Indoles

Chadha, Navriti; Silakari, Om

doi:10.1016/b978-0-08-102083-8.00008-x

Cited by 16 publications

(8 citation statements)

References 137 publications

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“…The choice of structures was based on preliminary calculations of the Bergman cyclization’s free activation energies and the synthetic accessibility of acyclic enediyne precursors. − According to the calculated free activation energy values, these heterocycles help to attenuate activation barriers in an ∼3 kcal/mol interval, providing target 10-membered structures with a different balance of stability/reactivity . Moreover, indole and isocoumarine scaffolds can be found in numerous natural products, biologically active compounds, and drugs. A variety of synthetic approaches to indole- , and isocoumarin-containing molecules are known along with the increasing importance of alkynes in the creation of such heterocycles. − Synthetic accessibility of 1 H -1,2,3-triazoles starting mainly from alkynes through a click approach − as well as from aldehydes and ketones led to a widespread application of triazole derivatives.…”

Section: Resultsmentioning

confidence: 99%

Intramolecular Nicholas Reactions in the Synthesis of Heteroenediynes Fused to Indole, Triazole, and Isocoumarin

et al. 2020

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The applicability of an intramolecular Nicholas reaction for the preparation of 10-membered O- and N-enediynes fused to indole, 1,2,3-triazole, and isocoumarin was investigated. The general approach to acyclic enediyne precursors fused to heterocycles includes inter- and intramolecular buta-1,3-diyne cyclizations with the formation of iodoethynylheterocycles, followed by Sonogashira coupling. The nature of both a heterocycle and a nucleophilic group affects the possibility of a 10-membered ring closure by the Nicholas reaction. Among oxacycles, an isocoumarin-fused enediyne was obtained. In the case of O-enediyne annulated with indole, instead of the formation of a 10-membered cycle, BF3-promoted addition of an OH-group to the proximal triple bond at the C3 position afforded dihydrofuryl-substituted indole. For 1,2,3-triazole-fused analogues, using NH-Ts as a nucleophilic functional group allowed obtaining 10-membered azaenediyne, while the substrate with a hydroxyl group gave only traces of the desired 10-membered oxacycle. An improved method for the deprotection of Co-complexes of cyclic enediynes using tetrabutylammonium fluoride in an acetone/water mixture and the investigation of the 10-membered enediynes’ reactivity in the Bergman cyclization are also reported. In the solid state, all synthesized iodoethynylheterocycles were found to be involved in halogen bond (XB) formation with either O or N atoms as XB acceptors.

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Section: Resultsmentioning

confidence: 99%

Intramolecular Nicholas Reactions in the Synthesis of Heteroenediynes Fused to Indole, Triazole, and Isocoumarin

et al. 2020

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“…Indole is a prominent phytoconstituent across various plant species and is produced by a variety of bacteria [ 270 ]. The indole-derived phytoconstituents and bacterial metabolites are a result of biosynthesis via the coupling of tryptophan with other amino acids.…”

Section: Indole Derivativesmentioning

confidence: 99%

From Hybrids to New Scaffolds: The Latest Medicinal Chemistry Goals in Multi-target Directed Ligands for Alzheimer’s Disease

Alarcón-Espósito

Mallea

Rodríguez-Lavado

2021

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: Alzheimer’s disease (AD) is a chronic, progressive, and fatal neurodegenerative disorder affecting cognition, behavior, and function, being one of the most common causes of mental deterioration in elderly people. Once thought as being just developed because of β amyloid depositions or neurofibrillary Tau tangles, during the last decades, numerous ADrelated targets have been established, the multifactorial nature of AD became evident. In this context, the one drug-one target paradigm has resulted to be inefficient in facing AD and other disorders with complex etiology, opening the field for the emergence of the multitarget approach. In this review, we highlight the recent advances within this area, emphasizing in hybridization tools of well-known chemical scaffolds endowed with pharmacological properties concerning AD, such as curcumin-, resveratrol-, chromone- and indole-. We focus mainly on well stablished and incipient AD therapeutic targets, AChE, BuChE, MAOs, β-amyloid deposition, 5-HT4 and Serotonin transporter, with the aim to shed light about new insights in the AD multitarget therapy.

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“…Indoles are a heterocyclic ring that has a wide range of therapeutic applications in disorders such as cancer, viral infections, depression, migraine, hypertension, and vomiting. 11 Bazedoxifene ( 11 ) is an indole-based ER ligand with unique structural characteristics, similar to tamoxifen and raloxifene, and has been shown to have strong estrogenic and antiestrogenic effects in both in vivo and in vitro assays (Fig. 2).…”

Section: Introductionmentioning

confidence: 99%

“…13 It has been observed that the fluorine atom in the oxindole ring in sunitinib (12) forms hydrophobic interactions with DNA amino acids. 11 Birinapant ( 13) is a novel bivalent apoptosis inhibitor (IAP) in clinical development for the treatment of cancer and hepatitis B virus infection, and a clinical drug candidate for hematological and solid malignancies, as well as leukemia at the same time (Fig. 2).…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis, and biological evaluation of indole-modified tamoxifen relatives as potent anticancer agents

et al. 2023

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Indoles

Cited by 16 publications

References 137 publications

Intramolecular Nicholas Reactions in the Synthesis of Heteroenediynes Fused to Indole, Triazole, and Isocoumarin

Intramolecular Nicholas Reactions in the Synthesis of Heteroenediynes Fused to Indole, Triazole, and Isocoumarin

From Hybrids to New Scaffolds: The Latest Medicinal Chemistry Goals in Multi-target Directed Ligands for Alzheimer’s Disease

Design, synthesis, and biological evaluation of indole-modified tamoxifen relatives as potent anticancer agents

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