crystallogr., 2001, 57(Pt 6), 847-849.
[http://dx.doi.org/10.1107/S0907444901004371] [PMID: 11375504]
[40]
Lai, C.; Gum, R.J.; Daly, M.; Fry, E.H.; Hutchins, C.; Abad-Zapatero, C.; von Geldern, T.W. Benzoxazole benzenesulfonamides as allosteric inhibitors of fructose-1,6-bisphosphatase. Bioorg. Med. Chem. Lett., 2006, 16(7), 1807-1810.
[http://dx.doi.org/10.1016/j.bmcl.2006.01.014] [PMID: 16446092]
[41]
Reddy, M.R.; Erion, M.D. Relative binding affinities of fructose-1,6-bisphosphatase inhibitors calculated using a quantum mechanics-based free energy perturbation method. J. Am. Chem. Soc., 2007, 129(30), 9296-9297.
[http://dx.doi.org/10.1021/ja072905j] [PMID: 17616196]
[42]
Erion, M.D.; Dang, Q.; Reddy, M.R.; Kasibhatla, S.R.; Huang, J.; Lipscomb, W.N.; van Poelje, P.D. Structure-guided design of AMP mimics that inhibit fructose-1,6-bisphosphatase with high affinity and specificity. J. Am. Chem. Soc., 2007, 129(50), 15480-15490.
[http://dx.doi.org/10.1021/ja074869u] [PMID: 18041833]
[43]
Dang, Q.; Kasibhatla, S.R.; Reddy, K.R.; Jiang, T.; Reddy, M.R.; Potter, S.C.; Fujitaki, J.M.; van Poelje, P.D.; Huang, J.; Lipscomb, W.N.; Erion, M.D. Discovery of potent and specific fructose-1,6-bisphosphatase inhibitors and a series of orally-bioavailable phosphoramidase-sensitive prodrugs for the treatment of type 2 diabetes. J. Am. Chem. Soc., 2007, 129(50), 15491-15502.
[http://dx.doi.org/10.1021/ja074871l] [PMID: 18041834]
[44]
Erion, M.D.; van Poelje, P.D.; Dang, Q.; Kasibhatla, S.R.; Potter, S.C.; Reddy, M.R.; Reddy, K.R.; Jiang, T.; Lipscomb, W.N. MB06322 (CS-917): A potent and selective inhibitor of fructose 1,6-bisphosphatase for controlling gluconeogenesis in type 2 diabetes. Proc. Natl. Acad. Sci. USA, 2005, 102(22), 7970-7975.
[http://dx.doi.org/10.1073/pnas.0502983102] [PMID: 15911772]
[45]
van Poelje, P.D.; Potter, S.C.; Chandramouli, V.C.; Landau, B.R.; Dang, Q.; Erion, M.D. Inhibition of fructose 1,6-bisphosphatase reduces excessive endogenous glucose production and attenuates hyperglycemia in Zucker diabetic fatty rats. Diabetes, 2006, 55(6), 1747-1754.
[http://dx.doi.org/10.2337/db05-1443] [PMID: 16731838]
[46]
Dang, Q.; Kasibhatla, S.R.; Jiang, T.; Fan, K.; Liu, Y.; Taplin, F.; Schulz, W.; Cashion, D.K.; Reddy, K.R.; van Poelje, P.D.; Fujitaki, J.M.; Potter, S.C.; Erion, M.D. Discovery of phosphonic diamide prodrugs and their use for the oral delivery of a series of fructose 1,6-bisphosphatase inhibitors. J. Med. Chem., 2008, 51(14), 4331-4339.
[http://dx.doi.org/10.1021/jm8001235] [PMID: 18570362]
[47]
Magnusson, I.; Rothman, D.L.; Katz, L.D.; Shulman, R.G.; Shulman, G.I. Increased rate of gluconeogenesis in type II diabetes mellitus. A 13C nuclear magnetic resonance study. J. Clin. Invest., 1992, 90(4), 1323-1327.
[http://dx.doi.org/10.1172/JCI115997] [PMID: 1401068]
[48]
Yoshida, T.; Okuno, A.; Izumi, M.; Takahashi, K.; Hagisawa, Y.; Ohsumi, J.; Fujiwara, T. CS-917, a fructose 1,6-bisphosphatase inhibitor, improves postprandial hyperglycemia after meal loading in non-obese type 2 diabetic Goto-Kakizaki rats. Eur. J. Pharmacol., 2008, 601(1-3), 192-197.
[http://dx.doi.org/10.1016/j.ejphar.2008.10.050] [PMID: 19014931]
[49]
Török, B.; Abid, M.; London, G.; Esquibel, J.; Török, M.; Mhadgut, S.C.; Yan, P.; Prakash, G.K.S. Highly enantioselective organocatalytic hydroxyalkylation of indoles with ethyl trifluoropyruvate. Angew. Chem. Int. Ed. Engl., 2005, 44(20), 3086-3089.
[http://dx.doi.org/10.1002/anie.200462877] [PMID: 15844111]
[50]
Török, M.; Abid, M.; Mhadgut, S.C.; Török, B. Organofluorine inhibitors of amyloid fibrillogenesis. Biochemistry, 2006, 45(16), 5377-5383.
[http://dx.doi.org/10.1021/bi0601104] [PMID: 16618127]
[51]
Abid, M.; Teixeira, L.; Török, B. Triflic acid-catalyzed highly stereoselective friedel-crafts aminoalkylation of indoles and pyrroles. Org. Lett., 2008, 10(5), 933-935.
[http://dx.doi.org/10.1021/ol703095d] [PMID: 18254637]
[52]
Rudnitskaya, A.; Huynh, K.; Török, B.; Stieglitz, K. Novel heteroaromatic organofluorine inhibitors of fructose-1,6-bisphosphatase. J. Med. Chem., 2009, 52(3), 878-882.
[http://dx.doi.org/10.1021/jm800720a] [PMID: 19143528]
[53]
Hebeisen, P.; Kuhn, B.; Kohler, P.; Gubler, M.; Huber, W.; Kitas, E.; Schott, B.; Benz, J.; Joseph, C.; Ruf, A. Allosteric FBPase inhibitors gain 10(5) times in potency when simultaneously binding two neighboring AMP sites. Bioorg. Med. Chem. Lett., 2008, 18(16), 4708-4712.
[http://dx.doi.org/10.1016/j.bmcl.2008.06.103] [PMID: 18650089]
[54]
Dang, Q.; Brown, B.S.; Liu, Y.; Rydzewski, R.M.; Robinson, E.D.; van Poelje, P.D.; Reddy, M.R.; Erion, M.D. Fructose-1,6-bisphosphatase inhibitors. 1. Purine phosphonic acids as novel AMP mimics. J. Med. Chem., 2009, 52(9), 2880-2898.
[http://dx.doi.org/10.1021/jm900078f] [PMID: 19348494]
[55]
Tsukada, T.; Takahashi, M.; Takemoto, T.; Kanno, O.; Yamane, T.; Kawamura, S.; Nishi, T. Synthesis, SAR, and X-ray structure of tricyclic compounds as potent FBPase inhibitors. Bioorg. Med. Chem. Lett., 2009, 19(20), 5909-5912.
[http://dx.doi.org/10.1016/j.bmcl.2009.08.081] [PMID: 19762234]
[56]
Tsukada, T.; Takahashi, M.; Takemoto, T.; Kanno, O.; Yamane, T.; Kawamura, S.; Nishi, T. Structure-based drug design of tricyclic 8H-indeno[1,2-d][1,3]thiazoles as potent FBPase inhibitors. Bioorg. Med. Chem. Lett., 2010, 20(3), 1004-1007.
[http://dx.doi.org/10.1016/j.bmcl.2009.12.056] [PMID: 20045638]
[57]
Tsukada, T.; Kanno, O.; Yamane, T.; Tanaka, J.; Yoshida, T.; Okuno, A.; Shiiki, T.; Takahashi, M.; Nishi, T. Discovery of potent and orally active tricyclic-based FBPase inhibitors. Bioorg. Med. Chem., 2010, 18(14), 5346-5351.
[http://dx.doi.org/10.1016/j.bmc.2010.05.041] [PMID: 20542703]
[58]
Heng, S.; Gryncel, K.R.; Kantrowitz, E.R. A library of novel allosteric inhibitors against fructose 1,6-bisphosphatase. Bioorg. Med. Chem., 2009, 17(11), 3916-3922.
[http://dx.doi.org/10.1016/j.bmc.2009.04.030] [PMID: 19419876]
[59]
Dang, Q.; Reddy, K.R.; Kasibthatla, S.R.; Jiang, T.; Taplin, F.; Gibson, T.; Potter, S.C.; Poelje, P.D.; Reddy, M.R.; Erion, M.D. Discovery of Phosphonic acid-containing desaminobenzimidazoles as fructose 1,6-bisphosphatase inhibitors that are suitable for oral delivery via prodrugs. J. Diabetes Metab., 2010, 1, 105-108.
[http://dx.doi.org/10.4172/2155-6156.1000105]
[60]
Dang, Q.; Kasibhatla, S.R.; Xiao, W.; Liu, Y.; Dare, J.; Taplin, F.; Reddy, K.R.; Scarlato, G.R.; Gibson, T.; van Poelje, P.D.; Potter, S.C.; Erion, M.D. Fructose-1,6-bisphosphatase Inhibitors. 2. Design, synthesis, and structure-activity relationship of a series of phosphonic acid containing benzimidazoles that function as 5′-adenosinemonophosphate (AMP) mimics. J. Med. Chem., 2010, 53(1), 441-451.
[http://dx.doi.org/10.1021/jm901420x] [PMID: 20055427]
[61]
Dang, Q.; Liu, Y.; Cashion, D.K.; Kasibhatla, S.R.; Jiang, T.; Taplin, F.; Jacintho, J.D.; Li, H.; Sun, Z.; Fan, Y.; DaRe, J.; Tian, F.; Li, W.; Gibson, T.; Lemus, R.; van Poelje, P.D.; Potter, S.C.; Erion, M.D. Discovery of a series of phosphonic acid-containing thiazoles and orally bioavailable diamide prodrugs that lower glucose in diabetic animals through inhibition of fructose-1,6-bisphosphatase. J. Med. Chem., 2011, 54(1), 153-165.
[http://dx.doi.org/10.1021/jm101035x] [PMID: 21126019]
[62]
Triscari, J.; Walker, J.; Feins, K.; Tao, B.; Bruce, S.R. In multiple ascending dose of CS-917, a novel fructose 1,6-bisphosphatase (FBPase) Inhibitor, in subjects with type 2 diabetes treated for 14 days; American Diabetes Association: Alexandria, VA, 2006.
[63]
Dang, Q.; Kasibthatla, S.R.; Jiang, T.; Taplin, F.; Gibson, T.; Potter, S.C.; Poeljek, P.D.; Erion, M.D. Oxazole phosphonic acids as fructose 1,6-bisphosphatase inhibitors with potent glucose-lowering activity. MedChemComm, 2011, 2, 287-290.
[http://dx.doi.org/10.1039/c0md00269k]
[64]
Kitas, E.; Mohr, P.; Kuhn, B.; Hebeisen, P.; Wessel, H.P.; Haap, W.; Ruf, A.; Benz, J.; Joseph, C.; Huber, W.; Sanchez, R.A.; Paehler, A.; Benardeau, A.; Gubler, M.; Schott, B.; Tozzo, E. Sulfonylureido thiazoles as fructose-1,6-bisphosphatase inhibitors for the treatment of type-2 diabetes. Bioorg. Med. Chem. Lett., 2010, 20(2), 594-599.
[http://dx.doi.org/10.1016/j.bmcl.2009.11.093] [PMID: 19969452]
[65]
Hebeisen, P.; Haap, W.; Kuhn, B.; Mohr, P.; Wessel, H.P.; Zutter, U.; Kirchner, S.; Ruf, A.; Benz, J.; Joseph, C.; Alvarez-Sánchez, R.; Gubler, M.; Schott, B.; Benardeau, A.; Tozzo, E.; Kitas, E. Orally active aminopyridines as inhibitors of tetrameric fructose-1,6-bisphosphatase. Bioorg. Med. Chem. Lett., 2011, 21(11), 3237-3242.
[http://dx.doi.org/10.1016/j.bmcl.2011.04.044] [PMID: 21550236]
[66]
He, H.B.; Gao, L.X.; Zhou, Y.Y.; Liu, T.; Tang, J.; Gong, X.P.; Qiu, W.W.; Li, J.Y.; Li, J.; Yang, F. Design, synthesis and biological activity evaluation of 2,5-diphenyl-1,3,4-oxadiazole derivatives as novel inhibitors of fructose-1,6-bisphosphatase. Heterocycles, 2012, 85, 2693-2712.
[http://dx.doi.org/10.3987/COM-12-12565]
[67]
Liao, B.R.; He, H.B.; Yang, L.L.; Gao, L.X.; Chang, L.; Tang, J.; Li, J.Y.; Li, J.; Yang, F. Synthesis and structure-activity relationship of non-phosphorus-based fructose-1,6-bisphosphatase inhibitors: 2,5-Diphenyl-1,3,4-oxadiazoles. Eur. J. Med. Chem., 2014, 83, 15-25.
[http://dx.doi.org/10.1016/j.ejmech.2014.06.011] [PMID: 24946215]
[68]
Bie, J.; Liu, S.; Zhou, J.; Xu, B.; Shen, Z. Design, synthesis and biological evaluation of 7-nitro-1H-indole-2-carboxylic acid derivatives as allosteric inhibitors of fructose-1,6-bisphosphatase. Bioorg. Med. Chem., 2014, 22(6), 1850-1862.
[http://dx.doi.org/10.1016/j.bmc.2014.01.047] [PMID: 24530031]
[69]
Bie, J.; Liu, S.; Li, Z.; Mu, Y.; Xu, B.; Shen, Z. Discovery of novel indole derivatives as allosteric inhibitors of fructose-1,6-bisphosphatase. Eur. J. Med. Chem., 2015, 90, 394-405.
[http://dx.doi.org/10.1016/j.ejmech.2014.11.049] [PMID: 25461330]
[70]
Wright, S.W.; Carlo, A.A.; Carty, M.D.; Danley, D.E.; Hageman, D.L.; Karam, G.A.; Levy, C.B.; Mansour, M.N.; Mathiowetz, A.M.; McClure, L.D.; Nestor, N.B.; McPherson, R.K.; Pandit, J.; Pustilnik, L.R.; Schulte, G.K.; Soeller, W.C.; Treadway, J.L.; Wang, I.K.; Bauer, P.H. Anilinoquinazoline inhibitors of fructose 1,6-bisphosphatase bind at a novel allosteric site: synthesis, in vitro characterization, and X-ray crystallography. J. Med. Chem., 2002, 45(18), 3865-3877.
[http://dx.doi.org/10.1021/jm010496a] [PMID: 12190310]
[71]
Rosini, M.; Mancini, F.; Tarozzi, A.; Colizzi, F.; Andrisano, V.; Bolognesi, M.L.; Hrelia, P.; Melchiorre, C. Design, synthesis, and biological evaluation of substituted 2,3-dihydro-1H-cyclopenta[b]quinolin-9-ylamine related compounds as fructose-1,6-bisphosphatase inhibitors. Bioorg. Med. Chem., 2006, 14(23), 7846-7853.
[http://dx.doi.org/10.1016/j.bmc.2006.07.059] [PMID: 16908175]
[72]
Choe, J.Y.; Nelson, S.W.; Arienti, K.L.; Axe, F.U.; Collins, T.L.; Jones, T.K.; Kimmich, R.D.A.; Newman, M.J.; Norvell, K.; Ripka, W.C.; Romano, S.J.; Short, K.M.; Slee, D.H.; Fromm, H.J.; Honzatko, R.B. Inhibition of fructose-1,6-bisphosphatase by a new class of allosteric effectors. J. Biol. Chem., 2003, 278(51), 51176-51183.
[http://dx.doi.org/10.1074/jbc.M308396200] [PMID: 14530289]

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