Chem Biol Drug Des, 2019, 93(4):605-616

Enzymatic Synthesis of Novel Purine Nucleosides Bearing a Chiral Benzoxazine Fragment.

A series of ribo- and deoxyribonucleosides bearing 2-aminopurine as a nucleobase with 7,8-difluoro- 3,4-dihydro-3-methyl-2H-[1,4]benzoxazine (conjugated directly or through an aminohexanoyl spacer) was synthesized using an enzymatic transglycosylation reaction. Nucleosides 3-6 were resistant to deamination under action of adenosine deaminase (ADA) E. coli and ADA from calf intestine. The antiviral activity of the modified nucleosides was evaluated against herpes simplex virus type 1 (HSV-1, strain L2). It has been shown that at sub-toxic concentrations, nucleoside (S)-4-[2-amino-9-(β-D-ribofuranosyl)-purin-6-yl]-7,8-difluoro-3,4-dihydro-3-methyl-2H-[1,4]benzoxazine exhibit significant antiviral activity (SI32) on the model of HSV-1 in vitro, including an acyclovir-resistant virus strain (HSV-1, strain L2/R).

Eletskaya BZ, Gruzdev DA, Krasnov VP, Levit GL, Kostromina MA, Paramonov AS, Kayushin AL, Muzyka IS, Muravyova TI, Esipov RS, Andronova VL, Galegov GA, Charushin VN, Miroshnikov AI, Konstantinova ID

IBCH: 7480
Ссылка на статью в журнале: http://doi.wiley.com/10.1111/cbdd.13458
Кол-во цитирований на 04.2024: 12
Данные статьи проверены модераторами 2018-12-18

Список научных проектов, где отмечена публикация

  1. 14-13-01077. . Сommercial.
  2. CKP IBCH (January 6, 2019 — December 31, 2022). . Сommercial.