Keywords
beyeran
diterpenoids
fullerene
isosteviol
macrocycles
Abstract
Macrocycle having two isosteviol moieties and malonate fragment has been synthesised, and its ability to inhibit the growth of Mycobacterium tuberculosis H37Rv in vitro with MIC value of 1mg cm–3 has been demonstrated. The macrocycle adds fullerene C60 at the activated methylene group to furnish the corresponding methanofullerene conjugate.
References
1.
10.1016/j.mencom.2011.04.006_bib0005_1
Vögtle
Host Guest Complex Chemistry Macrocycles: Synthesis, Strucrures, Applications,
1985
2.
10.1016/j.mencom.2011.04.006_bib0005_2
Karsten
Macrocyclic Chemistry: Current Trends and Future Perspectives,
2005
3.
Cronin L.
Annual Reports Section A (Inorganic Chemistry),
2003
4.
Lipkowitz K.B., Raghothama S., Yang J.A.
Journal of the American Chemical Society,
1992
5.
Bongiorno D., Ceraulo L., Mele A., Panzeri W., Selva A., Turco Liveri V.
Carbohydrate Research,
2002
6.
Uekama K., Hirayama F., Irie T.
Chemical Reviews,
1998
7.
Redenti E., Szente L., Szejtli J.
Journal of Pharmaceutical Sciences,
2001
8.
H. M. Merkus, Patent EP 867181, 1998.
9.
C. Zhang, R. Tan, H. Tang and X. Tan, Patent CN 1195525, 2000.
10.
J. MacMillan and M. H. Beale, in Comprehensive Natural Products Chemistry, eds. D. Barton, K. Nakanishi and O. Meth-Cohn, Elsevier, Amsterdam, 1999, vol. 2, p. 217.
11.
Wessjohann L.A., Ruijter E., Garcia-Rivera D., Brandt W.
Molecular Diversity,
2005
12.
Gray C.A., Davies-Coleman M.T., Schleyer M.H.
Journal of Natural Products,
2000
13.
Corea G., Fattorusso E., Lanzotti V., Taglialatela-Scafati O., Appendino G., Ballero M., Simon P., Dumontet C., Di Pietro A.
Journal of Medicinal Chemistry,
2003
14.
Corea G., Fattorusso E., Lanzotti V., Motti R., Simon P., Dumontet C., Di Pietro A.
Journal of Medicinal Chemistry,
2004
15.
Tamminen J., Kolehmainen E.
Molecules,
2001
16.
Petukhov P.A., Bagryanskaya I.Y., Gatilov Y.V., Tkachev A.V.
Mendeleev Communications,
2000
17.
Álvaro E., de la Torre M.C., Sierra M.A.
Chemical Communications,
2006
18.
Ojima I., Lin S., Inoue T., Miller M.L., Borella C.P., Geng X., Walsh J.J.
Journal of the American Chemical Society,
2000
19.
Larroque A., Dubois J., Thoret S., Aubert G., Guénard D., Guéritte F.
Bioorganic and Medicinal Chemistry Letters,
2005
20.
Larroque A., Dubois J., Thoret S., Aubert G., Chiaroni A., Guéritte F., Guénard D.
Bioorganic and Medicinal Chemistry,
2007
21.
10.1016/j.mencom.2011.04.006_bib0035_4
Strobykina
Zh. Obshch. Khim.,
2007
22.
10.1016/j.mencom.2011.04.006_bib0035_5
Strobykina
Zh. Obshch. Khim.,
2007
23.
MOSETTIG E., NES W.R.
Journal of Organic Chemistry,
1955
24.
10.1016/j.mencom.2011.04.006_bib0040_2
Liu
Acta Card. Sinica,
2001
25.
10.1016/j.mencom.2011.04.006_bib0040_3
Kataev
Khim. Farm. Zh.,
2006
26.
Diesters on the basis of 16-hydroxyisosteviol and dicarboxylic acids as carriers of Fe(III) picrates
Kataev V.E., Militsina O.I., Strobykina I.Y., Gubaidullin A.T., Zverev V.V., Kataeva O.N., Fedorova O.V., Valova M.S., Rusinov G.L.
Journal of Inclusion Phenomena and Macrocyclic Chemistry,
2007
27.
Kataev V.E., Strobykina I.Y., Militsina O.I., Korochkina M.G., Fedorova O.V., Ovchinnikova I.G., Valova M.S., Rusinov G.L.
Tetrahedron Letters,
2006
28.
Alfonsov V.A., Bakaleynik G.A., Gubaidullin A.T., Kataev V.E., Kovyljaeva G.I., Konovalov A.I., Litvinov I.A., Strobykina I.J., Andreeva O.V., Korochkina M.G.
Mendeleev Communications,
1999
29.
10.1016/j.mencom.2011.04.006_bib0040_7
Andreeva
Zh. Strukt. Khim.,
2007
30.
31.
Bradshaw J.S., Hansen L.D., Nielsen S.F., Thompson M.D., Reeder R.A., Izatt R.M., Christensen J.J.
Journal of the Chemical Society Chemical Communications,
1975
32.
Izatt R.M., Bradshaw J.S., Nielsen S.A., Lamb J.D., Christensen J.J., Sen D.
Chemical Reviews,
1985
33.
Reuther U., Brandmüller T., Donaubauer W., Hampel F., Hirsch A.
Chemistry - A European Journal,
2002
34.
Carano M., Corvaja C., Garlaschelli L., Maggini M., Marcaccio M., Paolucci F., Pasini D., Righetti P., Sartori E., Toffoletti A.
European Journal of Organic Chemistry,
2003
35.
Pasini D., Righetti P.P., Rossi V.
Organic Letters,
2001
36.
Pasini D., Klopp J.M., Fréchet J.M.
Chemistry of Materials,
2001
37.
Felder-Flesch D., Rupnicki L., Bourgogne C., Donnio B., Guillon D.
Journal of Materials Chemistry A,
2006
38.
10.1016/j.mencom.2011.04.006_bib0060
Al’fonsov
Zh. Obshch. Khim.,
2000
39.
10.1016/j.mencom.2011.04.006_bib0065_1
Derome
Modern NMR Techniques for Chemistry Research,
1988
40.
10.1016/j.mencom.2011.04.006_bib0065_2
Atta-ur-Rahman
One and Two Dimensional NMR Spectroscopy,
1989
41.
Latypov S., Balandina A., Boccalini M., Matteucci A., Usachev K., Chimichi S.
European Journal of Organic Chemistry,
2008
42.
Latypov S.K., Kozlov A.V., Hey-Hawkins E., Balueva A.S., Karasik A.A., Sinyashin O.G.
Journal of Physical Chemistry A,
2010
43.
M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle and J. A. Pople, Gaussian 98, revision A.3, Gaussian, Inc., Pittsburgh, PA, 1998. 16 P. R. Donald, Tuberculosis, 2010, 90, 279.