• 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

从 α-羟基酮、3-氧代丁腈和苯胺出发简明合成吡咯类药物候选物。

A Concise Synthesis of Pyrrole-Based Drug Candidates from α-Hydroxyketones, 3-Oxobutanenitrile, and Anilines.

机构信息

School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, 62 Nanyang Drive, N1.2-B1-14, Singapore 637459, Singapore.

Department of Chemistry, Faculty of Science, Institut Teknologi Sepuluh Nopember, Sukolilo, Surabaya 60111, Indonesia.

出版信息

Molecules. 2023 Jan 28;28(3):1265. doi: 10.3390/molecules28031265.

DOI:10.3390/molecules28031265
PMID:36770934
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9918993/
Abstract

A simple and concise three-component synthesis of a key pyrrole framework was developed from the reaction between α-hydroxyketones, oxoacetonitriles, and anilines. The synthesis was used to obtain several pyrrole-based drug candidates, including COX-2 selective NSAID, antituberculosis lead candidates BM212, BM521, and BM533, as well as several analogues. This route has potential to obtain diverse libraries of these pyrrole candidates in a concise manner to develop optimum lead compounds.

摘要

从α-羟基酮、氧代乙腈和苯胺之间的反应出发，开发了一种简单而简洁的三组分合成关键吡咯骨架的方法。该合成方法用于获得几种基于吡咯的药物候选物，包括 COX-2 选择性 NSAID、抗结核先导候选物 BM212、BM521 和 BM533 以及几种类似物。这条路线有可能以简洁的方式获得这些吡咯候选物的各种文库，从而开发出最佳的先导化合物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/69a4/9918993/1b5f69029bdc/molecules-28-01265-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/69a4/9918993/33b23e63e671/molecules-28-01265-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/69a4/9918993/2539b06c4b06/molecules-28-01265-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/69a4/9918993/022e4b714962/molecules-28-01265-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/69a4/9918993/1b5f69029bdc/molecules-28-01265-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/69a4/9918993/33b23e63e671/molecules-28-01265-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/69a4/9918993/2539b06c4b06/molecules-28-01265-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/69a4/9918993/022e4b714962/molecules-28-01265-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/69a4/9918993/1b5f69029bdc/molecules-28-01265-sch005.jpg

相似文献

1
A Concise Synthesis of Pyrrole-Based Drug Candidates from α-Hydroxyketones, 3-Oxobutanenitrile, and Anilines.从 α-羟基酮、3-氧代丁腈和苯胺出发简明合成吡咯类药物候选物。
Molecules. 2023 Jan 28;28(3):1265. doi: 10.3390/molecules28031265.
2
Selective One-Pot Multicomponent Synthesis of -Substituted 2,3,5-Functionalized 3-Cyanopyrroles via the Reaction between α-Hydroxyketones, Oxoacetonitriles, and Primary Amines.α-羟基酮、氧代乙腈和伯胺通过反应选择性一锅法多组分合成 -取代的 2,3,5-三取代 3-氰基吡咯。
Molecules. 2022 Aug 18;27(16):5285. doi: 10.3390/molecules27165285.
3
New derivatives of BM212: A class of antimycobacterial compounds based on the pyrrole ring as a scaffold.BM212的新衍生物：一类以吡咯环为骨架的抗分枝杆菌化合物。
Mini Rev Med Chem. 2007 Jan;7(1):65-78. doi: 10.2174/138955707779317786.
4
Antimycobacterial compounds. New pyrrole derivatives of BM212.抗分枝杆菌化合物。BM212的新型吡咯衍生物。
Bioorg Med Chem. 2004 Mar 15;12(6):1453-8. doi: 10.1016/j.bmc.2003.12.037.
5
Pyrrole versus quinoline formation in the palladium catalyzed reaction of 2-alkynyl-3-bromothiophenes and 2-alkynyl-3-bromofurans with anilines. A combined experimental and computational study.钯催化 2-炔基-3-溴噻吩和 2-炔基-3-溴呋喃与苯胺反应中吡咯与喹啉的形成。实验与计算研究的结合。
Org Biomol Chem. 2012 Dec 21;10(47):9464-73. doi: 10.1039/c2ob26689j. Epub 2012 Nov 5.
6
Bactericidal activities of the pyrrole derivative BM212 against multidrug-resistant and intramacrophagic Mycobacterium tuberculosis strains.吡咯衍生物BM212对耐多药和巨噬细胞内结核分枝杆菌菌株的杀菌活性。
Antimicrob Agents Chemother. 1998 Nov;42(11):3035-7. doi: 10.1128/AAC.42.11.3035.
7
One-pot three-component tandem reaction of diazo compounds with anilines and unsaturated ketoesters: a novel synthesis of 2,3-dihydropyrrole derivatives.重氮化合物与苯胺和不饱和酮酯的一锅三组分串联反应：2,3-二氢吡咯衍生物的新合成方法
Chem Commun (Camb). 2009 Mar 21(11):1362-4. doi: 10.1039/b822626a. Epub 2009 Feb 9.
8
Antimycobacterial agents. Novel diarylpyrrole derivatives of BM212 endowed with high activity toward Mycobacterium tuberculosis and low cytotoxicity.抗分枝杆菌药物。BM212的新型二芳基吡咯衍生物，对结核分枝杆菌具有高活性且细胞毒性低。
J Med Chem. 2006 Aug 10;49(16):4946-52. doi: 10.1021/jm0602662.
9
MmpL3 is the cellular target of the antitubercular pyrrole derivative BM212.MmpL3 是抗结核吡咯衍生物 BM212 的细胞靶标。
Antimicrob Agents Chemother. 2012 Jan;56(1):324-31. doi: 10.1128/AAC.05270-11. Epub 2011 Oct 24.
10
New pyrrole derivatives as antimycobacterial agents analogs of BM212.新型吡咯衍生物作为BM212的抗分枝杆菌剂类似物。
Bioorg Med Chem Lett. 1999 Oct 18;9(20):2983-8. doi: 10.1016/s0960-894x(99)00510-7.

本文引用的文献

1
Selective One-Pot Multicomponent Synthesis of -Substituted 2,3,5-Functionalized 3-Cyanopyrroles via the Reaction between α-Hydroxyketones, Oxoacetonitriles, and Primary Amines.α-羟基酮、氧代乙腈和伯胺通过反应选择性一锅法多组分合成 -取代的 2,3,5-三取代 3-氰基吡咯。
Molecules. 2022 Aug 18;27(16):5285. doi: 10.3390/molecules27165285.
2
Design, synthesis and biological evaluation of novel pyrrole derivatives as potential ClpP1P2 inhibitor against Mycobacterium tuberculosis.新型吡咯衍生物的设计、合成及作为潜在结核分枝杆菌 ClpP1P2 抑制剂的生物评价。
Bioorg Chem. 2018 Oct;80:422-432. doi: 10.1016/j.bioorg.2018.06.004. Epub 2018 Jun 4.
3
Pyrrole and Fused Pyrrole Compounds with Bioactivity against Inflammatory Mediators.
具有抗炎症介质生物活性的吡咯及稠合吡咯化合物。
Molecules. 2017 Mar 17;22(3):461. doi: 10.3390/molecules22030461.
4
N-substituted pyrrole-based scaffolds as potential anticancer and antiviral lead structures.基于N-取代吡咯的支架作为潜在的抗癌和抗病毒先导结构。
Med Chem. 2015;11(6):602-8. doi: 10.2174/1573406411666150313161225.
5
A class of pyrrole derivatives endowed with analgesic/anti-inflammatory activity.一类具有镇痛/抗炎活性的吡咯衍生物。
Bioorg Med Chem. 2013 Jul 1;21(13):3695-701. doi: 10.1016/j.bmc.2013.04.031. Epub 2013 Apr 26.
6
Discovery of disubstituted piperidines and homopiperidines as potent dual NK1 receptor antagonists-serotonin reuptake transporter inhibitors for the treatment of depression.发现二取代哌啶和高哌啶作为有效的双重NK1受体拮抗剂-5-羟色胺再摄取转运体抑制剂用于治疗抑郁症。
Bioorg Med Chem. 2013 Apr 15;21(8):2217-2228. doi: 10.1016/j.bmc.2013.02.010. Epub 2013 Feb 19.
7
Improved BM212 MmpL3 inhibitor analogue shows efficacy in acute murine model of tuberculosis infection.改良的 BM212 MmpL3 抑制剂类似物在急性结核感染的小鼠模型中显示出疗效。
PLoS One. 2013;8(2):e56980. doi: 10.1371/journal.pone.0056980. Epub 2013 Feb 21.
8
Molecular basis for sunitinib efficacy and future clinical development.舒尼替尼疗效的分子基础及未来临床发展
Nat Rev Drug Discov. 2007 Sep;6(9):734-45. doi: 10.1038/nrd2380.
9
New derivatives of BM212: A class of antimycobacterial compounds based on the pyrrole ring as a scaffold.BM212的新衍生物：一类以吡咯环为骨架的抗分枝杆菌化合物。
Mini Rev Med Chem. 2007 Jan;7(1):65-78. doi: 10.2174/138955707779317786.
10
Design of the Collaborative AtoRvastatin Diabetes Study (CARDS) in patients with type 2 diabetes.2型糖尿病患者阿托伐他汀协作糖尿病研究（CARDS）的设计
Diabet Med. 2002 Mar;19(3):201-11. doi: 10.1046/j.1464-5491.2002.00643.x.