Indole is a significant nitrogen-based heterocycle with particular importance in the synthesis of heterocyclic scaffolds. Indole based compounds have been recently attracting much attention due to their biological and pharmaceutical activities. 3-Substituted indoles such as cyanoacetyl indoles (CAIs) are nitrogen-heterocyclic compounds which are easily obtained from the reaction of indoles and cyanoacetic acid. They are versatile starting materials utilized for the construction of a wide variety of molecules containing indole moieties in organic synthesis. In this study, we provide an overview on the synthesis of 3-cyanoacetyl indoles (CAIs) and their recent applications in the multi-component reactions for the synthesis of various heterocyclic compounds such as pyranes, pyridines, dihydropyridines, pyrimidines, tetrahydropyrimidines, pyrazoles, pyrazolopyridines, pyrazolopyrimidines, pyridopyrimidines, tetrazolopyrimidines, triazolopyrimidines, furans, dihydrofurans, coumarins, pyrimido naphthyridines, chromenes, thiazoles, pyrimidoindazoles, pyrazoloquinolines, isoxazolopyridines, and carbazoles and their biological activities during the period of 2013 to 2022.
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http://dx.doi.org/10.1039/d3ra04385a | DOI Listing |
RSC Adv
May 2024
Department of Biomolecular Sciences, University of Urbino Carlo Bo 61029 Urbino (PU) Italy +39-0722303333 +39-0722303444.
A chemoselective one-pot synthesis of pharmaceutically prospective indole-pyrrole hybrids by the formal [3 + 2] cycloaddition of 3-cyanoacetyl indoles (CAIs) with 1,2-diaza-1,3-dienes (DDs) has been developed. The new indole-pyrrole hybrids were phenotypically screened for efficacy against promastigotes. The most active compounds 3c, 3d, and 3j showed IC < 20 μM and moderate cytotoxicity, lower than miltefosine.
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July 2023
Department of Chemistry, Qazvin Branch, Islamic Azad University Qazvin Iran +0098-28-33365275.
Indole is a significant nitrogen-based heterocycle with particular importance in the synthesis of heterocyclic scaffolds. Indole based compounds have been recently attracting much attention due to their biological and pharmaceutical activities. 3-Substituted indoles such as cyanoacetyl indoles (CAIs) are nitrogen-heterocyclic compounds which are easily obtained from the reaction of indoles and cyanoacetic acid.
View Article and Find Full Text PDFSci Rep
August 2022
Organic and Nano Group (ONG), Department of Chemistry, Iran University of Science and Technology (IUST), PO Box 16846-13114, Tehran, Iran.
In this study, a novel nano-magnetic metal-organic frameworks based on FeO namely FeO@MIL-101(Cr)-N(CHPO) was synthesized and fully characterized. The prepared sample was used as catalyst in the synthesis of pyrazolo [3,4-b] pyridines as convenient medicine by condensation reaction of aldehydes, 5-(1H-Indol-3-yl)- 2H-pyrazol-3-ylamine and 3-(cyanoacetyl)indole via a CVABO. The products were obtained with high yields at 100 °C and under solvent-free conditions.
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March 2021
Department of Chemistry, Qom Branch, Islamic Azad University, Qom, 37491-13191, Islamic Republic of Iran.
A one-pot three component reaction of benzaldehydes, 1H-tetrazole-5-amine, and 3-cyanoacetyl indole in the presence of a new hexamethylenetetramine-based ionic liquid/MIL-101(Cr) metal-organic framework as a recyclable catalyst was explored. This novel catalyst, which was fully characterized by XRD, FE-SEM, EDX, FT-IR, TGA, BET, and TEM exhibited outstanding catalytic activity for the preparation of a range of pharmaceutically important tetrazolo[1,5-a]pyrimidine-6-carbonitriles with good to excellent yields in short reaction time.
View Article and Find Full Text PDFAnticancer Agents Med Chem
October 2021
Department of Chemistry, A.S.P. College, Devrukh, Dist-Ratnagiri- 415 804, Maharashtra, India.
Background: Indole and pyrazole constitute a major class of biologically active scaffolds. The amalgamation of two or more pharmacophores would generate novel molecular templates that are likely to unveil remarkable biological properties.
Objective: An efficient and high yielding synthesis of indole-pyrazole integrated α-cyano substituted chalcones and their in vitro anti-breast cancer and antioxidant evaluation.
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