405-09-4Relevant articles and documents
Unusual Kinetic Profiles for Lewis Base-Catalyzed Sulfenocyclization of ortho -Geranylphenols in Hexafluoroisopropyl Alcohol
Robb, Kevin A.,Athavale, Soumitra V.,Denmark, Scott E.
supporting information, p. 1656 - 1661 (2019/08/26)
The kinetic behavior of the Lewis base-catalyzed sulfenocyclization of polyenes in hexafluoroisopropyl alcohol (HFIP) was explored. The rate of reaction is not dependent on the electronic properties of the terminal nucleophile, suggesting that this captur
PHARMACEUTICAL COMPOSITION COMPRISING A PYRAZOLE-O-GLUCOSIDE DERIVATIVE
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Page/Page column 47-48, (2008/12/07)
The invention relates toa pharmaceutical composition comprising a pyrazole-O-glucoside derivative selected from the group of compounds (1) to (29) according to claim 1 in combination with at least one second therapeutic agent which is suitable in the trea
Synthesis, biological evaluation and molecular modeling studies of N6-benzyladenosine analogues as potential anti-toxoplasma agents
Kim, Young Ah,Sharon, Ashoke,Chu, Chung K.,Rais, Reem H.,Al Safarjalani, Omar N.,Naguib, Fardos N.M.,el Kouni, Mahmoud H.
, p. 1558 - 1572 (2008/02/08)
Toxoplasma gondii is an opportunistic pathogen responsible for toxoplasmosis. T. gondii is a purine auxotroph incapable of de novo purine biosynthesis and depends on salvage pathways for its purine requirements. Adenosine kinase (EC.2.7.1.20) is the major enzyme in the salvage of purines in these parasites. 6-Benzylthioinosine and analogues were established as "subversive substrates" for the T. gondii, but not for the human adenosine kinase. Therefore, these compounds act as selective anti-toxoplasma agents. In the present study, a series of N6-benzyladenosine analogues were synthesized from 6-chloropurine riboside with substituted benzylamines via solution phase parallel synthesis. These N6-benzyladenosine analogues were evaluated for their binding affinity to purified T. gondii adenosine kinase. Furthermore, the anti-toxoplasma efficacy and host toxicity of these compounds were tested in cell culture. Certain substituents on the aromatic ring improved binding affinity to T. gondii adenosine kinase when compared to the unsubstituted N6-benzyladenosine. Similarly, varying the type and position of the substituents on the aromatic ring led to different degrees of potency and selectivity as anti-toxoplasma agents. Among the synthesized analogues, N6-(2,4-dimethoxybenzyl)adenosine exhibited the most favorable anti-toxoplasma activity without host toxicity. The binding mode of the synthesized N6-benzyladenosine analogues were characterized to illustrate the role of additional hydrophobic effect and van der Waals interaction within an active site of T. gondii adenosine kinase by induced fit molecular modeling.