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

ChemInform Abstract: Synthesis, Antitumor Activity, and Electrochemical Properties of Uracil Derivatives in the Furan Series.

ChemInform ◽  
2010 ◽  
Vol 23 (47) ◽  
pp. no-no
Author(s):  
M. TRUSULE ◽  
E. KUPCE ◽  
I. AUGUSTANE ◽  
N. V. VEROVSKII ◽  
E. LUKEVICS ◽  
...  
Keyword(s):  
Antitumor Activity ◽  
Electrochemical Properties ◽  
Furan Series ◽  
Uracil Derivatives

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.

Analogs of pyrimidine nucleosides. 14. Synthesis and antitumorigenic activity of alkoxyalkyl derivatives of 5-fluorouracil

1980 ◽  
Vol 16 (11) ◽  
pp. 1176-1179 ◽  
Author(s):  
M. Ya. Karpeiskii ◽  
S. M. Mikhailov ◽  
A. S. Tsieminya ◽  
A. A. Ziderman ◽  
I. M. Kravchenko ◽  
...  
Keyword(s):  
Antitumorigenic Activity ◽  
Pyrimidine Nucleosides ◽  
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

Optical and electrochemical properties of polyether derivatives of perylenediimides adsorbed on nanocrystalline metal oxide films

2008 ◽  
Vol 9 (5) ◽  
pp. 757-766 ◽  
Author(s):  
Mahmut Kus ◽  
Özgül Hakli ◽  
Ceylan Zafer ◽  
Canan Varlikli ◽  
Serafettin Demic ◽  
...  
Keyword(s):  
Metal Oxide ◽  
Electrochemical Properties ◽  
Oxide Films ◽  
Metal Oxide Films ◽  
Nanocrystalline Metal ◽  
Derivatives Of

Effect of fused indanedione (IND) groups and antipodal β-substituents on electrochemical properties of unsymmetrical metalloporphyrins

2020 ◽  
Vol 24 (10) ◽  
pp. 1155-1165
Author(s):  
W. Ryan Osterloh ◽  
Yuanyuan Fang ◽  
Nivedita Chaudhri ◽  
Lei Cong ◽  
Muniappan Sankar ◽  
...  
Keyword(s):  
Electrochemical Properties ◽  
Metal Ion ◽  
Anion Radical ◽  
Pyrrole Ring ◽  
Supporting Electrolyte ◽  
Central Metal ◽  
Tetrabutylammonium Perchlorate ◽  
Free Base ◽  
Reduction Potentials ◽  
Derivatives Of

The interacting effect of fused indanedione (IND) groups and antipodal Br [Formula: see text]-substituents on the electroreduction of free-base and transition metal tetraphenylporphyrins (TPPs) are elucidated through the use of cyclic voltammetry. A systematic study of the reduction potentials for mono- and di-fused derivatives of MTPP(IND)(R)2 and MTPP(IND)2(R)2 where R = Br or H and M = Cu[Formula: see text], Ni[Formula: see text], Zn[Formula: see text] or H2 is carried out in pyridine containing 0.1 M tetrabutylammonium perchlorate (TBAP) as supporting electrolyte and demonstrates how the overall electrochemical properties of these compounds can be tuned by systematic changes in the number of meso-[Formula: see text]fused IND groups on the molecule and the presence or absence of electron-withdrawing Br [Formula: see text]-substituents. Under these solution conditions, two reversible one-electron reductions are seen for H2TPP, while three reversible reductions are obtained for H2TPP(IND) or H2TPP(IND)Br2 and four for H2TPP(IND)2Br2. Multiple reductions also occur for the other investigated mono- and di-fused metalloporphyrins. Plots of measured [Formula: see text] values for the two ring-centered reductions of compounds in a given series vs. the number of fused IND groups are linear and with slopes varying in magnitude between 15 and 230 mV/IND depending upon the product of the electron transfer (anion radical or dianion), the specific central metal ion and the presence or absence of Br substituents on the pyrrole ring opposite the fused IND group(s). It is anticipated that the information from this study can be used for predicting the reduction potentials for yet to be synthesized compounds where a specific redox reactivity is desired.

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