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Volumn 16, Issue 4, 2010, Pages 1312-1318

Ring-opening/ring-closing protocols from nitrothiophenes: Six-membered versus unusual eight-membered sulfur heterocycles through michael-type addition on nitrobutadienes

Author keywords

Fused ring systems; Medium ring compounds; Nitrothiophenes; Ring expansion; Sulfur heterocycles

Indexed keywords

AROMATIC RINGS; AROMATICITIES; CONTROLLED PROCESS; FUSED-RING SYSTEM; HETEROCYCLES; HETEROSYSTEMS; LOW TEMPERATURES; RING COMPOUNDS; RING EXPANSION; RING OPENING; SULFUR HETEROCYCLES;

EID: 76549119703     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200902528     Document Type: Article
Times cited : (8)

References (38)
  • 7
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    • Several drugs showing different therapeutic approaches contain the nitrogroup: from nifedipine and nicardipine (L-type calcium channel blockers) to clonazepan, nimetazepan, and nitrazepan (anticonvulsant); from nitrofurantoin (bacteriocidal) to metronidazole and tinidazole (antiparasitic) and to tolcapone, entacapone, and dantrolene sodium (spasmolitic); and so on. Recently, some of us have observed that some nitro- and dinitronaphthylbutadienes show promising antitumor activity and references therein
    • b) Several drugs showing different therapeutic approaches contain the nitrogroup: from nifedipine and nicardipine (L-type calcium channel blockers) to clonazepan, nimetazepan, and nitrazepan (anticonvulsant); from nitrofurantoin (bacteriocidal) to metronidazole and tinidazole (antiparasitic) and to tolcapone, entacapone, and dantrolene sodium (spasmolitic); and so on. Recently, some of us have observed that some nitro- and dinitronaphthylbutadienes show promising antitumor activity. See, for example: M. Viale, G. Petrillo, M. Maccagno, P. Castagnola, C. Aiello, C. Cordazzo, M. A. Mariggiò, S. A. Jadhav, L. Bianchi, G. Leto, E. Rizzato, A. Poggi, D. Spinelli, Eur. J. Pharmacol. 2008, 588, 47-51, and references therein;
    • (2008) Eur. J. Pharmacol. , vol.588 , pp. 47-51
    • Viale, M.1    Petrillo, G.2    Maccagno, M.3    Castagnola, P.4    Aiello, C.5    Cordazzo, C.6    Mariggiò, M.A.7    Jadhav, S.A.8    Bianchi, L.9    Leto, G.10    Rizzato, E.11    Poggi, A.12    Spinelli, D.13
  • 12
    • 76549134001 scopus 로고    scopus 로고
    • R. Budriesi, A. Chiarini, G. Petrillo, D. Spinelli, et al., unpublished results
    • R. Budriesi, A. Chiarini, G. Petrillo, D. Spinelli, et al., unpublished results.
  • 15
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    • and references therein
    • L. Yet, Chem. Rev. 2000, 100, 2963-3007, and references therein;
    • (2000) Chem. Rev. , vol.100 , pp. 2963-3007
    • Yet, L.1
  • 25
    • 0026584775 scopus 로고
    • and references therein
    • C. W. Bird, Tetrahedron 1992, 48, 335-340, and references therein. See also:
    • (1992) Tetrahedron , vol.48 , pp. 335-340
    • Bird, C.W.1
  • 29
    • 76549131441 scopus 로고    scopus 로고
    • note
    • a) DFT calculations have been carried out using the Gaussian 03 series of programs. The structures of the various minima points have been fully optimized with the gradient method. After gas-phase optimization, single-point calculations in solution were performed. The correctness of such a methodology was checked by means of a fulloptimization calculation considering the solvent. In each case the solvent (ε = 46.7) was treated with the SCRF-CPCM method. The calculations were performed using the DFT level and the B3LYP functional available in Gaussian 03. All atoms were assigned the double-ζ DZVP basis set;
  • 33
    • 76549093449 scopus 로고    scopus 로고
    • The DZVP basis set is a local spin density (LSD)-optimized basis set of double-ζ quality in the valence shell plus polarization functions
    • e) The DZVP basis set is a local spin density (LSD)-optimized basis set of double-ζ quality in the valence shell plus polarization functions;


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.