Synthesis of new heteroaryl and heteroannulated indoles from dehydrophenylalanines: Antitumor evaluation

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 10, 2008, Pages 5584-5589

  Queiroz, Maria João R P ^a   Abreu, Ana S ^a   Carvalho, M Solange D ^a   Ferreira, Paula M T ^a   Nazareth, Nair ^b   Sao Jose Nascimento M ^b  

^a UNIVERSITY OF MINHO   (Portugal)

^b UNIVERSITY OF PORTO   (Portugal)

Author keywords

Antitumor evaluation; Dehydrophenylalanines; Heteroannulated indoles; Heteroarylindoles; Metal assisted C N intramolecular cyclization; Suzuki coupling

Indexed keywords

DEHYDROPHENYLALANINE DERIVATIVE; INDOLE DERIVATIVE; METHYL 1 PHENYL 3H BENZOFURO[2,3 E]INDOLE 2 CARBOXYLATE; METHYL 1 PHENYL 3H BENZOTHIENO[2,3 E]INDOLE 2 CARBOXYLATE; METHYL 3 (DIBENZOFUR 4 YL) 1H INDOLE 2 CARBOXYLATE; METHYL 3 (DIBENZOTHIEN 4 YL) 1H INDOLE 2 CARBOXYLATE; N BUTYLOXYCARBONYL BETA DIBENZOFUR 4 YL DEHYDROPHENYLALANINE; N BUTYLOXYCARBONYL BETA DIBENZOTHIEN 4 YL DEHYDROPHENYLALANINE; PHENYLALANINE DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CELL STRAIN MCF 7; CONTROLLED STUDY; CULTURE MEDIUM; CYCLIZATION; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; ISOMERIZATION; NEOPLASM; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUZUKI REACTION; THIN LAYER CHROMATOGRAPHY;

ANTINEOPLASTIC AGENTS; BREAST NEOPLASMS; CARCINOMA, NON-SMALL-CELL LUNG; CELL PROLIFERATION; CENTRAL NERVOUS SYSTEM NEOPLASMS; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; INDOLES; MOLECULAR STRUCTURE; PHENYLALANINE; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED;

EID: 43949131415     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.04.004     Document Type: Article

References (12)

1. Demeunynck M., Bailly C., and Wilson W.D. Small Molecule DNA and RNA Binders (2003), Wiley-VHC Verlag GmbH & Co. KGaA, Weinheim
2. Kaufmann D., Pojarová M., Vogel S., Liebl R., Gastpar R., Gross D., Nishino T., Pfaller T., and von Angerer E. Bioorg. Med. Chem. 15 (2007) 5122-5136
3. For a recent review on indoles as potent inhibitors of tubulin polymerization see:. Brancale A., and Silvestri R. Med. Res. Rev. 27 (2007) 209-238
4. Cacchi S., and Fabrizi G. Chem. Rev. 105 (2005) 2873-2920
5. Abreu A.S., Silva N.O., Ferreira P.M.T., and Queiroz M.-J.R.P. Tetrahedron Lett. 44 (2003) 3377-3379
6. Abreu A.S., Silva N.O., Ferreira P.M.T., Queiroz M.-J.R.P., and Venanzi M. Eur. J. Org. Chem. (2003) 4792-4796
7. Queiroz M.-J.R.P., Abreu A.S., Castanheira E.M.S., and Ferreira P.M.T. Tetrahedron 63 (2007) 2215-2222
8. Queiroz M.-J.R.P., Castanheira E.M.S., Carvalho M.S.D., Abreu A.S., Ferreira P.M.T., Karadeniz H., and Erdem A. Tetrahedron 64 (2008) 382-391
9. Abreu A.S., Ferreira P.M.T., Queiroz M.-J.R.P., Ferreira I.C.F.R., Calhelha R.C., and Estevinho L.M. Eur. J. Org. Chem. (2005) 2951-2957
10. Abreu A.S., Ferreira P.M.T., Monteiro L.S., Queiroz M.-J.R.P., Ferreira I.C.F.R., Calhelha R.C., and Estevinho L.M. Tetrahedron 60 (2004) 11821-11828
11. Skehan P., Storeng R., Scudiero D., Monks A., McMahon J., Vistica D., Warren J.T., Bokesch H., Kenny S., and Boyd M.R. J. Natl. Cancer Inst. 82 (1990) 1107-1112
12. Monks A., Scudiero D., Skehan P., Shoemaker R., Paul K., Vistica D., Hose C., Langley J., Cronise P., Vaigro-Wolff A., Gray-Goodrich M., Campbell H., Mayo J., and Boyd M. J. Natl. Cancer Inst. 83 (1991) 757-776