Synthesis and properties of spiro nucleosides containing the barbituric acid moiety

被引：68
|
作者：
Renard, A [1 ]
Lhomme, J [1 ]
Kotera, M [1 ]
机构：
[1] Univ Grenoble 1, LEDSS, CNRS, F-38041 Grenoble 9, France
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 04期
关键词：
D O I：
10.1021/jo016194y
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The two chiral spiro nucleosides 4 and 5 containing the barbituric acid moiety were efficiently synthesized from optically pure precursors, and their properties were studied. The carbocyclic nucleoside 5 is considerably more stable against ring opening than the deoxyribosyl derivative 4. Both compounds present enhanced hydrogen bonding capacity with diacetyladenosine.
引用
收藏
页码：1302 / 1307
页数：6
相关论文
共 50 条
  • [21] SYNTHESIS OF NUCLEOSIDES FLUORINATED IN THE SUGAR MOIETY - THE APPLICATION OF DIETHYLAMINOSULFUR TRIFLUORIDE TO THE SYNTHESIS OF FLUORINATED NUCLEOSIDES
    HERDEWIJN, P
    VANAERSCHOT, A
    KERREMANS, L
    NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 1989, 8 (01): : 65 - 96
  • [22] Synthesis, Crystal Structure, Hirshfeld Surface Analysis and Interaction Energy and Energy Framework Studies of Novel Hydrazone Derivative Containing Barbituric Acid Moiety
    Kincal, Sultan
    Topkaya, Cansu
    Gokturk, Tolga
    Hokelek, Tuncer
    Gup, Ramazan
    JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, 2023, 53 (01) : 81 - 92
  • [23] Synthesis of copolymers containing a spiro orthocarbonate moiety and evaluation of the volume change during their cationic crosslinking
    Kume, Makoto
    Maki, Yuya
    Ochiai, Bungo
    Endo, Takeshi
    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2006, 44 (24) : 7040 - 7053
  • [24] Synthesis of the first sialic acid analogue containing a γ-pyrone moiety
    Ooi, HC
    Marcuccio, SM
    Jackson, WR
    Keefe, DFO
    AUSTRALIAN JOURNAL OF CHEMISTRY, 1999, 52 (12) : 1127 - 1130
  • [25] Synthesis and characterization of a polymethacrylate containing photoreactive abietic acid moiety
    Tae Hoon Kim
    Ji Young Chang
    Jae-Ung Choi
    Woo-Sik Kim
    Macromolecular Research, 2005, 13 : 545 - 548
  • [26] Synthesis and characterization of a polymethacrylate containing photoreactive abietic acid moiety
    Kim, TH
    Chang, JY
    Choi, JU
    Kim, WS
    MACROMOLECULAR RESEARCH, 2005, 13 (06) : 545 - 548
  • [27] Synthesis of trehalose type analogues containing glucuronic acid moiety
    Nashed, MA
    Soliman, SE
    Bassily, RW
    El-Sokkary, RI
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 227 : U271 - U271
  • [28] Synthesis of barbituric acid containing nucleotides and their implications for the origin of primitive informational polymers
    Mungi, Chaitanya V.
    Singh, Sachin Kumar
    Chugh, Jeetender
    Rajamani, Sudha
    PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2016, 18 (30) : 20144 - 20152
  • [29] Synthesis and properties of nitrogenous heterocycles containing a spiro cyclopropane fragment
    Tomilov, YV
    Kostyuchenko, IV
    Nefedov, OM
    USPEKHI KHIMII, 2000, 69 (06) : 507 - 527
  • [30] Oligonucleotides containing disaccharide nucleosides: Synthesis, physicochemical, and substrate properties
    Mikhailov, SN
    Efimtseva, EV
    Ertnolinsky, BS
    Bobkov, GV
    Andreeva, OI
    Golubeva, AS
    Kochetkov, SN
    Van Aerschot, A
    Schepers, G
    Herdewijn, P
    NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2003, 22 (5-8): : 1117 - 1118
12345