cas 23192-63-4, 5-Amino-1-(2’,3’,5’-tri-O-acetyl--D-ribofuranosyl)-imidazole-4-carbonitrile | Articles data ｜lookchem

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23192-63-4

Articles about 23192-63-4Total 5 be found

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ISOLATION AND SYNTHESYS OF 1-METHYLISOGUANOSINE, A POTENT PHARMACOLOGICALLY ACTIVE CONSTITUENT FROM THE MARINE SPONGE TEDANIA DIGITATA
A new pharmacologically active agent isolated from the marine sponge Tedania digitata has been identified as 1-methylisoguanosine(1) by spectral and degradative chemical methods and synthesis from a β-D-ribofuranosylimidazole (2).
Quinn, Ronald J.,Gregson, Richard P.,Cook, Alan F.,Bartlett, Robert T.
p. 567 - 568
(1980)
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Synthesis of bredinin from 1-β-D-ribofuranosyl-5-aminoimidazole-4-carboxamide by a photo-reaction
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Fukukawa,Shuto,Hirano,Ueda
p. 3653 - 3657
(1986)
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Nucleosides and nucleotides. 96. Synthesis and antitumor activity of 5-ethynyl-1-β-D-ribofuranosylimidazole-4-carboxamide (EICAR) and its derivatives
The palladium-catalyzed cross-coupling reaction of 5-iodo-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl) imidazole-4-carboxamide (8) with various terminal alkynes in the presence of bis(benzonitrile)palladium dichloride in acetonitrile containing triethylamine gave the desired 5-alkynyl derivatives 9 in high yields. However, when (trimethylsilyl)acetylene was used, the only isolable product was the undesired dimer, 1,2-bis(4-carbamoyl-1-β-D-ribofuranosylimidazol-5-yl)acetylene derivative 10a. To circumvent such dimer formation, the reaction was done with use of trimethyl[(tributylstannyl)ethynyl]silane in the absence of triethylamine to afford the desired 5-(2-trimethylsilyl)ethynyl derivative 9a in good yield. Furthermore, the similar cross-coupling reaction of 5-iodo-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl) imidazole-4-carbonitrile (12) with (trimethylsilyl)acetylene also afforded the desired nucleoside 13a. Deprotection of these compounds furnished 5-alkynyl-1-β-D-ribofuranosylimidazole-4-carboxamides (6b-k) and -carbonitriles (14b-f). Among these, 5-ethynyl-1-β-D-ribofuranosylimidazole-4-carboxamide (6b, EICAR) is the most potent inhibitor of growth of the various tumor cells in culture including human solid tumor cells. Preliminary results of in vivo antitumor activity against murine leukemias L1210 and P388 are also described.
Minakawa,Takeda,Sasaki,Matsuda,Ueda
p. 778 - 786
(2007/10/02)

SYNTHESIS OF 2-FORMYLADENOSINE USING DIETHOXYACETONITRILE AS A SYNTHON
Diethoxyacetonitrile has been utilized for the effective synthesis of adenine derivatives as a synthon.Novel 2-formyladenine (2b) and 2-formyladenosine (5b) have been prepared in high yields starting from AICN (1) and AICNR (4b), respectively.
Murakami, Teiichi,Otsuka, Masami,Kobayashi, Susumu,Ohno, Masaji
p. 1315 - 1319
(2007/10/02)

1-Methylisoguanosine, a pharmacologically active agent from a marine sponge
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Cook,Bartlett,Gregson,Quinn
p. 4020 - 4025
(2007/10/02)

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Chemical Properties

Boiling Point: 601.911°C at 760 mmHg
Flash Point:317.825°C
Density: 1.518g/cm³
Solubility:Chloroform, Ethanol
Vapor Pressure: 0mmHg at 25°C
PKA: 1.28±0.61(Predicted)
PSA: 155.76000
LogP: 0.24208

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