Abstract
The present review relates to the synthesis and structure-activity relationship studies of Arbidol and its structural analogues. The latter are roughly divided into several unequal parts: indole- and benzofuran-based compounds, benzimidazole and imidazopyridine bioisosteres, and ring-expanded quinoline derivatives. Much attention is focused on various types of antiviral activity of the above-mentioned Arbidol congeners, as well as of the parent compound itself. Features of Arbidol synthesis and metabolic changes are also discussed.
Bibliography --- 166 references.
Funders
Russian Foundation for Basic Research
16-33-6003 mol_a_dk
Ministry of Education and Science of the Russian Federation
References
1.
rcr_87_6_509_bib1
Petrov
Lech. Vrach. ,
2011
2.
Schoggins J., Randall G.
Cell Host and Microbe ,
2013
3.
rcr_87_6_509_bib3
1991
4.
Trofimov F.A., Tsyshkova N.G., Zotova S.A., Grinev A.N.
Pharmaceutical Chemistry Journal ,
1993
5.
rcr_87_6_509_bib5
Rubtsov
1971
6.
rcr_87_6_509_bib6
Zhai
Appl. Chem. Ind. ,
2013
7.
Zhao H., Dietrich J.
Expert Opinion on Drug Discovery ,
2015
8.
rcr_87_6_509_bib8
Trofimov
Pharm. Chem. J ,
1969
9.
rcr_87_6_509_bib9
1969
10.
11.
Blaising J., Polyak S.J., Pécheur E.
Antiviral Research ,
2014
12.
Glushkov R.G., Gus'kova T.A.
Pharmaceutical Chemistry Journal ,
1999
13.
Boriskin Y.S., Pécheur E., Polyak S.J.
Virology Journal ,
2006
14.
rcr_87_6_509_bib14
2005
15.
rcr_87_6_509_bib15
Chen
J. Wuhan Inst. Tech. ,
2012
16.
Silin D., Lyubomska O., Ershov F., Frolov V., Kutsyna G.
Current Pharmaceutical Design ,
2009
17.
rcr_87_6_509_bib17
Mashkovskiy
2016
18.
Oliynyk S., Oh S.
Biomolecules and Therapeutics ,
2012
19.
Anisimova O.S., Frolova L.V., Chistyakov V.V., Ermachenkov I.A., Golovanova I.V., Zotova S.A., Pleshkova A.P., Yadrovskaya V.A., Sheinker Y.N.
Pharmaceutical Chemistry Journal ,
1995
20.
rcr_87_6_509_bib20
Chistyakov
2004
21.
rcr_87_6_509_bib21
Li
CAJ. ,
2013
22.
rcr_87_6_509_bib22
Ren
Pharm. Affairs ,
2009
23.
Wang Y., Chen X., Li Q., Zhong D.
Journal of Mass Spectrometry ,
2008
24.
Deng P., Zhong D., Yu K., Zhang Y., Wang T., Chen X.
Antimicrobial Agents and Chemotherapy ,
2013
25.
rcr_87_6_509_bib25
Song
J. Shenyang Inst. Chem. Tech. ,
2006
26.
rcr_87_6_509_bib26
1993
27.
rcr_87_6_509_bib27
Song
Chin. J. New Drugs ,
2004
28.
rcr_87_6_509_bib28
2012
29.
Monti S.A.
Journal of Organic Chemistry ,
1966
30.
Granik V.G., Lyubchanskaya V.M., Mukhanova T.I.
Pharmaceutical Chemistry Journal ,
1993
31.
Banwell M.G., Jones M.T., Loong D.T., Lupton D.W., Pinkerton D.M., Ray J.K., Willis A.C.
Tetrahedron ,
2010
32.
Hodgson H.H., Moore F.H.
Journal of the Chemical Society Transactions ,
1925
33.
rcr_87_6_509_bib33
Hodgson
1927
34.
Tetere Z., Kumpiņš V., Belyakov S., Zicāne D., Turks M.
Journal of Heterocyclic Chemistry ,
2011
35.
rcr_87_6_509_bib35
Krasovskii
Gig. Sanit. ,
1994
36.
Dubinskii R.A., Krivtsova I.Y., Grigor'ev N.B., Degterev E.V., Filimonova L.D., Kalinkina M.A.
Pharmaceutical Chemistry Journal ,
1994
37.
rcr_87_6_509_bib37
Wen
Chin. J. Pharm. ,
2006
38.
rcr_87_6_509_bib38
Zhai
Appl. Chem. Ind. ,
2013
39.
Schreiber S.L.
Science ,
2000
40.
Burke M.D., Schreiber S.L.
Angewandte Chemie - International Edition ,
2004
41.
ZHAO C., ZHAO Y., CHAI H., GONG P.
Chemical Research in Chinese Universities ,
2006
42.
rcr_87_6_509_bib42
Ma
Appl. Chem. Ind. ,
2013
43.
rcr_87_6_509_bib43
Xie
Chem. Prod. Tech. ,
2007
44.
Zhao C., Zhao Y., Chai H., Gong P.
Bioorganic and Medicinal Chemistry ,
2006
45.
Karg E., Luderer S., Pergola C., Bühring U., Rossi A., Northoff H., Sautebin L., Troschütz R., Werz O.
Journal of Medicinal Chemistry ,
2009
46.
rcr_87_6_509_bib46
2007
47.
rcr_87_6_509_bib47
48.
Bell M.R., Oesterlin R., Beyler A.L., Harding H.R., Potts G.O.
Journal of Medicinal Chemistry ,
1967
49.
Chai H., Liang X., Li L., Zhao C., Gong P., Liang Z., Zhu W., Jiang H., Luo C.
Journal of Molecular Modeling ,
2010
50.
Chai H., Zhao Y., Zhao C., Gong P.
Bioorganic and Medicinal Chemistry ,
2006
51.
rcr_87_6_509_bib51
2006
52.
rcr_87_6_509_bib52
Wang
Chin. J. Med. Chem. ,
2003
53.
Ivashchenko A.V., Yamanushkin P.M., Mit’kin O.D., Kisil’ V.M., Korzinov O.M., Vedenskii V.Y., Leneva I.A., Bulanova E.A., Bychko V.V., Okun’ I.M.
Pharmaceutical Chemistry Journal ,
2014
54.
rcr_87_6_509_bib54
Song
Chin. J. Synth. Chem. ,
2012
55.
rcr_87_6_509_bib55
Song
Chem. Bioengineering ,
2011
56.
rcr_87_6_509_bib56
Zhang
Fine Specialty Chem. ,
2007
57.
Scuotto M., Abdelnabi R., Collarile S., Schiraldi C., Delang L., Massa A., Ferla S., Brancale A., Leyssen P., Neyts J., Filosa R.
Bioorganic and Medicinal Chemistry ,
2017
58.
Ivachtchenko A.V., Yamanushkin P.M., Mitkin O.D., Kisil V.M., Korzinov O.M., Vedenskii V.Y., Leneva I.A., Bulanova E.A., Bichko V.V., Okun’ I.M., Ivashchenko A.A., Ivanenkov Y.A.
Pharmaceutical Chemistry Journal ,
2015
59.
Peduto A., Bruno F., Dehm F., Krauth V., de Caprariis P., Weinigel C., Barz D., Massa A., De Rosa M., Werz O., Filosa R.
European Journal of Medicinal Chemistry ,
2014
60.
rcr_87_6_509_bib60
Wang
Chin. J. Pharmaceut. ,
2004
61.
rcr_87_6_509_bib61
Zhang
Fine Chem. Intermediates ,
2011
62.
rcr_87_6_509_bib62
Gao
Chem. Reagents ,
2010
63.
rcr_87_6_509_bib63
Zhao
Chin. J. Med. Chem. ,
2004
64.
Di Mola A., Peduto A., La Gatta A., Delang L., Pastorino B., Neyts J., Leyssen P., de Rosa M., Filosa R.
Bioorganic and Medicinal Chemistry ,
2014
65.
Ivachtchenko Alexandre Vasil'evich, Yamanushkin Pavel Mikhailovich, Mitkin Oleg Dmitrievich, Kiselev Oleg Ivanovich
Mendeleev Communications ,
2010
66.
rcr_87_6_509_bib66
Trofimov
Chem. Heterocycl. Comp. ,
1973
67.
Zotova S.A., Korneeva T.M., Shvedov V.I., Fadeeva N.I., Leneva I.A., Fedyakina I.T., Khristova M.L., Nikolaeva I.S., Peters V.V., Gus'kova T.A.
Pharmaceutical Chemistry Journal ,
1995
68.
Mezentseva M.V., Nikolaeva I.S., Golovanova E.A., Krylova L.Y., Fomina A.N.
Pharmaceutical Chemistry Journal ,
1991
69.
Mezentseva M.V., Nikolaeva I.S., Golovanova E.A., Fomina A.N.
Pharmaceutical Chemistry Journal ,
1990
70.
Ivashchenko A.V., Yamanushkin P.M., Mit’kin O.D., Kisil’ V.M., Korzinov O.M., Vedenskii V.Y., Leneva I.A., Bulanova E.A., Bychko V.V., Okun’ I.M., Ivashchenko A.A., Ivanenkov Y.A.
Pharmaceutical Chemistry Journal ,
2014
71.
rcr_87_6_509_bib71
1958
72.
rcr_87_6_509_bib72
Joshi
J. Ind. Chem. Soc. ,
1994
73.
Novakov I.A., Artico M., Mai A., Rotili D., Orlinson B.S., Brunilina L.L., Nawrozkij M.B.
Russian Chemical Bulletin ,
2012
74.
Grinev A.N., Latypova S.V., Mashkovskii M.D., Panisheva E.K., Shvedov V.I.
Pharmaceutical Chemistry Journal ,
1967
75.
rcr_87_6_509_bib75
1958
76.
Wright Z.V., Wu N.C., Kadam R.U., Wilson I.A., Wolan D.W.
Bioorganic and Medicinal Chemistry Letters ,
2017
77.
Paredes A., de Campos Lourenço T., Marzal M., Rivera A., Dorny P., Mahanty S., Guerra-Giraldez C., García H.H., Nash T.E., Cass Q.B.
Antimicrobial Agents and Chemotherapy ,
2013
78.
Erlandsson P., Isaksson R., Lorentzon P., Lindberg P.
Journal of Chromatography B Biomedical Sciences and Applications ,
1990
79.
Liu Z., Peng Y., Ma B., Bi K., Liu Y., Sun G., Ping G., Guo Y.
International Journal of Pharmaceutics ,
2014
80.
Sheridan R.P.
Journal of Chemical Information and Computer Sciences ,
2002
81.
rcr_87_6_509_bib81
2009
82.
rcr_87_6_509_bib82
2016
83.
Velezheva V.S., Kornienko A.G., Topilin S.V., Turashev A.D., Peregudov A.S., Brennan P.J.
Journal of Heterocyclic Chemistry ,
2006
84.
A Practical, Nenitzescu-Based Synthesis of LY311727, the First Potent and Selective s-PLA2 Inhibitor
Pawlak J.M., Khau V.V., Hutchison D.R., Martinelli M.J.
Journal of Organic Chemistry ,
1996
85.
Balzarini J., Ruchko E.A., Zakharova E.K., Kameneva I.Y., Nawrozkij M.B.
Chemistry of Heterocyclic Compounds ,
2014
86.
Schols D., Ruchko E.A., Lavrenov S.N., Kachala V.V., Nawrozkij M.B., Babushkin A.S.
Chemistry of Heterocyclic Compounds ,
2015
87.
rcr_87_6_509_bib87
Allen
Org. React. ,
2011
88.
Kuckländer U.
Archiv der Pharmazie ,
1977
89.
Kuckländer U.
Archiv der Pharmazie ,
1971
90.
Kuckländer U.
Tetrahedron ,
1972
91.
Peduto A., Krauth V., Collarile S., Dehm F., Ambruosi M., Belardo C., Guida F., Massa A., Esposito V., Maione S., de Rosa M., Werz O., Filosa R.
European Journal of Medicinal Chemistry ,
2016
92.
Shvedov V.I., Kurilo G.N., Grinev A.N.
Chemistry of Heterocyclic Compounds ,
1972
93.
Shvedov V.I., Kurilo G.N., Grinev A.N.
Chemistry of Heterocyclic Compounds ,
1971
94.
Landwehr J., George S., Karg E., Poeckel D., Steinhilber D., Troschuetz R., Werz O.
Journal of Medicinal Chemistry ,
2006
95.
Grinev A.N., Panisheva E.K., Cherkasova A.A., Fomina A.N., Nikolaeva I.S., Golovanova E.A., Il'ina M.G.
Pharmaceutical Chemistry Journal ,
1987
96.
Fadeeva N.I., Panisheva E.K., Fomina A.N., Fedyakina I.T., Nikolaeva I.S., Mikerova N.I., Tikhomirova G.Y., Cherkasova A.A., Granik V.G.
Pharmaceutical Chemistry Journal ,
1991
97.
rcr_87_6_509_bib97
2011
98.
rcr_87_6_509_bib98
Zhai
Chin. J. Med. Chem. ,
2008
99.
Ivashchenko A.V., Yamanushkin P.M., Mit’kin O.D., Leneva I.A., Fedyakina I.T.
Pharmaceutical Chemistry Journal ,
2011
100.
Sellitto G., Faruolo A., de Caprariis P., Altamura S., Paonessa G., Ciliberto G.
Bioorganic and Medicinal Chemistry ,
2010
101.
Kadam R.U., Wilson I.A.
Proceedings of the National Academy of Sciences of the United States of America ,
2016
102.
Brancato V., Peduto A., Wharton S., Martin S., More V., Di Mola A., Massa A., Perfetto B., Donnarumma G., Schiraldi C., Tufano M.A., de Rosa M., Filosa R., Hay A.
Antiviral Research ,
2013
103.
rcr_87_6_509_bib103
Wang
Chin. Chem. Lett. ,
2004
104.
rcr_87_6_509_bib104
Zhao
Chin. Chem. Lett. ,
2004
105.
Fadeeva N.I., Leneva I.L., Panisheva E.K., Busse T.L., Khristova M.L., Kharitonenkov I.G., Granik V.G.
Pharmaceutical Chemistry Journal ,
1992
106.
rcr_87_6_509_bib106
Ivashchenko
Exp. Clin. Pharm. ,
2014
107.
rcr_87_6_509_bib107
Olesen
Curr. Opin. Drug Disc. Dev. ,
2001
108.
Karpov P.V., Baskin I.I., Zhokhova N.I., Nawrozkij M.B., Zefirov A.N., Yablokov A.S., Novakov I.A., Zefirov N.S.
Russian Chemical Bulletin ,
2011
109.
Blaising J., Lévy P.L., Polyak S.J., Stanifer M., Boulant S., Pécheur E.
Antiviral Research ,
2013
110.
rcr_87_6_509_bib110
Gasparini
J. Prev. Med. Hyg. ,
2014
111.
Delogu I., Pastorino B., Baronti C., Nougairède A., Bonnet E., de Lamballerie X.
Antiviral Research ,
2011
112.
da Silva-Júnior E.F., Leoncini G.O., Rodrigues É.E., Aquino T.M., Araújo-Júnior J.X.
Bioorganic and Medicinal Chemistry ,
2017
113.
Abdelnabi R., Neyts J., Delang L.
Antiviral Research ,
2015
114.
Liu N., Zhao F., Jia H., Rai D., Zhan P., Jiang X., Liu X.
MedChemComm ,
2015
115.
Zhang F., Wang G.
European Journal of Medicinal Chemistry ,
2014
116.
Jia H., Rai D., Zhan P., Chen X., Jiang X., Liu X.
Future Medicinal Chemistry ,
2015
117.
Roman G.
European Journal of Medicinal Chemistry ,
2015
118.
Lai C., Gane E., Liaw Y., Hsu C., Thongsawat S., Wang Y., Chen Y., Heathcote E.J., Rasenack J., Bzowej N., Naoumov N.V., Di Bisceglie A.M., Zeuzem S., Moon Y.M., Goodman Z., et. al.
New England Journal of Medicine ,
2007
119.
Bisacchi G.S., Chao S.T., Bachard C., Daris J.P., Innaimo S., Jacobs G.A., Kocy O., Lapointe P., Martel A., Merchant Z., Slusarchyk W.A., Sundeen J.E., Young M.G., Colonno R., Zahler R., et. al.
Bioorganic and Medicinal Chemistry Letters ,
1997
120.
Honkoop P., de Man R.
Expert Opinion on Investigational Drugs ,
2003
121.
rcr_87_6_509_bib121
2006
122.
rcr_87_6_509_bib122
Chai
Chin. J. Med. Chem. ,
2006
123.
Perfetto B., Filosa R., De Gregorio V., Peduto A., La Gatta A., de Caprariis P., Tufano M.A., Donnarumma G.
Journal of Medical Microbiology ,
2014
124.
Xu H., Lv M.
Current Pharmaceutical Design ,
2009
125.
Ghosh A.K., Osswald H.L., Prato G.
Journal of Medicinal Chemistry ,
2016
126.
Koshland D.E.
Proceedings of the National Academy of Sciences of the United States of America ,
1958
127.
Fischer E.
Berichte der deutschen chemischen Gesellschaft ,
1894
128.
Lozinskaya Natalia Alexandrovna, Volkova Maria Sergeevna, Seliverstov Mikhail Yurievitch, Temnov Victor Vyacheslavovich, Sosonyuk Sergey Evgen'evich, Proskurnina Marina Valentinovna, Zefirov Nikolai Serafimovich
Mendeleev Communications ,
2014
129.
rcr_87_6_509_bib129
Zefirova
2012
130.
rcr_87_6_509_bib130
Zefirova
Rus. J. Org. Chem. ,
2000
131.
Morellato L., Lefas-Le Gall M., Langlois M., Caignard D., Renard P., Delagrange P., Mathé-Allainmat M.
Bioorganic and Medicinal Chemistry Letters ,
2013
132.
De Esch I.J., Vollinga R.C., Goubitz K., Schenk H., Appelberg U., Hacksell U., Lemstra S., Zuiderveld O.P., Hoffmann M., Leurs R., Menge W.M., Timmerman H.
Journal of Medicinal Chemistry ,
1999
133.
Yonezawa S., Yamamoto T., Yamakawa H., Muto C., Hosono M., Hattori K., Higashino K., Yutsudo T., Iwamoto H., Kondo Y., Sakagami M., Togame H., Tanaka Y., Nakano T., Takemoto H., et. al.
Journal of Medicinal Chemistry ,
2012
134.
Lovering F., Bikker J., Humblet C.
Journal of Medicinal Chemistry ,
2009
135.
rcr_87_6_509_bib135
Moody
Anticancer Drug Des. ,
1998
136.
rcr_87_6_509_bib136
Leneva
Antibiot. Khimioter. ,
2014
137.
Das B., Rudra S., Yadav A., Ray A., Rao A.V., Srinivas A.S., Soni A., Saini S., Shukla S., Pandya M., Bhateja P., Malhotra S., Mathur T., Arora S.K., Rattan A., et. al.
Bioorganic and Medicinal Chemistry Letters ,
2005
138.
Naruganahalli K.S., Shirumalla R.K., Bansal V., Gupta J.B., Das B., Ray A.
European Journal of Pharmacology ,
2006
139.
Yanez M., Fernando Padin J., Alberto Arranz-Tagarro J., Camina M., Laguna R.
Current Topics in Medicinal Chemistry ,
2012
140.
rcr_87_6_509_bib140
Yu
Chin. Chem. Lett. ,
2005
141.
rcr_87_6_509_bib141
Zhai
Yaoxue Xuebao ,
2006
142.
Barbachyn M.R., Ford C.W.
Angewandte Chemie - International Edition ,
2003
143.
rcr_87_6_509_bib143
2011
144.
Aparoy P., Suresh G.K., Kumar Reddy K., Reddanna P.
Bioorganic and Medicinal Chemistry Letters ,
2011
145.
Zheng J., Xiao G., Guo J., Zheng Y., Gao H., Zhao S., Zhang K., Sun P.
Chemical Biology and Drug Design ,
2011
146.
Pergola C., Werz O.
Expert Opinion on Therapeutic Patents ,
2010
147.
Ford-Hutchinson A.W., Gresser M., Young R.N.
Annual Review of Biochemistry ,
1994
148.
149.
rcr_87_6_509_bib149
1989
150.
Ajani O.O., Aderohunmu D.V., Ikpo C.O., Adedapo A.E., Olanrewaju I.O.
Archiv der Pharmazie ,
2016
151.
Rajasekhar S., Maiti B., M. Balamurali M., Chanda K.
Current Organic Synthesis ,
2016
152.
Keri R.S., Hiremathad A., Budagumpi S., Nagaraja B.M.
Chemical Biology and Drug Design ,
2014
153.
Zhao Y., Liu Y., Chen D., Wei Z., Liu W., Gong P.
Bioorganic and Medicinal Chemistry Letters ,
2010
154.
Chen D., Zhai X., Yuan Q.H., Luo J., Xie S.C., Gong P.
Chinese Chemical Letters ,
2010
155.
Luo Y., Yao J., Yang L., Feng C., Tang W., Wang G., Zuo J., Lu W.
Bioorganic and Medicinal Chemistry ,
2010
156.
Chen D., Liu Y., Zhang S., Guo D., Liu C., Li S., Gong P.
Archiv der Pharmazie ,
2010
157.
Liu Y., Zhao Y., Zhai X., Feng X., Wang J., Gong P.
Bioorganic and Medicinal Chemistry ,
2008
158.
rcr_87_6_509_bib158
Li
2004
159.
Patteux C., Foucout L., Bohn P., Dupas G., Leprince J., Tonon M., Dehouck B., Marsais F., Papamicaël C., Levacher V.
Organic and Biomolecular Chemistry ,
2006
160.
Liu Y., Zhao Y., Zhai X., Liu X., Sun L., Ren Y., Gong P.
Archiv der Pharmazie ,
2008
161.
Synthesis andIn-VitroAnti-Hepatitis-B Virus Activity of 6H-[1]Benzothiopyrano[4,3-b] quinolin-10-ols
Jia W., Zhao Y., Li R., Wu Y., Li Z., Gong P.
Archiv der Pharmazie ,
2009
162.
Synthesis and in vitro anti-hepatitis B virus activity of 6H-[1]benzothiopyrano[4,3-b]quinolin-9-ols
Jia W., Liu Y., Li W., Liu Y., Zhang D., Zhang P., Gong P.
Bioorganic and Medicinal Chemistry ,
2009
163.
Liu Y., Feng G., Ma Z., Xu C., Guo Z., Gong P., Xu L.
Archiv der Pharmazie ,
2015
164.
Stahl M., Baier S.
ChemMedChem ,
2015
165.
rcr_87_6_509_bib165
166.
rcr_87_6_509_bib166