204716-94-9Relevant academic research and scientific papers
Quantitative evaluation of the chloride template effect in the formation of dicationic [14]imidazoliophanes
Ramos, Susana,Alcalde, Ermitas,Doddi, Giancarlo,Mencarelli, Paolo,Perez-Garcia, Lluisa
, p. 8463 - 8468 (2007/10/03)
The formation of macrocycles containing two imidazolium rings such as 1·2X and 2·2X is anion-directed through hydrogen bonding. The template effect exerted by the chloride anion in the ring-closure reaction of the monocationic model intermediate 9+ to yield the [14]imidazoliophane 22+ has been evaluated. This effect was quantified following the kinetics of the macrocyclization by using a UV-vis technique. The rate of the ring closure of monocation 9+ is increased up to 10 times, in the presence of Bu4NCl 0.04 M. This finding confirms that the template effect is operative in the macrocyclization leading to dicationic [14]imidazoliophanes.
Synthesis and in vitro evaluation of substituted aryl- and hetarylmethyl phosphonate and phosphate - UMP derivatives as potential glucosyltransferase inhibitors
Bhattacharya, Asish K.,Stolz, Florian,Kurzeck, Juergen,Rger, Wolfgang,Schmidt, Richard R.
, p. 973 - 982 (2007/10/03)
The enzyme β (1→4)-glucosyltransferase (BGT) catalyses the transfer of glucose from uridine diphospho-glucose (UDP-Glc) to 5-hydroxymethylcytosine (5-HMC) bases in double-stranded DNA. Potential inhibitors of BGT were developed by structure-based design and synthesized. The designed inhibitors 1-6 provide conformational mimicry of the transition state in glucosyltransfer reactions. The key synthetic steps involve a Michaelis-Arbuzov reaction followed by coupling with uridine-5′-morpholidophosphate as activated UMP derivative. The compounds were tested for in vitro inhibitory activity against BGT and the inhibition kinetics were examined. Three of the designed molecules were found to be potential inhibitors of BGT having IC50 values in the micromolar (μM) range. Useful structure-activity relationships were established which provide guidelines for the design of future generations of inhibitors of BGT.
Design and synthesis of aryl/hetarylmethyl phosphonate-UMP derivatives as potential glucosyltransferase inhibitors
Bhattacharya, Asish K.,Stolz, Florian,Schmidt, Richard R.
, p. 5393 - 5395 (2007/10/03)
A novel class of glucosyltransferase inhibitors has been designed and synthesised. The designed inhibitors 1-4 provide conformational mimicry of the transition-state in glucosyltransfer reactions. The key synthetic steps involve a Michaelis-Arbuzov reaction followed by coupling with uridine-5′-morpholidophosphate as activated UMP derivative.
