Fluorofuroxans: Synthesis and Application as Photoinduced Nitric Oxide Donors

被引:21
作者
Ando, Akihiro [1 ]
Matsubara, Ryosuke [1 ]
Takazawa, Saori [1 ]
Shimada, Toshiyuki [1 ]
Hayashi, Masahiko [1 ]
机构
[1] Kobe Univ, Dept Chem, Nada Ku, Kobe, Hyogo 6578501, Japan
关键词
aromatic substitution; furoxans; nitrogen oxides; photochemistry; synthetic methods; UNSYMMETRICALLY SUBSTITUTED FUROXANS; BIOLOGICAL EVALUATION; GENERATION; FURAZANS; NO; SPECTROSCOPY; SULFONES; RELEASE; ACIDS;
D O I
10.1002/ajoc.201600149
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of 3- and 4-fluorofuroxans is reported for the first time. Under photoirradiation and physiological conditions, 4-fluorofuroxans with weaker nitric oxide-releasing ability are converted into 3-fluorofuroxans, which show remarkable thiol-mediated nitric oxide-releasing properties, thereby suggesting that 4-fluorofuroxans are potent photoinduced nitric oxide donors.
引用
收藏
页码:886 / 890
页数:5
相关论文
共 51 条
[1]  
[Anonymous], ANGEW CHEM
[2]   New reactions of furoxans: Formation of alkynes and cyclobutaphenanthrenes [J].
Auricchio, S ;
Selva, A ;
Truscello, AM .
TETRAHEDRON, 1997, 53 (51) :17407-17416
[3]  
Birckenbach L, 1931, LIEBIGS ANN CHEM, V489, P7
[4]   Unsymmetrically substituted furoxans. Part 18. Smiles rearrangement in furoxan systems and in related furazans [J].
Boschi, D ;
Sorba, G ;
Bertinaria, M ;
Fruttero, R ;
Calvino, R ;
Gasco, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (15) :1751-1757
[5]   UNSYMMETRICALLY SUBSTITUTED FUROXANS .8. CHLOROMETHYLFUROXANS [J].
CALVINO, R ;
GASCO, A ;
MENZIANI, E ;
SERAFINO, A .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1983, 20 (03) :783-785
[6]  
CALVINO R, 1977, EUR J MED CHEM, V12, P157
[7]   4-METHYL-3-(ARYLSULFONYL)FUROXANS - A NEW CLASS OF POTENT INHIBITORS OF PLATELET-AGGREGATION [J].
CALVINO, R ;
FRUTTERO, R ;
GHIGO, D ;
BOSIA, A ;
PESCARMONA, GP ;
GASCO, A .
JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (17) :3296-3300
[8]   SYNTHESES, STRUCTURES AND ANTIMICROBIAL PROPERTIES OF SOME HALOGENOFUROXANS AND RELATED FURAZANS [J].
CALVINO, R ;
SERAFINO, A ;
FERRAROTTI, B ;
GASCO, A ;
SANFILIPPO, A .
ARCHIV DER PHARMAZIE, 1984, 317 (08) :695-701
[9]   UNSYMMETRICALLY SUBSTITUTED FUROXANS .7. A C-13 NMR-STUDY OF A SERIES OF ISOMERIC PAIRS OF FUROXANS AND THE STRUCTURE OF THE 2 ISOMERIC CHLORO-PHENYL-FUROXANS [J].
CALVINO, R ;
FRUTTERO, R ;
GASCO, A ;
MORTARINI, V ;
AIME, S .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1982, 19 (02) :427-430
[10]   PHOTOCHROMISM OF 4-SUBSTITUTED BENZOFUROXANS [J].
CALZAFERRI, G ;
GLEITER, R ;
KNAUER, KH ;
MARTIN, HD ;
SCHMIDT, E .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1974, 13 (01) :86-88