Palladium catalyzed reaction in aqueous DMF: Synthesis of 3-alkynyl substituted flavones in the presence of prolinol

Tetrahedron

Volumn 59, Issue 48, 2003, Pages 9563-9570

  Pal, Manojit ^a   Subramanian, Venkataraman ^a   Parasuraman, Karuppasamy ^a   Yeleswarapu, Koteswar Rao ^a  

^a DR REDDY'S LABORATORIES LTD   (India)

Author keywords

3 alkynyl flavones; Aqueous media; Palladium catalyst; Prolinol

Indexed keywords

3 IODOFLAVONE; ALCOHOL DERIVATIVE; ALKYNE DERIVATIVE; ALKYNYL GROUP; COPPER; FLAVONE DERIVATIVE; PALLADIUM; PROLINOL; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CHEMICAL REACTION; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; THIN LAYER CHROMATOGRAPHY;

EID: 0242352616     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.10.003     Document Type: Article

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18. Alkenyl or alkynyl side chain attached to an appropriate heterocycle has been found to be beneficial for their interesting anti-cancer as well as other biological activities. For selected examples see: in the case of uracil (a) Spector T., Porter D.J.T., Nelson D.J., Baccanari D.P., Davis S.T., Almond M.R., Khor S.P., Amyx H., Cao S., Rustum Y.M. Drugs Future. 19:1994;565 (b) Kundu N.G., Das B., Spears C.P., Majumdar A., Kang S.I. J. Med. Chem. 33:1990;1975 (c) Kundu N.G., Dasgupta S.K., Chaudhuri L.N., Mahanty J.S., Spears C.J., Shahinian A.H. Eur. J. Med. Chem. 28:1993;473. For pyrone (d) Marrision L.R., Dickinson J.M., Ahmed R., Fairlamb I.J.S. Tetrahedron Lett. 43:2002;8853 (e) Marrision L.R., Dickinson J.M., Fairlamb I.J.S. Bioorg. Med. Chem. Lett. 12:2002;3509 (f) Lee J.-H., Park J.-S., Cho C.-G. Org. Lett. 4:2002;1171. For purin (g) Hocek M., Votruba I. Bioorg. Med. Chem. Lett. 12:2002;1055. For adenosine (h) Volpini R., Costanzi S., Lambertucci C., Vittori S., Klotz K.-N., Lorenzen A., Cristalli G. Bioorg. Med. Chem. Lett. 11:2001;1931. For quinolines (i) Nolan J.M., Comins D.L. J. Org. Chem. 68:2003;3736.
19. Alkenyl or alkynyl side chain attached to an appropriate heterocycle has been found to be beneficial for their interesting anti-cancer as well as other biological activities. For selected examples see: in the case of uracil (a) Spector T., Porter D.J.T., Nelson D.J., Baccanari D.P., Davis S.T., Almond M.R., Khor S.P., Amyx H., Cao S., Rustum Y.M. Drugs Future. 19:1994;565 (b) Kundu N.G., Das B., Spears C.P., Majumdar A., Kang S.I. J. Med. Chem. 33:1990;1975 (c) Kundu N.G., Dasgupta S.K., Chaudhuri L.N., Mahanty J.S., Spears C.J., Shahinian A.H. Eur. J. Med. Chem. 28:1993;473. For pyrone (d) Marrision L.R., Dickinson J.M., Ahmed R., Fairlamb I.J.S. Tetrahedron Lett. 43:2002;8853 (e) Marrision L.R., Dickinson J.M., Fairlamb I.J.S. Bioorg. Med. Chem. Lett. 12:2002;3509 (f) Lee J.-H., Park J.-S., Cho C.-G. Org. Lett. 4:2002;1171. For purin (g) Hocek M., Votruba I. Bioorg. Med. Chem. Lett. 12:2002;1055. For adenosine (h) Volpini R., Costanzi S., Lambertucci C., Vittori S., Klotz K.-N., Lorenzen A., Cristalli G. Bioorg. Med. Chem. Lett. 11:2001;1931. For quinolines (i) Nolan J.M., Comins D.L. J. Org. Chem. 68:2003;3736.
20. Alkenyl or alkynyl side chain attached to an appropriate heterocycle has been found to be beneficial for their interesting anti-cancer as well as other biological activities. For selected examples see: in the case of uracil (a) Spector T., Porter D.J.T., Nelson D.J., Baccanari D.P., Davis S.T., Almond M.R., Khor S.P., Amyx H., Cao S., Rustum Y.M. Drugs Future. 19:1994;565 (b) Kundu N.G., Das B., Spears C.P., Majumdar A., Kang S.I. J. Med. Chem. 33:1990;1975 (c) Kundu N.G., Dasgupta S.K., Chaudhuri L.N., Mahanty J.S., Spears C.J., Shahinian A.H. Eur. J. Med. Chem. 28:1993;473. For pyrone (d) Marrision L.R., Dickinson J.M., Ahmed R., Fairlamb I.J.S. Tetrahedron Lett. 43:2002;8853 (e) Marrision L.R., Dickinson J.M., Fairlamb I.J.S. Bioorg. Med. Chem. Lett. 12:2002;3509 (f) Lee J.-H., Park J.-S., Cho C.-G. Org. Lett. 4:2002;1171. For purin (g) Hocek M., Votruba I. Bioorg. Med. Chem. Lett. 12:2002;1055. For adenosine (h) Volpini R., Costanzi S., Lambertucci C., Vittori S., Klotz K.-N., Lorenzen A., Cristalli G. Bioorg. Med. Chem. Lett. 11:2001;1931. For quinolines (i) Nolan J.M., Comins D.L. J. Org. Chem. 68:2003;3736.
21. Alkenyl or alkynyl side chain attached to an appropriate heterocycle has been found to be beneficial for their interesting anti-cancer as well as other biological activities. For selected examples see: in the case of uracil (a) Spector T., Porter D.J.T., Nelson D.J., Baccanari D.P., Davis S.T., Almond M.R., Khor S.P., Amyx H., Cao S., Rustum Y.M. Drugs Future. 19:1994;565 (b) Kundu N.G., Das B., Spears C.P., Majumdar A., Kang S.I. J. Med. Chem. 33:1990;1975 (c) Kundu N.G., Dasgupta S.K., Chaudhuri L.N., Mahanty J.S., Spears C.J., Shahinian A.H. Eur. J. Med. Chem. 28:1993;473. For pyrone (d) Marrision L.R., Dickinson J.M., Ahmed R., Fairlamb I.J.S. Tetrahedron Lett. 43:2002;8853 (e) Marrision L.R., Dickinson J.M., Fairlamb I.J.S. Bioorg. Med. Chem. Lett. 12:2002;3509 (f) Lee J.-H., Park J.-S., Cho C.-G. Org. Lett. 4:2002;1171. For purin (g) Hocek M., Votruba I. Bioorg. Med. Chem. Lett. 12:2002;1055. For adenosine (h) Volpini R., Costanzi S., Lambertucci C., Vittori S., Klotz K.-N., Lorenzen A., Cristalli G. Bioorg. Med. Chem. Lett. 11:2001;1931. For quinolines (i) Nolan J.M., Comins D.L. J. Org. Chem. 68:2003;3736.
22. Alkenyl or alkynyl side chain attached to an appropriate heterocycle has been found to be beneficial for their interesting anti-cancer as well as other biological activities. For selected examples see: in the case of uracil (a) Spector T., Porter D.J.T., Nelson D.J., Baccanari D.P., Davis S.T., Almond M.R., Khor S.P., Amyx H., Cao S., Rustum Y.M. Drugs Future. 19:1994;565 (b) Kundu N.G., Das B., Spears C.P., Majumdar A., Kang S.I. J. Med. Chem. 33:1990;1975 (c) Kundu N.G., Dasgupta S.K., Chaudhuri L.N., Mahanty J.S., Spears C.J., Shahinian A.H. Eur. J. Med. Chem. 28:1993;473. For pyrone (d) Marrision L.R., Dickinson J.M., Ahmed R., Fairlamb I.J.S. Tetrahedron Lett. 43:2002;8853 (e) Marrision L.R., Dickinson J.M., Fairlamb I.J.S. Bioorg. Med. Chem. Lett. 12:2002;3509 (f) Lee J.-H., Park J.-S., Cho C.-G. Org. Lett. 4:2002;1171. For purin (g) Hocek M., Votruba I. Bioorg. Med. Chem. Lett. 12:2002;1055. For adenosine (h) Volpini R., Costanzi S., Lambertucci C., Vittori S., Klotz K.-N., Lorenzen A., Cristalli G. Bioorg. Med. Chem. Lett. 11:2001;1931. For quinolines (i) Nolan J.M., Comins D.L. J. Org. Chem. 68:2003;3736.
23. Alkenyl or alkynyl side chain attached to an appropriate heterocycle has been found to be beneficial for their interesting anti-cancer as well as other biological activities. For selected examples see: in the case of uracil (a) Spector T., Porter D.J.T., Nelson D.J., Baccanari D.P., Davis S.T., Almond M.R., Khor S.P., Amyx H., Cao S., Rustum Y.M. Drugs Future. 19:1994;565 (b) Kundu N.G., Das B., Spears C.P., Majumdar A., Kang S.I. J. Med. Chem. 33:1990;1975 (c) Kundu N.G., Dasgupta S.K., Chaudhuri L.N., Mahanty J.S., Spears C.J., Shahinian A.H. Eur. J. Med. Chem. 28:1993;473. For pyrone (d) Marrision L.R., Dickinson J.M., Ahmed R., Fairlamb I.J.S. Tetrahedron Lett. 43:2002;8853 (e) Marrision L.R., Dickinson J.M., Fairlamb I.J.S. Bioorg. Med. Chem. Lett. 12:2002;3509 (f) Lee J.-H., Park J.-S., Cho C.-G. Org. Lett. 4:2002;1171. For purin (g) Hocek M., Votruba I. Bioorg. Med. Chem. Lett. 12:2002;1055. For adenosine (h) Volpini R., Costanzi S., Lambertucci C., Vittori S., Klotz K.-N., Lorenzen A., Cristalli G. Bioorg. Med. Chem. Lett. 11:2001;1931. For quinolines (i) Nolan J.M., Comins D.L. J. Org. Chem. 68:2003;3736.
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63. 2 in water has been documented earlier, see Ref. 12e. (e) Amatore C., Jutand A. J. Am. Chem. Soc. 115:1993;9531.
64. 2 in water has been documented earlier, see Ref. 12e. (e) Amatore C., Jutand A. J. Am. Chem. Soc. 115:1993;9531.
65. 2 in water has been documented earlier, see Ref. 12e. (e) Amatore C., Jutand A. J. Am. Chem. Soc. 115:1993;9531.
66. 50 of 30 μM when tested against same panel of cancer cell lines [e.g. HT29 (colon), H460 (lung), LoVo (colon) etc.]. A detailed study on biological activities of these compounds will be published elsewhere.
67. Yu W.-Y., Alper H. J. Org. Chem. 62:1997;5684.