158810-74-3Relevant academic research and scientific papers
No auxiliary, no byproduct strategy for water-soluble prodrugs of taxoids: Scope and limitation of O-N intramolecular acyl and acyloxy migration reactions
Skwarczynski, Mariusz,Sohma, Youhei,Noguchi, Mayo,Kimura, Maiko,Hayashi, Yoshio,Hamada, Yoshio,Kimura, Tooru,Kiso, Yoshiaki
, p. 2655 - 2666 (2005)
Since numerous new taxoids active against multidrug resistant (MDR) tumors have been developed and their poor water-solubility is a very real problem in intravenous administration, we have designed and synthesized a series of novel water-soluble taxoid prodrugs (isotaxoids). These prodrugs, a 2′-O-isoform of taxoids, showed promising results with higher water solubility (0.8-1.1 mg/mL) and proper kinetics for parent drug release by a simple pH-dependent chemical mechanism via O-N intramolecular acyl migration. No additional functional auxiliaries are released during the conversion to parent drugs, which would be an advantage in toxicology and general pharmacology, and the cost for the evaluations of auxiliary units in these fields could be saved in prodrug development. In addition, we demonstrate for the first time the successful application of the O-N intramolecular acyloxy migration reaction in the prodrug design, with the exception of the tert-butyloxycarbonyl group, and that this reaction can be provided with no organic solvent and no side products.
Synthesis and evaluation of phenylisoserine derivatives for the SARS-CoV 3CL protease inhibitor
Konno, Hiroyuki,Onuma, Takumi,Nitanai, Ikumi,Wakabayashi, Masaki,Yano, Shigekazu,Teruya, Kenta,Akaji, Kenichi
, p. 2746 - 2751 (2017)
Synthesis and evaluation of new scaffold phenylisoserine derivatives connected with the essential functional groups against SARS CoV 3CL protease are described. The phenylisoserine backbone was found by simulation on GOLD software and the structure activi
Synthesis and Antifeedant Properties of N-Acylphenylisoserinates of Lactarius Sesquiterpenoid Alcohols
Kopczacki,Gumulka,Masnyk,Sarosiek,Barycki,Ignacak,Zochowski,Grabarczyk,Nowak,Daniewski
, p. 89 - 108 (2007/10/03)
The esterification of various sesquiterpenoid alcohols of Lactarius origin with N-benzoyl-[2R,3S]-phenylisoserine (side chain of Taxol), N-acetyl-[2R,3S]-phenylisoserine and N-tert-butoxy-[2R,3S]-phenylisoserine (side chain of Taxotere) produced compounds whose antifeedant properties against storage pests Tribolium confusum, Trogoderma granarium, Sitophylus granarius and Rhizoperta dominica were measured. The introduction of the ester moiety in these molecules, in comparison to original compounds, moderately enhanced their antifeedant activities, as well as changed their selectivity of activity towards the test insects.
Synthesis of N-Acetyl-3-phenylisoserinates of sesquiterpenoid alcohols of Lactarius origin
Barycki, Rafal,Gumulka, Maria,Masynk, Marek,Daniewski, Wlodzimierz M.,Kobus, Miroslaw,Luczak, Miroslaw
, p. 75 - 82 (2007/10/03)
Important biological properties of Taxol i.e. 13-N-benzoyl-(2R,3S)-3-phenylisoserinate of baccatin III and also N-benzoyl-(2R,3S)-3-phenylisoserinates of several sesquiterpenoid alcohols of Lactarius origin prompted us to synthesize N-acetyl-3-phenylisose
Erhoehung der Effizienz der katalytischen asymmetrischen Aminohydroxylierung durch N-Halogencarbamat-Salze
Li, Guigen,Angert, Hubert H.,Sharpless, K. Barry
, p. 2995 - 2999 (2007/10/03)
Keywords: Aminoalkohole; Asymmetrische Aminohydroxylierung; Carbamate; Katalyse
