• 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

（）-2-亚苄基环烷酮：第二十部分——环状查尔酮类似物与细胞硫醇的反应：在硫杂迈克尔反应中，与1-四氢萘酮类似物相比，4-色满酮意外地具有更高的反应活性。

()-2-Benzylidenecyclanones: Part XX-Reaction of Cyclic Chalcone Analogs with Cellular Thiols: Unexpected Increased Reactivity of 4-Chromanone- Compared to 1-Tetralone Analogs in Thia-Michael Reactions.

作者信息

Bognár Gábor, Kenari Fatemeh, Pintér Zoltán, Borges Igor D, Camargo Ademir J, Oliveira Heibbe C B, Sanches-Neto Flávio Olimpio, Carvalho-Silva Valter H, Napolitano Hamilton B, Perjési Pál

机构信息

Institute of Pharmaceutical Chemistry, University of Pécs, H-7624 Pécs, Hungary.

Grupo de Química Teórica e Estrutural de Anápolis, Universidade Estadual de Goiás, Anápolis 75132-903, GO, Brazil.

出版信息

Molecules. 2024 Nov 21;29(23):5493. doi: 10.3390/molecules29235493.

DOI:10.3390/molecules29235493
PMID:39683654
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11643487/
Abstract

In vitro relative cytotoxicity (IC ()/IC () of ()-3-(4'-methylbenzylidene)-4-chromanone () towards human Molt 4/C8 and CEM T-lymphocytes showed a >50-fold increase in comparison to those of the respective tetralone derivative (). On the other hand, such an increase was not observed in the analogous 4-OCH ( and ) derivatives. In order to study whether thiol reactivity-as a possible basis of the mechanism of action-correlates with the observed cytotoxicities, the kinetics of the non-enzyme catalyzed reactions with reduced glutathione (GSH) and N-acetylcysteine (NAC) of and were investigated. The reactivity of the compounds and the stereochemical outcome of the reactions were evaluated using high-pressure liquid chromatography-mass spectrometry (HPLC-MS). Molecular modeling calculations were performed to rationalize the unexpectedly higher thiol reactivity of the chromanones () compared to the carbocyclic analog tetralones (). The results indicate the possible role of spontaneous thiol reactivity of compounds in their recorded biological effects.

摘要

体外相对细胞毒性（()-3-(4'-甲基亚苄基)-4-色满酮（）对人Molt 4/C8和CEM T淋巴细胞的IC()/IC()）与相应的四氢萘酮衍生物（）相比增加了50倍以上。另一方面，在类似的4-OCH（和）衍生物中未观察到这种增加。为了研究作为可能作用机制基础的硫醇反应性是否与观察到的细胞毒性相关，研究了与还原型谷胱甘肽（GSH）和N-乙酰半胱氨酸（NAC）的非酶催化反应动力学。使用高压液相色谱-质谱（HPLC-MS）评估化合物的反应性和反应的立体化学结果。进行分子建模计算以解释色满酮（）与碳环类似物四氢萘酮（）相比硫醇反应性意外更高的原因。结果表明化合物的自发硫醇反应性在其记录的生物学效应中可能发挥的作用。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0b40/11643487/ea406f4df5f6/molecules-29-05493-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0b40/11643487/14ca9f592d88/molecules-29-05493-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0b40/11643487/e65c0e657fb2/molecules-29-05493-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0b40/11643487/5aaf5b344fb4/molecules-29-05493-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0b40/11643487/abb69864a00b/molecules-29-05493-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0b40/11643487/ea406f4df5f6/molecules-29-05493-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0b40/11643487/14ca9f592d88/molecules-29-05493-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0b40/11643487/e65c0e657fb2/molecules-29-05493-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0b40/11643487/5aaf5b344fb4/molecules-29-05493-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0b40/11643487/abb69864a00b/molecules-29-05493-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0b40/11643487/ea406f4df5f6/molecules-29-05493-g011.jpg

相似文献

1
()-2-Benzylidenecyclanones: Part XX-Reaction of Cyclic Chalcone Analogs with Cellular Thiols: Unexpected Increased Reactivity of 4-Chromanone- Compared to 1-Tetralone Analogs in Thia-Michael Reactions.（）-2-亚苄基环烷酮：第二十部分——环状查尔酮类似物与细胞硫醇的反应：在硫杂迈克尔反应中，与1-四氢萘酮类似物相比，4-色满酮意外地具有更高的反应活性。
Molecules. 2024 Nov 21;29(23):5493. doi: 10.3390/molecules29235493.
2
()-2-Benzylidenecyclanones: Part XIX. Reaction of ()-2-(4'-X-Benzylidene)-1-tetralones with Cellular Thiols: Comparison of Thiol Reactivities of Open-Chain Chalcones and Their Six- and Seven-Membered Cyclic Analogs.()-2-亚苄基环庚酮：第十九部分。()-2-(4'-X-亚苄基)-1-四氢萘酮与细胞硫醇的反应：开链查耳酮及其六元和七元环类似物的硫醇反应活性比较。
Int J Mol Sci. 2024 Jul 16;25(14):7773. doi: 10.3390/ijms25147773.
3
()-2-Benzylidenecyclanones: Part XVIII Study the Possible Link between Glutathione Reactivity and Cancer Cell Cytotoxic Effects of Some Cyclic Chalcone Analogs A Comparison of the Reactivity of the Open-Chain and the Seven-Membered Homologs.()-2-苯亚甲基环庚酮：第十八部分 研究某些环状查尔酮类似物的谷胱甘肽反应性与癌细胞细胞毒性作用之间的可能联系 比较开链和七元同系物的反应性。
Int J Mol Sci. 2023 May 10;24(10):8557. doi: 10.3390/ijms24108557.
4
Reagent-induced asymmetric induction in addition reaction of reduced glutathione onto bis-Mannich chalcones.试剂诱导的还原型谷胱甘肽与双曼尼希查尔酮加成反应的不对称诱导。
Arch Pharm (Weinheim). 2018 Jul;351(7):e1700386. doi: 10.1002/ardp.201700386. Epub 2018 May 18.
5
The evaluation of 1-tetralone and 4-chromanone derivatives as inhibitors of monoamine oxidase.评价 1-四氢萘酮和 4-色满酮衍生物作为单胺氧化酶抑制剂。
Mol Divers. 2021 Feb;25(1):491-507. doi: 10.1007/s11030-020-10143-w. Epub 2020 Sep 24.
6
Different effects of two cyclic chalcone analogues on redox status of Jurkat T cells.两种环状查尔酮类似物对Jurkat T细胞氧化还原状态的不同影响。
Toxicol In Vitro. 2014 Dec;28(8):1359-65. doi: 10.1016/j.tiv.2014.06.006. Epub 2014 Jul 8.
7
Synthesis and Evaluation of 2-benzylidene-1-tetralone Derivatives for Monoamine Oxidase Inhibitory Activity.用于单胺氧化酶抑制活性的2-亚苄基-1-四氢萘酮衍生物的合成与评价
Cent Nerv Syst Agents Med Chem. 2018;18(2):136-149. doi: 10.2174/1871524918666180501121638.
8
Introduction of amino moiety enhances the inhibitory potency of 1-tetralone chalcone derivatives against LPS-stimulated reactive oxygen species production in RAW 264.7 macrophages.引入氨基部分可增强 1-四氢萘酮查尔酮衍生物对 LPS 刺激的 RAW 264.7 巨噬细胞中活性氧产生的抑制作用。
Bioorg Chem. 2019 Jun;87:495-505. doi: 10.1016/j.bioorg.2019.03.055. Epub 2019 Mar 20.
9
Effect of selected dimethylaminochalcones on some mitochondrial activities.某些二甲基氨基查耳酮对某些线粒体活性的影响。
In Vitro Cell Dev Biol Anim. 2013 May;49(5):354-9. doi: 10.1007/s11626-013-9600-x. Epub 2013 Apr 19.
10
Design, Synthesis, and Evaluation of (2-(Pyridinyl)methylene)-1-tetralone Chalcones for Anticancer and Antimicrobial Activity.用于抗癌和抗菌活性的(2-(吡啶基)亚甲基)-1-四氢萘酮查耳酮的设计、合成与评价
Med Chem. 2018;14(4):333-343. doi: 10.2174/1573406413666171020121244.

本文引用的文献

1
()-2-Benzylidenecyclanones: Part XIX. Reaction of ()-2-(4'-X-Benzylidene)-1-tetralones with Cellular Thiols: Comparison of Thiol Reactivities of Open-Chain Chalcones and Their Six- and Seven-Membered Cyclic Analogs.()-2-亚苄基环庚酮：第十九部分。()-2-(4'-X-亚苄基)-1-四氢萘酮与细胞硫醇的反应：开链查耳酮及其六元和七元环类似物的硫醇反应活性比较。
Int J Mol Sci. 2024 Jul 16;25(14):7773. doi: 10.3390/ijms25147773.
2
The expanding repertoire of covalent warheads for drug discovery.用于药物发现的共价弹头的不断扩大的库。
Drug Discov Today. 2023 Dec;28(12):103799. doi: 10.1016/j.drudis.2023.103799. Epub 2023 Oct 13.
3
Synthesis, reactions and application of chalcones: a systematic review.
查耳酮的合成、反应及应用：系统综述。
Org Biomol Chem. 2023 Jul 5;21(26):5317-5346. doi: 10.1039/d3ob00792h.
4
Anticancer Activity of Chalcones and Its Derivatives: Review and In Silico Studies.查耳酮及其衍生物的抗癌活性：综述及计算机研究。
Molecules. 2023 May 10;28(10):4009. doi: 10.3390/molecules28104009.
5
()-2-Benzylidenecyclanones: Part XVIII Study the Possible Link between Glutathione Reactivity and Cancer Cell Cytotoxic Effects of Some Cyclic Chalcone Analogs A Comparison of the Reactivity of the Open-Chain and the Seven-Membered Homologs.()-2-苯亚甲基环庚酮：第十八部分 研究某些环状查尔酮类似物的谷胱甘肽反应性与癌细胞细胞毒性作用之间的可能联系 比较开链和七元同系物的反应性。
Int J Mol Sci. 2023 May 10;24(10):8557. doi: 10.3390/ijms24108557.
6
Chalcone: A Promising Bioactive Scaffold in Medicinal Chemistry.查尔酮：药物化学中一种有前景的生物活性骨架。
Pharmaceuticals (Basel). 2022 Oct 11;15(10):1250. doi: 10.3390/ph15101250.
7
Two Important Anticancer Mechanisms of Natural and Synthetic Chalcones.天然和合成查尔酮的两种重要抗癌机制。
Int J Mol Sci. 2022 Sep 30;23(19):11595. doi: 10.3390/ijms231911595.
8
Licochalcone A Induces Cholangiocarcinoma Cell Death Via Suppression of Nrf2 and NF-κB Signaling Pathways.甘草查尔酮 A 通过抑制 Nrf2 和 NF-κB 信号通路诱导胆管癌细胞死亡。
Asian Pac J Cancer Prev. 2022 Jan 1;23(1):115-123. doi: 10.31557/APJCP.2022.23.1.115.
9
Reaction of Chalcones with Cellular Thiols. The Effect of the 4-Substitution of Chalcones and Protonation State of the Thiols on the Addition Process. Diastereoselective Thiol Addition.查耳酮与细胞硫醇的反应。查耳酮的 4-取代基和硫醇的质子化状态对加成过程的影响。立体选择性硫醇加成。
Molecules. 2021 Jul 17;26(14):4332. doi: 10.3390/molecules26144332.
10
Mechanism of inhibition of SARS-CoV-2 M by peptidyl Michael acceptor explained by QM/MM simulations and design of new derivatives with tunable chemical reactivity.通过量子力学/分子力学模拟解释肽基迈克尔受体对SARS-CoV-2 M的抑制机制以及设计具有可调化学反应性的新衍生物
Chem Sci. 2020 Nov 27;12(4):1433-1444. doi: 10.1039/d0sc06195f.