ChemInform Abstract: STUDIES ON URACIL DERIVATIVES AND ANALOGS; VII. SYNTHESIS OF N1-IODOMETHYL DERIVATIVES OF URACIL AND DIHYDROURACIL

1985 ◽  
Vol 16 (34) ◽  
Author(s):  
N. G. KUNDU ◽  
S. G. KHATRI
Keyword(s):  
Uracil Derivatives ◽  
Derivatives Of

Preparation of Chloro and Sulfanyl Derivatives of 1-(2-Deoxy-4-C-hydroxymethyl-α-L-threo-Pentofuranosyl)uracil

1997 ◽  
Vol 62 (7) ◽  
pp. 1114-1127 ◽  
Author(s):  
Hubert Hřebabecký ◽  
Jan Balzarini ◽  
Antonín Holý
Keyword(s):  
Nucleophilic Substitution ◽  
Hydrogen Chloride ◽  
Thionyl Chloride ◽  
Sodium Methoxide ◽  
Thioacetic Acid ◽  
Uracil Derivatives ◽  
Derivatives Of ◽  
Hiv 1

3'-Chloro and 3'-acetylsulfanyl derivatives of 1-(2-deoxy-4-C-hydroxymethyl-α-L-threo-pentofuranosyl)uracil were prepared by reaction of 2,3'-anhydro-1-{5'-O-benzoyl-4'-C-[(benzoyloxy)methyl]-2'-deoxy-α-L-erythro-pentofuranosyl}uracil (3) with hydrogen chloride and thioacetic acid, respectively. The reaction with hydrogen chloride gave a mixture of N-1 and N-3 substituted uracil derivatives 12 and 14. Reaction of 1-{3-O-benzoyl-4-C-[(benzoyloxy)methyl]-2-deoxy-α-L-threo-pentofuranosyl}uracil (7) with thionyl chloride and subsequent debenzoylation afforded 1-(4-C-chloromethyl-2-deoxy-β-D-erythro-pentofuranosyl)uracil (19). Nucleophilic substitution with lithium thioacetate, followed by deacylation, converted 1-{3-O-benzoyl-4-C-[(benzoyloxy)methyl]-2-deoxy-5-O-p-toluenesulfonyl-α-L-threo-pentofuranosyl}uracil (9) into 1-(2-deoxy-4-C-sulfanylmethyl-β-D-erythro-pentofuranosyl)uracil (21). The obtained thiols were oxidized with iodine or air to give 1,1'-[disulfandiylbis(2,3-dideoxy-4-hydroxymethyl-α-L-threo-pentofuranose-3,1-diyl]di(pyrimidine-2,4-(1H,3H)-dione) (17) and 1,1'-[disulfandiylbis(2,5-dideoxy-4-hydroxymethyl-α-L-threo-pentofuranose-5,1-diyl]di(pyrimidine-2,4(1H,3H)-dione) (22). Reaction of 1-{3-acetylsulfanyl-5-O-methanesulfonyl-4-C-[(benzoyloxy)methyl]-2,3-dideoxy-α-L-threo-pentofuranosyl)}uracil (24) with methanolic sodium methoxide afforded 1-(3,5-anhydro-2,3-dideoxy-4-C-hydroxymethyl-3-sulfanyl-α-L-threo-pentofuranosyl)uracil (25). The same reagent was used in the preparation of 1-(3,5-anhydro-2-deoxy-4-C-hydroxymethyl-α-L-threo-pentofuranosyl)uracil (26) from 1-{4-C-[(benzoyloxy)methyl]-2-deoxy-5-O-p-toluenesulfonyl-α-L-threo-pentofuranosyl}uracil (8). From the series of 4'-substituted 2'-deoxyuridine derivatives, synthesized in this study, solely the 4'-chloromethyl derivative 19 and the oxetane derivative 26 exhibited an appreciable activity against HIV-1 and HIV-2.

Synthesis, antitumorigenic activity, and electrochemical properties of uracil derivatives of the furan series

1991 ◽  
Vol 27 (12) ◽  
pp. 1358-1364 ◽  
Author(s):  
M. Trushule ◽  
�. Kupche ◽  
I. Augustane ◽  
N. V. Verovskii ◽  
�. Lukevits ◽  
...  
Keyword(s):  
Electrochemical Properties ◽  
Antitumorigenic Activity ◽  
Furan Series ◽  
Uracil Derivatives ◽  
Derivatives Of

The novel C-5 aryl, alkenyl, and alkynyl substituted uracil derivatives of l-ascorbic acid: Synthesis, cytostatic, and antiviral activity evaluations

2007 ◽  
Vol 15 (2) ◽  
pp. 749-758 ◽  
Author(s):  
Tatjana Gazivoda ◽  
Silvana Raić-Malić ◽  
Marko Marjanović ◽  
Marijeta Kralj ◽  
Krešimir Pavelić ◽  
...  
Keyword(s):  
Ascorbic Acid ◽  
Antiviral Activity ◽  
Acid Synthesis ◽  
The Novel ◽  
Uracil Derivatives ◽  
Ascorbic Acid Synthesis ◽  
Derivatives Of

New Boron-Nitrogen Analogues of Uracil Derivatives [1]

1989 ◽  
Vol 44 (11) ◽  
pp. 1421-1426 ◽  
Author(s):  
Ludwik Komorowski ◽  
Kurt Niedenzu
Keyword(s):  
Thermal Stability ◽  
Uracil Derivatives ◽  
Derivatives Of ◽  
Boron Nitrogen ◽  
Nitrogen Analogues

The reaction of Ν,N′-dimethylurea with 1,5-dimethyl-2,4-bis-(dimethylamino)-1,5-diaza-2,4-dibora-3-oxacyclohexan-6-one (2) in the melt proceeds with condensation of the urea to yield two major products: the acid 1,3,5-trimethyl-2-hydroxy-1,3,5-triaza-2-boracyclohexa-4,5-dione (la); and a mixture of the methylammonium (4 a) and dimethylammonium salt (4b) of the anion [{CH3N(u-CONCH3)2}2B]-. Analogous products were obtained from the reaction of 2 with Ν,Ν′,N″-triorganylbiurets. The 2-hydroxy derivatives of type 1 form 1:1 molar adducts with amines (3) of variable thermal stability. The anhydride of la was obtained as the bis(dimethylamine) adduct [CH3N(μ-CONCH3)2B]2O · 2 (CH3)2NH (6) from the reaction of [(CH3)2N]2BOB[N(CH3)2]2 with N,N′,N″-trimethylbiuret.

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