一锅法合成 2-氨基吲哚-3-甲酰胺及类似物。
One-pot synthesis of 2-amino-indole-3-carboxamide and analogous.
机构信息
Drug Discovery Institute, University of Pittsburgh, Pittsburgh, PA 15261, United States.
出版信息
ACS Comb Sci. 2011 Mar 14;13(2):140-6. doi: 10.1021/co100040z. Epub 2010 Dec 17.
Abstract
An efficient one-pot, two-step solution-phase synthetic method was developed to synthesize twenty-three 2-amino-indole-3-carboxamides (3) from 2-halonitrobenzene (1) or heterocyclic analogous and cyanoacetamides (2). In this sequence, first, intermediate 2-cyano-2-(2-nitrophenyl)acetamide (4) was generated under basic condition via S(NAr) reaction; after direct addition of hydrochloric acid solution, FeCl(3), and Zn powder, indole 3 was generated via reduction/cyclization process.
摘要
开发了一种高效的一锅两步溶液相合成方法，从 2-卤代硝基苯（1）或杂环类似物和氰基乙酰胺（2）合成了 23 种 2-氨基-3-吲哚甲酰胺（3）。在这个序列中，首先，在碱性条件下通过 S（NAr）反应生成中间体 2-氰基-2-（2-硝基苯基）乙酰胺（4）；直接加入盐酸溶液、FeCl(3)和 Zn 粉后，通过还原/环化过程生成吲哚 3。
相似文献
1
One-pot synthesis of 2-amino-indole-3-carboxamide and analogous.一锅法合成 2-氨基吲哚-3-甲酰胺及类似物。
ACS Comb Sci. 2011 Mar 14;13(2):140-6. doi: 10.1021/co100040z. Epub 2010 Dec 17.
2
Novel synthetic methods for N-cyano-1H-imidazole-4-carboxamides and their fungicidal activity.新型 N-氰基-1H-咪唑-4-甲酰胺的合成方法及其杀菌活性。
Bioorg Med Chem Lett. 2012 Feb 1;22(3):1455-8. doi: 10.1016/j.bmcl.2011.11.115. Epub 2011 Dec 4.
3
Synthesis of 5-Aminoimidazole-4-Carboxamide Riboside (AICAR) and Its Derivatives Using Inosine as Starting Material.
Curr Protoc Nucleic Acid Chem. 2015 Dec 1;63:1.35.1-1.35.24. doi: 10.1002/0471142700.nc0135s63.
4
Synthesis and enzymatic polymerisation of 5-amino-1-(2'-deoxy-beta-D-ribofuranosyl)imidazole-4-carboxamide-5'- triphosphate.5-氨基-1-(2'-脱氧-β-D-呋喃核糖基)咪唑-4-甲酰胺-5'-三磷酸的合成与酶促聚合
Nucleic Acids Res. 1990 Dec 11;18(23):7127-31. doi: 10.1093/nar/18.23.7127.
5
Synthesis of a methylene analog of 5-amino-1-beta-D-ribofuranosylimidazole-4-carboxamide monophosphate (ZMP).5-氨基-1-β-D-呋喃核糖基咪唑-4-甲酰胺单磷酸（ZMP）的亚甲基类似物的合成。
Biosci Biotechnol Biochem. 2005 Apr;69(4):836-8. doi: 10.1271/bbb.69.836.
6
Synthesis of nucleosides as potential inhibitors of purine biosynthesis.作为嘌呤生物合成潜在抑制剂的核苷的合成。
Nucleic Acids Symp Ser. 1991(25):53-4. doi: 10.1002/chin.199031303.
7
Solid-phase synthesis of a new diphosphate 5-aminoimidazole-4-carboxamide riboside (AICAR) derivative and studies toward cyclic AICAR diphosphate ribose.新型二磷酸 5-氨基咪唑-4-甲酰胺核苷（AICAR）衍生物的固相合成及环状 AICAR 二磷酸核糖的研究。
Molecules. 2011 Sep 21;16(9):8110-8. doi: 10.3390/molecules16098110.
8
Rhodium-Catalyzed Cyclization of 2-Ethynylanilines in the Presence of Isocyanates: Approach toward Indole-3-carboxamides.铑催化的异氰酸酯存在下2-乙炔基苯胺的环化反应：吲哚-3-甲酰胺的合成方法
Org Lett. 2016 Feb 19;18(4):748-51. doi: 10.1021/acs.orglett.6b00007. Epub 2016 Feb 3.
9
Synthesis and antifungal activity of N-(substituted pyridinyl)-1-methyl(phenyl)-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide derivatives.N-(取代吡啶基)-1-甲基(苯基)-3-(三氟甲基)-1H-吡唑-4-甲酰胺衍生物的合成及抑菌活性。
Molecules. 2012 Nov 30;17(12):14205-18. doi: 10.3390/molecules171214205.
10
Regiocontrolled synthesis of carbocycle-fused indoles via arylation of silyl enol ethers with o-nitrophenylphenyliodonium fluoride.通过硅基烯醇醚与邻硝基苯基苯基氟化碘鎓的芳基化反应实现区域可控的碳环稠合吲哚的合成。
Org Lett. 1999 Aug 26;1(4):673-6. doi: 10.1021/ol990759j.
引用本文的文献
1
Heteroannulations of cyanoacetamide-based MCR scaffolds utilizing formamide.基于氰基乙酰胺的多组分反应支架利用甲酰胺进行的杂环化反应
Beilstein J Org Chem. 2025 Jan 24;21:217-225. doi: 10.3762/bjoc.21.13. eCollection 2025.
2
A multicomponent tetrazolo indole synthesis.多组分四唑吲哚合成。
Chem Commun (Camb). 2021 Jul 6;57(54):6652-6655. doi: 10.1039/d1cc02384e.
3
Discovery of chromenes as inhibitors of macrophage migration inhibitory factor.发现色烯类化合物作为巨噬细胞移动抑制因子抑制剂。
Bioorg Med Chem. 2018 Mar 1;26(5):999-1005. doi: 10.1016/j.bmc.2017.12.032. Epub 2017 Dec 24.
4
Cyanoacetamides (IV): versatile one-pot route to 2-quinoline-3-carboxamides.氰基乙酰胺（IV）：一种通用的一锅法合成 2-喹啉-3-甲酰胺的方法。
ACS Comb Sci. 2012 May 14;14(5):316-22. doi: 10.1021/co3000133. Epub 2012 Apr 18.
本文引用的文献
1
Design of a versatile multicomponent reaction leading to 2-amino-5-ketoaryl pyrroles.设计一种通用的多组分反应，生成 2-氨基-5-芳基吡咯酮。
Chem Biol Drug Des. 2010 Mar;75(3):277-83. doi: 10.1111/j.1747-0285.2009.00942.x. Epub 2010 Jan 19.
2
Robust generation of lead compounds for protein-protein interactions by computational and MCR chemistry: p53/Hdm2 antagonists.通过计算化学和多组分反应化学稳健生成用于蛋白质-蛋白质相互作用的先导化合物：p53/Hdm2拮抗剂
Angew Chem Int Ed Engl. 2010 Jul 19;49(31):5352-6. doi: 10.1002/anie.201001343.
3
Discovery of piperidin-4-yl-aminopyrimidines as HIV-1 reverse transcriptase inhibitors. N-benzyl derivatives with broad potency against resistant mutant viruses.发现哌啶-4-基-氨基嘧啶作为 HIV-1 逆转录酶抑制剂。具有广谱抗耐药突变病毒活性的 N-苄基衍生物。
Bioorg Med Chem Lett. 2010 Jul 15;20(14):4215-8. doi: 10.1016/j.bmcl.2010.05.040. Epub 2010 May 16.
4
Dabigatran etexilate, a new oral direct thrombin inhibitor, for stroke prevention in patients with atrial fibrillation.达比加群酯，一种新型的口服直接凝血酶抑制剂，用于预防心房颤动患者的中风。
Expert Opin Pharmacother. 2010 Jun;11(8):1403-11. doi: 10.1517/14656566.2010.482931.
5
Structures of low molecular weight inhibitors bound to MDMX and MDM2 reveal new approaches for p53-MDMX/MDM2 antagonist drug discovery.小分子抑制剂与 MDMX 和 MDM2 结合的结构揭示了用于 p53-MDMX/MDM2 拮抗剂药物发现的新方法。
Cell Cycle. 2010 Mar 15;9(6):1104-11. doi: 10.4161/cc.9.6.10956.
6
Intramolecular hydrogen bonding in medicinal chemistry.分子内氢键在药物化学中的作用。
J Med Chem. 2010 Mar 25;53(6):2601-11. doi: 10.1021/jm100087s.
7
Discovery of cyclic acylguanidines as highly potent and selective beta-site amyloid cleaving enzyme (BACE) inhibitors: Part I--inhibitor design and validation.环状酰胍类化合物作为高效、选择性β-淀粉样肽 cleaving 酶（BACE）抑制剂的发现：第一部分——抑制剂设计与验证。
J Med Chem. 2010 Feb 11;53(3):951-65. doi: 10.1021/jm901408p.
8
Cyanoacetamide MCR (III): three-component Gewald reactions revisited.氰基乙酰胺MCR（III）：对三组分格瓦尔德反应的重新审视
J Comb Chem. 2010 Jan-Feb;12(1):111-8. doi: 10.1021/cc9001586.
9
Potent and orally active small-molecule inhibitors of the MDM2-p53 interaction.强效、口服有效的小分子 MDM2-p53 相互作用抑制剂。
J Med Chem. 2009 Dec 24;52(24):7970-3. doi: 10.1021/jm901400z.
10
Cyanoacetamide multicomponent reaction (I): Parallel synthesis of cyanoacetamides.氰基乙酰胺多组分反应（I）：氰基乙酰胺的平行合成
J Comb Chem. 2009 Sep-Oct;11(5):920-7. doi: 10.1021/cc9000778.
Zotero 插件