Synthesis, X-ray crystal structure and biological properties of acetylenic flavone derivatives

Farmaco

Volumn 58, Issue 9, 2003, Pages 875-881

  Artali, Roberto ^a   Barili, Pier Luigi ^b   Bombieri, Gabriella ^a   Da Re, Paolo ^a   Marchini, Nicoletta ^a   Meneghetti, Fiorella ^a   Valenti, Piero ^c  

^a UNIVERSITY OF MILAN   (Italy)

^b Dipto Chim Bioorganica Biofarmacia   (Italy)

^c Dipartimento di Chimica   (Italy)

Author keywords

Antimicrobial and cytotoxic activities; Flavone derivatives; Synthesis; X ray structures

Indexed keywords

3 METHYL 3 HYDROXYBUT 1 YNE; 3 METHYLBUT 3 EN 2 YNE; 4' (3 HYDROXY 3 METHYLBUT 1 YNYL)FLAVONE; 4' (3 METHYLBUT 3 EN 1 YNYL)FLAVONE; 6 (3 HYDROXY 3 METHYLBUT 1 YNYL)FLAVONE; 6 (3 METHYLBUT 3 EN 1 YNYL)FLAVONE; 7 (3 HYDROXY 3 METHYLBUT 1 YNYL)FLAVONE; 7 (3 METHYLBUT 3 EN 1 YNYL)FLAVONE; ALKYNE DERIVATIVE; FLAVONE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CONTROLLED STUDY; CRYSTAL STRUCTURE; CYTOTOXICITY; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; X RAY CRYSTALLOGRAPHY;

EID: 0141676091     PISSN: 0014827X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0014-827X(03)00145-9     Document Type: Article

References (19)

1. Ben-Zvi Z., Danon A. Pharmacology of acetylenic derivatives. Patai S. The Chemistry of Triple Bounded Functional Group. 1994;739-787 J. Wiley, Chichester UK.
2. Banthorpe P.V. Biochemistry of triple bonded functional group. Patai S. The Chemistry of Triple Bounded Functional Group. 2:1994;689-737 J. Wiley, Chichester UK.
3. Bleicher L.S., Cosford N.D.P., Herbaut A., McCallum J.S., McDonald I.A. A practical and efficient synthesis of the selective neuronal acetylcholine-gated ion channel agonist (S)-(-)-5-ethynyl-3(1-methyl-2-pyrrolidinyl)pyridine maleate (SIB-1508Y). J. Org. Chem. 63:1998;1109-1118.
4. Wong G., Koehler K.F., Skolnick P., Gu Z.-Q., Ananthan S., Schönholzer P., Hunkeler W., Zhang W., Cook J.M. Synthetic and computer-assisted analysis of the structural requirements for selective, high-affinity ligand binding to diazepam-insensitive benzodiazepine receptors. J. Med. Chem. 36:1993;1820-1830.
5. Cocuzza A.J., Chidester D.R., Cordova B.C., Jeffrey S., Parsons R.L., Bacheler L.T., Erickson-Viitanen S., Trainor G.L., Ko S.S. Synthesis and evaluation of efavirenz (Sustiva) analogues as HIV-1 reverse transcriptase inhibitors: replacement of the cyclopropylacetylene side chain. Bioorg. Med. Chem. Lett. 11:2001;1177-1179.
6. Legraverend M.L.O., Bisagni E., Leclerc S., Meijer L. Synthesis of C2 alkynylated purines, a new family of potent inhibitors of cyclin-dependent kinases. Bioorg. Med. Chem. Lett. 8:1998;793-798.
7. Faulkner D.J. Marine natural products. Nat. Prod. Rep. 18:2001;1-49.
8. Mari S., Rossi M., Valenti P., Dare P. Flavone and xanthone derivatives related to fluoroquinolones. Farmaco. 54:1999;411-415. and references therein.
9. Barili P.L., Valenti P., Artali R., Bombieri G., Da Re P. Synthesis and properties of 6-fluoro-7-chloro-4-oxo-4H-chromene-3-carboxylic acid. X-ray structure of achiral heterotopic 3-diethoxymethyl-6-fluoro-7-chloro-4-oxo-4H-chromene. Z. Kristallogr. 216:2001;600-603.
10. Fkyerat A., Dubin G.-M., Tabacchi R. The synthesis of natural acetylenic compounds from stereum hirsutum. Helv. Chim. Acta. 82:1999;1418-1422.
11. Ishibashi K., Nose K., Shindo T., Asai M., Mishima H. Seccaine: acetylenic metabolite of helminthosporium siccans. Sankyo Kenkyusho Nempo. 20:1968;76-79.
12. Sonogashira K., Tohda Y., Hagihara N. Convenient synthesis of acetylenes. Catalytic substitution of acetylenic hydrogen with bromo-alkenes, iodo-arenes and bromo-pyridenes. Tetrahedron Lett. 1975;4467-4470.
13. Rossi M., Cantrell J.S., Farber A.J., Dyott T., Carrell H.L., Glusker J.P. Molecular structures of 5,6- and 7,8-benzoflavones, inhibitors of aryl hydrocarbon hydroxylase. Cancer Res. 40:1980;2774-2784.
14. Wallet J.C., Gaydou E.M., Jaud J., Baldy A. Structures of 2′-methoxyflavone and 2′,4′,5,7-tetramethoxyflavone. Acta Crystallogr. Sect. C. 46:1990;1536-1540.
15. C.K. Johnson, ORTEP 11, Report ORNL-5138 Oak Ridge National Laboratory, TN, 1976.
16. Gale J.D. GULP - a computer program for the symmetry adapted simulation of solids. J. Chem. Soc. Faraday Trans. 93:1997;629-637.
17. Schmidt M.W., Baldridge K.K., Boatz J.A., Elbert S.T., Gordon M.S., Jensen J.H., Koseki S., Matsunaga N., Nguyen K.A., Su S., Windus T.L., Dupuis M., Montgomery J.A. General atomic and molecular electronic structure system. J. Comput. Chem. 14:1993;1347-1363.
18. Altomare A., Burla M.C., Camalli M., Cascarano G., Giacovazzo C., Gagliardi A., Polidori G. SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Crystallogr. 27:1994;435.
19. G.M. Sheldrick, SHELX-97 Program for the Refinement of Crystal Structures, University of Göttingen, Germany.