Rapid synthesis of 4-arylchromenes from ortho-substituted alkynols: A versatile access to restricted iso combretastatin A-4 analogues as antitumor agents

European Journal of Medicinal Chemistry

Volumn 90, Issue , 2015, Pages 834-844

  Renko, Dolor ^a   Provot, Olivier ^a   Rasolofonjatovo, Evelia ^a   Bignon, Jérôme ^b   Rodrigo, Jordi ^a   Dubois, Joëlle ^b   Brion, Jean Daniel ^a   Hamze, Abdallah ^a   Alami, Mouad ^a  

^a UNIVERSITÉ PARIS SACLAY   (France)

^b CNRS   (France)

Author keywords

4 Arylchromenes; 4 Chromanones; Combretastatin A 4; Cytotoxicity; N Tosylhydrazones; Tubulin

Indexed keywords

4 (3,5 DIMETHOXYPHENYL) 6 METHYL 2H CHROMENE; 4 (4 FLUOROPHENYL) 6 METHYL 2H CHROMENE; 4 (4 FLUOROPHENYL) 7 METHOXY 2H CHROMENE; 4 (4 METHOXY 2 NITROPHENYL) 6 METHYL 2H CHROMENE; 4 (6 METHYL 2H CHROMEN 4 YL)BENZONITRILE; 4 (7 METHOXY 2H CHROMEN 4 YL) N,N DIMETHYLANILINE; 4 (P TOLYL) 2H CHROMENE; 4 ARYL 2H CHROMENE; 4 METHYL N" (6 METHYLCHROMAN 4 YLIDENE)BENZENE SULFONOHYDRAZIDE; 4 METHYL N" (6 PHENYLCHROMAN 4 YLIDENE)BENZENE SULFONOHYDRAZIDE; 6 METHYLCHROMAN 4 ONE; 6 PHENYLCHROMAN 4 ONE; 7 (HYDROXYMETHYL)CHROMAN 4 ONE; 7 FLUORO 4 (3,4,5 TRIMETHOXYPHENYL) 2H CHROMENE; 7 FLUOROCHROMAN 4 ONE; 7 METHOXY 4 (3,4,5 TRIMETHOXYPHENYL) 2H CHROMENE; 7 METHOXY 4 (P TOLYL) 2H CHROMENE; 7 METHOXYCHROMAN 4 ONE; 8 BROMO 7 METHOXYCHROMAN 4 ONE; ANTINEOPLASTIC AGENT; ARYLPROPYNOL; CHROMAN 4 ONE; COMBRETASTATIN A4; N TOSYLHYDRAZONE; N' (7 FLUOROCHROMAN 4 YLIDENE) 4 METHYLBENZENE SULFONOHYDRAZIDE; N' (7 METHOXYCHROMAN 4 YLIDENE) 4 METHYLBENZENE SULFONOHYDRAZIDE; N' (8 BROMO 7 METHOXYCHROMAN 4 YLIDENE) 4 METHYLBENZENESULFONOHYDRAZIDE; N' (CHROMAN 4 YLIDENE) 4 METHYLBENZENESULFONOHYDRAZIDE; N' [7 (HYDROXYMETHYL)CHROMAN 4 YLIDENE) 4 METHYLBENZENESULFONOHYDRAZIDE; UNCLASSIFIED DRUG; UNINDEXED DRUG; ALCOHOL DERIVATIVE; BENZOPYRAN DERIVATIVE; COMBRETASTATIN A4 PHOSPHATE; STILBENE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG CYTOTOXICITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MELTING POINT; MICROTUBULE ASSEMBLY; PROTON NUCLEAR MAGNETIC RESONANCE; CELL PROLIFERATION; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; DRUG SCREENING; K562 CELL LINE; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL CULTURE;

ALCOHOLS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; BENZOPYRANS; CELL PROLIFERATION; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; K562 CELLS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STILBENES; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED;

EID: 84918812498     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.12.024     Document Type: Article

References (57)

1. G.R. Pettit S.B. Singh E. Hamel C.M. Lin D.S. Alberts D. Garcia-Kendall Isolation and structure of the strong cell growth and tubulin inhibitor combretastatin A-4 Experientia 45 1989 209 211
2. G.R. Pettit G.M. Cragg D.L. Herald J.M. Schmidt P. Lohavanijaya Isolation and structure of combretastatin Can. J. Chem. 60 1982 1374 1376
3. E. Hamel Antimitotic natural products and their interactions with tubulin Med. Res. Rev. 16 1996 207 231
4. A. McGown B. Fox Differential cytotoxicity of combretastatins A1 and A4 in two daunorubicin-resistant P388 cell lines Cancer Chemother. Pharmacol. 26 1990 79 81
5. G.M. Tozer C. Kanthou C.S. Parkins S.A. Hill The biology of the combretastatins as tumour vascular targeting agents Int. J. Exp. Pathol. 83 2002 21 38
6. J. Griggs J.C. Metcalfe R. Hesketh Targeting tumour vasculature: the development of combretastatin A4 Lancet Oncol. 2 2001 82 87
7. K. Ohsumi R. Nakagawa Y. Fukuda T. Hatanaka Y. Morinaga Y. Nihei K. Ohishi Y. Suga Y. Akiyama T. Tsuji Novel combretastatin analogues effective against murine solid tumors: design and structure-activity relationships J. Med. Chem. 41 1998 3022 3032
8. L. Wang K.W. Woods Q. Li K.J. Barr R.W. McCroskey S.M. Hannick L. Gherke R.B. Credo Y.-H. Hui K. Marsh R. Warner J.Y. Lee N. Zielinski-Mozng D. Frost S.H. Rosenberg H.L. Sham Potent, orally active heterocycle-based combretastatin A-4 analogues: synthesis, structure-activity relationship, pharmacokinetics, and in vivo antitumor activity evaluation J. Med. Chem. 45 2002 1697 1711
9. S. Aprile E. Del Grosso G.C. Tron G. Grosa In vitro metabolism study of combretastatin A-4 in rat and human liver microsomes Drug Metab. Dispos. 35 2007 2252 2261
10. J. Lee S. Bae S.-H. Lee H. Choi Y.H. Kim S.J. Kim G.T. Park S.K. Moon D.-H. Kim S. Lee S.K. Ahn N.S. Choi K.J. Lee Discovery of a potent tubulin polymerization inhibitor: synthesis and evaluation of water-soluble prodrugs of benzophenone analog Bioorg. Med. Chem. Lett. 20 2010 6327 6330
11. D.M. Patterson G.J. Rustin Vascular damaging agents Clin. Oncol. R. Coll. Radiol. 19 2007 443 456
12. C. Mousset A. Giraud O. Provot A. Hamze J. Bignon J.M. Liu S. Thoret J. Dubois J.D. Brion M. Alami Synthesis and antitumor activity of benzils related to combretastatin A-4 Bioorg. Med. Chem. Lett. 18 2008 3266 3271
13. O. Provot A. Hamze J.-F. Peyrat J.-D. Brion M. Alami Discovery and hit to lead optimization of novel combretastatin A-4 analogues: dependence of C-linker length and hybridization Anticancer Agents Med. Chem. 13 2013 1614 1635
14. A. Hamze D. Veau O. Provot J.D. Brion M. Alami Palladium-catalyzed Markovnikov terminal arylalkynes hydrostannation: application to the synthesis of 1,1-diarylethylenes J. Org. Chem. 74 2009 1337 1340
15. A. Hamze J.-D. Brion M. Alami Synthesis of 1,1-diarylethylenes via efficient iron/copper co-catalyzed coupling of 1-arylvinyl halides with Grignard reagents Org. Lett. 14 2012 2782 2785
16. M. Roche A. Hamze O. Provot J.-D. Brion M. Alami Synthesis of ortho/ortho'-substituted 1,1-diarylethylenes through cross-coupling reactions of sterically encumbered hydrazones and aryl halides J. Org. Chem. 78 2013 445 454
17. M. Roche A. Hamze J.-D. Brion M. Alami Catalytic three-component one-pot reaction of hydrazones, dihaloarenes, and amines Org. Lett. 15 2013 148 151
18. S. Messaoudi B. Treguier A. Hamze O. Provot J.-F. Peyrat J.R. De Losada J.-M. Liu J. Bignon J. Wdzieczak-Bakala S. Thoret J. Dubois J.-D. Brion M. Alami Isocombretastatins a versus combretastatins a: the forgotten isoCA-4 isomer as a highly promising cytotoxic and antitubulin agent J. Med. Chem. 52 2009 4538 4542
19. A. Hamze A. Giraud S. Messaoudi O. Provot J.-F. Peyrat J. Bignon J.-M. Liu J. Wdzieczak-Bakala S. Thoret J. Dubois J.-D. Brion M. Alami Synthesis, biological evaluation of 1,1-diarylethylenes as a novel class of antimitotic agents Chem Med Chem 4 2009 1912 1924
20. A. Hamze E. Rasolofonjatovo O. Provot C. Mousset D. Veau J. Rodrigo J. Bignon J.-M. Liu J. Wdzieczak-Bakala S. Thoret J. Dubois J.-D. Brion M. Alami B-ring-modified isoCombretastatin A-4 analogues endowed with interesting anticancer activities Chem Med Chem 6 2011 2179 2191
21. J. Aziz E. Brachet A. Hamze J.-F. Peyrat G. Bernadat E. Morvan J. Bignon J. Wdzieczak-Bakala D. Desravines J. Dubois M. Tueni A. Yassine J.-D. Brion M. Alami Synthesis, biological evaluation, and structure-activity relationships of tri-and tetrasubstituted olefins related to isocombretastatin A-4 as new tubulin inhibitors Org. Biomol. Chem. 11 2013 430 442
22. M. Farhat A. Poissonnier A. Hamze C. Ouk-Martin J.D. Brion M. Alami J. Feuillard C. Jayat-Vignoles Reversion of apoptotic resistance of TP53-mutated Burkitt lymphoma B-cells to spindle poisons by exogenous activation of JNK and p38 MAP kinases Cell. Death Dis. 5 2014 e1201
23. A. Maksimenko M. Alami F. Zouhiri J.-D. Brion A. Pruvost J. Mougin A. Hamze T. Boissenot O. Provot D. Desmaële P. Couvreur Therapeutic modalities of squalenoyl nanocomposites in colon cancer: an ongoing search for improved efficacy ACS Nano 2014 2018 2032
24. S. Messaoudi A. Hamze O. Provot B. Treguier J.R. De Losada J. Bignon J.M. Liu J. Wdzieczak-Bakala S. Thoret J. Dubois J.D. Brion M. Alami Discovery of isoerianin analogues as promising anticancer agents Chem Med Chem 6 2011 488 497
25. K.G. Pinney, V.P. Mocharla, Z. Chen, C.M. Garner, A. Ghatak, M. Hadimani, J. Kessler, J.M. Dorsey, K. Edvardsen, D.J. Chaplin, J. Prezioso, U.R. Ghatak, U.S. Patent Appl., (2004), 20040043969.
26. E. Rasolofonjatovo O. Provot A. Hamze J. Rodrigo J. Bignon J. Wdzieczak-Bakala C. Lenoir D. Desravines J. Dubois J.-D. Brion M. Alami Design, synthesis and anticancer properties of 5-arylbenzoxepins as conformationally restricted isocombretastatin A-4 analogs Eur. J. Med. Chem. 62 2013 28 39
27. T. Eguchi Y. Hoshino A. Ayame Synthesis of neoflavenes by a palladium-catalyzed cross-coupling reaction of 4-Trifluoromethylsulfonyloxy-2H-Chromenes with arylboronic acids Bull. Chem. Soc. Jpn. 75 2002 581 585
28. D.M.X. Donnelly J.-P. Finet P.J. Guiry K. Nesbitt Synthesis of neoflavenes by ligand coupling reactions with aryllead triacetates Tetrahedron 57 2001 413 423
29. S.A. Worlikar T. Kesharwani T. Yao R.C. Larock Synthesis of 3,4-disubstituted 2H-benzopyrans through Cg'C bond formation via electrophilic cyclization J. Org. Chem. 72 2007 1347 1353
30. G. Savitha K. Felix P.T. Perumal Synthesis of novel 3-Bromo-2H-chromene derivatives: palladium-mediated intramolecular cyclization of aryl propargyl ethers Synlett 2009 2079 2082
31. S.J. Pastine S.W. Youn D. Sames PtIV-catalyzed cyclization of arene-alkyne substrates via intramolecular electrophilic hydroarylation Org. Lett. 5 2003 1055 1058
32. X. Xu J. Liu L. Liang H. Li Y. Li Iron-catalyzed regioselective hydroaryloxylation of C-C triple bonds: an efficient synthesis of 2H-1-benzopyran derivatives Adv. Synth. Catal. 351 2009 2599 2604
33. A. Aponick B. Biannic M.R. Jong A highly adaptable catalyst/substrate system for the synthesis of substituted chromenes Chem. Commun. 46 2010 6849 6851
34. C. Commandeur J.-C. Florent P. Rousselle E. Bertounesque Easy access to pyranoacridines, pyranoxanthenes, and arylchromenes through a domino reaction Eur. J. Org. Chem. 2011 2011 1447 1451
35. E. Rasolofonjatovo B. Tréguier O. Provot A. Hamze E. Morvan J.-D. Brion M. Alami Palladium-catalyzed coupling of N-tosylhydrazones with ortho substituted aryl halides: synthesis of 4-arylchromenes and related heterocycles Tetrahedron Lett. 52 2011 1036 1040
36. E. Rasolofonjatovo B. Tréguier O. Provot A. Hamze J.-D. Brion M. Alami A one-pot three-step synthesis of z-trisubstituted olefins from arylalkynes and their cyclization into 4-aryl-2H-chromenes Eur. J. Org. Chem. 2012 1603 1615
37. K. Sonogashira Y. Tohda N. Hagihara A convenient synthesis of acetylenes: catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes and bromopyridines Tetrahedron Lett. 16 1975 4467 4470
38. M. Alami F. Ferri G. Linstrumelle An efficient palladium-catalyzed reaction of vinyl and aryl halides or triflates with terminal alkynes Tetrahedron Lett. 34 1993 6403 6406
39. N. Olivi E. Thomas J.F. Peyrat M. Alami J.D. Brion Highly efficient p-toluenesulfonic acid-catalyzed alcohol addition or hydration of unsymmetrical arylalkynes Synlett 2004 2175 2179
40. G. Le Bras O. Provot J.F. Peyrat M. Alami J.D. Brion Rapid microwave assisted hydration of internal arylalkynes in the presence of PTSA: an efficient regioselective access to carbonyl compounds Tetrahedron Lett. 47 2006 5497 5501
41. M. Jacubert O. Provot J.-F. Peyrat A. Hamze J.-D. Brion M. Alami p-Toluenesulfonic acid-promoted selective functionalization of unsymmetrical arylalkynes: a regioselective access to various arylketones and heterocycles Tetrahedron 66 2010 3775 3787
42. J. Barluenga P. Moriel C. Valdes F. Aznar N-tosylhydrazones as reagents for cross-coupling reactions: a route to polysubstituted olefins Angew. Chem. Int. Ed. 46 2007 5587 5590
43. B. Treguier A. Hamze O. Provot J.D. Brion M. Alami Expeditious synthesis of 1,1-diarylethylenes related to isocombretastatin A-4 (isoCA-4) via palladium-catalyzed arylation of N-tosylhydrazones with aryl triflates Tetrahedron Lett. 50 2009 6549 6552
44. G. Le Bras A. Hamze S. Messaoudi O. Provot P.-B. Le Calvez J.-D. Brion M. Alami Synthesis of isocoumarin via PTSA-catalyzed annulation of diarylalkynes Synthesis 2008 1607 1611
45. M. Lawson A. Hamze J.F. Peyrat J. Bignon J. Dubois J.D. Brion M. Alami An efficient coupling of N-tosylhydrazones with 2-halopyridines: synthesis of 2-alpha-styrylpyridines endowed with antitumor activity Org. Biomol. Chem. 11 2013 3664 3673
46. K.W. Anderson T. Ikawa R.E. Tundel S.L. Buchwald The selective reaction of aryl halides with KOH:g‰ synthesis of phenols, aromatic ethers, and benzofurans J. Am. Chem. Soc. 128 2006 10694 10695
47. S. Messaoudi J.D. Brion M. Alami An expeditious copper-catalyzed access to 3-aminoquinolinones, 3-aminocoumarins and anilines using sodium azide Adv. Synth. Catal. 352 2010 1677 1687
48. A. Giraud O. Provot A. Hamzé J.-D. Brion M. Alami One-pot hydrosilylation-protodesilylation of functionalized diarylalkynes: a highly selective access to Z-stilbenes. Application to the synthesis of combretastatin A-4 Tetrahedron Lett. 49 2008 1107 1110
49. T.L. Nguyen C. McGrath A.R. Hermone J.C. Burnett D.W. Zaharevitz B.W. Day P. Wipf E. Hamel R. Gussio A common pharmacophore for a diverse set of colchicine site inhibitors using a structure-based approach J. Med. Chem. 48 2005 6107 6116
50. V. Siddaiah C.V. Rao S. Venkateswarlu A.V. Krishnaraju G.V. Subbaraju Synthesis, stereochemical assignments, and biological activities of homoisoflavonoids Bioorg. Med. Chem. 14 2006 2545 2551
51. A. Arcadi F. Blesi S. Cacchi G. Fabrizi A. Goggiamani F. Marinelli Gold versus silver catalyzed intramolecular hydroarylation reactions of [(3-arylprop-2-ynyl)oxy]benzene derivatives Org. Biomol. Chem. 10 2012 9700 9708
52. M.L. Shelanski F. Gaskin C.R. Cantor Microtubule assembly in the absence of added nucleotides Proc. Natl. Acad. Sci. USA 70 1973 765 768
53. D.M. Barron S.K. Chatterjee R. Ravindra R. Roof E. Baloglu D.G.I. Kingston S. Bane A fluorescence-based high-throughput assay for antimicrotubule drugs Anal. Biochem. 315 2003 49 56
54. J. Sadowski J. Gasteiger G. Klebe Comparison of automatic three-dimensional model builders using 639 X-ray structures J. Chem. Inf. Comput. Sci. 34 1994 1000 1008
55. G. Jones P. Willett R.C. Glen A.R. Leach R. Taylor Development and validation of a genetic algorithm for flexible docking J. Mol. Biol. 267 1997 727 748
56. O. Korb T. Stützle T.E. Exner Empirical scoring functions for advanced protein-ligand docking with plants J. Chem. Inf. Model 49 2009 84 96
57. E.F. Pettersen T.D. Goddard C.C. Huang G.S. Couch D.M. Greenblatt E.C. Meng T.E. Ferrin UCSF chimera-A visualization system for exploratory research and analysis J. Comput. Chem. 25 2004 1605 1612