Syntheses of Isoxazoline-Based Amino Acids by Cycloaddition of Nitrile Oxides and Their Conversion into Highly Functionalized Bioactive Amino Acid Derivatives

被引：35
作者：
Kiss, Lorand [1 ]
Nonn, Melinda [1 ,2 ]
Fueloep, Ferenc [1 ,2 ]
机构：
[1] Univ Szeged, Inst Pharmaceut Chem, H-6720 Szeged, Hungary
[2] Univ Szeged, Hungarian Acad Sci, Stereochem Res Grp, H-6720 Szeged, Hungary
来源：
SYNTHESIS-STUTTGART | 2012年 / 44卷 / 13期
关键词：
amino acids; amino alcohols; cycloaddition; diastereo-selectivity; heterocycles; ring opening; stereoselective synthesis; 1,3-DIPOLAR CYCLOADDITION; NEURAMINIDASE INHIBITORS; CYCLOPENTANE DERIVATIVES; REDUCTION; NUCLEOSIDES; DISCOVERY; OXIDATION; HOMOLOGS;
D O I：
10.1055/s-0031-1290373
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The present account illustrates the syntheses of isoxazoline-based amino acids by the cycloaddition of 1,3-dipolar nitrile oxides to the C-C double bond of unsaturated amino acid derivatives, with focus on the regio- and stereoselectivities of the transformations. Emphasis is also placed on the syntheses of highly functionalized amino acids by means of isoxazoline ring opening. The syntheses of various pharmacologically active compounds and their analogues via the above strategies are described.
引用
收藏
页码：1951 / 1963
页数：13
相关论文
共 62 条
[1]   Identification of phenylisoxazolines as novel and viable antibacterial agents active against gram-positive pathogens [J].
Barbachyn, MR ;
Cleek, GJ ;
Dolak, LA ;
Garmon, SA ;
Morris, J ;
Seest, EP ;
Thomas, RC ;
Toops, DS ;
Watt, W ;
Wishka, DG ;
Ford, CW ;
Zurenko, GE ;
Hamel, JC ;
Schaadt, RD ;
Stapert, D ;
Yagi, BH ;
Adams, WJ ;
Friis, JM ;
Slatter, JG ;
Sams, JP ;
Oien, NL ;
Zaya, MJ ;
Wienkers, LC ;
Wynalda, MA .
JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (02) :284-302
[2]   Solution-phase synthesis of novel Δ2-isoxazoline libraries via 1,3-dipolar cycloaddition and their antifungal properties [J].
Basappa ;
Sadashiva, MP ;
Mantelingu, K ;
Swamy, SN ;
Rangappa, KS .
BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (21) :4539-4544
[3]  
Bode JW, 2001, ANGEW CHEM INT EDIT, V40, P2082, DOI 10.1002/1521-3773(20010601)40:11<2082::AID-ANIE2082>3.0.CO
[4]  
2-1
[5]   A mild and chemoselective method for the reduction of conjugated isoxazolines to β-hydroxy ketones [J].
Bode, JW ;
Carreira, EM .
ORGANIC LETTERS, 2001, 3 (10) :1587-1590
[6]   Comparison of the anti-influenza virus activity of cyclopentane derivatives with oseltamivir and zanamivir in vivo [J].
Chand, P ;
Bantia, S ;
Kotian, PL ;
El-Kattan, Y ;
Lin, TH ;
Babu, YS .
BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (12) :4071-4077
[7]   Systematic structure-based design and stereoselective synthesis of novel multisubstituted cyclopentane derivatives with potent antiinfluenza activity [J].
Chand, P ;
Kotian, PL ;
Dehghani, A ;
El-Kattan, Y ;
Lin, TH ;
Hutchison, TL ;
Babu, YS ;
Bantia, S ;
Elliott, AJ ;
Montgomery, JA .
JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (25) :4379-4392
[8]   Syntheses and neuraminidase inhibitory activity of multisubstituted cyclopentane amide derivatives [J].
Chand, P ;
Babu, YS ;
Bantia, S ;
Rowland, S ;
Dehghani, A ;
Kotian, PL ;
Hutchison, TL ;
Ali, S ;
Brouillette, W ;
El-Kattan, Y ;
Lin, TH .
JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (08) :1919-1929
[9]   Synthesis and anticonvulsant activity of novel bicyclic acidic amino acids [J].
Conti, P ;
De Amici, M ;
di Ventimiglia, SJ ;
Stensbol, TB ;
Madsen, U ;
Bräuner-Osborne, H ;
Russo, E ;
De Sarro, G ;
Bruno, G ;
De Micheli, C .
JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (14) :3102-3108
[10]   Synthesis and pharmacological evaluation of novel conformationally constrained homologues of glutamic acid [J].
Conti, Paola ;
Caligiuri, Antonio ;
Pinto, Andrea ;
Roda, Gabriella ;
Tamborini, Lucia ;
Nielsen, Birgitte ;
Madsen, Ulf ;
Frydenvang, Karla ;
Colombo, Alessio ;
De Micheli, Carlo .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2007, 42 (08) :1059-1068
1234567