• 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

一种简单易行的区域选择性氘代吖唑并[1,5-]嘧啶分子的方法。

A Simple and Easily Implemented Method for the Regioselective Introduction of Deuterium into Azolo[1,5-]pyrimidines Molecules.

机构信息

Laboratory of Bioactive Azaheterocycles, Institute of Biomedicine and Pharmacy, Russian-Armenian University, Hovsep Emin Str. 123, Yerevan 0051, Armenia.

Scientific and Technological Center of Organic and Pharmaceutical Chemistry, The National Academy of Sciences of the Republic of Armenia, Azatutyan Ave. 26, Yerevan 0014, Armenia.

出版信息

Molecules. 2023 Mar 22;28(6):2869. doi: 10.3390/molecules28062869.

DOI:10.3390/molecules28062869
PMID:36985841
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10054722/
Abstract

A method for the technically easy-to-implement synthesis of deuterium-labeled pyrazolo[1,5-]pyrimidines and 1,2,4-triazolo[1,5-]pyrimidines have been developed. The regioselectivity of such transformations has been shown. H NMR and mass spectrometric methods have proved the quantitative nature of such transformations and the kinetics of deuterium exchange has been studied. Spectrally, at different temperatures (+30 °C, -10 °C and -15 °C), the kinetics of the process was studied both in CDOD and in deuterated alkali.

摘要

已经开发出一种技术上易于实施的合成氘标记的吡唑并[1,5-a]嘧啶和 1,2,4-三唑并[1,5-a]嘧啶的方法。已经显示了这种转化的区域选择性。H NMR 和质谱方法证明了这种转化的定量性质,并研究了氘交换的动力学。在不同温度(+30°C、-10°C 和-15°C)下,通过 CDOD 和氘化碱对该过程的动力学进行了光谱研究。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/62ed/10054722/fe1ed83a2c03/molecules-28-02869-sch010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/62ed/10054722/ea642afdd502/molecules-28-02869-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/62ed/10054722/c7a8ce8398e4/molecules-28-02869-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/62ed/10054722/70c45bbf560a/molecules-28-02869-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/62ed/10054722/4583754bde57/molecules-28-02869-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/62ed/10054722/4febc6326315/molecules-28-02869-g004a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/62ed/10054722/2dc2a55630a2/molecules-28-02869-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/62ed/10054722/6cee785d8c0b/molecules-28-02869-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/62ed/10054722/fc10e0da30ab/molecules-28-02869-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/62ed/10054722/5f5ed72800d4/molecules-28-02869-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/62ed/10054722/d3e00a0fb808/molecules-28-02869-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/62ed/10054722/1f2a83a5defb/molecules-28-02869-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/62ed/10054722/863070b0db20/molecules-28-02869-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/62ed/10054722/5464b9d9e35c/molecules-28-02869-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/62ed/10054722/42e64c2e30c5/molecules-28-02869-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/62ed/10054722/1a21531a2933/molecules-28-02869-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/62ed/10054722/b1a677c1d97a/molecules-28-02869-sch006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/62ed/10054722/457c866de48d/molecules-28-02869-sch007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/62ed/10054722/23dd0253ba7a/molecules-28-02869-sch008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/62ed/10054722/ffb5b6059328/molecules-28-02869-sch009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/62ed/10054722/fe1ed83a2c03/molecules-28-02869-sch010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/62ed/10054722/ea642afdd502/molecules-28-02869-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/62ed/10054722/c7a8ce8398e4/molecules-28-02869-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/62ed/10054722/70c45bbf560a/molecules-28-02869-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/62ed/10054722/4583754bde57/molecules-28-02869-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/62ed/10054722/4febc6326315/molecules-28-02869-g004a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/62ed/10054722/2dc2a55630a2/molecules-28-02869-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/62ed/10054722/6cee785d8c0b/molecules-28-02869-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/62ed/10054722/fc10e0da30ab/molecules-28-02869-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/62ed/10054722/5f5ed72800d4/molecules-28-02869-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/62ed/10054722/d3e00a0fb808/molecules-28-02869-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/62ed/10054722/1f2a83a5defb/molecules-28-02869-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/62ed/10054722/863070b0db20/molecules-28-02869-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/62ed/10054722/5464b9d9e35c/molecules-28-02869-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/62ed/10054722/42e64c2e30c5/molecules-28-02869-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/62ed/10054722/1a21531a2933/molecules-28-02869-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/62ed/10054722/b1a677c1d97a/molecules-28-02869-sch006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/62ed/10054722/457c866de48d/molecules-28-02869-sch007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/62ed/10054722/23dd0253ba7a/molecules-28-02869-sch008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/62ed/10054722/ffb5b6059328/molecules-28-02869-sch009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/62ed/10054722/fe1ed83a2c03/molecules-28-02869-sch010.jpg

相似文献

1
A Simple and Easily Implemented Method for the Regioselective Introduction of Deuterium into Azolo[1,5-]pyrimidines Molecules.一种简单易行的区域选择性氘代吖唑并[1,5-]嘧啶分子的方法。
Molecules. 2023 Mar 22;28(6):2869. doi: 10.3390/molecules28062869.
2
Design, synthesis, and biological evaluation of C9- and C2-substituted pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidines as new A2A and A3 adenosine receptors antagonists.新型 A2A 和 A3 腺苷受体拮抗剂 C9 和 C2 取代的吡唑并[4,3-e]-1,2,4-三唑并[1,5-c]嘧啶的设计、合成及生物学评价
J Med Chem. 2003 Mar 27;46(7):1229-41. doi: 10.1021/jm021023m.
3
New approach toward the synthesis of deuterated pyrazolo[1,5-]pyridines and 1,2,4-triazolo[1,5-]pyridines.合成氘代吡唑并[1,5 - ]吡啶和1,2,4 - 三唑并[1,5 - ]吡啶的新方法。
Beilstein J Org Chem. 2017 May 2;13:800-805. doi: 10.3762/bjoc.13.80. eCollection 2017.
4
Solvent-Controlled, Site-Selective N-Alkylation Reactions of Azolo-Fused Ring Heterocycles at N1-, N2-, and N3-Positions, Including Pyrazolo[3,4- d]pyrimidines, Purines, [1,2,3]Triazolo[4,5]pyridines, and Related Deaza-Compounds.溶剂控制的氮杂并环杂环化合物在N1-、N2-和N3-位的位点选择性N-烷基化反应,包括吡唑并[3,4-d]嘧啶、嘌呤、[1,2,3]三唑并[4,5]吡啶及相关脱氮化合物。
J Org Chem. 2018 Jun 15;83(12):6334-6353. doi: 10.1021/acs.joc.8b00540. Epub 2018 Jun 6.
5
Synthesis and antimicrobial activity of some new pyrazole, fused pyrazolo[3,4-d]-pyrimidine and pyrazolo[4,3-e][1,2,4]-triazolo[1,5-c]pyrimidine derivatives.一些新型吡唑、稠合吡唑并[3,4-d]嘧啶和吡唑并[4,3-e][1,2,4]三唑并[1,5-c]嘧啶衍生物的合成及抗菌活性
Molecules. 2008 Jul 29;13(7):1501-17. doi: 10.3390/molecules13071501.
6
N-Labelling and structure determination of adamantylated azolo-azines in solution.溶液中金刚烷基化氮杂嗪的N-标记与结构测定
Beilstein J Org Chem. 2017 Nov 29;13:2535-2548. doi: 10.3762/bjoc.13.250. eCollection 2017.
7
Synthesis of dihydrotestosterone derivatives modified in the A-ring with (hetero)arylidene, pyrazolo[1,5-a]pyrimidine and triazolo[1,5-a]pyrimidine moieties and their targeting of the androgen receptor in prostate cancer.A 环中带有(杂)芳基、吡唑并[1,5-a]嘧啶和三唑并[1,5-a]嘧啶部分的二氢睾酮衍生物的合成及其在前列腺癌中对雄激素受体的靶向作用。
J Steroid Biochem Mol Biol. 2021 Jul;211:105904. doi: 10.1016/j.jsbmb.2021.105904. Epub 2021 Apr 29.
8
Vinylation of α-Aminoazoles with Triethylamine: A General Strategy to Construct Azolo[1,5-]pyrimidines with a Nonsubstituted Ethylidene Fragment.α-氨基唑与三乙胺的乙烯基化:构建具有非取代亚乙基片段的唑并[1,5-a]嘧啶的一般策略。
Org Lett. 2021 Apr 2;23(7):2664-2669. doi: 10.1021/acs.orglett.1c00571. Epub 2021 Mar 18.
9
Biosynthesis of the pyrimidine moiety of thiamin in Escherichia coli: incorporation of stable isotope-labeled glycines.大肠杆菌中硫胺素嘧啶部分的生物合成:稳定同位素标记甘氨酸的掺入
Biochemistry. 1979 Jun 12;18(12):2632-6. doi: 10.1021/bi00579a031.
10
Anhydrous versus hydrated N4-substituted 1H-pyrazolo[3,4-d]pyrimidine-4,6-diamines: hydrogen bonding in two and three dimensions.无水与水合的N4-取代的1H-吡唑并[3,4-d]嘧啶-4,6-二胺:二维和三维中的氢键作用
Acta Crystallogr B. 2008 Oct;64(Pt 5):610-22. doi: 10.1107/S0108768108019903. Epub 2008 Sep 15.

本文引用的文献

1
Pyrazolo[1,5-]pyrimidines-based fluorophores: a comprehensive theoretical-experimental study.基于吡唑并[1,5 - ]嘧啶的荧光团:一项全面的理论 - 实验研究
RSC Adv. 2020 Oct 29;10(65):39542-39552. doi: 10.1039/d0ra07716j. eCollection 2020 Oct 27.
2
Trends in the Hydrogen-Deuterium Exchange at the Carbon Centers. Preparation of Internal Standards for Quantitative Analysis by LC-MS.碳中心氢氘交换的趋势。通过 LC-MS 进行定量分析的内标制备。
Molecules. 2021 May 18;26(10):2989. doi: 10.3390/molecules26102989.
3
I-Catalyzed Aerobic α,β-Dehydrogenation and Deamination of Tertiary Alkylamines: Highly Selective Synthesis of Polysubstituted Pyrimidines via Hidden Acyclic Enamines.
I 催化的叔胺的有氧 α,β-脱氢和脱氨反应:通过隐藏的无环烯胺高选择性合成多取代嘧啶。
Org Lett. 2020 Jul 17;22(14):5645-5649. doi: 10.1021/acs.orglett.0c02001. Epub 2020 Jul 7.
4
Differences in lipid metabolism between anagliptin and sitagliptin in patients with type 2 diabetes on statin therapy: a secondary analysis of the REASON trial.在他汀类药物治疗的 2 型糖尿病患者中,阿格列汀与西格列汀的脂质代谢差异:REASON 试验的二次分析。
Cardiovasc Diabetol. 2019 Nov 16;18(1):158. doi: 10.1186/s12933-019-0965-3.
5
Efficacy of anagliptin as compared to linagliptin on metabolic parameters over 2 years of drug consumption: A retrospective cohort study.与利格列汀相比,阿格列汀在两年药物服用期内对代谢参数的疗效:一项回顾性队列研究。
World J Diabetes. 2018 Oct 15;9(10):165-171. doi: 10.4239/wjd.v9.i10.165.
6
Inflammatory responses and inflammation-associated diseases in organs.器官中的炎症反应及炎症相关疾病。
Oncotarget. 2017 Dec 14;9(6):7204-7218. doi: 10.18632/oncotarget.23208. eCollection 2018 Jan 23.
7
First deuterated drug approved.首个氘代药物获批。
Nat Biotechnol. 2017 Jun 7;35(6):493-494. doi: 10.1038/nbt0617-493.
8
New approach toward the synthesis of deuterated pyrazolo[1,5-]pyridines and 1,2,4-triazolo[1,5-]pyridines.合成氘代吡唑并[1,5 - ]吡啶和1,2,4 - 三唑并[1,5 - ]吡啶的新方法。
Beilstein J Org Chem. 2017 May 2;13:800-805. doi: 10.3762/bjoc.13.80. eCollection 2017.
9
Medication induced sleepwalking: A systematic review.药物诱导性梦游:系统评价。
Sleep Med Rev. 2018 Feb;37:105-113. doi: 10.1016/j.smrv.2017.01.005. Epub 2017 Jan 29.
10
Synthesis, Characterization, and Cytotoxicity of Some New 5-Aminopyrazole and Pyrazolo[1,5-a]pyrimidine Derivatives.一些新型5-氨基吡唑和吡唑并[1,5-a]嘧啶衍生物的合成、表征及细胞毒性
Sci Pharm. 2014 Oct 24;83(1):27-39. doi: 10.3797/scipharm.1409-14. Print 2015 Jan-Mar.