16205-60-0Relevant academic research and scientific papers
Nucleobase-Functionalized 5-Aza-7-deazaguanine Ribo- A nd 2′-Deoxyribonucleosides: Glycosylation, Pd-Assisted Cross-Coupling, and Photophysical Properties
Leonard, Peter,Kondhare, Dasharath,Jentgens, Xenia,Daniliuc, Constantin,Seela, Frank
supporting information, p. 13313 - 13328 (2019/11/11)
The special nucleobase recognition pattern of 5-aza-7-deazaguanine nucleosides makes them valuable for construction of homo purine DNA, silver-mediated base pairs, and expansion of the four letter genetic coding system. To widen the utility of 5-aza-7-deazaguanine nucleosides, side chains were introduced at position-7 of the nucleobase. As key compounds, 7-iodo nucleosides were synthesized. Nucleobase anion glycosylation of the iodo derivative of isobutyrylated 5-aza-7-deazaguanine with the bromo sugar of 2,3,5-tri-O-benzoyl-1-O-acetyl-d-ribofuranose gave the pure β-D anomeric N-9 glycosylation product (67%), whereas one-pot Vorbrüggen conditions gave only 42% of the iodinated nucleoside. The noniodinated nucleoside was formed in 84%. For the synthesis of 2′-deoxyribonucleosides, anion glycosylation performed with Hoffer's 2′-deoxyhalogenose yielded an anomeric mixture (α-D = 33% and β-D = 39%) of 2′-deoxyribonucleosides. Various side chain derivatives were prepared from nonprotected nucleosides by Pd-assisted Sonogashira or Suzuki-Miyaura cross-coupling. Among the functionalized ribonucleosides and anomeric 2′-deoxyribonucleosides, some of them showed strong fluorescence. Benzofuran and pyrene derivatives display high quantum yields in non-aqueous solvents and solvatochromism. Single-crystal X-ray analysis of 7-iodo-5-aza-7-deaza-2′-deoxyguanosine displayed intermolecular iodo-oxygen interactions in the crystal and channels filled with solvent molecules.
COMPOUNDS AND METHODS USED IN ASSESSING MONO-PARP ACTIVITY
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Paragraph 0126; 0128, (2017/07/08)
Mutant mono ADP-ribose-polymerases (mono-PARP) proteins and small molecule compound substrates specific for the mutant mono-PARP proteins as well as methods of using these compositions to identify protein targets of the mono-PARPs and to screen for antagonists of the mono-PARPs are described.
Engineering the substrate specificity of ADP-ribosyltransferases for identifying direct protein targets
Carter-O'Connell, Ian,Jin, Haihong,Morgan, Rory K.,David, Larry L.,Cohen, Michael S.
supporting information, p. 5201 - 5204 (2014/05/06)
Adenosine diphosphate ribosyltransferases (ARTDs; ARTD1-17 in humans) are emerging as critical regulators of cell function in both normal physiology and disease. These enzymes transfer the ADP-ribose moiety from its substrate, nicotinamide adenine dinucle
A novel one pot room temperature ionic liquid mediated synthesis of 1,5-benzodiazepine ribofuranosides
Yadav, Ashok K.,Kumar, Manoj,Yadav, Tripti,Jain, Renuka
experimental part, p. 461 - 468 (2010/10/20)
A novel one pot ecofriendly synthesis of 7-substituted/7,8-disubstituted-2, 2,4-trisubstituted-l-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-2, 3-dihydro-1,5-benzodiazepines have been accomplished stepwise, i.e. reacting o-phenylenediamine and a ketone in
Synthesis of ribonucleosides of 2-thioxopyrido [2,3-d]pyrimidines by phase transfer catalysis and their antimicrobial activity
Agrawal, Hemlata,Swati,Yadav, Ashok K.,Prakash, Lalit
, p. 159 - 166 (2007/10/03)
The ribonucleosides viz; 2-thioxo-3,5,7-trisubstituted-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl) pyrido[2,3-d]pyrimidine-4 (1H)-ones have been synthesized via phase transfer ribosylation of 2-thioxo- 3,5,7-trisubstituted pyrido[2,3-d)pyrimidine-4(1H)-ones with 2,3,5-tri-O-benzoyl-β-D- ribofuranosyl bromide in biphasic solvent such as CH2Cl2-50% aqueous NaOH using tetrabutylammonium bromide as phase transfer catalysis (PTC). The synthesized compounds have been characterized by elemental analyses, spectral data and screened for their antimicrobial activity.
New C2 symmetrical and semisymmetrical substituted imidazolium ribonucleoside. Imidazolic nucleosides analogues
Al Mourabit,Beckmann,Poupat,Ahond,Potier
, p. 3455 - 3464 (2007/10/03)
New C2 symmetrical imidazolium ribonucleosides have been synthesized. The silyl Hilbert Johnson-Vorbrugen method was used. Subsequent coupling of trimethylsilylimidazole with the peracylated D-ribofuranose 1, followed by removal of the protecting groups, afforded 1,3-bis(β-D-ribofuranosyl)imidazolium 7 and 1-(β-D-ribofuranosyl)imidazole 8. In a similar synthetic sequence, 4(5)-substituted bis-ribofuranosylimidazolium 14 was also prepared. For the selective preparation of the monoglycosylated imidazole 15, the classical method starting from 2,3,5-tri-O-benzoyl-D-ribofuranosyl bromide in acetonitrile and using Hg(CN)2 was employed. These new base modified nucleosides were devoid of activity, against HIV and cytotoxicity.
A Stereocontrolled Synthesis of 1,3,6-Tri-O-benzoyl-α-D-ribofuranose
Brodfuehrer, Paul R.,Sapino, Chester,Howell, Henry G.
, p. 2597 - 2598 (2007/10/02)
The synthesis of a valuable carbohydrate intermediate, 1,3,5-tri-O-benzoyl-α-D-ribofuranose (4), has been achieved in a convenient, one-step process from commercially available 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (7).
