30747-23-0Relevant articles and documents
Synthetic (p)ppGpp analogue is an inhibitor of stringent response in mycobacteria
Syal, Kirtimaan,Flentie, Kelly,Bhardwaj, Neerupma,Maiti, Krishnagopal,Jayaraman, Narayanaswamy,Stallings, Christina L.,Chatterji, Dipankar
, (2017)
Bacteria elicit an adaptive response against hostile conditions such as starvation and other kinds of stresses. Their ability to survive such conditions depends, in part, on stringent response pathways. (p)ppGpp, considered to be the master regulator of t
2′-Modified Guanosine Analogs for the Treatment of HCV
Girijavallabhan, Vinay,Arasappan, Ashok,Bennett, Frank,Chen, Kevin,Dang, Qun,Huang, Ying,Kerekes, Angela,Nair, Latha,Pissarnitski, Dmitri,Verma, Vishal,Alvarez, Carmen,Chen, Ping,Cole, David,Esposite, Sara,Huang, Yuhua,Hong, Qingmei,Liu, Zhidan,Pan, Weidong,Pu, Haiyan,Rossman, Randall,Truong, Quang,Vibulbhan, Bancha,Wang, Jun,Zhao, Zhiqiang,Olsen, David,Stamford, Andrew,Bogen, Stephane,Njoroge, F. George
, p. 277 - 294 (2016/07/06)
Novel 2′-modified guanosine nucleosides were synthesized from inexpensive starting materials in 7–10 steps via hydroazidation or hydrocyanation reactions of the corresponding 2′-olefin. The antiviral effectiveness of the guanosine nucleosides was evaluated by converting them to the corresponding 5′-O-triphosphates (compounds 38–44) and testing their biochemical inhibitory activity against the wild-type NS5B polymerase.
2'-CYANO SUBSTITUTED NUCLEOSIDE DERIVATIVES AND METHODS OF USE THEREOF USEFUL FOR THE TREATMENT OF VIRAL DISEASES
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Paragraph 0232, (2014/06/24)
The present invention relates to 2′-Cyano Substituted Nucleoside Derivatives of Formula (I): and pharmaceutically acceptable salts thereof, wherein B, X, R1, R2 and R3 are as defined herein. The present invention also relates to compositions comprising at least one 2′-Cyano Substituted Nucleoside Derivative, and methods of using the 2′-Cyano Substituted Nucleoside Derivatives for treating or preventing HCV infection in a patient.
2'-AZIDO SUBSTITUTED NUCLEOSIDE DERIVATIVES AND METHODS OF USE THEREOF FOR THE TREATMENT OF VIRAL DISEASES
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Paragraph 0241; 0242, (2014/08/06)
The present invention relates to 2′-Azido Substituted Nucleoside Derivatives of Formula (I): and pharmaceutically acceptable salts thereof, wherein B, X, R1, R2 and R3 are as defined herein. The present invention also relates to compositions comprising at least one 2′-Azido Substituted Nucleoside Derivative, and methods of using the 2′-Azido Substituted Nucleoside Derivatives for treating or preventing HCV infection in a patient.
2'-SUBSTITUTED NUCLEOSIDE DERIVATIVES AND METHODS OF USE THEREOF FOR THE TREATMENT OF VIRAL DISEASES
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Page/Page column 57-58, (2012/11/06)
The present invention relates to 2'-Substituted Nucleoside Derivatives of Formula (I): and pharmaceutically acceptable salts thereof, wherein A, B, X, R1, R2 and R3 are as defined herein. The present invention also relates
Nucleobase and ribose modifications control immunostimulation by a MicroRNA-122-mimetic RNA
Peacock, Hayden,Fucini, Raymond V.,Jayalath, Prasanna,Ibarra-Soza, Jose M.,Haringsma, Henry J.,Flanagan, W. Michael,Willingham, Aarron,Beal, Peter A.
supporting information; scheme or table, p. 9200 - 9203 (2011/08/04)
Immune stimulation is a significant hurdle in the development of effective and safe RNA interference therapeutics. Here, we address this problem in the context of a mimic of microRNA-122 by employing novel nucleobase and known 2′-ribose modifications. The
Kinetics and mechanism of the defluorination of 8-fluoropurine nucleosides in basic and acidic media
Liu, Jie,Barrio, Jorge R.,Satyamurthy, Nagichettiar
, p. 1175 - 1187 (2008/12/20)
For investigating the stability of C(8)-fluorine bond in 8-fluoropurine nucleosides some protected 8-fluoroguanosine, 8-fluoroinosine and 8-fluoroadenosine derivatives were prepared by direct fluorination of acetyl-protected purine nucleosides with elemental fluorine in solvents such as chloroform, acetonitrile and nitromethane. Fluorination reactions conducted in chloroform medium gave better yields of 8-fluoropurines. The fluorination yields were slightly lower when acetonitrile or nitromethane was used as solvent, but the product purification was found to be much easier. When the synthesized, protected fluoronucleosides were subjected to standard basic (NH3 in methanol or 2-propanol) and acidic (HCl in methanol) deprotection conditions relevant to nucleoside chemistry, an efficient defluorination reaction took place. The kinetics of these defluorination reactions were conveniently followed, under pseudo-first-order reaction conditions, using 19F NMR spectroscopy. 1H NMR, LC-MS and mass spectroscopy identified the products of the kinetic reaction mixtures. The defluorination reaction rate constants (kobs) in basic media depended upon the electron density at C(8) while the kobs data in acidic medium were determined by the pKa of N7. An addition-elimination based mechanism (SNAr) has been proposed for the defluorination reactions of these 8-fluoropurine nucleosides.
Reliable chemical synthesis of oligoribonucleotides (RNA) with 2′-O-[(triisopropylsilyl)oxy]methyl(2′-O-tom)-protected phosphoramidites
Pitsch, Stefan,Weiss, Patrick A.,Jenny, Luzi,Stutz, Alfred,Wu, Xiaolin
, p. 3773 - 3795 (2007/10/03)
A method for the introduction of the 2′-O-[(triisopropylsilyl)oxy]methyl (=tom) group into N-acetylated, 5′-O-dimethoxytritylated ribonucleosides is presented. The corresponding 2′-O-tom-protected phosphoramidite building blocks were obtained in pure form and were successfully employed for the routine synthesis of oligoribonucleotides on DNA synthesizers. Under DNA coupling conditions (2.5 min coupling time for a 1.5-μmol synthesis scale) and with 5-(benzylthio)-1H-tetrazole (BTT) as activator, 2′-O-tom-protected phosphoramidites exhibited average coupling yields >99.4%. The combination of N-acetyl and 2′-O-tom protecting groups allowed a reliable and complete two-step deprotection, first with MeNH2 in EtOH/H2O and then with Bu4NF in THF, without concomitant destruction of the product RNA sequences.
Selective cleavage of the O6-diphenylcarbamoyl group from sugar-modified guanosines for incorporation into oligo-RNA
Foeldesi, Andras,Trifonova, Anna,Dinya, Zoltan,Chattopadhyaya, Jyoti
, p. 7283 - 7284 (2007/10/03)
A facile conversion of 2',3',5'-O-tri-(Bz, Tol or Ac)-N2-(Ac or iBu)-O6-DPC-guanosine to N2-(Ac or iBu)-guanosine has been achieved in 89-98% yield by short treatment with 90% aqueous TFA for smooth cleavage of the DPC gro
Purine nucleoside analogues. 8*. N2-acetylation of guanine derivatives
Madre,Zhuk,Golankiewicz
, p. 2242 - 2246 (2007/10/03)
A method for the acetylation of the exocyclic amino group of guanine derivatives has been developed. A series of N2-acetylguanines was synthesized by reacting of N9(7)-alkoxyalkylguanines with an excess of acetic anhydride in the pre