152006-17-2Relevant articles and documents
Design, synthesis and biological evaluation of novel hamamelitannin analogues as potentiators for vancomycin in the treatment of biofilm related Staphylococcus aureus infections
Vermote, Arno,Brackman, Gilles,Risseeuw, Martijn D.P.,Coenye, Tom,Van Calenbergh, Serge
, p. 4563 - 4575 (2016)
Staphylococcus aureus is a frequent cause of biofilm-related infections. Bacterial cells within a biofilm are protected from attack by the immune system and conventional antibiotics often fail to penetrate the biofilm matrix. The discovery of hamamelitannin as a potentiator for antibiotics, recently led to the design of a more drug-like lead. In the present study, we want to gain further insight into the structure–activity relationship (S.A.R.) of the 5-position of the molecule, by preparing a library of 21 hamamelitannin analogues.
Design and synthesis of 2,6-disubstituted-4′-selenoadenosine- 5′-N,N-dimethyluronamide derivatives as human A3 adenosine receptor antagonists
Choi, Hongseok,Jacobson, Kenneth A.,Yu, Jinha,Jeong, Lak Shin
, (2021/05/03)
A new series of 4′-selenoadenosine-5′-N,N-dimethyluronamide derivatives as highly potent and selective human A3 adenosine receptor (hA3AR) antagonists, is described. The highly selective A3AR agonists, 4′-selenoadenosine-5′-N-methyluronamides were successfully converted into selective antagonists by adding a second N-methyl group to the 5′-uronamide position. All the syn-thesized compounds showed medium to high binding affinity at the hA3AR. Among the synthe-sized compounds, 2-H-N6-3-iodobenzylamine derivative 9f exhibited the highest binding affinity at hA3AR. (Ki = 22.7 nM). The 2-H analogues generally showed better binding affinity than the 2-Cl analogues. The cAMP functional assay with 2-Cl-N6-3-iodobenzylamine derivative 9l demonstrated hA3AR antagonist activity. A molecular modelling study suggests an important role of the hydrogen of 5′-uronamide as an essential hydrogen bonding donor for hA3AR activation.
Stereoselective synthesis of selenium-containing glycoconjugates via the mitsunobu reaction
Cermola, Flavio,De Nisco, Mauro,Manfra, Michele,Pedatella, Silvana,Serpico, Luigia
, (2021/05/26)
A simple and efficient route for the synthesis of new glycoconjugates has been developed. The approach acts as a model for a mini-library of compounds with a deoxy-selenosugar core joined to a polyphenolic moiety with well-known antioxidant properties. An unexpected stereocontrol detected in the Mitsunobu key reaction led to the most attractive product showing a natural Dconfiguration. Thus, we were able to obtain the target molecules from the commercially available D-ribose via a shorter and convenient sequence of reactions.
Practical synthesis of 4′-selenopurine nucleosides by combining chlorinated purines and ‘armed’ 4-selenosugar
Ishii, Kazuki,Saito-Tarashima, Noriko,Ota, Masashi,Yamamoto, Seigi,Okamoto, Yasuko,Tanaka, Yoshiyuki,Minakawa, Noriaki
, p. 6589 - 6594 (2016/09/23)
The synthesis of a variety of chemically modified oligonucleotides requires the development of a practical synthetic method for its building block, i.e., nucleoside analogs. The one-pot Pummerer-like reaction using hypervalent iodine in combination with 6-chloropurine and an ‘armed’ 4-selenosugar bearing an electron-donating group at the 2-position gave the desired 4′-seleno-6-chloropurine derivative in higher yield as compared to the previous method using a ‘disarmed’ 4-selenosugar bearing an electron-withdrawing group at the 2-position. In addition, the use of 2,6-dichloropurine as a nucleobase transformable into guanine skeleton enabled an effective Pummerer-like reaction followed by isomerization to the desired N9 isomer under the acidic conditions. This Pummerer-like reaction between chlorinated purine bases and an ‘armed’ 4-selenosugar is advantageous because it affords 4′-selenopurine nucleosides in one-pot without the need for isolation of the unstable selenoxide derivative.
