Document Type : Review Article
Authors
Taxus Research Laboratory, Bocskai u. 22., H-4080 Hajdúnánás, Hungary
Abstract
The isoindole scaffolds and their related compounds are very important as they have a wide range of biological activities such as anti-inflammatory, antiarrhythmic, nootropic, anxiolytic, sedative, and antimicrobial activities. The design, synthesis and biological evaluation of novel antiviral agents have seen an increased relevance over the past few years. Several promising and successful results have been collected and reported in this mini review that could be useful for their further development and application in antiviral therapy. Furthermore, the main types of drug targets, the mechanism of actions, and the structure–activity relationship have also been studied to find potent and safe antiviral agents. This review summarises the considerable antiviral activities of isoindoline derivatives against several human viruses. The isoindole framework has and comprises many advantageous physicochemical- and biological properties. Several promising results showed that linkage, fusion, substitution or hybridization of the isoindole ring with various other rings or side chains led to effective antivirals. Results reported refer to versatile mechanism of action of thesecompounds.
Graphical Abstract
)
Keywords
Main Subjects
[1] Nannini G., Giraldi P.N., Molgora G., Biasoli G., Spinelli F., Logemann W., Dradi E., Zanni G., Buttinoni A., Tommasini R., Arzneim. Forsch., 1973, 23: 1090.
[2] Okazaki K., Oshima E., Obase H., Oiji Y., Nito M., Kubo K., Isoindolin-1-one derivative and antiarrhythmic agent. U.S. Patent:4,849,441, 1988
[3] Csende F., Porkoláb A., Matíz K., Szabó Z., Csorvássy I., Frank L., Sci. Pharm., 1999, 67: 149.
[4] Reyes A., Huerta L., Alfaro M., Navarrete A. Chem. Biodivers., 2010, 7:2718
[5] Wada T., Fukuda N. Pharmacol. Biochem. Behav., 1992, 41:573.
[6] de Wit H., Vicini L., Haig G. M., Hunt T., Feltner D. J. Clin. Psychopharmacol., 2006, 26:268.
[7] Zsotér T.T., Hart F., Radde I.C., Endrenyi L. J. Pharmacol. Exp. Ther., 1972, 180:723.
[8] Zhuang Z.P., Kung M.P., Mu M., Kung H.F. J. Med. Chem., 1998, 41:157.
[9] Hamprecht D., Micheli F., Tedesco G., Checchia A., Donati D., Petrone M., Terreni S., Wood M. Bioorg. Med. Chem. Lett., 2007, 17:428.
[10] Mukai T., Yamaguchi E., Goto J., Takagi K., Jpn. J. Pharmacol., 1981, 31:147.
[11] Chiba S., Nishiyama T., Yamada Y., Anesth. Analg., 2009, 108:1008.
[12] Kanamitsu N., Osaki T., Itsuji Y., Yoshimura M., Tsujimoto H., Soga M., Chem. Pharm. Bull., 2007, 55:1682.
[13] Usifoh C.O., Lambert D.M., Wouters J., Scriba G.K.E., Arch. Pharm., 2001, 334:323.
[14] Sale A.O., Consonni P., Lerner L.J., Lepetit G., Triazolo isoindole derivatives. U.S. Patent 4, 007, 276, 1977
[15] Csende F., Porkoláb A., Der Pharma Chem., 2018, 10:43.
[16] Speth P.A.J., Gore M.E., Pateman A.J., Newell D.R., Bishop J.A.M., Fllis W.J., Green J.A., Gumbrell L.A., Linssen P.C.M., Miller A. Smith I.E., McVie J.G., de Mulder P.H.M., de Pauw B.E., Griggs J.V., Brown G.W., Cancer Chemother. Pharmacol., 1988, 21:343.
[17] Meegalla S.K., Stevens G.J., McQueen C.A., Chen A.Y., Yu C., Liu L.F., Barrows L.R., La Voie E., J. Med. Chem., 1994, 37:3434.
[18] Kato Y., Takemoto M., Achiwa K., Chem. Pharm. Bull., 1999, 47:529.
[19] Kato Y., Tebiike H., Achiwa K., Ashizawa N., Kurihara T., Kobayashi F., Chem. Pharm. Bull., 1990, 38:2060.
[20] Marsili A., 2-(Omega-alkylaminoalkyl)- and 2-(omega-dialkylaminoalkyl)-3-(4-X-benzylidene)-phthalimidines. U.S. Patent 0105131A1, 1984
[21] Cohen F.S., Biophys. J. 2016, 110, 1028.
[22] Emmelkamp J.M., Rockstroh J.K., Eur. J. Med. Res., 2007, 12: 409.
[23] Zhou Y., Simmons G., Expert Rev. Anti-Infect. Ther., 2012, 10: 1129.
[24] Wang Y., Wang H., Jiang X., Jiang Z., Guo T., Ji X., Li Y., Li Z., Molecules, 2019, 24: 985.
[25] Jamil H., Gordon D.A., Eustice D.C., Brooks C. M., Dickson Jr J.K., Chen Y., Ricci B., Chu C.H., Harrity T.W., Ciosek Jr C.P., Biller S.A., Gregg R.E., Wetterau J.R., Proc. Natl. Acad. Sci. U.S.A., 1996, 93: 11991.
[26] Jamil H., Chu C.H., Dickson Jr.J.K., Chen Y., Yan M., Biller S.A., Gregg R.E., Wetterau J.R., Gordon D.A ., J. Lipid Res., 1998, 39: 1448.
[27] Burrows J.N., Cumming J.G., Fillery S.M., HamLin G.A., Hudson J.A., Jackson R.J., McLaughlin S., Shaw J.S., Bioorg. Med. Chem. Lett., 2005, 15: 25.
[28] Diana G.D., Pevear D.C., Otto M.J., McKinlay M.A., Rossmann M.G., Smith T., Badger J., Pharmacol. Therap., 1989, 42: 289.
[29] Minagawa K., Kouzuki S., Yoshimoto J., Kawamura Y., Tani H., Iwata T., Terui Y., Nakai H., Yagi S., Hattori N., Fujiwara T., Kamigauchi T., J. Antibiot., 2002, 55: 155.
[30] Minagawa K., Kouzuki S., Kamigauchi T. J. Antibiot., 2002, 55: 165.
[31] Motohashi Y., Igarashi M., Okamatsu M., Noshi T., Sakoda Y., Yamamoto N., Ito K., Yoshida R., Kida H., Virol. J., 2013, 10: 118.
[32] Pedersen O.S., Pedersen E.B., Antiviral Chem. Chemother., 1999, 10: 285.
[33] Mertens A., Zilch H., König B., Schäfer W., Poll T., Kampe W., Seidel H., Leser U., Leinert H., J. Med. Chem., 1993, 36: 2526.
[34] Maass G., Immendoerfer U., Koenig B., Leser U., Mueller B., Goody R., Pfaff E., Antimicrob. Agents Chemother., 1993, 37: 2612.
[35] Ren J., Esnouf R.M., Hopkins A.L., Stuart D.I., Stammers D.K., J. Med. Chem., 1999, 42:3845.
[36] König B., Leser U., Mertens A., Schäfer W., Poll T., Use of oxazolo[2, 3-a]isoindole and imidazo[2, 1-a]isoindole derivatives as antiviral drugs and new oxazolo[2, 3-a]isoindole derivatives. U.S. Patent: 3,336,306,1992
[37] Samee W., Ungwitayatorn J., Matayatsuk C., Pimthon J., Sci. Asia., 2004, 30:81.
[38] Spallarossa A., Cesarini S., Ranise A., Bruno O., Schenone S., La Colla P., Collu G., Sanna G., Secci B., Loddo R., Eur. J. Med. Chem., 2009, 44:1650.
[39] Spallarossa A., Cesarini S., Ranise A., Schenone S., Bruno O., Borassi A., La Colla P., Pezzullo M., Sanna G., Collu G., Secci B., Loddo R., Eur. J. Med. Chem., 2009, 44:2190.
[40] Penta A., Ganguly S., Murugesan S., Org. Med. Chem. Lett., 2013, 3:8.
[41] Kumari G., Singh R.K., Chem. Biol. Drug Des., 2016, 87:200.
[42] Gussio R., Pattabiraman N., Zaharevitz D.W., Kellogg G.E., Topol I.A., Rice W.G., Schaeffer C.A., Erickson J.W., Burt S.K., J. Med. Chem., 1996, 39:1645.
[43] Vanangamudi M., Poongavanam V., Namasivayam V., Curr. Med. Chem., 2017, 24:3774.
[44] Craigie R., Future Virol., 2012, 7:679.
[45] Delelis O., Carayon K., Saïb A., Deprez E., J.- F. Mouscadet, Retrovirology, 2008, 5:114.
[46] Hajimahdi Z., Zarghi A., Iran. J. Pharm. Res., 2016, 15:595.
[47] Zhao X.Z., Maddali K., Vu B.C., Marchand C., Hughes S.H., Pommier Jr.Y., Burke T.R., Bioorg. Med. Chem. Lett., 2009, 19:2714.
[48] Zhao X.Z., Semenova E.A., Vu B.C., Maddali K., Marchand C., Hughes S.H., Pommier Y., Burke, Jr.T.R., J. Med. Chem., 2008, 51:251.
[49] Zhao X.Z., Maddali K., Marchand C., Pommier Y., Burke Jr.T.R., , Bioorg. Med. Chem., 2009, 17:5318.
[50] Zhao X. Z., Maddali K., Smith S.J., Métifiot M., Johnson B.C., Marchand C., Hughes S.H., Pommier Y., Burke, Jr.T.R., Bioorg. Med. Chem. Lett., 2012, 22: 7309.
[51] Penta A., Babu K.K., Ganguly S., Murugesan S., J. Pharm. Negative Results, 2013, 4:13.
[52] Verschueren W.G., Dierynck I., Amssoms K.I.E., Hu L., Boonants P.M.J.G., Pille G.M.E., Daeyaert F.F.D., Hertogs K., Surleraux D.L.N.G., Wigerinck P.B.T.P., J. Med. Chem., 2005, 48:1930.
[53] Jin H., Cai R.Z., Schacherer L., Jabri S., Tsiang M., Fardis M., Chen X., Chen J.M., Kim C. U., Bioorg. Med. Chem. Lett., 2006, 16:3989.
[54] Metobo S.E., Jin H., Tsiang M., Kim C.U., Bioorg. Med. Chem. Lett., 2006, 16:3985.
[55] Fardis M., Jin H., Jabri S., Cai R.Z., Mish M., Tsiang M., Kim C.U., Bioorg. Med. Chem. Lett., 2006, 16:4031.
[56] Jin H., Wright M., Pastor R., Mish M., Metobo S., Jabri S., Lansdown R., Cai R., Pyun P., Tsiang M., Chen X., Kim C. U., Bioorg. Med. Chem. Lett., 2008, 18:1388.
[57] Jin H., Metobo S., Jabri S., Mish M., Lansdown R., Chen X., Tsiang M., Wright M., Kim C.U., Bioorg. Med. Chem. Lett., 2009, 19:2263.
[58] Metobo S., Mish M., Jin H., Jabri S., Lansdown R., Chen X., Tsiang M., Wright M., Kim C.U., Bioorg. Med. Chem. Lett., 2009, 19:1187.
[59] Avolio S., Robertson K., Hernando J.I.M., DiMuzio J., Summa V., Bioorg. Med. Chem. Lett., 2009, 19:2295.
[60] Pompei M., Francesco M. E. Di, Koch U., Liverton N. J., Summa V., Bioorg. Med. Chem. Lett., 2009, 19:2574.
[61] McCauley J.A., McIntyre C.J., Rudd M.T., Nguyen K.T., Romano J.J., Butcher J.W., Gilbert K.F., Bush K.J., Holloway M.K., Swestock J., Wan B.L., Carroll S.S., DiMuzio J.M., Graham D.J., Ludmerer S.W., Mao S.S., Stahlhut M.W., Fandozzi C.M., Trainor N., Olsen D.B., Vacca J.P., Liverton N.J., J. Med. Chem., 2010, 53:2443.
[62] Pompei M., Di Francesco M.E., Pesci S., Koch U., Vignetti S.E ., Veneziano M., Pace P., Summa V., Bioorg. Med. Chem. Lett., 2010, 20:168.
[63] Blatt L.M., Wenglowsky S.M., Andrews S.W., Jiang Y., Kennedy A.L., Condroski K.R., Josey J.A., Stengel P.J., Madduru M.R., Doherty G.A., Woodard B.T., Macrocyclic carboxylic acids and acylsulfonamides as inhbitors of HCV replication. PCT Int. Appl. WO, 2005/037214, 2004
[64] Jiang Y., Andrews S.W., Condroski K.R., Buckman B., Serebryany V., Wenglowsky S., Kennedy A.L., Madduru M.R., Wang B., Lyon M., Doherty G.A., Woodard B.T., Lemieux C., Do M.G., Zhang H., Ballard J., Vigers G., Brandhuber B.J., Stengel P., Josey J.A., Beigelman L., Blatt L., Seiwert S.D., J. Med. Chem., 2014, 57:1753.
[65] Rajagopalan R., Misialek S., Stevens S.K., Myszka D.G., Brandhuber B.J., Ballard J.A., Andrews S.W., Seiwert S.D., Kossen K., Biochemistry, 2009, 48:2559.
[66] Seiwert S.D., Andrews S.W., Jiang Y., Serebryany V., Tan H., Kossen K., Rajagopalan P. T.R., Misialek S., Stevens S.K., Stoycheva A., Hong J., Lim S.R., Qin X., Rieger R., Condroski K.R., Zhang H., Do M.G., Lemieux C., Hingorani G.P., Hartley D.P., Josey J.A., Pan L., Beigelman L., Blatt L.M., Antimicrob. Agents Chemother., 2008, 52:4432.
[67] Boloor A., Hanway D., Joshi M., Winn D.T., Mendez G., Walls M., Wei P., Qian F., Zhang X., Zhang Y., Hepperle M.E., Li X., Campbell D.A., Betancort J.M., Bioorg. Med. Chem. Lett., 2009, 19:5708.
[68] Li X., Zhang Y.K., Liu Y., Ding C.Z., Li Q., Zhou Y., Plattner J.J., Baker S.J., Qian X., Fan D., Liao L., Ni Z.J., White G.V., Mordaunt J.E., Lazarides L.X., Slater M.J., Jarvest R.L., Thommes P., Ellis M., Edge C.M., Hubbard J.A., Somers D., Rowland P., Nassau P., McDowell B., Skarzynski T.J., Kazmierski W.M., Grimes R.M., Wright L.L., Smith G.K., Zou W., Wright J., Pennicott L.E., Bioorg. Med. Chem. Lett., 2010, 20:3550.
[69] Kim Y., Lovell S., Tiew K.C., Mandadapu S.R., Alliston K.R., Battaile K.P., Groutas W.C., Chang K.O., J. Virol., 2012, 86:11754.
[70] Kuo C.J., Liu H.G., Lo Y.K., Seong C.M., Lee K.I., Jung Y.S., Liang P.H., FEBS Lett., 2009, 583:549.
[71] Timiri A.K., Subasri S., Kesherwani M., Vishwanathan V., Sinha B.N., Velmurugan D., Jayaprakash V., Bioorg. Chem., 2015, 62:74.
[72] Bailey T.R., Rippin S.R., Opsitnick E., Burns C.J., Pevear D.C., Collett M.S., Rhodes G., Tohan S., Huggins J.W., Baker R.O., Kern E.R., Keith K.A., Dai D., Yang G., Hruby D., Jordan R., J. Med. Chem., 2007, 50:1442.
[73] Grosenbach D.W., Jordan R., Hruby D.E., Future Virol., 2011, 6:653.
[74] Duraffour S., Lorenzo M.M., Zöller G., Topalis D., Grosenbach D., Hruby D.E., Andrei G., Blasco R., Meyer H., J. Antimicrob. Chemother., 2015, 70:1367.
[75] Dong M.x., Zhang J., Peng X.q., Lu H., Yun L.h., Jiang S., Dai Q.y., Eur. J. Med. Chem., 2010, 45:4096.
[76] Kovaleva K.S., Zubkov F.I., Bormotov N.I., Novikov R.A., Dorovatovskii P.V., Khrustalev V.N., Gatilov Y.V., Zarubaev V.V., Yarovaya O.I., Shishkina L.N., Salakhutdinov N.F., Med. Chem. Commun., 2018, 9:2072.
[77] Deore R.R., Jagtap A.D., Chang P.T., Trimethasil W., Chern J.W., J. Asian Assoc. Schools Pharm., 2012, 1:210.
[78] Li Y.F., Wang G.F., He P.L., Huang W.G., Zhu F.H., Gao H.Y., Tang W., Luo Y., Feng C.L., Shi L.P., Ren Y.D., Lu W., Zuo J.P., J. Med. Chem., 2006, 49:4790.
[79] Voronov A.A., Alekseeva K.A., Ryzhkova E.A., Zarubaev V.V., Galochkina A.V., Zaytsev V.P., Majik M.S., Tilve S.G., Gurbanov A.V., Zubkov F. I., Tetrahedron Lett., 2018, 59:1108.
[80] S. Bond, Sanford V.A., Lambert J.N., Yu C., Mitchell J.P., Draffan A. G., Nearn R. H., Polycyclic agents for the treatment of respiratory syncytial virus infections. U.S. Patent 2007/0287700, 2007
[81] Bond S., Draffan A.G., Fenner J.E., Lambert J., Lim C.Y., Lin B., Luttick A., Mitchell J.P., Morton C.J., Nearn R.H., Sanford V., Stanislawski P.C., Tucker S.P., Bioorg. Med. Chem. Lett., 2015, 25:969.
[82] Liu L., Zhai Y., Chang Y., Yan W., Huang R., Sun P., Huang W., Guo J., Lett. Drug Des. Discov., 2018, 15:304.
[83] Yang Y.J., Zhao J.H., Pan X.D., Zhang P.C., Chem. Pharm. Bull., 2010, 58:208.
[84] Yang Y., Feng Z., Jiang J., Yang Y., Pan X., Zhang P., Chem. Pharm. Bull., 2011, 59:1016
)