• 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

不同酸促进的 4-(4-硫代氨基甲酰基)丁-2-酮腙环氧化聚合模式：14 元环与 28 元聚氮大环的形成。

Different Modes of Acid-Promoted Cyclooligomerization of 4-(4-Thiosemicarbazido)butan-2-one Hydrazone: 14-Membered versus 28-Membered Polyazamacrocycle Formation.

机构信息

N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Avenue, 119991 Moscow, Russian Federation.

Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, 31 Leninsky Avenue, Bldg 4, 119071 Moscow, Russian Federation.

出版信息

J Org Chem. 2022 Dec 2;87(23):15722-15731. doi: 10.1021/acs.joc.2c01199. Epub 2022 Nov 16.

DOI:10.1021/acs.joc.2c01199
PMID:36383744
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9724087/
Abstract

Unprecedented self-assembly of a novel 14-membered cyclic bis-thiosemicarbazone or/and a 28-membered cyclic tetrakis-thiosemicarbazone upon acid-promoted cyclooligomerization of 4-(4-thiosemicarbazido)butan-2-one hydrazone has been discovered. A thorough study of the influence of various factors on the direction of macrocyclization provided the optimal conditions for the highly selective formation of each of the macrocycles in excellent yields. Plausible pathways for macrocyclizations have been discussed. The macrocycle precursor was prepared by the reaction of readily available 4-isothiocyanatobutan-2-one with an excess of hydrazine.

摘要

在酸促进的 4-(4-硫代氨基甲酰基)丁-2-酮腙的环齐聚反应中，发现了一种新型的 14 元环双硫代缩氨基脲和/或 28 元环四硫代缩氨基脲的前所未有的自组装。对各种因素对大环化方向的影响进行了深入研究，为每种大环化合物的高产率高选择性形成提供了最佳条件。讨论了大环化的可能途径。大环前体通过与过量的肼反应由易得的 4-异硫氰酸丁-2-酮制备。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9c51/9724087/ec41614b5436/jo2c01199_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9c51/9724087/a7e385b666d9/jo2c01199_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9c51/9724087/632e4e791022/jo2c01199_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9c51/9724087/9457b54d51a2/jo2c01199_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9c51/9724087/47cc2bdc9568/jo2c01199_0010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9c51/9724087/6f3c1ae10d3a/jo2c01199_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9c51/9724087/864aa717d544/jo2c01199_0011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9c51/9724087/b1eaf2a73043/jo2c01199_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9c51/9724087/3727b9b4b203/jo2c01199_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9c51/9724087/6cb23d2cf168/jo2c01199_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9c51/9724087/ec41614b5436/jo2c01199_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9c51/9724087/a7e385b666d9/jo2c01199_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9c51/9724087/632e4e791022/jo2c01199_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9c51/9724087/9457b54d51a2/jo2c01199_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9c51/9724087/47cc2bdc9568/jo2c01199_0010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9c51/9724087/6f3c1ae10d3a/jo2c01199_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9c51/9724087/864aa717d544/jo2c01199_0011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9c51/9724087/b1eaf2a73043/jo2c01199_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9c51/9724087/3727b9b4b203/jo2c01199_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9c51/9724087/6cb23d2cf168/jo2c01199_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9c51/9724087/ec41614b5436/jo2c01199_0006.jpg

相似文献

1
Different Modes of Acid-Promoted Cyclooligomerization of 4-(4-Thiosemicarbazido)butan-2-one Hydrazone: 14-Membered versus 28-Membered Polyazamacrocycle Formation.不同酸促进的 4-(4-硫代氨基甲酰基)丁-2-酮腙环氧化聚合模式：14 元环与 28 元聚氮大环的形成。
J Org Chem. 2022 Dec 2;87(23):15722-15731. doi: 10.1021/acs.joc.2c01199. Epub 2022 Nov 16.
2
Effective self-assembly of 21- and 14-membered azamacrocycles condition-controlled cyclotrimerization or cyclodimerization of different thiosemicarbazide-based precursors.21元和14元氮杂大环的有效自组装：不同硫代氨基脲基前体的条件控制环三聚或环二聚反应。
Org Biomol Chem. 2024 Nov 27;22(46):9078-9093. doi: 10.1039/d4ob01384k.
3
Structure activity relationships of imido N-alkyl semicarbazones, thiosemicarbazones and acethydrazones as hypolipidemic agents in rodents.
Lipids. 1990 Jul;25(7):391-7. doi: 10.1007/BF02537982.
4
Computational and Experimental Evidence for Templated Macrocyclization: The Role of a Hydrogen Bond Network in the Quantitative Dimerization of 24-Atom Macrocycles.计算与实验证据支持模板化大环化：氢键网络在 24 原子大环定量二聚反应中的作用。
Molecules. 2023 Jan 23;28(3):1144. doi: 10.3390/molecules28031144.
5
[Benzoquinone-guanyl-hydrazone-thiosemicarbazone in the treatment of acute tonsillitis].[苯醌-胍基-腙-硫代半卡巴腙治疗急性扁桃体炎]
Nord Med. 1960 Nov 10;64:1413-5.
6
Structural studies and investigation on the activity of imidazole-derived thiosemicarbazones and hydrazones against crop-related fungi.结构研究及咪唑衍生的硫代缩氨基脲和腙类化合物对作物相关真菌活性的研究。
Molecules. 2013 Oct 14;18(10):12645-62. doi: 10.3390/molecules181012645.
7
Synthesis, characterization, and antiviral activity of novel fluorinated isatin derivatives.新型氟化异吲哚酮衍生物的合成、表征及抗病毒活性
Monatsh Chem. 2013;144(11):1725-1733. doi: 10.1007/s00706-013-1034-3. Epub 2013 Jul 12.
8
Exo-selective reductive macrocyclization of ynals.烯醛的外选择性还原大环化反应
Org Lett. 2015 Mar 20;17(6):1493-6. doi: 10.1021/acs.orglett.5b00381. Epub 2015 Mar 6.
9
Synthesis and Characterization of Biologically Significant 5-[N,N-dialkylamino alkoxy] azaindole 2-one, 3-thiosemicarbazones and 5-[N,N-dialkylamino alkoxy] azaindole 3-hydrazone, 2-ones.具有生物意义的 5-[N,N-二烷基氨基烷氧基] 氮杂吲哚 2-酮、3-硫代缩氨基脲和 5-[N,N-二烷基氨基烷氧基] 氮杂吲哚 3-腙、2-酮的合成与表征。
Adv Exp Med Biol. 2020;1195:189-198. doi: 10.1007/978-3-030-32633-3_27.
10
Synthesis and antiproliferative activity of some steroidal thiosemicarbazones, semicarbazones and hydrozones.某些甾体硫代半卡巴腙、半卡巴腙和腙的合成及其抗增殖活性
Steroids. 2014 Sep;87:99-107. doi: 10.1016/j.steroids.2014.05.026. Epub 2014 Jun 11.

引用本文的文献

1
Unprecedented synthesis of a 14-membered hexaazamacrocycle.首次合成14元六氮杂大环化合物。
Beilstein J Org Chem. 2023 Nov 15;19:1728-1740. doi: 10.3762/bjoc.19.126. eCollection 2023.

本文引用的文献

1
A general and stereoselective approach to 14-membered cyclic bis-semicarbazones involving BF-catalyzed amidoalkylation of 2-(trimethylsilyloxy)propene.一种涉及 BF 催化的 2-(三甲基甲硅氧基)丙烯酰胺烷基化的 14 元环双半卡巴腙的通用和立体选择性方法。
Org Biomol Chem. 2022 Jun 8;20(22):4569-4588. doi: 10.1039/d2ob00644h.
2
Nickel(II), Copper(II) and Palladium(II) Complexes with Bis-Semicarbazide Hexaazamacrocycles: Redox-Noninnocent Behavior and Catalytic Activity in Oxidation and C-C Coupling Reactions.镍(II)、铜(II)和钯(II)与双缩二氨基己六氮杂大环配合物：氧化和 C-C 偶联反应中的氧化还原非惰性行为和催化活性。
Inorg Chem. 2020 Aug 3;59(15):10650-10664. doi: 10.1021/acs.inorgchem.0c01119. Epub 2020 Jul 10.
3
Biosynthesis and Chemical Applications of Thioamides.
硫代酰胺的生物合成与化学应用。
ACS Chem Biol. 2019 Feb 15;14(2):142-163. doi: 10.1021/acschembio.8b01022. Epub 2019 Jan 30.
4
New AMD3100 derivatives for CXCR4 chemokine receptor targeted molecular imaging studies: synthesis, anti-HIV-1 evaluation and binding affinities.新型 AMD3100 衍生物用于 CXCR4 趋化因子受体靶向分子成像研究：合成、抗 HIV-1 评估和结合亲和力。
Dalton Trans. 2015 Mar 21;44(11):5004-16. doi: 10.1039/c4dt02972k.
5
Polyazamacrocycles as potential antitumor agents for human prostate cancer cells.多氮大环作为潜在的抗肿瘤药物用于人类前列腺癌细胞。
Chem Biol Drug Des. 2013 Apr;81(4):517-26. doi: 10.1111/cbdd.12098.
6
Macrocycles are great cycles: applications, opportunities, and challenges of synthetic macrocycles in drug discovery.大环化合物是重要的环状化合物：合成大环化合物在药物研发中的应用、机遇与挑战
J Med Chem. 2011 Apr 14;54(7):1961-2004. doi: 10.1021/jm1012374. Epub 2011 Mar 7.
7
Medical applications of macrocyclic polyamines.大环多胺的医学应用。
Curr Med Chem. 2006;13(6):711-27. doi: 10.2174/092986706776055706.
8
Taking advantage of luminescent lanthanide ions.利用发光镧系离子。
Chem Soc Rev. 2005 Dec;34(12):1048-77. doi: 10.1039/b406082m. Epub 2005 Sep 20.
9
Radiolabeled peptide conjugates for targeting of the bombesin receptor superfamily subtypes.用于靶向胃泌素释放肽受体超家族亚型的放射性标记肽缀合物。
Nucl Med Biol. 2005 Oct;32(7):733-40. doi: 10.1016/j.nucmedbio.2005.05.005.
10
Cyclam complexes and their applications in medicine.环戊二烯配合物及其在医学中的应用。
Chem Soc Rev. 2004 May 10;33(4):246-66. doi: 10.1039/b313659k. Epub 2004 Mar 22.