85908-57-2Relevant articles and documents
Phosphate linkers with traceable cyclic intermediates for self-immolation detection and monitoring
Procházková, Eli?ka,?imon, Petr,Straka, Michal,Filo, Juraj,Májek, Michal,Cigáň, Marek,Baszczyňski, Ond?ej
supporting information, p. 211 - 214 (2021/01/14)
Self-immolation (SI) is the key principle of ProTide nucleotide prodrugs such as remdesivir, which is currently used to treat COVID-19 patients. Developing novel tailor-made SI systems requires new analytical methods for the detection and monitoring of SI. We developed a robust method for SI analysis using novel phosphate-based SI linkers with NMR traceable cyclic intermediates to distinguish SI from alternative fragmentation pathways and to monitor cargo release in real time.
Sterically-Controlled Self-Immolation in Phosphoramidate Linkers Triggered by Light
Baszczyňski, Ond?ej,Cigáň, Marek,Filo, Juraj,Procházková, Eli?ka
, (2020/02/18)
Phosphoramidate prodrugs stand out for their applications as drug delivery systems. However, information on their activation remains limited to prodrug half-live and metabolite structure, which hinders their development. Considering the lack of data on ph
Kinetics and mechanism of the anilinolysis of aryl ethyl isothiocyanophosphates in acetonitrile
Barai, Hasi Rani,Adhikary, Keshab Kumar,Lee, Hai Whang
, p. 1829 - 1834 (2013/07/26)
The nucleophilic substitution reactions of Y-aryl ethyl isothiocyanophosphates with substituted X-anilines and deuterated X-anilines were investigated kinetically in acetonitrile at 75.0 oC. The free energy relationships with X in the nucleophiles exhibited biphasic concave downwards with a break point at X = H. A stepwise mechanism with rate-limiting bond formation for strongly basic anilines and with rate-limiting bond breaking for weakly basic anilines is proposed based on the negative and positive ?XY values, respectively. The deuterium kinetic isotope effects (DKIEs; kH/kD) changed gradually from primary normal with strongly basic anilines, via primary normal and secondary inverse with aniline, to secondary inverse with weakly basic anilines. The primary normal and secondary inverse DKIEs were rationalized by frontside attack involving hydrogen bonded, four-center-type TSf and backside attack involving in-line-type TSb, respectively.