41244-53-5Relevant articles and documents
Synthesis of 5-(Dihydroxyboryl)-2'-deoxyuridine and Related Boron-Containing Pyrimidines
Schinazi, Raymond F.,Prusoff, William H.
, p. 841 - 847 (1985)
Organoboron derivatives of pyrimidines and of 2'-deoxyribonucleosides have been synthesized as potential antiviral and anticancer agents.The first 5-boron-substituted pyrimidine nucleoside, 5-(dihydroxyboryl)-2'-deoxyuridine, has been prepared via a metal-halogen exchange at -50 deg C in tetrahydrofuran on 5-bromo-3',5'-bis (O-trimethylsilyl)-2'-deoxyuridine using n-butyllithium followed by boronation at -65 deg C with tri-n-butyl borate in the presence of HMPT.After hydrolysis, the product was purified by column chromatography and repeated fractional crystallization and the purity determined by HPLC.This hydrolytically stable compound showed no activity against Sarcoma 180 (S-180) but inhibited herpes simplex virus type 1 at a nontoxic concentration.The compound sensitized hamster V-79 cells to neutrons and could be of potential use in boron neutron capture therapy. 5-(Dihydroxyboryl)uracil and 6-(dihydroxyboryl)uracil were prepared also by a similar route from the corresponding 5- or 6-bromo-2,4-bis(benzyloxy)pyrimidine.However, the mixture was maintained at -85 deg C during the whole reaction sequence and the product was obtained by hydrolysis followed by catalytic hydrogenation.The physical characteristics of these analogues, as well as those of their iminodiethanol esters, are described.
Synthesis and coordination chemistry of pyrimidine-substituted phosphine ligands
Nixon, Tracy D.,Gamble, Aimee J.,Thatcher, Robert J.,Whitwood, Adrian C.,Lynam, Jason M.
scheme or table, p. 252 - 260 (2012/04/10)
Reaction of PPh2H with UrI (Ur = uracil) in the presence of Pd(OAc)2 affords PPh2Ur. In the solid state, PPh 2Ur crystallises as a methanol solvate in the monoclinic space group P21/c. Reaction of PPh2Ur with CuI in dry and deoxygenated THF solution results in the formation of [Cu4(μ3-I) 4(PPh2Ur)4]. A single crystal X-ray diffraction study demonstrated that this species contains a distorted tetrahedral core of copper atoms, with facially-capping iodides. The uracil groups in the clusters are engaged in hydrogen bonding to groups on neighbouring molecules to form an extended array. A similar reaction between PPh2Ur and CuI in unpurified THF allows for the isolation of the phosphine oxide P(O)PPh 2Ur. The synthesis of the benzyl-protected phosphine PPh 2UrP is also described [UrP = 2,4-bis(benzyloxy)pyrimidine]. Reaction of PPh2UrP with [Ru(η5-C5H5)(NCMe)3]PF 6 allows for isolation of [Ru(η5-C5H 5)(NCMe)(PPh2UrP)2]PF6.
"Molecular chameleons". Design and synthesis of a second series of flexible nucleosides
Seley, Katherine L.,Salim, Samer,Zhang, Liang,O'Daniel, Peter I.
, p. 1612 - 1619 (2007/10/03)
(Chemical Equation Presented) The second series of flexible shape-modified nucleosides is introduced. The "fleximers" feature the purine ring systems split into their individual imidazole and pyrimidine components. This structural modification serves to introduce flexibility to the nucleoside while still retaining the elements essential for recognition. As a consequence, these structurally innovative nucleosides can more readily adapt to their environment and should find use as bioprobes for investigating enzyme-coenzyme binding sites as well as nucleic acid and protein interactions. Their design and synthesis is described.