Synthesis, evaluation and CoMFA/CoMSIA study of nitrofuranyl methyl N-heterocycles as novel antitubercular agents
Apeng Wang
1
,
Yang Yang
1
,
Yangsheng Jun
2
,
Bin Wang
3
,
Kai Lv
1
,
Mingliang Liu
1
,
Huiyuan Guo
1
,
Yu Y. Lu
3
2
Hebei General Hospital, Shijiazhuang, Hebei 050051, China.
|
Publication type: Journal Article
Publication date: 2018-05-01
scimago Q2
wos Q1
SJR: 0.608
CiteScore: 6.7
Impact factor: 3.0
ISSN: 09680896, 14643391
PubMed ID:
29551372
Organic Chemistry
Drug Discovery
Biochemistry
Molecular Biology
Pharmaceutical Science
Clinical Biochemistry
Molecular Medicine
Abstract
A series of novel nitrofuranyl methyl N-heterocycles based on the structure of IIIM-MCD-211 were designed and synthesized. Compounds 6d, 8b and 12a show excellent activity against MTB H37Rv strain (MIC: 0.031-0.062 μg/mL) roughly comparable to INH and IIIM-MCD-211. In addition, a three-dimensional quantitative structure-activity relationship (3D-QSAR) study was performed on the above mentioned chemical series employing comparative molecular field analysis (CoMFA) and comparative molecular similarity index analysis (CoMSIA) techniques. The developed CoMFA and CoMSIA models display high external predictability (r2pred of 0.954 and 0.935, respectively) and good statistical robustness. More importantly, the newly designed compounds 16a and 16b (MIC: <0.016 μg/mL) based on the two models, as expected, were found to be more active than 12a and IIIM-MCD-21. Design and synthesis of more potent nitrofuranyl methyl N-heterocycles as anti-TB agents are currently in progress.
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GOST
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Wang A. et al. Synthesis, evaluation and CoMFA/CoMSIA study of nitrofuranyl methyl N-heterocycles as novel antitubercular agents // Bioorganic and Medicinal Chemistry. 2018. Vol. 26. No. 8. pp. 2073-2084.
GOST all authors (up to 50)
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Wang A., Yang Y., Jun Y., Wang B., Lv K., Liu M., Guo H., Lu Yu. Y. Synthesis, evaluation and CoMFA/CoMSIA study of nitrofuranyl methyl N-heterocycles as novel antitubercular agents // Bioorganic and Medicinal Chemistry. 2018. Vol. 26. No. 8. pp. 2073-2084.
Cite this
RIS
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TY - JOUR
DO - 10.1016/j.bmc.2018.03.004
UR - https://doi.org/10.1016/j.bmc.2018.03.004
TI - Synthesis, evaluation and CoMFA/CoMSIA study of nitrofuranyl methyl N-heterocycles as novel antitubercular agents
T2 - Bioorganic and Medicinal Chemistry
AU - Wang, Apeng
AU - Yang, Yang
AU - Jun, Yangsheng
AU - Wang, Bin
AU - Lv, Kai
AU - Liu, Mingliang
AU - Guo, Huiyuan
AU - Lu, Yu Y.
PY - 2018
DA - 2018/05/01
PB - Elsevier
SP - 2073-2084
IS - 8
VL - 26
PMID - 29551372
SN - 0968-0896
SN - 1464-3391
ER -
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BibTex (up to 50 authors)
Copy
@article{2018_Wang,
author = {Apeng Wang and Yang Yang and Yangsheng Jun and Bin Wang and Kai Lv and Mingliang Liu and Huiyuan Guo and Yu Y. Lu},
title = {Synthesis, evaluation and CoMFA/CoMSIA study of nitrofuranyl methyl N-heterocycles as novel antitubercular agents},
journal = {Bioorganic and Medicinal Chemistry},
year = {2018},
volume = {26},
publisher = {Elsevier},
month = {may},
url = {https://doi.org/10.1016/j.bmc.2018.03.004},
number = {8},
pages = {2073--2084},
doi = {10.1016/j.bmc.2018.03.004}
}
Cite this
MLA
Copy
Wang, Apeng, et al. “Synthesis, evaluation and CoMFA/CoMSIA study of nitrofuranyl methyl N-heterocycles as novel antitubercular agents.” Bioorganic and Medicinal Chemistry, vol. 26, no. 8, May. 2018, pp. 2073-2084. https://doi.org/10.1016/j.bmc.2018.03.004.