Synthesis of new α-Aryl-α-tetralones and α-Fluoro-α-aryl-α-tetralones, preliminary antiproliferative evaluation on drug resistant cell lines and in silico prediction of ADMETox properties

Souza, de; Salustiano, Eduardo J.; Costa, Kelli Monteiro da; Costa, Angela T.; Rumjanek, Vivian M.; Domingos, Jorge L. O.; Rennó, Magdalena N.; Costa, Paulo R. R.

doi:10.1016/j.bioorg.2021.104790

Cited by 7 publications

(2 citation statements)

References 41 publications

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“…The LRF considers that oral drug candidates need to have the cLogP ≤ 5, MW ≤ 500, HBD ≤ 5, HBA ≤ 10, and PSA ≤ 120 Å 2 . [53] The results presented in Table 2 (≤120). Hence, these 10 chalcones should theoretically exhibit good passive oral absorption.…”

Section: In Silico Prediction Of Drug-likeness Physicochemical Proper...mentioning

confidence: 99%

Synthesis and evaluation of hybrid sulfonamide‐chalcones with potential antileishmanial activity

de Oliveira,

de Souza,

de Almeida

et al. 2023

Archiv der Pharmazie

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Leishmaniasis is an emerging tropical infectious disease caused by a protozoan parasite of the genus Leishmania. In this work, the molecular hybridization between a trimethoxy chalcone and a sulfonamide group was used to generate a series of sulfonamide‐chalcones. A series of eight sulfonamide‐chalcone hybrids were made with good yields (up to 95%). These sulfonamide‐chalcones were tested against promastigotes of Leishmania amazonensis and cytotoxicity against mouse macrophages, which showed good antileishmanial activity with IC50 = 1.72–3.19 µM. Three of them (10c, 10g, and 10h) were also highly active against intracellular amastigotes and had a good selectivity index (SI > 9). Thus, those three compounds were docked in the cytosolic tryparedoxin peroxidase (cTXNPx) enzyme of the parasite, and molecular dynamics simulations were carried out. This enzyme was selected as a target protein for the sulfonamide‐chalcones due to the fact of the anterior report, which identified a strong and stable interaction between the chalcone NAT22 (6) and the cTXNPx. In addition, a prediction of the drug‐likeness, and the pharmacokinetic profile of all compounds were made, demonstrating a good profile of those chalcones.

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Section: In Silico Prediction Of Drug-likeness Physicochemical Proper...mentioning

confidence: 99%

Synthesis and evaluation of hybrid sulfonamide‐chalcones with potential antileishmanial activity

de Oliveira,

de Souza,

de Almeida

et al. 2023

Archiv der Pharmazie

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“…Tetralone is a key fragment found in a variety of natural products possessing a broad spectrum of biological activities. − Among noteworthy examples is hopeanol 1 , originally isolated from the bark of Hopea exalata , which exhibits cytotoxic and acetylcholinesterase inhibition activity . Enantioselective synthesis of hopeanol and other resveratrol-derived natural and unnatural analogs was reported by Nicolaou et al Alkaloid galdosol 2 , an active inhibitor of squalene synthase in rat liver, was recently isolated from Salvia canariensis plants .…”

Section: Introductionmentioning

confidence: 99%

A Diastereoselective Assembly of Tetralone Derivatives via a Tandem Michael Reaction and ipso-Substitution of the Nitro Group

Аксенов

Ganusenko

et al. 2023

J. Org. Chem.

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Enantioselective Synthesis of Isoflavanones and Pterocarpans through a Ru^II‐Catalyzed ATH‐DKR of Isoflavones

et al. 2021

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Noyori‐Ikariya RuII complexes promoted the one‐pot C=C/C=O bonds reduction of isoflavones using sodium formate as the hydrogen source through Asymmetric Transfer Hydrogenation‐Dynamic Kinetic Resolution (ATH‐DKR). Due to the neutral conditions employed, isoflavones with different substituents at the 2’‐position of B‐ring (H, OH, OMe and Br) were successfully reduced. Ten cis‐3‐phenylchroman‐4‐ols were selectively obtained (>20 : 1 dr) in good yields (up to 86 %) and excellent enantioselectivities (up to >99 : 1 er). The synthetic applications of these chiral compounds were also demonstrated. Enantioenriched isoflavanones were obtained under mild metal‐free oxidation of the cis‐3‐phenylchroman‐4‐ols while pterocarpans were synthesized by two strategies: an acid‐catalyzed cyclization and a novel approach based on a Pd‐catalyzed C−O intramolecular cross‐coupling reaction.

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Synthesis of new α-Aryl-α-tetralones and α-Fluoro-α-aryl-α-tetralones, preliminary antiproliferative evaluation on drug resistant cell lines and in silico prediction of ADMETox properties

Cited by 7 publications

References 41 publications

Synthesis and evaluation of hybrid sulfonamide‐chalcones with potential antileishmanial activity

Synthesis and evaluation of hybrid sulfonamide‐chalcones with potential antileishmanial activity

A Diastereoselective Assembly of Tetralone Derivatives via a Tandem Michael Reaction and ipso-Substitution of the Nitro Group

Enantioselective Synthesis of Isoflavanones and Pterocarpans through a Ru^II‐Catalyzed ATH‐DKR of Isoflavones

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Synthesis of new α-Aryl-α-tetralones and α-Fluoro-α-aryl-α-tetralones, preliminary antiproliferative evaluation on drug resistant cell lines and in silico prediction of ADMETox properties

Cited by 7 publications

References 41 publications

Synthesis and evaluation of hybrid sulfonamide‐chalcones with potential antileishmanial activity

Synthesis and evaluation of hybrid sulfonamide‐chalcones with potential antileishmanial activity

A Diastereoselective Assembly of Tetralone Derivatives via a Tandem Michael Reaction and ipso-Substitution of the Nitro Group

Enantioselective Synthesis of Isoflavanones and Pterocarpans through a RuII‐Catalyzed ATH‐DKR of Isoflavones

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Product

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Enantioselective Synthesis of Isoflavanones and Pterocarpans through a Ru^II‐Catalyzed ATH‐DKR of Isoflavones