Synthesis and biological evaluation of aryl phosphoramidate prodrugs of fosfoxacin and its derivatives

被引：11

作者：

Munier, Mathilde ^{[1
]}

Tritsch, Denis ^{[1
]}

Lievremont, Didier ^{[1
]}

Rohmer, Michel ^{[1
]}

Grosdemange-Billiard, Catherine ^{[1
]}

机构：

[1] Univ Strasbourg, CNRS, Lab Chim & Biochim Mol Bioactives, UMR 7177,Inst Bel, 4 Rue Blaise Pascal, F-67081 Strasbourg, France

来源：

BIOORGANIC CHEMISTRY | 2019年 / 89卷

关键词：

Phosphate prodrug; Antimicrobials; MEP pathway; DXR; Mycobacterium tuberculosis; PHOSPHONIC ACID ANTIBIOTICS; MYCOBACTERIUM-SMEGMATIS; ISOPRENOID BIOSYNTHESIS; PROTIDE TECHNOLOGY; FOSMIDOMYCIN; INHIBITORS; FR-31564; PATHWAY; ANALOGS; GROWTH;

D O I：

10.1016/j.bioorg.2019.103012

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Aryl phosphoramidate prodrugs of fosfoxacin derivatives 15a-b and 8a-b were synthesized and investigated for their ability to target bacteria. No growth inhibition was observed neither for Mycobacterium smegmatis nor for Escherichia coli on solid medium, demonstrating the absence of release of the active compounds in the bacterial cells. Investigation of the stability of the prodrugs and their multienzymatic cleavage in abiotic and biotic conditions showed that the use of aryl phosphoramidate prodrug approach to deliver non-nucleotides compounds is not obvious and might not be appropriate for an antimicrobial drug.

引用

页数：10

共 50 条

[41] Synthesis and biological evaluation of 3-aryl-3-arylmethoxytropane derivatives at monoamine transporters
Kaur, Harneet
Izenwasser, Sari
Trudell, Mark L.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233 : 709 - 709
[42] Synthesis and biological evaluation of α-aryl-α-tetralone derivatives as hepatitis C virus inhibitors
Manvar, Dinesh
Fernandes, Talita de A.
Domingos, Jorge L. O.
Baljinnyam, Erdenechimeg
Basu, Amartya
Junior, Eurides F. T.
Costa, Paulo R. R.
Kaushilc-Basu, Neerja
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 93 : 51 - 54
[43] Synthesis and biological evaluation of novel N-aryl maleimide derivatives clubbed with α-hydroxyphosphonates
Patil, Nilesh S.
Deshmukh, Ganesh B.
Patil, Sambhaji V.
Bholay, Avinash D.
Gaikwad, Nitin D.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 83 : 490 - 497
[44] Novel Aryl Alkamidazole Derivatives as Multifunctional Antifungal Inhibitors: Design, Synthesis, and Biological Evaluation
Liu, Yating
Liu, Wenxia
Yu, Shuai
Wang, Qingpeng
Liu, Min
Han, Jun
Sun, Bin
JOURNAL OF MEDICINAL CHEMISTRY, 2022, 65 (21) : 14916 - 14937
[45] S-acyl-2-thioethyl phosphoramidate diester derivatives as mononucleotide prodrugs
Egron, D
Imbach, JL
Gosselin, G
Aubertin, AM
Périgaud, C
JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (21) : 4564 - 4571
[46] Synthesis and biological evaluation of FUDR monophosphate prodrugs as anticancer agents
Gonczy, Blanka
Slusarczyk, Magdalena
Murziani, Paola
McGuigan, Christopher
Vande Voorde, Johan
Liekens, Sandra
Balzarini, Jan
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
[47] Synthesis, Biological Evaluation, and Pharmacokinetic Study of Novel Liguzinediol Prodrugs
Liu, Zheng
Li, Wei
Wen, Hong-Mei
Bian, Hui-Min
Zhang, Jing
Chen, Lei
Chen, Long
Yang, Kun-Di
MOLECULES, 2013, 18 (04) : 4561 - 4572
[48] Efficient synthesis of nucleoside aryloxy phosphoramidate prodrugs utilizing benzyloxycarbonyl protection
Cho, Jong Hyun
Amblard, Franck
Coats, Steven J.
Schinazi, Raymond F.
TETRAHEDRON, 2011, 67 (30) : 5487 - 5493
[49] Synthesis and Biological Evaluation of Oral Prodrugs Based on the Structure of Gemcitabine
Zhao, Cuirong
Xue, Xiaoxia
Li, Gang
Sun, Cuicui
Sun, Changjun
Qu, Xianjun
Li, Wenbao
CHEMICAL BIOLOGY & DRUG DESIGN, 2012, 80 (03) : 479 - 488
[50] Design, synthesis and biological evaluation of uridine analogs as phosphate prodrugs
Meneghesso, Silvia
McGuigan, Christopher
Naesens, Lieve
Balzarini, Jan
Vanderlinden, Evelien
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241

← 1 2 3 4 5 →