The Synthesis of Diverse Annulated Pyridines with 6-Membered Functionalized Saturated Cycles for Medical Chemistry Research

Author:

Yehorov Dmytro V.1ORCID,Subota Andrii I.1ORCID

Affiliation:

1. Institute of Organic Chemistry of the National Academy of Sciences of Ukraine; Enamine Ltd., Ukraine

Abstract

The article describes a set of pyridines annulated with functionalized 6-membered saturated rings, which are attractive building blocks for the synthesis of diversified compound libraries in medical chemistry. A certain array of compounds includes pyridines with condensed cyclohexane, piperidine and tetrahydropyran cycles containing keto-, amino-, carboxylic groups, as well as fluorinated fragments. The synthesis of the compounds using the procedure previously developed by us via CuCl2-catalyzed condensation of propargylamine with ketones was performed. The limits of application of this reaction were further expanded and determined in this work compared to our previous results. Condensed pyridines, which proved problematic or impossible to obtain by this method, were synthesized using other synthetic pathways. Thus, the study offers a number of new building blocks for use in drug discovery.

Publisher

National University of Pharmacy

Subject

General Medicine

Reference24 articles.

1. Catalano, J. G.; Gudmundsson, K. S.; Svolto, A.; Boggs, S. D.; Miller, J. F.; Spaltenstein, A.; Thomson, M.; Wheelan, P.; Minick, D. J.; Phelps, D. P.; Jenkinson, S. Synthesis of a novel tricyclic 1,2,3,4,4a,5,6,10b-octahydro-1,10-phenanthroline ring system and CXCR4 antagonists with potent activity against HIV-1. Bioorg. Med. Chem. Lett. 2010, 20, 2186–2190. https://doi.org/10.1016/j.bmcl.2010.02.030.

2. Ebetino, F. H.; Degenhardt, Ch. R; Jamieson, L. A; Burdsall, D. C. Recent Work on the Synthesis of Phosphonate-containing, Bone-active Heterocycles. Heterocycles 1990, 30, 855–862. http://doi.org/10.3987/COM-89-S62.

3. Structure-activity relationships of new heterocycle-containing bisphosphonates as inhibitors of bone resorption and as inhibitors of growth of Dictyostelium discoideum amoebae;Rogers;Mol. Pharmacol.,1995

4. Paget, S. D.; Foleno, B. D.; Boggs, C. M.; Goldschmidt, R. M.; Hlasta, D. J.; Weidner-Wells, M. A.; Werblood, H. M.; Wira, E.; Bush, K.; Macielag, M. J. Synthesis and antibacterial activity of pyrroloaryl-substituted oxazolidinones. Bioorg. Med. Chem. Lett. 2003, 13, 4173–4177. https://doi.org/10.1016/j.bmcl.2003.08.031.

5. Horne, D. B.; Biswas, K.; Brown, J.; Bartberger, M. D.; Clarine, J.; Davis, C. D.; Gore, V. K.; Harried, S.; Horner, M.; Kaller, M. R.; Lehto, S. G.; Liu, Q.; Ma, V. V.; Monenschein, H.; Nguyen, T. T.; Yuan, Ch. C.; Youngblood, B. D.; Zhang, M.; Zhong, W.; Allen, J. R.; Chen, J. J.; Gavva, N. R. Discovery of TRPM8 Antagonist (S)-6-(((3-Fluoro-4-(trifluoromethoxy)phenyl)(3-fluoropyridin-2-yl)methyl)carbamoyl)nicotinic Acid (AMG 333), a Clinical Candidate for the Treatment of Migraine. J. Med. Chem. 2018, 61, 8186–8201. https://doi.org/10.1021/acs.jmedchem.8b00518.

同舟云学术

1.学者识别学者识别

2.学术分析学术分析

3.人才评估人才评估

"同舟云学术"是以全球学者为主线,采集、加工和组织学术论文而形成的新型学术文献查询和分析系统,可以对全球学者进行文献检索和人才价值评估。用户可以通过关注某些学科领域的顶尖人物而持续追踪该领域的学科进展和研究前沿。经过近期的数据扩容,当前同舟云学术共收录了国内外主流学术期刊6万余种,收集的期刊论文及会议论文总量共计约1.5亿篇,并以每天添加12000余篇中外论文的速度递增。我们也可以为用户提供个性化、定制化的学者数据。欢迎来电咨询!咨询电话:010-8811{复制后删除}0370

www.globalauthorid.com

TOP

Copyright © 2019-2024 北京同舟云网络信息技术有限公司
京公网安备11010802033243号  京ICP备18003416号-3