Abstract
Data on furo[2,3-{\it b}]pyridines published in the last 15 years are integrated and analyzed for the first time. Information on the methods of synthesis, chemical transformations and biological action of these systems is described systematically. Particular attention is paid to the preparation and study of properties of polycondensed derivatives as the most promising and rapidly developing line of research of furo[2,3-{\it b}]pyridine chemistry. The biological properties of this class of compounds are discussed, and examples of furo[2,3-{\it b}]pyridines that exhibit high biological activities are given.
The bibliography includes 88 references.
References
1.
2.
2
A. A. Krasnovskii
Zhur. Fiz. Khim. ,
1956
3.
3
M. F. Shostakovskii
"Prostye Vinilovye Efiry" (Vinyl Ethers) ,
1952
4.
4
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1949
5.
5
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1953
6.
6
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1953
7.
Beutner G.L., Kuethe J.T., Yasuda N.
Tetrahedron Letters ,
2009
8.
Su T., Lin C., Lin Y., Lo Y., Chen K.
Heterocycles ,
2000
9.
9
V. H. Lynch
Carnegie Inst. Year Book ,
1954
10.
Kaigorodova E.A., Vasilin V.K., Sidorova E.A., Zavodnik V.E., Krapivin G.D.
Chemistry of Heterocyclic Compounds ,
2004
11.
11
T. T. Bannister
Diss. Abstr. ,
1959
12.
Mazina O.S., Rybakov V.B., Chernyshev V.V., Babaev E.V., Aslanov L.A.
Crystallography Reports ,
2004
13.
13
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1954
14.
Dabaeva V.V., Bagdasaryan M.R., Noravyan A.S.
Chemistry of Heterocyclic Compounds ,
2007
15.
15
A. S. Holt
"Research in Photosynthesis" ,
1957
16.
Sirakanyan S.N., Paronikyan E.G., Ghukasyan M.S., Noravyan A.S.
Chemistry of Heterocyclic Compounds ,
2010
17.
17
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1958
18.
Debenham J.S., Madsen-Duggan C.B., Toupence R.B., Walsh T.F., Wang J., Tong X., Kumar S., Lao J., Fong T.M., Xiao J.C., Huang C.R., Shen C., Feng Y., Marsh D.J., Stribling D.S., et. al.
Bioorganic and Medicinal Chemistry Letters ,
2010
19.
19
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1959
20.
Taltavull J., Serrat J., Gràcia J., Gavaldà A., Córdoba M., Calama E., Montero J.L., Andrés M., Miralpeix M., Vilella D., Hernández B., Beleta J., Ryder H., Pagès L.
European Journal of Medicinal Chemistry ,
2011
21.
21
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1958
22.
Sirakanyan S.N., Kartsev V.G., Hovakimyan A.A., Noravyan A.S., Shakhatuni A.A.
Chemistry of Heterocyclic Compounds ,
2013
23.
23
N. V. Vostrilova
Dokl. Akad. Nauk Uzbek. SSR ,
1958
24.
Sirakanyan S.N., Geronikaki A., Spinelli D., Hovakimyan A.A., Noravyan A.S.
Tetrahedron ,
2013
25.
Sirakanyan S.N., Ovakimyan A.A., Noravyan A.S., Dzhagatspanyan I.A., Shakhatuni A.A., Nazaryan I.M., Akopyan A.G.
Pharmaceutical Chemistry Journal ,
2013
26.
26
B. Ya. Dain
1957
27.
Dabaeva V.V., Bagdasaryan M.R., Noravyan A.S., Nazaryan I.M., Akopyan A.G., Tadevosyan A.A.
Pharmaceutical Chemistry Journal ,
2013
28.
28
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1955
29.
29
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1951
30.
30
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1954
31.
31
A. A. Krasnovskii
Biokhimiya ,
1960
32.
32
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1952
33.
Yakovlev M.Y., Kadushkin A.V., Solov'eva N.P., Granik V.G.
Heterocyclic Communications ,
1998
34.
34
G. W. Robinson
J. Chem. Phys. ,
1886
35.
35
Z. K. Maizus
Dokl. Akad. Nauk SSSR ,
1960
36.
36
J. Billon
Bull. Soc. chim. France ,
1960
37.
37
L. M. Kosobutskaya
Dokl. Akad. Nauk SSSR ,
1950
38.
Zheng G.Z., Bhatia P., Daanen J., Kolasa T., Patel M., Latshaw S., El Kouhen O.F., Chang R., Uchic M.E., Miller L., Nakane M., Lehto S.G., Honore M.P., Moreland R.B., Brioni J.D., et. al.
Journal of Medicinal Chemistry ,
2005
39.
Hayakawa M., Kaizawa H., Moritomo H., Koizumi T., Ohishi T., Yamano M., Okada M., Ohta M., Tsukamoto S., Raynaud F.I., Workman P., Waterfield M.D., Parker P.
Bioorganic and Medicinal Chemistry Letters ,
2007
40.
Wu Z., Robinson R.G., Fu S., Barnett S.F., Defeo-Jones D., Jones R.E., Kral A.M., Huber H.E., Kohl N.E., Hartman G.D., Bilodeau M.T.
Bioorganic and Medicinal Chemistry Letters ,
2008
41.
Arcadi A., Cacchi S., Di Giuseppe S., Fabrizi G., Marinelli F.
Synlett ,
2002
42.
Malamas M.S., Sredy J., Moxham C., Katz A., Xu W., McDevitt R., Adebayo F.O., Sawicki D.R., Seestaller L., Sullivan D., Taylor J.R.
Journal of Medicinal Chemistry ,
2000
43.
Viaud-Massuard M., Van de Poël H., Guillaumet G.
Heterocycles ,
2002
44.
44
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1953
45.
Ackermann L., Kaspar L.T.
Journal of Organic Chemistry ,
2007
46.
Arcadi A., Cacchi S., Di Giuseppe S., Fabrizi G., Marinelli F.
Organic Letters ,
2002
47.
Bossharth E., Desbordes P., Monteiro N., Balme G.
Organic Letters ,
2003
48.
Martin M.W., Newcomb J., Nunes J.J., Bemis J.E., McGowan D.C., White R.D., Buchanan J.L., DiMauro E.F., Boucher C., Faust T., Hsieh F., Huang X., Lee J.H., Schneider S., Turci S.M., et. al.
Bioorganic and Medicinal Chemistry Letters ,
2007
49.
49
A. A. Krasnovskii
Biofizika ,
1958
50.
Aillaud I., Bossharth E., Conreaux D., Desbordes P., Monteiro N., Balme G.
Organic Letters ,
2006
51.
Bossharth E., Desbordes P., Monteiro N., Balme G.
Tetrahedron Letters ,
2009
52.
Yue W.S., Li J.J.
Organic Letters ,
2002
53.
Parmentier M., Gros P., Fort Y.
Tetrahedron ,
2005
54.
Liu J., Fitzgerald A.E., Mani N.S.
Journal of Organic Chemistry ,
2008
55.
Willis M.C., Taylor D., Gillmore A.T.
Tetrahedron ,
2006
56.
Tadd A.C., Fielding M.R., Willis M.C.
Tetrahedron Letters ,
2007
57.
Ramsden C.A., Milata V.
Advances in Heterocyclic Chemistry ,
2006
58.
Volochnyuk D.M., Pushechnikov A.O., Krotko D.G., Sibgatulin D.A., Kovalyova S.A., Tolmachev A.A.
Synthesis ,
2003
59.
59
H. Linshitz
"Research in Photosynthesis" ,
1957
60.
de los Ríos C.
Bioorganic and Medicinal Chemistry ,
2002
61.
10.1002/1521-4184(200209)335:7<347::AID-ARDP347>3.0.CO;2-G
62.
Martins C., Carreiras M.C., León R., de los Ríos C., Bartolini M., Andrisano V., Iriepa I., Moraleda I., Gálvez E., García M., Egea J., Samadi A., Chioua M., Marco-Contelles J.
European Journal of Medicinal Chemistry ,
2011
63.
Li W., Lai F., Lee G., Peng S., Liu R.
Journal of the American Chemical Society ,
1998
64.
Schnute M.E., Brideau R.J., Collier S.A., Cudahy M.M., Hopkins T.A., Knechtel M.L., Oien N.L., Sackett R.S., Scott A., Stephan M.L., Wathen M.W., Wieber J.L.
Bioorganic and Medicinal Chemistry Letters ,
2008
65.
Hirota T., Tomita K., Sasaki K., Okuda K., Yoshida M., Kashino S.
Heterocycles ,
2001
66.
Okuda K., Yoshida M., Hirota T., Sasaki K.
Chemical and Pharmaceutical Bulletin ,
2010
67.
Okuda K., Deguchi H., Kashino S., Hirota T., Sasaki K.
Chemical and Pharmaceutical Bulletin ,
2010
68.
Okuda K., Watanabe N., Hirota T., Sasaki K.
Tetrahedron Letters ,
2010
69.
Okuda K., Takechi H., Hirota T., Sasaki K.
Heterocycles ,
2011
70.
Okuda K., Takano J., Hirota T., Sasaki K.
Journal of Heterocyclic Chemistry ,
2011
71.
Hajbi Y., Suzenet F., Khouili M., Lazar S., Guillaumet G.
Tetrahedron ,
2007
72.
Tverdokhlebov A.V., Zavada A.V., Tolmachev A.A., Kostyuk A.N., Chernega A.N., Rusanov E.B.
Tetrahedron ,
2005
73.
73
T. Skwarski
Chem. Abs. ,
1957
74.
Yamaguchi S., Kurosaki M., Orito K., Yokayama H., Hirai Y., Shiotani S.
Journal of Heterocyclic Chemistry ,
1998
75.
Yamaguchi S., Awajima K., Hirai Y., Yokoyama H., Shiotani S.
Journal of Heterocyclic Chemistry ,
1998
76.
Yamaguchi S., Kurosaki M., Yokoyama H., Hirai Y., Shiotani S.
Journal of Heterocyclic Chemistry ,
1998
77.
Yamaguchi S., Saitoh H., Kurosaki M., Yokoyama H., Hirai Y., Shiotani S.
Journal of Heterocyclic Chemistry ,
1999
78.
Lipshutz B.H., Kim S., Mollard P., Blomgren P.A., Stevens K.L.
Tetrahedron ,
1998
79.
Charton I., Mamai A., Bennejean C., Renard P., Delagrange P., Morgan P.J., Howell H.E., Gourdel-Martin M.E., Viaud M.C., Guillaumet G.
Pharmacy and Pharmacology Communications ,
2000
80.
80
N. N. Mel'nikov
Zhur. Obshch. Khim. ,
1937
81.
Paronikyan E.G., Oganisyan A.K., Noravyan A.S., Paronikyan R.G., Dzhagatspanyan I.A.
Pharmaceutical Chemistry Journal ,
2002
82.
82
G. P. Brin
Biokhimiya ,
1957
83.
83
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1947
84.
Shiotani S., Yamaguchi S., Kurosaki M., Yokoyama H., Hirai Y.
Journal of Heterocyclic Chemistry ,
1999
85.
85
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1947
86.
86
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1958
87.
Sirakanyan S.N., Ovakimyan A.A., Noravyan A.S., Minasyan N.S., Dzhagatspanyan I.A., Nazaryan I.M., Akopyan A.G.
Pharmaceutical Chemistry Journal ,
2014
88.
88
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1946
89.
89
A. A. Krasnovskii
Izd. Akad. Nauk SSSR, Moscow ,
1955
90.
Fokialakis N., Magiatis P., Aligiannis N., Mitaku S., Tillequin F., Sévenet T.
Phytochemistry ,
2001
91.
Dorsey B.D., McDonough C., McDaniel S.L., Levin R.B., Newton C.L., Hoffman J.M., Darke P.L., Zugay-Murphy J.A., Emini E.A., Schleif W.A., Olsen D.B., Stahlhut M.W., Rutkowski C.A., Kuo L.C., Lin J.H., et. al.
Journal of Medicinal Chemistry ,
2000
92.
Bateman K.P., Baker J., Wilke M., Lee J., LeRiche T., Seto C., Day S., Chauret N., Ouellet M., Nicoll-Griffith D.A.
Chemical Research in Toxicology ,
2004
93.
93
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1956
94.
Knight Z.A., Gonzalez B., Feldman M.E., Zunder E.R., Goldenberg D.D., Williams O., Loewith R., Stokoe D., Balla A., Toth B., Balla T., Weiss W.A., Williams R.L., Shokat K.M.
Cell ,
2006
95.
Rückle T., Schwarz M.K., Rommel C.
Nature Reviews Drug Discovery ,
2006
96.
Fan Q., Knight Z.A., Goldenberg D.D., Yu W., Mostov K.E., Stokoe D., Shokat K.M., Weiss W.A.
Cancer Cell ,
2006
97.
Marco J., Carreiras M.
Mini-Reviews in Medicinal Chemistry ,
2003