One‐Pot, Step‐Wise, Alternative Syntheses of Quinoline‐Substituted Bis(Indolyl)Methanes Using a Green Approach

Madhu, Bandi; Reddy, Venkata Ramana

doi:10.1002/jhet.2922

Cited by 4 publications

(3 citation statements)

References 24 publications

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“…Noteworthy, performing a similar reaction in the absence of dimedone (2a) resulted in the detection of compound 4b (Figure 2B), indicating that the rewired Yonemitsu-type MCR may afford indolocarbazoles with a variety of substituents positioned at C-6 [18]. In sharp contrast, indole 3-carboxaldehyde (1b) gives the standard Yonemitsu adducts [19]. After tuning the stoichiometry and reaction conditions (See SI), the scope of the reaction was studied.…”

Section: Resultsmentioning

confidence: 99%

Streamlined Access to Novel Activators and Degraders of the Aryl Hydrocarbon Receptor through a Rewired Multicomponent Reaction

Ghashghaei

Hartung

Pedrola³

et al. 2022

Preprint

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A rewired Yonemitsu multicomponent reaction was designed to readily synthesize a family of 6-substituted indolocarbazoles. In this approach, indole 2-carboxaldehyde and nucleophilic species directly yield the final adducts through a domino reaction. The scope of the new process was analyzed, and the range of the indole aldehydes and nucleophiles was established. Comparative studies with analogous compounds reveal important details on the reaction mechanism. Experimental and computational studies address the conformational behavior of representative adducts, determining their potential chirality. These novel structures are potent activating ligands of the human aryl hydrocarbon receptor, importantly being non-toxic. Furthermore, the scaffold may be included in a 2-step synthesis of (homo)-PROTACs that efficiently and specifically degrade the receptor. Our approach allows the control of this important target in biomedicine through a designed new chemistry.

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Section: Resultsmentioning

confidence: 99%

Streamlined Access to Novel Activators and Degraders of the Aryl Hydrocarbon Receptor through a Rewired Multicomponent Reaction

Ghashghaei

Hartung

Pedrola³

et al. 2022

Preprint

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“…Madhu Bandi et al . developed a method for synthesis of quinoline substituted bi(indoyl)methanes 298(a – I) by carrying out condensation reaction between 1,4‐hydroxy‐1‐methyl‐2‐oxo‐1,2‐dihydroquinoline‐3‐carbaldehyde 297 a and substituted indoles 296(a – f) in presence of L‐proline with water keeping at temperature 100 °C for 2–3 hours [72] . (Scheme 58 )…”

Section: Introductionmentioning

confidence: 99%

Chemistry of Quinoline Based Heterocycle Scaffolds: A Comprehensive Review

et al. 2022

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Quinoline is a significant scaffold among heterocyclic compounds and can be used as a key building block for the development of novel medications. Quinoline and its derivatives are recognised as biologically active substances with a number of pharmacological properties. Nowadays, quinolinebased heterocycle scaffolds have achieved a prominent position in medicinal chemistry due to their significant pharmaco-logical and biological properties. The discovery and creation of cutting-edge medications to treat a variety of diseases is an example of the usefulness of these compounds. The current study outlines the range of methods available to create different quinolone-based heterocycle scaffolds and their advantageous therapeutic applications using the literature that has been published up to 2022.

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“…13 Reported synthetic methylene-bridged hybrid dimers of 4-hydroxy-1-methyl-2(1H)-quinolone and indole are similar to natural dimers (Figures S1 and S2). 14,15 Quinolone−indole dimers show significant chymase inhibitory and antitumor and antifungal activities. Additionally, dimeric compounds often exhibit stronger activities than their corresponding monomers.…”

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confidence: 99%

Penicilloneines A and B, Quinolone–Citrinin Hybrids from a Starfish-Derived Penicillium sp.

Fan,

Shao,

Zhang

et al. 2024

J. Nat. Prod.

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Penicilloneines A (1) and B (2) are the first reported quinolone−citrinin hybrids. They were isolated from the starfish-derived fungus Penicillium sp. GGF16-1-2, and their structures were elucidated using spectroscopic, chemical, computational, and single-crystal X-ray diffraction methods. Penicilloneines A (1) and B (2) share a common 4-hydroxy-1-methyl-2(1H)-quinolone unit; however, they differ in terms of citrinin moieties, and these two units are linked via a methylene bridge. Penicilloneines A (1) and B (2) exhibited antifungal activities against Colletotrichum gloeosporioides, with lethal concentration 50 values of 0.02 and 1.51 μg/mL, respectively. A mechanistic study revealed that 1 could inhibit cell growth and promote cell vacuolization and consequent disruption of the fungal cell walls via upregulating nutrient-related hydrolase genes, including putative hydrolase, acetylcholinesterase, glycosyl hydrolase, leucine aminopeptidase, lipase, and beta-galactosidase, and downregulating their synthase genes 3-carboxymuconate cyclase, pyruvate decarboxylase, phosphoketolase, and oxalate decarboxylase.

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One‐Pot, Step‐Wise, Alternative Syntheses of Quinoline‐Substituted Bis(Indolyl)Methanes Using a Green Approach

Cited by 4 publications

References 24 publications

Streamlined Access to Novel Activators and Degraders of the Aryl Hydrocarbon Receptor through a Rewired Multicomponent Reaction

Streamlined Access to Novel Activators and Degraders of the Aryl Hydrocarbon Receptor through a Rewired Multicomponent Reaction

Chemistry of Quinoline Based Heterocycle Scaffolds: A Comprehensive Review

Penicilloneines A and B, Quinolone–Citrinin Hybrids from a Starfish-Derived Penicillium sp.

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