52940-48-4Relevant academic research and scientific papers
HFIP Promoted Low-Temperature SNAr of Chloroheteroarenes Using Thiols and Amines
Bhujabal, Yuvraj B.,Vadagaonkar, Kamlesh S.,Gholap, Aniket,Sanghvi, Yogesh S.,Dandela, Rambabu,Kapdi, Anant R.
, p. 15343 - 15354 (2019/12/04)
A highly efficient and an unprecedented hexafluoro-2-propanol, promoting low-temperature aromatic nucleophilic substitutions of chloroheteroarenes, has been performed using thiols and (secondary) amines under base-free and metal-free conditions. The developed protocol also provides excellent regio-control for the selective functionalization of dichloroheteroarenes, while the utility of the protocol was demonstrated by the modification of a commercially available drug ceritinib.
Pd/PTABS: Catalyst for Room Temperature Amination of Heteroarenes
Murthy Bandaru, Siva Sankar,Bhilare, Shatrughn,Chrysochos, Nicolas,Gayakhe, Vijay,Trentin, Ivan,Schulzke, Carola,Kapdi, Anant R.
supporting information, p. 473 - 476 (2018/01/28)
A mild and highly efficient catalytic amination procedure for chloroheteroarenes at ambient temperature using the Pd/PTABS catalytic system is reported. The protocol is selective for the amination of chloroheteroarenes using secondary amines such as piperidine, pyrrolidine, and several others. The exceptional mildness of the developed protocol is beneficial for the synthesis of a crucial Buparlisib intermediate as well as the formal synthesis of Alogliptin in competitive yields.
O6-(benzotriazol-1-yl)inosine derivatives: Easily synthesized, reactive nucleosides
Bae, Suyeal,Lakshman, Mahesh K.
, p. 782 - 789 (2007/10/03)
A novel class of O6-(benzotriazol-1-yl)inosine as well as the corresponding 2′-deoxy derivatives can be conveniently prepared by a reaction between sugar-protected or -unprotected inosine or 2′- deoxyinosine nucleosides and 1H-benzotriazol-1-yloxy-tris(dimethylamino) phosphonium hexafluorophosphate (BOP). The reaction appears to proceed via a nucleoside phosphonium salt, and in the absence of any additional nucleophile, the released 1-hydroxybenzotriazole undergoes reaction with the formed phosphonium salt leading to the requisite O6-(benzotriazol-1-yl) inosine or 2′-deoxyinosine derivatives. Isolation and characterization of the phosphonium salt as well as analysis by 31P{1H} NMR appear to be consistent with this reaction pathway. The resulting O 6-(benzotriazol-1-yl)inosine derivatives are effective as electrophilic nucleosides, undergoing facile reactions with a variety of nucleophiles such as alcohols, phenols, amines, and a thiol. Unusual and challenging nucleoside derivatives such as an aryl-bridged dimer, a nucleoside-amino acid conjugate, and a nucleoside- nucleoside dimer have also been synthesized from the O6-(benzotriazol-1-yl)-2′- deoxyinosine derivative. Finally, a fully protected DNA building block, the O6-(benzotriazol-1-yl)-2′-deoxyinosine 5′-O-DMT 3′-O-phosphoramidite, has been prepared and a preliminary evaluation of its use for DNA modification has been performed. Results from these studies indicate several important facts: A single, simple methodological approach provides a class of stable, isolable ribo and 2′-deoxyribonucleoside derivatives that possess excellent reactivity for SNAr chemistry with a wide range of nucleophiles. Also, a benzotriazolyl nucleoside phosphoramidite appears to be a suitable reagent for incorporation into DNA for purposes of site-specific DNA modification.
Adenosine N1-oxide analogues as inhibitors of orthopox virus replication
Khandazhinskaya, Anastasiya L.,Shirokova, Elena A.,Shipitsin, Alexander V.,Karpenko, Inna L.,Belanov, Evgenii F.,Kukhanova, Marina K.,Yasko, Maksim V.
, p. 1107 - 1121 (2008/02/09)
Several new types of adenosine N1-oxide (ANO) derivatives including N1-alkoxy and N6-alkyl as well as the analogues with a trihydroxycyclopentane ring in place of the ribose residue were synthesized and their antiviral properties were evaluated in Vero and LLC-MK2 cell cultures infected with vaccinia, mousepox, monkeypox, cowpox, and different isolates of smallpox viruses. The antiviral activity of ANO and its derivatives significantly depended on the virus type and cell cultures. Mousepox and monkeypox viruses were the most sensitive to these compounds, while vaccinia and cowpox viruses were inhibited at the concentrations 1-1.5 orders of magnitude higher. The toxicity of the synthesized compounds was much lower than that of ANO. Modifications of the ANO N6-position did not offer any advantages over the parent compound. The synthesized N1-oxide derivatives of noraristeromycin retained the activity comparable with noraristeromycin and displayed a decreased toxicity. No direct correlation between antiviral activity and stability of the compounds was found.
Anti-HCV nucleoside derivatives
-
, (2008/06/13)
The present invention comprises novel and known purine and pyrimidine nucleoside derivatives which have been discovered to be active against hepatitis C virus (HCV). The use of these derivatives for the treatment of HCV infection is claimed as are the novel nucleoside derivatives disclosed herein.
Mild and efficient functionalization at C6 of purine 2′-deoxynucleosides and ribonucleosides
Lin, Xiaoyu,Robins, Morris J.
, p. 3497 - 3499 (2007/10/03)
(Equation Presented) Treatment of sugar-protected inosine and 2′-deoxyinosine derivatives with a cyclic secondary amine or imidazole and I2/Ph3P/EtN(i-Pr)2/(CH2-Cl 2 or toluene) gave quantitative conversions into 6-N-(substituted)purine nucleosides. SNAr reactions with (imidazol-1-yl) derivatives gave 6-(N, O, or S)-substituted products. The 6-(benzylsulfonyl) group underwent SNAr displacement with an arylamine at ambient temperature.
