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

[21] New and efficient approach to aryl phosphoramidate derivatives of AZT/d4T as anti-HIV prodrugs
Li, XS
Fu, H
Jiang, YY
Zhao, YF
Liu, JY
SYNLETT, 2004, (14) : 2600 - 2602
[22] Synthesis of telmisartan and its derivatives and evaluation of their biological activities
Yu, WF
Zhou, ZM
Zhu, HB
He, LS
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2006, 26 (03) : 318 - 323
[23] Synthesis and biological evaluation of ebselen and its acyclic derivatives
Chang, TC
Huang, ML
Hsu, WL
Hwang, JM
Hsu, LY
CHEMICAL & PHARMACEUTICAL BULLETIN, 2003, 51 (12) : 1413 - 1416
[24] Progress in the synthesis and biological evaluation of lipid A and its derivatives
Gao, Jian
Guo, Zhongwu
MEDICINAL RESEARCH REVIEWS, 2018, 38 (02) : 556 - 601
[25] Synthesis and antiproliferative evaluation of novel azido nucleosides and their phosphoramidate derivatives
Xavier, Nuno M.
Goncalves-Pereira, Rita
Jorda, Radek
Reznickova, Eva
Krystof, Vladimir
Conceicao Oliveira, M.
PURE AND APPLIED CHEMISTRY, 2017, 89 (09) : 1267 - 1281
[26] Design, synthesis and biological activity of novel benzimidazole and indolequinone phosphoramidate prodrugs targeted to DT-diaphorase.
Borch, RF
Flader, C
Hernick, M
CLINICAL CANCER RESEARCH, 2000, 6 : 4489S - 4489S
[27] Studies on the synthesis and biological evaluation of potential tetrahydropyridinyl prodrugs of indazolyl derivatives as neuroprotective agents.
Isin, EM
Castagnoli, N
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 222 : U294 - U294
[28] NEW DERIVATIVES OF ARYL-PROPIONIC ACID. SYNTHESIS AND BIOLOGICAL EVALUATION
Vasincu , Ioana
Apotrosoaei, Maria
Tuchilus, Cristina
Panzariu, Andreea Teodora
Dragostin, Oana
Lupascu, D.
Profire, Lenuta
MEDICAL-SURGICAL JOURNAL-REVISTA MEDICO-CHIRURGICALA, 2013, 117 (02): : 532 - 537
[29] Design, synthesis and biological evaluation of aryl pyrimidine derivatives as potential leishmanicidal agents
Suryawanshi, S. N.
Kumar, Santosh
Shivahare, Rahul
Pandey, Susmita
Tiwari, Avinash
Gupta, Suman
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (18) : 5235 - 5238
[30] NEW PHOSPHORAMIDATE DERIVATIVES OF 5-NITROQUINOLIN-8-OL: SYNTHESIS, SPECTRAL CHARACTERIZATION, AND EVALUATION OF BIOLOGICAL ACTIVITY
Reddy, S. Munichandra
Rao, D. Subba
Sudhamani, H.
Kumari, P. Gnana
Raju, C. Naga
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2015, 190 (11) : 2005 - 2012

← 1 2 3 4 5 →