• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利:CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法,用中文像聊天一样搜索,搜遍4000万医学文献。AI智能推荐,让科研检索更轻松。

立即免费搜索

文件翻译

保留排版,准确专业,支持PDF/Word/PPT等文件格式,支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述,25分钟生成高质量综述,智能提取关键信息,辅助科研写作。

立即免费体验

合成与氨基噁唑、氨基咪唑和氨基吡咯稠合的吡哆醇衍生的二甲基吡啶醇。

Synthesis of Pyridoxine-Derived Dimethylpyridinols Fused with Aminooxazole, Aminoimidazole, and Aminopyrrole.

机构信息

College of Pharmacy, Yeungnam University, Gyeongsan 38541, Korea.

Department of Chemistry and Howard Hughes Medical Institute, University of Illinois at Urbana-Champaign, 600 South Mathews Avenue, Urbana, IL 61801, USA.

出版信息

Molecules. 2022 Mar 23;27(7):2075. doi: 10.3390/molecules27072075.

DOI:10.3390/molecules27072075
PMID:35408475
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9000659/
Abstract

Described in this paper are studies on the preparation of three classes of dimethylpyridinols derived from pyridoxine fused with aminooxazole, aminoimidazole, and aminopyrrole. The key feature of this synthetic strategy is the manipulation of hydroxymethyl moiety of C(5)-position of the pyridoxine starting material along with the installation of an amino group at C(6)-position. Efficient and practical synthesis for the oxazole- and imidazole-fused targets was accomplished, while the instability of the pyrrole-fused one was observed.

摘要

本文介绍了三种二甲吡啶醇类化合物的制备研究,这些化合物是由吡哆醇与氨基噁唑、氨基咪唑和氨基吡咯缩合得到的。该合成策略的关键特点是对吡哆醇原料 C(5)位的羟甲基进行操作,并在 C(6)位上引入氨基。成功实现了噁唑和咪唑缩合目标物的高效、实用合成,而吡咯缩合产物则由于其不稳定性而无法获得。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/419f/9000659/903ed846485a/molecules-27-02075-sch010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/419f/9000659/66d2d2ab3052/molecules-27-02075-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/419f/9000659/b06241705dce/molecules-27-02075-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/419f/9000659/8d62a09796ca/molecules-27-02075-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/419f/9000659/c9418ee48475/molecules-27-02075-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/419f/9000659/9d08743ffae7/molecules-27-02075-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/419f/9000659/545f0d494032/molecules-27-02075-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/419f/9000659/e7c29d83cd4c/molecules-27-02075-sch006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/419f/9000659/fbdcca7f0513/molecules-27-02075-sch007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/419f/9000659/2d710c1b7fde/molecules-27-02075-sch008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/419f/9000659/d5b54e32fed6/molecules-27-02075-sch009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/419f/9000659/903ed846485a/molecules-27-02075-sch010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/419f/9000659/66d2d2ab3052/molecules-27-02075-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/419f/9000659/b06241705dce/molecules-27-02075-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/419f/9000659/8d62a09796ca/molecules-27-02075-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/419f/9000659/c9418ee48475/molecules-27-02075-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/419f/9000659/9d08743ffae7/molecules-27-02075-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/419f/9000659/545f0d494032/molecules-27-02075-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/419f/9000659/e7c29d83cd4c/molecules-27-02075-sch006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/419f/9000659/fbdcca7f0513/molecules-27-02075-sch007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/419f/9000659/2d710c1b7fde/molecules-27-02075-sch008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/419f/9000659/d5b54e32fed6/molecules-27-02075-sch009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/419f/9000659/903ed846485a/molecules-27-02075-sch010.jpg

相似文献

1
Synthesis of Pyridoxine-Derived Dimethylpyridinols Fused with Aminooxazole, Aminoimidazole, and Aminopyrrole.合成与氨基噁唑、氨基咪唑和氨基吡咯稠合的吡哆醇衍生的二甲基吡啶醇。
Molecules. 2022 Mar 23;27(7):2075. doi: 10.3390/molecules27072075.
2
Common and Potentially Prebiotic Origin for Precursors of Nucleotide Synthesis and Activation.核苷酸合成和激活前体的共同和潜在的前生物起源。
J Am Chem Soc. 2017 Jul 5;139(26):8780-8783. doi: 10.1021/jacs.7b01562. Epub 2017 Jun 22.
3
Synthesis of 3-pyridinols. 3. Synthesis of pyridoxine skeletons from 4-methyloxazole.3-吡啶醇的合成。3. 由4-甲基恶唑合成吡哆醇骨架。
Chem Pharm Bull (Tokyo). 1965 Jul;13(7):878-81. doi: 10.1248/cpb.13.878.
4
Formation of 6-Azaindoles by Intramolecular Diels-Alder Reaction of Oxazoles and Total Synthesis of Marinoquinoline A.通过恶唑的分子内狄尔斯-阿尔德反应形成6-氮杂吲哚以及马里诺喹啉A的全合成。
Org Lett. 2020 Mar 20;22(6):2215-2219. doi: 10.1021/acs.orglett.0c00417. Epub 2020 Feb 27.
5
Pyridoxine-derived bicyclic amido-, ureido-, and carbamato-pyridinols: synthesis and antiangiogenic activities.吡哆醇衍生的双环酰胺基、脲基和氨基甲酸酯基吡啶醇:合成及抗血管生成活性
Org Biomol Chem. 2014 Nov 21;12(43):8702-10. doi: 10.1039/c4ob01221f.
6
Solid-phase synthesis of 3-aminopyrrole-2,5-dicarboxylate analogues.3-氨基吡咯-2,5-二羧酸酯类似物的固相合成
J Comb Chem. 2006 Jan-Feb;8(1):117-26. doi: 10.1021/cc0500912.
7
Double isocyanide cyclization: a synthetic strategy for two-carbon-tethered pyrrole/oxazole pairs.双异氰环化反应:一种构建碳二键连接的吡咯/噁唑偶联物的合成策略。
J Am Chem Soc. 2011 Feb 16;133(6):1775-7. doi: 10.1021/ja110864t. Epub 2011 Jan 18.
8
A concise total synthesis of breitfussin A and B.布氏菌素 A 和 B 的简洁全合成。
Org Lett. 2015 Jan 2;17(1):122-5. doi: 10.1021/ol503348n. Epub 2014 Dec 16.
9
Modular and Stereoselective Approach to Highly Substituted Indole/Pyrrole-Fused Diazepanones.高度取代的吲哚/吡咯稠合二氮杂环庚酮的模块化和立体选择性方法。
J Org Chem. 2021 May 7;86(9):6458-6466. doi: 10.1021/acs.joc.1c00303. Epub 2021 Apr 28.
10
Pyridoxine-derived bicyclic aminopyridinol antioxidants: synthesis and their antioxidant activities.吡哆醇衍生的双环氨基吡啶醇抗氧化剂:合成及其抗氧化活性。
Org Biomol Chem. 2011 Dec 21;9(24):8475-82. doi: 10.1039/c1ob05144j. Epub 2011 Nov 1.

本文引用的文献

1
Synthesis and activity of N-(5-hydroxy-3,4,6-trimethylpyridin-2-yl)acetamide analogues as anticolitis agents via dual inhibition of TNF-α- and IL-6-induced cell adhesions.N-(5-羟基-3,4,6-三甲基吡啶-2-基)乙酰胺类似物的合成及其作为通过抑制 TNF-α 和 IL-6 诱导的细胞黏附双重作用的抗结肠炎剂的活性。
Bioorg Med Chem Lett. 2021 Jul 1;43:128059. doi: 10.1016/j.bmcl.2021.128059. Epub 2021 Apr 23.
2
Synthesis and anticancer evaluation of 6-azacyclonol-2,4,6-trimethylpyridin-3-ol derivatives: M3 muscarinic acetylcholine receptor-mediated anticancer activity of a cyclohexyl derivative in androgen-refractory prostate cancer.6-氮杂环壬醇-2,4,6-三甲基吡啶-3-醇衍生物的合成及抗癌活性评价:M3 毒蕈碱型乙酰胆碱受体介导的环己基衍生物在雄激素难治性前列腺癌中的抗癌活性。
Bioorg Chem. 2021 May;110:104805. doi: 10.1016/j.bioorg.2021.104805. Epub 2021 Mar 6.
3
Natural products in drug discovery: advances and opportunities.天然产物在药物发现中的应用:进展与机遇。
Nat Rev Drug Discov. 2021 Mar;20(3):200-216. doi: 10.1038/s41573-020-00114-z. Epub 2021 Jan 28.
4
The Resurrection of Phenotypic Drug Discovery.表型药物发现的复兴
ACS Med Chem Lett. 2020 Mar 6;11(10):1820-1828. doi: 10.1021/acsmedchemlett.0c00006. eCollection 2020 Oct 8.
5
Antioxidant Analogue 6-Amino-2,4,5-Trimethylpyridin-3-ol Ameliorates Experimental Colitis in Mice.抗氧化类似物6-氨基-2,4,5-三甲基吡啶-3-醇改善小鼠实验性结肠炎
Dig Dis Sci. 2021 Apr;66(4):1022-1033. doi: 10.1007/s10620-020-06267-6. Epub 2020 May 2.
6
Synthesis and Cytotoxic and Antiviral Activity Profiling of All-Four Isomeric Series of Pyrido-Fused 7-Deazapurine Ribonucleosides.合成及全四种异构系列吡啶并稠合 7-脱氮嘌呤核苷的细胞毒性和抗病毒活性分析。
Chemistry. 2020 Oct 9;26(57):13002-13015. doi: 10.1002/chem.202001124. Epub 2020 Sep 16.
7
Principle and design of pseudo-natural products.伪天然产物的原理与设计。
Nat Chem. 2020 Mar;12(3):227-235. doi: 10.1038/s41557-019-0411-x. Epub 2020 Feb 3.
8
Synthesis, activity and mechanism of alkoxy-, carbamato-, sulfonamido-, thioureido-, and ureido-derivatives of 2,4,5-trimethylpyridin-3-ol against inflammatory bowel disease.2,4,5-三甲基-3-羟基吡啶的烷氧基、氨基甲酰基、磺酰胺基、硫脲基和脲基衍生物的合成、活性和作用机制及其对炎症性肠病的影响。
J Enzyme Inhib Med Chem. 2020 Dec;35(1):1-20. doi: 10.1080/14756366.2019.1677637.
9
Down-regulation of cathepsin S and matrix metalloproteinase-9 via Src, a non-receptor tyrosine kinase, suppresses triple-negative breast cancer growth and metastasis.通过非受体酪氨酸激酶Src 下调组织蛋白酶 S 和基质金属蛋白酶-9 可抑制三阴性乳腺癌的生长和转移。
Exp Mol Med. 2018 Sep 5;50(9):1-14. doi: 10.1038/s12276-018-0135-9.
10
Synthesis and evaluation of 6-heteroarylamino-2,4,5-trimethylpyridin-3-ols as inhibitors of TNF-α-induced cell adhesion and inflammatory bowel disease.6-杂芳基氨基-2,4,5-三甲基吡啶-3-醇作为肿瘤坏死因子-α诱导的细胞黏附抑制剂及炎症性肠病药物的合成与评价
Medchemcomm. 2018 Jun 8;9(8):1305-1310. doi: 10.1039/c8md00156a. eCollection 2018 Aug 1.