SYNTHESIS OF NUCLEOSIDE ADDUCTS OF PORPHYRINS AND CHLOROPHYLL DERIVATIVES

被引:19
作者
JIANG, XQ
PANDEY, RK
SMITH, KM
机构
[1] LAWRENCE LIVERMORE NATL LAB,DEPT CHEM,DAVIS,CA 95616
[2] ROSWELL PK CANC INST,DEPT RADIAT BIOL,CTR PDT,DIV CHEM,BUFFALO,NY 14263
关键词
D O I
10.1016/0040-4039(94)02271-C
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of various vinyl-porphyrins and -chlorins with 2',3',5'-tri-O-acetyl-5-chloromercuriuridine under ''Heck conditions'' affords both trans- and gem-nucleoside adducts in ratios which depend upon the nature of the vinyl-porphyrin or -chlorin.
引用
收藏
页码:365 / 368
页数:4
相关论文
共 12 条
[1]   PALLADIUM-CATALYZED COUPLING REACTIONS OF URACIL NUCLEOSIDES AND NUCLEOTIDES [J].
BIGGE, CF ;
KALARITIS, P ;
DECK, JR ;
MERTES, MP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (06) :2033-2038
[2]   PORPHYRINYL-NUCLEOSIDES CONTAINING FLUORINATED NUCLEOBASES [J].
CZUCHAJOWSKI, L ;
PALKA, A ;
MORRA, M ;
WANDREKAR, V .
TETRAHEDRON LETTERS, 1993, 34 (34) :5409-5412
[3]   3-DIMENSIONAL STRUCTURE-ACTIVITY ANALYSIS OF A SERIES OF PORPHYRIN DERIVATIVES WITH ANTI-HIV-1 ACTIVITY TARGETED TO THE V3 LOOP OF THE GP120 ENVELOPE GLYCOPROTEIN OF THE HUMAN-IMMUNODEFICIENCY-VIRUS TYPE-1 [J].
DEBNATH, AK ;
JIANG, S ;
STRICK, N ;
LIN, K ;
HABERFIELD, P ;
NEURATH, AR .
JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (08) :1099-1108
[4]   INTERACTION OF DNA WITH A PORPHYRIN LIGAND - EVIDENCE FOR INTERCALATION [J].
FIEL, RJ ;
HOWARD, JC ;
MARK, EH ;
DATTAGUPTA, N .
NUCLEIC ACIDS RESEARCH, 1979, 6 (09) :3093-3118
[5]   MOLECULAR RECOGNITION VIA BASE-PAIRING - PHOTOINDUCED ELECTRON-TRANSFER IN HYDROGEN-BONDED ZINC PORPHYRIN BENZOQUINONE CONJUGATES [J].
HARRIMAN, A ;
KUBO, Y ;
SESSLER, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (01) :388-390
[6]  
Heck R. F., 1974, ORGANOTRANSITION MET
[7]   PORPHYRINS COUPLED WITH NUCLEOSIDE BASES - SYNTHESIS AND CHARACTERIZATION OF ADENINE-PORPHYRIN AND THYMINE-PORPHYRIN DERIVATIVES [J].
HISATOME, M ;
MARUYAMA, N ;
FURUTERA, T ;
ISHIKAWA, T ;
YAMAKAWA, K .
CHEMISTRY LETTERS, 1990, (12) :2251-2254
[8]   SYNTHETIC SAPPHYRIN CYTOSINE CONJUGATES - CARRIERS FOR SELECTIVE NUCLEOTIDE TRANSPORT AT NEUTRAL PH [J].
KRAL, V ;
SESSLER, JL ;
FURUTA, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (22) :8704-8705
[9]   SYNTHESIS AND ANTIVIRAL AND CYTOTOXIC ACTIVITY OF IODOHYDRIN AND IODOMETHOXY DERIVATIVES OF 5-VINYL-2'-DEOXYURIDINES, 2'-FLUORO-2'-DEOXYURIDINE, AND URIDINE [J].
KUMAR, R ;
XU, LH ;
KNAUS, EE ;
WIEBE, LI ;
TOVELL, DR ;
TYRRELL, DL ;
ALLEN, TM .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (02) :717-723
[10]   PRONOUNCED H-1 AND P-31 NMR SPECTRAL CHANGES ON MESO-TETRAKIS(N-METHYLPYRIDINIUM-4-YL)PORPHYRIN BINDING TO POLY[D(G-C)].POLY[D(G-C)] AND TO 3 TETRADECAOLIGODEOXYRIBONUCLEOTIDES - EVIDENCE FOR SYMMETRICAL, SELECTIVE BINDING TO 5'CG3' SEQUENCES [J].
MARZILLI, LG ;
BANVILLE, DL ;
ZON, G ;
WILSON, WD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (14) :4188-4192