2,2-Dimethyl-2H-pyran-derived alkaloids I. Practical synthesis of acronycine and benzo[b]acronycine and their biological properties

Archives of Pharmacal Research

Volumn 31, Issue 9, 2008, Pages 1087-1093

  Motiur Rahman, A F M ^a   Liang, Jing Lu ^a   Lee, Seung Ho ^a   Son, Jong Keun ^a   Jung, Mi Ja ^a,b   Kwon, Youngjoo ^a,b   Jahng, Yurngdong ^a  

^a Yeungnam University   (South Korea)

^b Ewha Womans University   (South Korea)

Author keywords

2,2 Dimethyl 2H pyran derived alkaloid; Acronycine; Benzo b acronycine; Cytotoxicity; Phenylboronic acid; Topoisomerase inhibitor

Indexed keywords

ACRONINE; ANTINEOPLASTIC AGENT; BENZO(B)ACRONYCINE; CAMPTOTHECIN; DNA; DNA TOPOISOMERASE; DNA TOPOISOMERASE (ATP HYDROLYSING); DRUG DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; ETOPOSIDE;

ARTICLE; CELL PROLIFERATION; CELL SURVIVAL; DRUG ANTAGONISM; DRUG EFFECT; DRUG SCREENING; HUMAN; SYNTHESIS; TUMOR CELL LINE;

ACRONINE; ANTINEOPLASTIC AGENTS, PHYTOGENIC; CAMPTOTHECIN; CELL LINE, TUMOR; CELL PROLIFERATION; CELL SURVIVAL; DNA; DNA TOPOISOMERASES, TYPE I; DNA TOPOISOMERASES, TYPE II; DRUG SCREENING ASSAYS, ANTITUMOR; ETOPOSIDE; HUMANS; INDICATORS AND REAGENTS;

EID: 52649092382     PISSN: 02536269     EISSN: 19763786     Source Type: Journal    
DOI: 10.1007/s12272-001-1273-7     Document Type: Article

References (45)

1. Anand, R. C. and Selvapalam, N., A practical regiospecific approach towards acronycine and related alkaloids. Chem. Commun., 199-200 (1996).
2. Bandaranayake, W. M., Crombie, L., and Whiting, D. A., Novel methods for the synthesis of 2-2-dimethylchromens. Chem. Commun., 970-971 (1969).
3. Bandaranayake, W. M., Crombie, L., and Whiting, D. A., Pyridine-catalysed chromenylation of mono-chelated metadihydric phenols with mono-, sesqui-and di-terpene aldehydes: synthesis of rubranine and flemingins A-, B-and C-methyl ethers. J. Chem. Soc. C, 804-810 (1971).
4. J. R. Beck R. Kwok R. N. Booher A. C. Brown L. E. Patterson P. Pranc B. Rockley A. Pohland 1968 Synthesis of acronycine J. Am. Chem. Soc. 90 4706 4710
5. Blechert, S., Fichter, K.-E., Lindner, J., and Winterfeldt, E., Cyclisierungen zu 9,11-disubstituierten Acronycin-Derivaten. Liebigs Ann. Chem., 503-511 (1980).
6. M. J. Broadhurst C. H. Hassall 1982 Anthracyclines. Part 1. The synthesis of racemic daunomycinone and some related tetrahydronaphthacenequinones J. Chem. Soc., Perkin Trans. 1 2227 2238
7. R. D. Brown L. J. Drummond F. N. Lahey W. C. Thomas 1949 Alkaloids of the Australian Rutaceae: Acronychia baueri. II. Some reactions of the alkaloid acronycine Aust. J. Sci. Res. A2 622 629
8. N. Costes S. Michel F. Tillequin M. Koch A. Pierre Gh. Atassi 1999 Chiral dihydroxylation of acronycine: Absolute configuration of natural cis-1,2-dihydroxy-1,2-dihydroacronycine and cytotoxicity of (1R,2R)-and (1S,2S)-1,2-diacetoxy-1,2-dihydroacronycine J. Nat. Prod. 62 490 492
9. N. Costes H. Le Deit S. Michel F. Tillequin M. Koch B. Pfeiffer P. Renard S. Léonce N. Guilbaud L. Kraus-Berthier A. Pierré Gh. Atassi 2000 Synthesis and cytotoxic and antitumor activity of benzo[b]pyrano[3,2-h]acridin- 7-one analogues of acronycine J. Med. Chem. 43 2395 2402
10. J. A. Diment E. Ritchie W. C. Taylor 1969 The Diels-Alder reaction of some styrenes and 2,2-dimethylchromenes with acetylenic esters Aust. J. Chem. 22 1721 1730
11. R. T. Dorr J. D. Liddil D. D. Von Hoff M. Soble C. K. Osborne 1989 Antitumor activity and murine pharmacokinetics of parenternal acronycine Cancer Res. 49 340 344
12. A. Elomri S. Mitaku S. Michel A.-L. Skaltsounis F. Tillequin M. Koch A. Pierre N. Guilbaud S. Leonce L. Kraus-Berthier Y. Rolland Gh. Atassi 1996 Synthesis and cytotoxic and antitumor activity of esters in the 1,2-dihydroxy-1,2-dihydroacronycine series J. Med. Chem. 39 4762 4766
13. M. Fukuda K. Nishio F. Kanazawa H. Ogasawara T. Ishida H. Arioka K. Bojanowsji M. Oka N. Saijo 1996 Synergism between cisplatin and topoisomerase I inhibitors, NB-506 and SN-38, in human small cell lung cancer cells Cancer Res. 56 789 793
14. T. R. Govindachari B. R. Pai P. S. Subramaniam 1966 Alkaloids of Glycosmis pentaphylla (Retz.) Correa Tetrahedron 22 3245 3252
15. J. Hlubucek E. Ritchie W. C. Taylor 1970 A synthesis of acronycine Aust. J. Chem. 23 1881 1889
16. G. I. Hughes F. N. Lahey J. R. Price L. J. Webb 1948 Alkaloids of the Australian Rutaceae Nature 162 223 224
17. Jahng, Y., Studies on the steric effect of substituent on N12 in acridones are in progress, which will be due in the future (2008).
18. H. W. Jung J. S. Oh S. H. Lee J. L. Liang D. H. Kim A. F. M. Rahman Y. Jahng 2007 A facile synthesis of mollugin Bull. Kor. Chem. Soc. 28 1863 1866
19. D. H. Kang J. S. Kim M. J. Jung E. S. Lee Y. Jahng Y. Kwon Y. Na 2008 New insight for fluoroquinophenoxazine derivatives as possibly new potent topoisomerase I inhibitor Bioorg Med Chem Lett. 18 1520 1524
20. S. Léonce L. Kraus-Berthier R. M. Golsteyn M.-H. David-Cordonnier C. Tardy A. Lansiaux V. Poindessous A. K. Larsen A. Pierré 2006 Generation of replication-dependent double-strand breaks by the novel N2-G-alkylator S23906-1 Cancer Res. 66 7203 7210
21. D. G. Longhhead 1990 Synthesis of des-N-methylacronycine and acronycine J. Org. Chem. 55 2245 2246
22. J.-P. Lumb D. Trauner 2005 Pericyclic reactions of prenylated naphthoquinones: Biomimetic syntheses of mollugin and microphyllaquinone Org. Lett. 7 5865 5868
23. J.-P. Lumb D. Trauner 2005 Biomimetic synthesis and structure elucidation of rubicordifolin, a cytotoxic natural product from Rubia cordifolia J. Am. Chem. Soc. 127 2870 2871
24. P. L. Macdonald A. V. Robertson 1966 The structure of acronycine Aust. J. Chem. 19 275 281
25. P. Magiatis S. Mitaku A.-L. Skaltsounis F. Tillequin M. Koch A. Pierre G. Atassi 1999 Synthesis and cytotoxic activity of 1-alkoxy-and 1-amino-2-hydroxy-1,2-dihydroacronycine derivatives Chem. Pharm. Bull. 47 611 614
26. S. Michel T. Gaslonde F. Tillequin 2004 Benzo[b]acronycine derivatives: a novel class of antitumor agents Eur. J. Med. Chem. 39 649 655
27. S. Mitaku A. L. Skaltsounis F. Tillequin M. Koch 1988 Chemistry of Acronycine; Part 1. Synthesis of 1-hydroxy-1,2-dihydroacronycine and 2-hydroxy-1,2-dihydroacronycine Planta Medica 54 24 27
28. Murphy, W. S., Tuladhar, S. M., and Duffy, B., Simple synthesis of hexahydrocannaninoids using phenylboric acid catalyst. J. Chem. Soc., Perkin Trans. 1, 605-609 (1992).
29. J. Nickl 1958 Synthese von β-Tubasäure und von Lonchocarpin Chem. Ber. 91 1372 1376
30. T. M. Nguyen C. Sittisombut S. Boutefnouchet M.-C. Lallemand S. Michel M. Koch F. Tillequin R. Mazinghien A. Lansiaux M.-H. David-Cordonnier B. Pfeiffer L. Kraus-Berthier S. Leonce A. Pierre 2006 Synthesis, antitumor activity, and mechanism of action of benzo[a]pyrano[3,2-h]acridin-7-one analogues of acronycine J. Med. Chem. 49 3383 3394
31. C. S. Oh C. V. Greco 1970 Synthesis of isoacronycine and its pyranone analog J. Heterocyclic Chem. 7 261 267
32. J. D. Pettigrew J. A. Cadieux S. S. S. So P. D. Wilson 2005 Phenylboronic acid mediated triple condensation reactions of phloroglucinol and unsaturated carbonyl compounds Org. Lett. 7 467 470
33. K. Ramesh R. S. Kapil 1986 Synthesis of acridone alkaloids: Glycocitrine-I, N-methylatalphyllidine, atalphyllidine 11-hydroxyacronycine and 14-hydroxynoracronycine Ind. J. Chem. Section B 25B 684 687
34. J. Reisch P. Dziemba T. Adam 1993 Natural Product Chemistry. Part 160. Synthesis of 8-, 9-, 10-and 11-methylacronycines to improve the cytostatic activity of acronycine J. Heterocyclic Chem. 30 1469 1476
35. J. Reisch M. Top 1991 Path to acronycine epoxide and acronycine diol Pharmazie 46 745
36. Reisch, J. and Schiwek, K., Naturstoffchemie, 180. Synthese von Acronycineepoxid. Liebigs Ann. Chem., 317-318 (1994).
37. J. Schneider E. L. Evans E. Grunberg R. I. Fryer 1972 Synthesis and biological activity of acronycine analogs J. Med. Chem. 15 266 270
38. L. I. Smith P. M. Ruoff 1940 The chemistry of vitamin E. XXII. The reaction between Grignard reagents and coumarins and hydrocoumarins J. Am. Chem. Soc. 62 145 148
39. R. R. Smolders A. Waefelaer R. Coomans D. Francart J. Hanuise N. Voglet 1982 Synthesis of 9-, 10-and 11-fluoroacronycines Bull. Soc. Chim. Belg. 91 33 42
40. R. R. Smolders J. Hanuise N. Voglet 1984 Synthesis of some hydroxylated 9-acridanones Bull. Soc. Chim. Belg. 93 239 240
41. G. H. Svoboda 1966 Alkaloids of Acronychia baueri. II. Extraction of the alkaloids and studies of structure-activity relationships Lloydia 29 206 224
42. G. H. Svoboda G. A. Poore P. J. Simpson G. B. Boder 1966 Alkaloids of Acronychia baueri. I. Isolation of the alkaloids and a study of the antitumor and other biological properties of acronycine J. Pharm. Sci. 55 758 768
43. E. Späth R. Hillel 1939 Die Synthese des Seselins (XLVI. Mitteil. über natürliche Cumarine) Chem. Ber. 72 963 965
44. H. D. Thi Mai T. Gaslonde S. Michel F. Tillequin M. Koch J.-B. Bongui A. Elomri E. Seguin B. Pfeiffer P. Renard M.-H. David-Cordonnier W. Laine C. Bailly L. Kraus-Berthier S. Léonce J. A. Hickman A. Pierré 2003 Structure-activity relationships and mechanism of action of antitumor benzo[b]pyrano[3,2-h]acridin-7-one acronycine analogues J. Med. Chem. 46 3072 3082
45. Tillequin, F., Michel, S., and Skaltsounis, A.-L., Acronycine-Type Alkaloids: Chemistry and Biology. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Elsevier: Amsterdam, 1998; Vol 12, pp 1-102.