A general synthesis of arylindoles and (1-arylvinyl)carbazoles: Via a one-pot reaction from N -tosylhydrazones and 2-nitro-haloarenes and their potential application to colon cancer

Chemical Communications

Volumn 52, Issue 88, 2016, Pages 13027-13030

  Bzeih, Tourin ^a,b   Naret, Timothée ^a   Hachem, Ali ^b   Jaber, Nada ^b   Khalaf, Ali ^b   Bignon, Jerome ^c   Brion, Jean Daniel ^a   Alami, Mouad ^a   Hamze, Abdallah ^a  

^a UNIVERSITÉ PARIS SUD   (France)

^b LEBANESE UNIVERSITY   (Lebanon)

^c CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; AROMATIC NITRO COMPOUND; CARBAZOLE DERIVATIVE; COMBRETASTATIN A4; HYDRAZONE DERIVATIVE; INDOLE DERIVATIVE; ISOCOMBRETASTATIN A4; PHENYL GROUP; UNCLASSIFIED DRUG; AROMATIC HYDROCARBON; NITRO DERIVATIVE; TOLUENESULFONIC ACID DERIVATIVE;

ANTIPROLIFERATIVE ACTIVITY; ARTICLE; COLON CANCER; CONTROLLED STUDY; CROSS COUPLING REACTION; CYCLIZATION; DRUG SCREENING; DRUG SYNTHESIS; HCT116 CELL LINE; HUMAN; HUMAN CELL; IC50; IN VITRO STUDY; ONE POT SYNTHESIS; STRUCTURE ACTIVITY RELATION; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COLON TUMOR; PATHOLOGY; SYNTHESIS; TUMOR CELL CULTURE;

CARBAZOLES; CATALYSIS; COLONIC NEOPLASMS; CYCLIZATION; HUMANS; HYDRAZONES; HYDROCARBONS, AROMATIC; INDOLES; MOLECULAR STRUCTURE; NITRO COMPOUNDS; TOSYL COMPOUNDS; TUMOR CELLS, CULTURED;

EID: 84993996161     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c6cc07666a     Document Type: Article

References (45)

1. C. Dumontet M. A. Jordan Nat. Rev. Drug Discovery 2010 9 790
2. L. M. Greene M. J. Meegan D. M. Zisterer J. Pharmacol. Exp. Ther. 2015 355 212
3. C. Gridelli A. Rossi P. Maione E. Rossi V. Castaldo P. C. Sacco G. Colantuoni Oncologist 2009 14 612
4. J. Yan J. Chen S. Zhang J. Hu L. Huang X. Li J. Med. Chem. 2016 59 5264
5. D. A. Horton G. T. Bourne M. L. Smythe Chem. Rev. 2003 103 893
6. M.-Z. Zhang Q. Chen G.-F. Yang Eur. J. Med. Chem. 2015 89 421
7. T. C. Barden, in Heterocyclic Scaffolds II: Reactions and Applications of Indoles, ed., W. G. Gribble, Springer Berlin Heidelberg, Berlin, Heidelberg, 2010, p. 31
8. A. W. Schmidt K. R. Reddy H.-J. Knölker Chem. Rev. 2012 112 3193
9. L.-X. Liu X.-Q. Wang B. Zhou L.-J. Yang Y. Li H.-B. Zhang X.-D. Yang Sci. Rep. 2015 5 13101
10. J.-P. Liou Y.-L. Chang F.-M. Kuo C.-W. Chang H.-Y. Tseng C.-C. Wang Y.-N. Yang J.-Y. Chang S.-J. Lee H.-P. Hsieh J. Med. Chem. 2004 47 4247
11. J.-P. Liou C.-Y. Wu H.-P. Hsieh C.-Y. Chang C.-M. Chen C.-C. Kuo J.-Y. Chang J. Med. Chem. 2007 50 4548
12. G. R. Reddy C.-C. Kuo U.-K. Tan M. S. Coumar C.-Y. Chang Y.-K. Chiang M.-J. Lai J.-Y. Yeh S.-Y. Wu J.-Y. Chang J.-P. Liou H.-P. Hsieh J. Med. Chem. 2008 51 8163
13. Y.-S. Wu M. S. Coumar J.-Y. Chang H.-Y. Sun F.-M. Kuo C.-C. Kuo Y.-J. Chen C.-Y. Chang C.-L. Hsiao J.-P. Liou C.-P. Chen H.-T. Yao Y.-K. Chiang U.-K. Tan C.-T. Chen C.-Y. Chu S.-Y. Wu T.-K. Yeh C.-Y. Lin H.-P. Hsieh J. Med. Chem. 2009 52 4941
14. A. Brancale R. Silvestri Med. Res. Rev. 2007 27 209
15. C. Mousset A. Giraud O. Provot A. Hamze J. Bignon J. M. Liu S. Thoret J. Dubois J. D. Brion M. Alami Bioorg. Med. Chem. Lett. 2008 18 3266
16. 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 J. Med. Chem. 2009 52 4538
17. 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 ChemMedChem 2009 4 1912
18. A. Hamze J.-D. Brion M. Alami Org. Lett. 2012 14 2782
19. 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 Org. Biomol. Chem. 2013 11 430
20. A. Maksimenko M. Alami F. Zouhiri J. D. Brion A. Pruvost J. Mougin A. Hamze T. Boissenot O. Provot D. Desmaele P. Couvreur ACS Nano 2014 8 2018
21. A. Penoni J. Volkmann K. M. Nicholas Org. Lett. 2002 4 699
22. T. Sakamoto Y. Kondo N. Takazawa H. Yamanaka Tetrahedron Lett. 1993 34 5955
23. L.-Z. Gong P. Knochel Synlett 2005 267
24. Z. Zhang Z. Hu Z. Yu P. Lei H. Chi Y. Wang R. He Tetrahedron Lett. 2007 48 2415
25. B. S. Lane M. A. Brown D. Sames J. Am. Chem. Soc. 2005 127 8050
26. S. Llona-Minguez M. Desroses A. Ghassemian S. A. Jacques L. Eriksson R. Isacksson T. Koolmeister P. Stenmark M. Scobie T. Helleday Chem.-Eur. J. 2015 21 7394
27. E. M. Woerly J. E. Miller M. D. Burke Tetrahedron 2013 69 7732
28. For reviews on N -tosylhydrazones, see
29. J. Barluenga C. Valdés Angew. Chem., Int. Ed. 2011 50 7486
30. Z. Liu J. Wang J. Org. Chem. 2013 78 10024
31. X. Liu X. Ma Y. Huang Z. Gu Org. Lett. 2013 15 4814
32. T. Naret P. Retailleau J. Bignon J. D. Brion M. Alami A. Hamze Adv. Synth. Catal. 2016 358 1833
33. M. Roche S. M. Salim J. Bignon H. Levaique J.-D. Brion M. Alami A. Hamze J. Org. Chem. 2015 80 6715
34. M. Roche J. Bignon J.-D. Brion A. Hamze M. Alami J. Org. Chem. 2014 79 7583
35. J. Barluenga P. Moriel C. Valdes F. Aznar Angew. Chem., Int. Ed. 2007 46 5587
36. E. Brachet A. Hamze J. F. Peyrat J. D. Brion M. Alami Org. Lett. 2010 12 4042
37. For copper-catalysis coupling with N -tosylhydrazones, see
38. J. Aziz G. Frison M. Gomez J. D. Brion A. Hamze M. Alami ACS Catal. 2014 4 4498
39. J. Aziz J.-D. Brion A. Hamze M. Alami Adv. Synth. Catal. 2013 355 2417
40. A. Hamze B. Treguier J.-D. Brion M. Alami Org. Biomol. Chem. 2011 9 6200
41. Q. Xiao Y. Xia H. Li Y. Zhang J. Wang Angew. Chem., Int. Ed. 2011 50 1114
42. 3 is used as the reducing reagent, the product obtained can be contaminated by the N -ethylated derivatives, most likely from the alkylation of the product by the triethyl phosphate byproduct generated in the reaction mixture.
43. J. I. G. Cadogan Q. Rev., Chem. Soc. 1968 22 222
44. H. Majgier-Baranowska J. D. Williams B. Li N. P. Peet Tetrahedron Lett. 2012 53 4785
45. L. Joucla L. Djakovitch Adv. Synth. Catal. 2009 351 673