An Insight into Common and Advanced Synthesis Methodologies of Acyl Urea Analogs Targeting the CNS

Page: [1006 - 1022] Pages: 17

  • * (Excluding Mailing and Handling)

Abstract

The acyl urea functionality and related analogs are increasingly used in medicinal chemistry and drug design to prove well-defined pharmacological actions and optimal physicochemical properties. This review paper aimed to summarize information related to synthesis methods of acyl urea derivatives, marketed products, and patents to explore their applications in counteracting CNS-related diseases by multiple targeting. Comprehensive data related to acyl urea and related compounds of the last 15 years is collected from various resources to provide enormous information to the readers. The content of the study uniformly includes considerable evidence linked to the common and unique synthesis techniques of acyl urea from starting materials like benzamide, isocyanates, substituted iodoglycals, 2 chloro nicotinic acid, and methyl hydrazines, as well as patents related to the same. This work describes the reactions of several substrates that can be used to manufacture various acyl urea derivatives. An understanding of patents related to acyl urea analogs with specific targets for CNS action may also help researchers working on additional synthesis of acyl urea derivatives with potential CNS action.

[1]
Blanco-Canosa, J.B.; Nardone, B.; Albericio, F.; Dawson, P.E. J. Am. Chem. Soc., 2015, 137(22), 7197-7209.
[http://dx.doi.org/10.1021/jacs.5b03504] [PMID: 25978693]
[2]
Zhou, J. Rossi. J. Nat. Rev. Drug Discov., 2017, 16(3), 181-202.
[http://dx.doi.org/10.1038/nrd.2016.199] [PMID: 27807347]
[3]
Todd, C.D.; Tipton, P.A.; Blevins, D.G.; Piedras, P.; Pineda, M.; Polacco, J.C. J. Exp. Bot., 2006, 57(1), 5-12.
[http://dx.doi.org/10.1093/jxb/erj013] [PMID: 16317038]
[4]
Ogawa, J.; Honda, M.; Soong, C.L.; Shimizu, S. Biosci. Biotechnol. Biochem., 1995, 59(10), 1960-1962.
[http://dx.doi.org/10.1271/bbb.59.1960]
[5]
Szostak, R.; Liu, C.; Lalancette, R.; Szostak, M. J. Org. Chem., 2018, 83(23), 14676-14682.
[http://dx.doi.org/10.1021/acs.joc.8b02691] [PMID: 30352152]
[6]
Jordá, A.; Portolés, M.; Guasch, R.; Bernal, D.; Saez, G.T. Biochem. Pharmacol., 1989, 38(16), 2727-2732.
[http://dx.doi.org/10.1016/0006-2952(89)90560-1] [PMID: 2764993]
[7]
Kleinmaier, R.; Keller, M.; Igel, P.; Buschauer, A.; Gschwind, R.M. J. Am. Chem. Soc., 2010, 132(32), 11223-11233.
[http://dx.doi.org/10.1021/ja103756y] [PMID: 20698689]
[8]
Arbuzov, B.A.; Fedotova, N.R.; Zobova, N.N.; Nazyrova, A.Z.; Anan’ev, E.V.; Gorbunov, S.M. Pharm. Chem. J., 1989, 23(6), 479-481.
[http://dx.doi.org/10.1007/BF01145802]
[9]
Chaudhary, P.M.; Tupe, S.G.; Deshpande, M.V. Mini Rev. Med. Chem., 2013, 13(2), 222-236.
[PMID: 22512590]
[10]
Agnihotri, T.G.; Jadhav, G.S.; Sahu, B.; Jain, A. Drug Deliv. Transl. Res., 2022, 12(12), 3104-3120.
[http://dx.doi.org/10.1007/s13346-022-01173-y] [PMID: 35570262]
[11]
Klabunde, T.; Wendt, K.U.; Kadereit, D.; Brachvogel, V.; Burger, H.J.; Herling, A.W.; Oikonomakos, N.G.; Kosmopoulou, M.N.; Schmoll, D.; Sarubbi, E.; von Roedern, E.; Schönafinger, K.; Defossa, E. J. Med. Chem., 2005, 48(20), 6178-6193.
[http://dx.doi.org/10.1021/jm049034y] [PMID: 16190745]
[12]
Sliskovic, D.R.; Trivedi, B.K. Curr. Med. Chem., 1994, 1(3), 204-255.
[http://dx.doi.org/10.2174/092986730103220214163743]
[13]
Goverdhan, G.; Raghupathi Reddy, A.; Himabindu, V.; Mahesh Reddy, G. J. Saudi Chem. Soc., 2014, 18(2), 129-138.
[http://dx.doi.org/10.1016/j.jscs.2011.06.002]
[14]
Ramazani, A.; Nasrabadi, F.Z.; Rezaei, A.; Rouhani, M.; Ahankar, H.; Asiabi, P.A.; Joo, S.W.; Ślepokura, K.; Lis, T. J. Chem. Sci., 2015, 127(12), 2269-2282.
[http://dx.doi.org/10.1007/s12039-015-0988-6]
[15]
Bialer, M. Epilepsia, 2012, 53(s8)(Suppl. 8), 3-11.
[http://dx.doi.org/10.1111/epi.12024] [PMID: 23205958]
[16]
Marson, A.G.; Williamson, P.R.; Hutton, J.L.; Clough, H.E.; Chadwick, D.W. Cochrane Libr., 2000, 2010(1)
[http://dx.doi.org/10.1002/14651858.CD001030] [PMID: 10908558]
[17]
Ahmad, S.; Fowler, L.J.; Whitton, P.S. Epilepsy Res., 2005, 63(2-3), 141-149.
[http://dx.doi.org/10.1016/j.eplepsyres.2005.02.002] [PMID: 15777732]
[18]
Zhou, C.H.; Wang, Y. Curr. Med. Chem., 2012, 19(2), 239-280.
[http://dx.doi.org/10.2174/092986712803414213] [PMID: 22320301]
[19]
Sobol, E.; Bialer, M.; Yagen, B. J. Med. Chem., 2004, 47(17), 4316-4326.
[http://dx.doi.org/10.1021/jm0498351] [PMID: 15294003]
[20]
Ravn, J.; Ankersen, M.; Begtrup, M.; Lau, J.F. Tetrahedron Lett., 2003, 44(36), 6931-6935.
[http://dx.doi.org/10.1016/S0040-4039(03)01676-9]
[21]
Spielman, M.A.; Geiszler, A.O.; Close, W.J. J. Am. Chem. Soc., 1948, 70(12), 4189-4191.
[http://dx.doi.org/10.1021/ja01192a063] [PMID: 18105968]
[22]
Smitha, S.; Pandeya, S.N.; Stables, J.P.; Ganapathy, S. Sci. Pharm., 2008, 76(4), 621-636.
[http://dx.doi.org/10.3797/scipharm.0806-14]
[23]
Ghosh, A.K.; Brindisi, M. J. Med. Chem., 2020, 63(6), 2751-2788.
[http://dx.doi.org/10.1021/acs.jmedchem.9b01541] [PMID: 31789518]
[24]
Zuliani, V.; Fantini, M.; Nigam, A.; Stables, J.P.; Patel, M.K.; Rivara, M. Bioorg. Med. Chem., 2010, 18(22), 7957-7965.
[http://dx.doi.org/10.1016/j.bmc.2010.09.029] [PMID: 20943396]
[25]
Gunia-Krzyżak, A.; Żesławska, E.; Słoczyńska, K.; Żelaszczyk, D.; Sowa, A.; Koczurkiewicz-Adamczyk, P.; Popiół, J.; Nitek, W.; Pękala, E.; Marona, H. Int. J. Mol. Sci., 2020, 21(12), 4372.
[http://dx.doi.org/10.3390/ijms21124372] [PMID: 32575479]
[26]
Brandenberger, H. Anal Toxicol Clin Forensic Pharm Chem, 1997, 399.
[http://dx.doi.org/10.1515/9783110881615.399]
[27]
Volwiler, E.H.; Tabern, D.L. J. Am. Chem. Soc., 1936, 58(8), 1352-1354.
[http://dx.doi.org/10.1021/ja01299a012]
[28]
Belleville, G. Can. J. Psychiatry, 2010, 55(9), 558-567.
[http://dx.doi.org/10.1177/070674371005500904] [PMID: 20840803]
[29]
Jorg, M.; Scammells, P.J.; Capuano, B. Curr. Med. Chem., 2014, 21(27), 3188-3210.
[http://dx.doi.org/10.2174/1389200215666140217110716] [PMID: 24533801]
[30]
Bialer, M.; Yagen, B.; Shimshoni, J.A.U.S. Patent 8846903, 2014.
[31]
de María, P.; de Gonzalo, G.; Alcántara, A. Catalysts, 2019, 9(10), 802.
[http://dx.doi.org/10.3390/catal9100802]
[32]
Bachhav, Y.G.; Heinrich, A.; Kalia, Y.N. Eur. J. Pharm. Biopharm., 2011, 78(3), 408-414.
[http://dx.doi.org/10.1016/j.ejpb.2011.03.006] [PMID: 21397689]
[33]
Cirit, Ü.; Bacinoglu, S.; Cangul, I.T.; Kaya, H.H.; Taş, M.; Ak, K. Anim. Reprod. Sci., 2007, 101(1-2), 134-144.
[http://dx.doi.org/10.1016/j.anireprosci.2006.09.005] [PMID: 17011145]
[34]
Stec, J.; Hernandez, A.; Grooms, G.; El-Alfy, A. Synthesis, 2017, 49(10), 2163-2176.
[http://dx.doi.org/10.1055/s-0036-1588724]
[35]
Chakraborty, K.; Vijayagopal, P.; Iyapparajanarasimapallavan, G.; Joseph, D.; Makkar, F.; Raola, V.K.; Joy, M. Mar. Fish. Infor. Serv., T & E Ser, 2015, 223 & 224, 3-8.
[36]
Singhuber, J.; Zhu, M.; Prinz, S.; Kopp, B. J. Ethnopharmacol., 2009, 126(1), 18-30.
[http://dx.doi.org/10.1016/j.jep.2009.07.031] [PMID: 19651200]
[37]
Limón, D.; Talló Domínguez, K.; Garduño-Ramírez, M.L.; Andrade, B.; Calpena, A.C.; Pérez-García, L. Colloids Surf. B Biointerfaces, 2019, 181, 657-670.
[http://dx.doi.org/10.1016/j.colsurfb.2019.06.018] [PMID: 31212138]
[38]
Limón, D.; Jiménez-Newman, C.; Rodrigues, M.; González-Campo, A.; Amabilino, D.B.; Calpena, A.C.; Pérez-García, L. ChemistryOpen, 2017, 6(4), 585-598.
[http://dx.doi.org/10.1002/open.201700040] [PMID: 28794954]
[39]
Shorvon, S.D. In: The treatment of epilepsy; Blackwell Publishing Oxford: UK, 1955.
[40]
Tolman, K.G.; Jubiz, W.; Sannella, J.J.; Madsen, J.A.; Belsey, R.E.; Goldsmith, R.S.; Freston, J.W. Pediatrics, 1975, 56(1), 45-51.
[http://dx.doi.org/10.1542/peds.56.1.45] [PMID: 1161362]
[41]
Murray, W.J.; Kier, L.B. In: Medicinal chemistry; Elsevier, 1977, Vol. 15, pp. 577-619.
[42]
Zhu, J.; Zhang, L.; Li, K. Int. J. Electrochem. Sci., 2022, 17(10), 22102.
[http://dx.doi.org/10.20964/2022.07.05]
[43]
WHO Expert Committee on Drug Dependence, World Health Organization WHO Expert Committee on Drug Dependence [meeting held in Geneva from 9 to 16 April 1987]: twenty-fourth report. World Health Organization, 1988.
[44]
Bulpitt, P.; Aeschlimann, D. J. Biomed. Mater. Res., 1999, 47(2), 152-169.
[http://dx.doi.org/10.1002/(SICI)1097-4636(199911)47:2<152::AID-JBM5>3.0.CO;2-I] [PMID: 10449626]
[45]
Asplund, K.; Wiholm, B.E.; Lithner, F. Diabetologia, 1983, 24(6), 412-417.
[http://dx.doi.org/10.1007/BF00257338] [PMID: 6411511]
[46]
Jacobson, R.A.U.S. Patent 2090594, 1937.
[47]
Greene, R.; Phoenix, T. E.P. Patent 0896532B1, 1999.
[48]
Joppien, Hartmut K.R. Patent 830002202B1, 1983.
[49]
Ruat, M.; Faure, H.; Traiffort, E.U.S. Patent 9073835B2, 2015.
[50]
Michael, F.U.S. Patent 5135953A, 1992.
[51]
Robert, C.U.S. Patent 2850530A, 1956.
[52]
Guckian, K.N. E.P. Patent 2877166B1, 2013.
[53]
Floyd, W.C. E.P. Patent EP0240370A2,
[54]
E.P. Patent, EP0193249A2,,
[55]
Linus, S.U.S. Patent 7576239B2, 2009.
[56]
E.P. Patent 0416250A2,
[57]
U.S. Patent 3933908A, 1976.
[58]
Raymond, Robert W.O. Patent 2001036403A1, 2000.
[59]
Breitfelder, S. D.E. Patent 60036726T2, 2002.
[60]
McSherry, D.D.; Richard, K.U.S. Patent 8017082B2, 2009.
[61]
Woonza, M.U.S. Patent 8197802B2, 2011.
[62]
Ishii, Yasutaka J.P. Patent 4920024B2, 2012.
[63]
Zhao, Xuan.; Michael, D. U.S Patent 20220079936A1, 2022.
[64]
Tanaka, Y J.P. Patent 5638085B2, 2013.
[65]
Kaiser-Wilhelm, A J.P. Patent 6906445B2, 2021.
[66]
Guillen, K.H.U.S. Patent 10905797B2, 2019.
[67]
Tamera, B.U.S. Patent 11541075B2, 2023.
[68]
Shenghong, A.U.S. Patent 20080161554A1, 2008.
[69]
Liu, Quan Lin Baiqiao C.N. Patent 101970097B, 2009.
[70]
V, Esbelin E.P. Patent 2797974B1, 2014.
[71]
Igor, K.U.S. Patent 8101375B2, 2012.
[72]
Sadozai U.S. Patent 6548081B2, 2003.
[73]
BorZilleri U.S. Patent 7989477B2, 2011.
[74]
Fäcke Thomas U.S. Patent 11000976B2, 2021.
[75]
Thapa, R.; Flores, R.; Cheng, K.H.; Mochona, B.; Sikazwe, D. Molecules, 2023, 28(5), 2319.
[http://dx.doi.org/10.3390/molecules28052319] [PMID: 36903567]
[76]
Tiwari, V.K.; Yadav, M.S.; Singh, S.K.; Agrahari, A.K.; Singh, A.S. Synthesis, 2021, 53(14), 2494-2502.
[http://dx.doi.org/10.1055/a-1399-3823]
[77]
Soares-Paulino, A.A.; Stefani, H.A. Eur. J. Org. Chem., 2020, 2020(25), 3847-3855.
[http://dx.doi.org/10.1002/ejoc.202000494]
[78]
Liptrot, D.; Alcaraz, L.; Roberts, B. Adv. Synth. Catal., 2010, 352(13), 2183-2188.
[http://dx.doi.org/10.1002/adsc.201000395]
[79]
Maqbool, T.; Younas, H.; Bilal, M.; Rasool, N.; Bajaber, M.A.; Mubarik, A.; Parveen, B.; Ahmad, G.; Ali Shah, S.A. ACS Omega, 2023, 8(33), 30306-30314.
[http://dx.doi.org/10.1021/acsomega.3c03183] [PMID: 37636953]
[80]
Caldwell, T.M.; Kaufman, M.D.; Wise, S.C.; Mi Ahn, Y.; Hood, M.M.; Lu, W.P.; Patt, W.C.; Samarakoon, T.; Vogeti, L.; Vogeti, S.; Yates, K.M.; Bulfer, S.L.; Le Bourdonnec, B.; Smith, B.D.; Flynn, D.L. Bioorg. Med. Chem. Lett., 2022, 74, 128929.
[http://dx.doi.org/10.1016/j.bmcl.2022.128929] [PMID: 35961461]
[81]
Saeed, A.; Hökelek, T.; Bolte, M.; Erben, M.F. J. Mol. Struct., 2021, 1245, 131271.
[http://dx.doi.org/10.1016/j.molstruc.2021.131271]
[82]
Zhang, P.P.; Wang, Q.; Min, L.J.; Wu, H.K.; Weng, J.Q.; Tan, C.X.; Zhang, Y.G.; Liu, X.H. J. Mol. Struct., 2020, 1205, 127485.
[http://dx.doi.org/10.1016/j.molstruc.2019.127485]
[83]
Qiao, L.; Zhai, Z.W.; Cai, P.P.; Tan, C.X.; Weng, J.Q.; Han, L.; Liu, X.H.; Zhang, Y.G. J. Heterocycl. Chem., 2019, 56(9), 2536-2541.
[http://dx.doi.org/10.1002/jhet.3648]
[84]
Maity, R.; Naskar, S.; Das, I. J. Org. Chem., 2018, 83(4), 2114-2124.
[http://dx.doi.org/10.1021/acs.joc.7b03054] [PMID: 29393648]
[85]
Chow, S.Y.; Odell, L.R. J. Org. Chem., 2017, 82(5), 2515-2522.
[http://dx.doi.org/10.1021/acs.joc.6b02894] [PMID: 28150496]
[86]
Soldatova, N.S.; Orlova, K.V.; Sarycheva, T.A. Key Eng. Mater., 2016, 685, 785-788.
[http://dx.doi.org/10.4028/www.scientific.net/KEM.685.785]
[87]
Sun, R.; Liu, C.; Zhang, H.; Wang, Q. J. Agric. Food Chem., 2015, 63(31), 6847-6865.
[http://dx.doi.org/10.1021/acs.jafc.5b02460] [PMID: 26168369]
[88]
McCoull, W.; Barton, P.; Brown, A.J.H.; Bowker, S.S.; Cameron, J.; Clarke, D.S.; Davies, R.D.M.; Dossetter, A.G.; Ertan, A.; Fenwick, M.; Green, C.; Holmes, J.L.; Martin, N.; Masters, D.; Moore, J.E.; Newcombe, N.J.; Newton, C.; Pointon, H.; Robb, G.R.; Sheldon, C.; Stokes, S.; Morgan, D. J. Med. Chem., 2014, 57(14), 6128-6140.
[http://dx.doi.org/10.1021/jm500610n] [PMID: 24967667]
[89]
Singh, A.K.; Chawla, R.; Yadav, L.D.S. Tetrahedron Lett., 2013, 54(37), 5099-5102.
[http://dx.doi.org/10.1016/j.tetlet.2013.07.045]
[90]
Zhang, J.F.; Xu, J.Y.; Wang, B.L.; Li, Y.X.; Xiong, L.X.; Li, Y.Q.; Ma, Y.; Li, Z.M. J. Agric. Food Chem., 2012, 60(31), 7565-7572.
[http://dx.doi.org/10.1021/jf302446c] [PMID: 22812664]
[91]
Häcker, H.G.; Meusel, M.; Aschfalk, M.; Gütschow, M. ACS Comb. Sci., 2011, 13(1), 59-64.
[http://dx.doi.org/10.1021/co100020b] [PMID: 21247126]
[92]
Shimshoni, J.A.; Yagen, B.; Pessah, N.; Wlodarczyk, B.; Finnell, R.H.; Bialer, M. Epilepsia, 2008, 49(7), 1202-1212.
[http://dx.doi.org/10.1111/j.1528-1167.2008.01624.x] [PMID: 18435754]
[93]
Grasso, S.; De Sarro, G.; De Sarro, A.; Micale, N.; Zappalà, M.; Puja, G.; Baraldi, M.; De Micheli, C. J. Med. Chem., 2000, 43(15), 2851-2859.
[http://dx.doi.org/10.1021/jm001002x] [PMID: 10956193]
[94]
Mrongovius, R.I.; Rand, M.J. Clin. Exp. Pharmacol. Physiol., 1977, 4(1), 7-15.
[http://dx.doi.org/10.1111/j.1440-1681.1977.tb02372.x] [PMID: 18311]
[95]
Cannizzaro, C.E.; Thiel, I.M.E.; D’Accorso, N.B. J. Heterocycl. Chem., 1998, 35(2), 481-484.
[http://dx.doi.org/10.1002/jhet.5570350238]
[96]
Korade, S.N.; Mhaldar, P.M.; Kulkarni, P.P.; Rashinkar, G.S.; Pore, D.M. Synth. Commun., 2021, 51(15), 2336-2348.
[http://dx.doi.org/10.1080/00397911.2021.1934875]
[97]
Kaufmann, D.; Bialer, M.; Shimshoni, J.A.; Devor, M.; Yagen, B. J. Med. Chem., 2009, 52(22), 7236-7248.
[http://dx.doi.org/10.1021/jm901229s] [PMID: 19877649]
[98]
Khan, S.A.; Singh, N.; Saleem, K. Eur. J. Med. Chem., 2008, 43(10), 2272-2277.
[http://dx.doi.org/10.1016/j.ejmech.2007.12.012] [PMID: 18294737]
[99]
Parmar, S.S.; Dwivedi, C.; Chaudhari, A.; Gupta, T.K. J. Med. Chem., 1972, 15(1), 99-101.
[http://dx.doi.org/10.1021/jm00271a030] [PMID: 4331920]
[100]
Stavropoulos, G.; Theodoropoulos, D. J. Heterocycl. Chem., 1977, 14(7), 1139-1143.
[http://dx.doi.org/10.1002/jhet.5570140703]
[101]
Mehta, S.J.; Hamor, G.H. J. Pharm. Sci., 1961, 50(8), 672-675.
[http://dx.doi.org/10.1002/jps.2600500811] [PMID: 13769010]
[102]
Stubbins, J.F. Synthesis of potential analgesics: N-(2-dialkylaminoethyl) 2-phenylacetanilides; University of Minnesota, 1965.
[103]
Cesarini, S.; Spallarossa, A.; Ranise, A.; Schenone, S.; Rosano, C.; La Colla, P.; Sanna, G.; Busonera, B.; Loddo, R. Eur. J. Med. Chem., 2009, 44(3), 1106-1118.
[http://dx.doi.org/10.1016/j.ejmech.2008.06.010] [PMID: 18667259]
[104]
Ke, S.; Li, Z.; Qian, X. Bioorg. Med. Chem., 2008, 16(16), 7565-7572.
[http://dx.doi.org/10.1016/j.bmc.2008.07.026] [PMID: 18678501]
[105]
Nims, R.W.; Sidhu, J.S.; Thomas, P.E.; Mellini, D.W.; Nelson, V.C.; Omiecinski, C.J.; Lubet, R.A. J. Biochem. Toxicol., 1994, 9(6), 279-288.
[http://dx.doi.org/10.1002/jbt.2570090602] [PMID: 7534352]
[106]
Irannejad, H.; Naderi, N.; Emami, S.; Ghadikolaei, R.Q.; Foroumadi, A.; Zafari, T.; Mazar-Atabaki, A.; Dadashpour, S. Med. Chem. Res., 2014, 23(5), 2503-2514.
[http://dx.doi.org/10.1007/s00044-013-0843-6]