Nucleophilic substitution of halogen in 4-halo genated derivatives of glutamic acid

1995 ◽  
Vol 44 (4) ◽  
pp. 635-638 ◽  
Author(s):  
V. P. Krasnov ◽  
M. A. Koroleva ◽  
N. G. Evstigneeva ◽  
I. A. Nizova
Keyword(s):  
Glutamic Acid ◽  
Nucleophilic Substitution ◽  
Derivatives Of

Nucleophilic substitution of halogen in 4-halo derivatives of glutamic acid

1996 ◽  
Vol 45 (3) ◽  
pp. 543-544
Author(s):  
V. P. Krasnov ◽  
M. A. Koroleva ◽  
G. L. Rusinov
Keyword(s):  
Glutamic Acid ◽  
Nucleophilic Substitution ◽  
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.

Heterocyclic derivatives of purines. 5. Nucleophilic substitution in series of imidazo[1,2-f]purine derivatives

1984 ◽  
Vol 20 (3) ◽  
pp. 330-334
Author(s):  
S. N. Garmash ◽  
B. A. Priimenko ◽  
N. A. Klyuev ◽  
N. I. Romanenko ◽  
A. K. Sheinkman
Keyword(s):  
Nucleophilic Substitution ◽  
Purine Derivatives ◽  
Heterocyclic Derivatives ◽  
In Series ◽  
Derivatives Of

ChemInform Abstract: HETEROCYCLIC DERIVATIVES OF PURINES. 5. NUCLEOPHILIC SUBSTITUTION IN THE IMIDAZO(1,2-F)PURINE SERIES.

1984 ◽  
Vol 15 (32) ◽  
Author(s):  
S. N. GARMASH ◽  
B. A. PRIIMENKO ◽  
N. A. KLYUEV ◽  
N. I. ROMANENKO ◽  
A. K. SHEINKMAN
Keyword(s):  
Nucleophilic Substitution ◽  
Heterocyclic Derivatives ◽  
Derivatives Of
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