Palladium-catalyzed synthesis of [E]-6-(2-acylvinyl)uracils and [E]-6-(2-acylvinyl)-1-[(2-hydroxyethoxy)methyl]uracils—their antiviral and cytotoxic activities

Kundu, Nitya G.; Das, Palas; Balzarini, Jan; Clercq, Erik De

doi:10.1016/s0968-0896(97)00114-4

Cited by 21 publications

(6 citation statements)

References 48 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…4) Formation of chalcones 8c-d under these conditions is dissimilar to results described in previous papers concerning the Sonogashira coupling between 1-phenyl-2-propyn-1-ol and different electron-deficient halides. [31][32][33][34][35] Several authors initially proposed that chalcone formation during these transformations could be related to the participation of organo-palladium intermediates, 31-33 but some recent results 35 (and our own findings 20 ) have confirmed that a base-catalysed isomerisation of the expected phenyl-substituted propargyl alcohol is a more likely explanation for this transformation. The detailed study of the Sonogashira coupling of 3b with 1-phenyl-2-propyn-1-ol [by carrying out the reaction at room temperature (25 8C) and after a careful work up] enabled the isolation of the expected phenyl-substituted propargyl alcohol 8e (30%) together with 8d (67%) (Scheme 5).…”

Section: Resultsmentioning

confidence: 96%

Pyridazine derivatives. Part 39: Reactivity of 5-iodopyridazin-3(2H)-ones in palladium-catalysed reactions

et al. 2004

View full text Add to dashboard Cite

Section: Resultsmentioning

confidence: 96%

Pyridazine derivatives. Part 39: Reactivity of 5-iodopyridazin-3(2H)-ones in palladium-catalysed reactions

et al. 2004

View full text Add to dashboard Cite

“…Unfortunately, 2-bromoethanol did not react with 5-iodouracil in the presence of K 2 CO 3 or Et 3 N as observed by TLC. N -Functionalizations of uracils at the N1- and N1,N3-positions were previously reported [ 10 , 11 , 12 , 13 ]. O -Alkylation of hydroxypyrimidines were also reported, e.g.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of N-Substituted 5-Iodouracils as Antimicrobial and Anticancer Agents

et al. 2009

View full text Add to dashboard Cite

This study reports the synthesis of some substituted 5-iodouracils and their bioactivities. Alkylation of 5-iodouracils gave predominately N1-substituted-(R)-5-iodouracil compounds 7a-d (R = n-C4H9, s-C4H9, CH2C6H11, CH2C6H5) together with N1,N3-disubstituted (R) analogs 8a-b (R = n-C4H9, CH2C6H11). Their antimicrobial activity was tested against 27 strains of microorganisms using the agar dilution method. The analogs 7a, 7c and 7d displayed 25-50% inhibition against Branhamella catarrhalis, Neisseria mucosa and Streptococcus pyogenes at 0.128 mg/mL. No antimalarial activity was detected for any of the analogs when tested against Plasmodium falciparum (T9.94). Their anticancer activity was also examined. Cyclohexylmethyl analogs 7c and 8b inhibited the growth of HepG2 cells. Significantly, N1,N3-dicyclohexylmethyl analog 8b displayed the most potent anticancer activity, with an IC50 of 16.5 μg/mL. These 5-iodouracil analogs represent a new group of anticancer and antibacterial agents with potential for development for medicinal applications.

show abstract

“…The development of new chemotherapeutic agents is becoming the major interest in many academic and industrial research laboratories all over the world with the aim to discover newer, more potent molecules with higher selectivity and reduced toxicity than the existing ones. Large arrays of uracil non-nucleoside derivatives possess variety of chemotherapeutic properties [1] including anticancer [2][3][4][5][6], antiviral [7][8][9][10][11][12][13][14][15] and antimicrobial activities [16]. Moreover, many purine and pyrimidine nucleoside analogues have been the object of intensive chemical and pharmacological investigation due to their potential anti-HIV activity [17].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, structural, conformational and DFT studies of N-3 and O-4 alkylated regioisomers of 5-(hydroxypropyl)pyrimidine

Salihović

Osmanović

Špirtović-Halilović

et al. 2015

Journal of Molecular Structure

View full text Add to dashboard Cite

Because of the great pharmacological potential of the pyrimidine motif, novel C-5 substituted N-3 acyclic and O-4 acyclic pyrimidine derivatives were prepared as an interesting class of compounds for biological evaluation. Introduction of the 2,3-dihydroxypropyl (DHP) and penciclovir (PCV)-like side chains to 2-methoxypyrimidin-4-one (2) afforded a mixture of Nand O-acyclic pyrimidine nucleosides in the ratio of 54 : 29 (3 : 4) and 57 : 21 (5 : 6) with N-3 isomer being dominant. Distinction between Nand Oalkylated pyrimidine moiety was deduced from extensive experimental FT-IR, HPLC-MS and 1D ( 1 H, 13 C) and 2D (COSY, HMQC and HMBC) NMR analyses. The N-, Oregioisomers were also examined by computational method at density functional theory (DFT) RB3LYP/6-31G(d), 6-31G** and 6-31+G* levels. DFT global chemical reactivity descriptors (total energy, chemical hardness, electronic chemical potential and electrophilicity) were calculated for the isomers and used to predict and describe their relative stability and reactivity. The chemical reactivity indices were related to the C 2 -N 3 -C 4 bond angle. Theoretical predictions can be used to compare chemical reactivity and stability with future biological evaluation and behavior of these compounds.

show abstract

Palladium-catalyzed synthesis of [E]-6-(2-acylvinyl)uracils and [E]-6-(2-acylvinyl)-1-[(2-hydroxyethoxy)methyl]uracils—their antiviral and cytotoxic activities

Cited by 21 publications

References 48 publications

Pyridazine derivatives. Part 39: Reactivity of 5-iodopyridazin-3(2H)-ones in palladium-catalysed reactions

Pyridazine derivatives. Part 39: Reactivity of 5-iodopyridazin-3(2H)-ones in palladium-catalysed reactions

Synthesis of N-Substituted 5-Iodouracils as Antimicrobial and Anticancer Agents

Synthesis, structural, conformational and DFT studies of N-3 and O-4 alkylated regioisomers of 5-(hydroxypropyl)pyrimidine

Contact Info

Product

Resources

About