Synthesis and characterization of benzenesulfonyl hydrazones and benzenesulfonamides

Synthetic Communications

Volumn 36, Issue 22, 2006, Pages 3401-3409

  De Oliveira, Kely Navakoski ^a   Nunes, Ricardo José ^a  

^a FEDERAL UNIVERSITY OF SANTA CATARINA   (Brazil)

Author keywords

Benzenesulfonyl chlorides; Diels Alder reaction; Sulfonamides; Sulfonylhydrazones

Indexed keywords

1 METHYL 4 [4 (MORPHOLIN 4 YLSULFONYL)PHENYL] 10 OXA 4 AZATRICYCLO[5.2.1.0 2,6]DEC 8 ENE 3,5 DIONE; 1 METHYL 4 [4 (PYRROLIDIN 1 YLSULFONYL)PHENYL] 10 OXA 4 AZATRICYCLO[5.2.1.0 2,6]DEC 8 ENE 3,5 DIONE; 4 [4 (MORPHOLIN 4 YLSULFONYL)PHENYL] 10 OXA 4 AZATRICYCLO[5.2.1.0 2,6]DEC 8 ENE 3,5 DIONE; 4 [4 (PYRROLIDIN 1 YLSULFONYL)PHENYL] 10 OXA 4 AZATRICYCLO[5.2.1.0 2,6]DEC 8 ENE 3,5 DIONE; 4-[3,5 DIOXO 10 OXA 4 AZATRICYCLO[5.2.1.0 2,6]DEC 8 EN 4 YL]BENZENESULFONOHYDRAZIDE; BENZENE DERIVATIVE; BENZENESULFONAMIDE DERIVATIVE; HYDRAZONE DERIVATIVE; N,N DIMETHYL 4 [1 METHYL 3,5 DIOXO 10 OXA 4 AZATRICYCLO[5.2.1.0 2,6]DEC 8 EN 4 YL]BENZENESULFONAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; DIELS ALDER REACTION; DRUG SYNTHESIS; POLYMERIZATION;

EID: 33751106933     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910600941455     Document Type: Article

References (12)

1. Rollas, S.; Gulerman, N.; Erdeniz, H. Synthesis and antimicrobial activity of some new hydrazones of 4-fluorobenzoic acid hydrazide and 3-acetyl-2,5-disubstituted-1,3,4-oxadiazolines. Farmaco 2002, 57 (2), 171-174.
2. Ozawa, Y.; Sugi, N. H.; Nagasu, T.; Owa, T.; Watanabe, T.; Koyanagi, N.; Yoshino, H.; Kitoh, K.; Yoshimatsu, K. E7070, a novel sulfonamide agent with potent antitumour activity in vitro and in vivo. Eur. J. Cancer 2001, 37, 2275-2282.
3. Betz, U. A. K.; Fischer, R.; Kleymann, G.; Hendrix, M.; Rübsamen-Waigmann, H. Potent in vivo antiviral activity of the herpes simplex virus primase-helicase inhibitor BAY 57-1293. Antimicrob. Agents Chemother. 2002, 46, 1766-1772.
4. Bhattacharya, G.; Herman, J.; Delfín, D.; Salem, M. M.; Barszcz, T.; Mollet, M.; Riccio, G.; Brun, R.; Werbovetz, K. A. Synthesis and antitubulin activity of N1- and N4-substituted 3,5-dinitro sulfanilamides against African trypanosomes and leishmania. J. Med. Chem. 2004, 47, 1823-1832.
5. Lima, L. M.; Amarante, E. G.; Miranda, A. L. P.; Fraga, C. A. M.; Barreiro, E. J. Syntheses and antinociceptive profile of novel acidic sulphonylhydrazone derivatives from natural safrole. Pharm. Pharmacol. Commun. 1999, 5, 673-678.
6. Kremlev, M. M.; Kul'chitskaya, M. E.; Biba, A. D.; Romanenko, V. D. Synthesis of derivatives of N-(sulfamoylaryl)maleinimides. Ukr. Khim Zh. 1971, 37 (9), 924-927;
7. Chem. Abstr. 1972, 77, 19296n.
8. Andrade, E. S.; Nunes, R. J.; Uieara, M. Synthesis and characterization of exoendo and endo-endo benzenesulfonylaziridine. Synth. Commun. 2004, 34, 3073-3081.
9. Baldwin, J. E.; Pinschmidt, R. K.; Andrist, A. H. Bicyclo[2.1.0]pent-2- ene: Tests for the retro-ene mechanism of thermal isomerization. J. Am. Chem. Soc. 1970, 92 (17), 5249-5250.
10. Chang, A. C.; Young, P. R. Characterization of geometric isomers of norbornene end-capped imides. J. Heterocycl. Chem. 1983, 20 (1), 177-182.
11. Lopez, S. N.; Sortino, M.; Escalante, A.; de Campos, F.; Correa, R.; Cechinel Filho, V.; Nunes, R. J.; Zacchino, S. A. Antifungal properties of novel N- and α,β-substituted succinimides against dermatophytes. Arzneimittel-Forschung 2003, 53 (4), 280-288.
12. Cremlyn, R.; Swinbourne, F.; Nunes, R. Diels-Alder reactions using N-[p-(chlorosulfonyl) phenyl]maleimide as dienophile. Phosphorus, Sulfur Rela. Elem. 1987, 33 (1-2), 65-75.