Indoles as therapeutics of interest in medicinal chemistry: Bird's eye view

Chadha, Navriti; Silakari, Om

doi:10.1016/j.ejmech.2017.04.003

Cited by 486 publications

(242 citation statements)

References 163 publications

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“…The well-known ability of gold catalysts to induce propargylic ester rearrangements, such as Rautenstrauch or [3,3] [125][126][127][128] After the first work by Zhang in 2005, [129] other research groups studied the reactivity of indoles and propargylic esters under gold catalysis conditions in both intra-and intermolecular processes. Very recently, Shi and co-workers prepared a series of indoles 110, N-substituted with propargylic ester systems, that were able to undergo tandem gold-catalyzed 1,2-acyloxy migration/[3+2] cycloaddition to afford a series of polycyclic indolines 111, each containing four contiguous stereocenters (Scheme 44).…”

Section: Initiated By the Rearrangement Of A Propargylic Estermentioning

confidence: 99%

“…[1][2][3][4] Therefore, since its discovery and characterization in 1866, [5] enormous efforts have been dedicated to the development of efficient methods for its preparation [6][7][8][9][10][11][12] and functionalization. Indole is probably one of the most important and intensively studied heterocyclic systems in different research areas, including pharmaceutical, agrochemical, and materials sciences.…”

Section: Introductionmentioning

confidence: 99%

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Gold‐Catalyzed Functionalization Reactions of Indole

Pirovano

2018

Eur J Org Chem

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This review summarizes the progress achieved in the last fifteen years by application of homogeneous gold catalysis in the field of indole functionalization. Several electrophilic species obtained through gold‐catalyzed π‐activation have in fact been found to react with the nucleophilic positions of indole, thus allowing its efficient manipulation. In order to furnish a complete and clear overview on the role of the catalyst, the review is organized from the perspective of the gold‐activated substrate that is reacting with the indole. In addition, in view of the ability of gold to catalyze tandem and cascade reactions, a separate section describes tandem/cascade protocols useful for the synthesis of complex polycyclic indole derivatives. Finally, gold catalysis has also been employed for the synthesis of indole‐based natural products. For this reason, a dedicated section collects all the work in which the key step to obtain these complex indoles is represented by a gold‐catalyzed reaction.

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Section: Initiated By the Rearrangement Of A Propargylic Estermentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Gold‐Catalyzed Functionalization Reactions of Indole

Pirovano

2018

Eur J Org Chem

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“…Chemically, this heterocyclic ring system is a fusion of six-membered benzene and five-membered pyrrole ring [2,3]. The indoles are privileged molecules in the chemical literature due to their diverse biological properties and found in a number of natural products and bioactive molecules [4][5][6][7][8].…”

Section: Introductionmentioning

confidence: 99%

Molecular self-assembly in indole-based benzamide derivative: Crystal structure, Hirshfeld surfaces and antimicrobial activity

et al. 2017

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Two new compounds, 1H-indole-7-amine (1) and N-(1H-indol-7-yl)-2-methylbenzamide (2)were synthesized and structurally characterized by NMR and FT-IR spectroscopic techniques. The molecular structure of compound 2 was further elucidated by single-crystal X-ray diffraction technique. Moreover, the crystal packing of compound 2 is analyzed in terms of non-covalent N-H···O, C-H···π, and parallel displaced π···π interactions. Hirshfeld surface analysis and decomposed fingerprint plots of the compound 2 were performed to visualize the presence of strong hydrogen bond N-H···O and C-H···π stacking interactions. Hirshfeld surface analysis and decomposed fingerprint plots show that the structure of compound 2 is stabilized by H···H, N-H···O, C-H···π and π···π intermolecular interactions and these interactions contribute mostly to molecular self-assembly in the crystal. In addition, compound 2 was evaluated for both their in-vitro antibacterial and antifungal activity. The obtained results have been reported, explained and compared with fluconazole and ampicillin used as reference drugs. KEYWORDSAntimicrobial activity Single crystal structure Molecular self-assembly Hirshfeld surface analysis Deformation electron density Indole-based benzamide derivative Cite this: Eur.

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“…[9] Accordingly, numerous synthetic methods leading to these structures can be found in the literature, and the frequently applied methods have been summarized in recent reviews. [10,11] 1H,2H,3H,4H,5H- [1,4]Diazepino [1,7-a]indole derivatives of general formula 1 are melanin-concentrating hormone receptor 1 (MCHr1) antagonists for the treatment of obesity through regulation of appetite. [12] Target molecules were first prepared by using the discovery chemistry route shown in Scheme 1, which provided material for in vitro and in vivo studies.…”

Section: Introductionmentioning

confidence: 99%

Environmentally Friendly Synthesis of Indoline Derivatives using Flow‐Chemistry Techniques

et al. 2017

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Flow chemistry proved to be a valuable technique to improve the synthesis route to melanin-concentrating hormone receptor 1 (MCHr1) antagonists with the 1H,2H,3H,4H,5H-[1,4]diazepino[1,7-a]indole scaffold. A one-step route for the heterogeneous catalytic hydrogenation of ethyl 4-(2-nitrophenyl)-3-oxobutanoate for the synthesis of ethyl 2-(2,3-dihydro-1H-indol-2-yl)acetate was developed, and the use of common reducing chemicals was avoided. N-Alkylation of the indoline nitrogen

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Indoles as therapeutics of interest in medicinal chemistry: Bird's eye view

Cited by 486 publications

References 163 publications

Gold‐Catalyzed Functionalization Reactions of Indole

Gold‐Catalyzed Functionalization Reactions of Indole

Molecular self-assembly in indole-based benzamide derivative: Crystal structure, Hirshfeld surfaces and antimicrobial activity

Environmentally Friendly Synthesis of Indoline Derivatives using Flow‐Chemistry Techniques

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