Diastereomeric N,S-Dialkyl Dithiocarbamates Derived from (E)-Chalcones and ʟ-Tryptophan: Microwave-Assisted Synthesis and In Vitro Studies Against Fusarium oxysporum DOI Creative Commons

Natalia Agudelo-Ibañez,

Sergio Alejandro Torres‐Cortés,

Ericsson Coy‐Barrera

и другие.

Organics, Год журнала: 2024, Номер 5(4), С. 598 - 613

Опубликована: Дек. 9, 2024

The synthesis of indole phytoalexin-like analogs related to alkyl (((1-(4-substitutedphenyl)-3-oxo-3-phenylpropyl)thio)carbonothioyl)-ʟ-tryptophanate 1a–d and the evaluation their antifungal activity against phytopathogen Fusarium oxysporum is reported. target compounds were synthesized in following two stages: (1) initial esterification ʟ-tryptophan, which reacted with trimethyl silane chloride simple aliphatic alcohols (R = Me, Et) under microwave irradiation (MWI) at 100 °C obtain respective ester 2a–b; (2) resulting mixture ʟ-tryptophanates 2a–b carbon disulfide (E)-chalcone 3a–b MWI 50 during 60 min, followed by purification through classical column chromatography (55–76% yields). products obtained as mixtures (S,R) (S,S) diastereoisomers. An LC-DAD-MS analysis allowed us establish ratio these diastereoisomers, subsequent DFT/B3LYP-based computational calculations NMR 1H chemical shifts suggested that major diastereoisomer involved an absolute configuration, comprising more than 60% mixture. subjected test F. using amended medium-based assay. Compound series 1 showed inhibition percentages 80% first concentration IC50 values between 0.33 5.71 mM, demonstrating greater potential agents compared other ʟ-tryptophan derivatives like (2S)-3-(1H-indol-3-yl)-2-{[(1Z)-3-oxobut-1-en-1-yl]amino}propanoate, presented lower percentages. In summary, phytoalexin derived from (E)-chalcones significantly inhibited mycelial growth oxysporum, indicating effective agents.

Язык: Английский

Synthesis, molecular docking and pharmacological evaluations of novel naphthalene-pyrazoline hybrids as new orally active anti-inflammatory agents DOI Creative Commons

D Vasudha,

A Jagadeesh,

Suraj N. Mali

и другие.

Chemical Physics Impact, Год журнала: 2024, Номер 8, С. 100500 - 100500

Опубликована: Янв. 29, 2024

The pyrazoline nucleus is widely present in diverse compounds as it serves a valuable template for the discovery of new class bioactive compounds. Various substituted 2-pyrazolines exhibit spectrum pharmacological activities, including antimicrobial, anti-inflammatory, analgesic, and antitumor properties. In view this, we have synthesized novel naphthalene-pyrazoline hybrids (PY1-PY20). All were thoroughly characterized by means standard spectroscopic techniques tested their in-vivo anti-inflammatory activity. Most exhibited significant activity particular bearing electron withdrawing groups had potential vivo Further, in-silico molecular docking studies carried out using 'Molegro Virtual Docker' tool against target proteins such COX-1 (PDB ID: 1EQH) COX-2 1PXX). results revealed that majority pyrazolines form hydrogen interactions with key residues (Ser 530, Tyr 385, 355, Arg 120, Ser 353, 83) active binding sites (1EQH) (1PXX). Notably, 530 COX-1, Gln 192, Leu 352, His 90, 38, 385 are crucial reported Ligand-protein inverse highlight specific bond interactions, PY-8, PY-11, PY-15, PY-17 showing interactions. study was able to identify derivatives.

Язык: Английский

Процитировано

3
Nickel-catalysed highly regioselective synthesis of β-acyl naphthalenes under reductive conditions DOI

Yujuan Wu,

Chen Ma,

Jia-Fan Qiao

и другие.

Chemical Communications, Год журнала: 2024, Номер 60(44), С. 5723 - 5726

Опубликована: Янв. 1, 2024

A nickel-catalysed reductive ring-opening reaction of 7-oxabenzonorbornadienes with acyl chlorides as the electrophilic coupling partner was developed, generating β-acyl naphthalene unique product without any α iso.

Язык: Английский

Процитировано

2
Naphthyl‐Based Chalcone Derivatives: A Multifaceted Player in Medicinal Chemistry DOI Creative Commons

Priyanka Mahesha,

Nitinkumar S. Shetty

ChemistrySelect, Год журнала: 2024, Номер 9(19)

Опубликована: Май 17, 2024

Abstract Research has placed a great deal of emphasis on molecule development and discovery with substantial biological profiling in recent years. Despite the significant side effects, medicinal chemists have long strived to synthesize drug molecules highest level therapeutic activity lowest possible toxicity. The naphthyl‐based chalcone derivatives drawn attention due their simple structures wide range pharmacological effects. main focus this review is outline biologically active based naphthyl moiety‐substituted developed over A synopsis screening, including relevant structure‐activity relationships, action mechanisms, applications, provided article. It true that prospective hybrids combining moiety different pharmacophores are needed address resistance improve specificity. Therefore, may be useful design new, highly successful drugs previously reported methodologies.

Язык: Английский

Процитировано

2
Novel Benzimidazole-Endowed Chalcones as α-Glucosidase and α-Amylase Inhibitors: An Insight into Structural and Computational Studies DOI Creative Commons

V. Prashasthi,

Ramith Ramu,

P. Akhileshwari

и другие.

Molecules, Год журнала: 2024, Номер 29(23), С. 5599 - 5599

Опубликована: Ноя. 27, 2024

In search of novel antidiabetic agents, we synthesized a new series chalcones with benzimidazole scaffolds by an efficient ‘one-pot’ nitro reductive cyclization method and evaluated their α-glucosidase α-amylase inhibition studies. The offered simple route for the preparation benzimidazoles excellent yield higher purity compared to other conventional acid- or base-catalyzed methods. 1H, 13C NMR, IR, mass spectrum data were used characterize compounds. Single-crystal XRD confirmed 3D structure compound 7c, which was crystalized in P1¯ space group triclinic crystal system. Hirshfeld surface analysis validates presence O-H..O, O-H…N, C-H…O intermolecular hydrogen bonds. From DFT calculations, energy gap between frontier molecular orbitals 7c found be 3.791 eV. series, 7l emerged as potent agent IC50 = 22.45 ± 0.36 µg/mL 20.47 0.60 against enzymes, respectively. silico docking studies revealed that has strong binding interactions proteins. Molecular dynamics also stability

Язык: Английский

Процитировано

1
Exploration of alpha-glucosidase inhibitors: A comprehensive in silico approach targeting a large set of triazole derivatives DOI Creative Commons
Oussama Abchır,

Meriem Khedraoui,

Imane Yamari

и другие.

PLoS ONE, Год журнала: 2024, Номер 19(9), С. e0308308 - e0308308

Опубликована: Сен. 6, 2024

Background The increasing prevalence of diabetes and the side effects associated with current medications necessitate development novel candidate drugs targeting alpha-glucosidase as a potential treatment option. Methods This study employed computer-aided drug design techniques to identify inhibitors from PubChem database. Molecular docking was used evaluate 81,197 compounds, narrowing set for further analysis providing insights into ligand-target interactions. An ADMET assessed pharmacokinetic properties these including absorption, distribution, metabolism, excretion, toxicity. dynamics simulations validated results. Results 9 compounds were identified based on their ability form stable complexes favorable profiles, three subjected molecular dynamics, which showed stability throughout entire 100 ns simulation. Conclusion These findings suggest promising new treatment. Further validation through in vitro vivo studies is recommended confirm efficacy safety.

Язык: Английский

Процитировано

0
Microwave-assisted synthesis, antiproliferative, antibacterial activities, in silico, computational studies and molecular dynamics simulation of new bis-(aryl-based chalcone) derivatives DOI
Muntadher Al-Kaabi,

Hanan A. Al-Hazam,

Lamiaa Al-Maliki

и другие.

Journal of Molecular Structure, Год журнала: 2024, Номер unknown, С. 139992 - 139992

Опубликована: Сен. 1, 2024

Язык: Английский

Процитировано

0
Diastereomeric N,S-Dialkyl Dithiocarbamates Derived from (E)-Chalcones and ʟ-Tryptophan: Microwave-Assisted Synthesis and In Vitro Studies Against Fusarium oxysporum DOI Creative Commons

Natalia Agudelo-Ibañez,

Sergio Alejandro Torres‐Cortés,

Ericsson Coy‐Barrera

и другие.

Organics, Год журнала: 2024, Номер 5(4), С. 598 - 613

Опубликована: Дек. 9, 2024

The synthesis of indole phytoalexin-like analogs related to alkyl (((1-(4-substitutedphenyl)-3-oxo-3-phenylpropyl)thio)carbonothioyl)-ʟ-tryptophanate 1a–d and the evaluation their antifungal activity against phytopathogen Fusarium oxysporum is reported. target compounds were synthesized in following two stages: (1) initial esterification ʟ-tryptophan, which reacted with trimethyl silane chloride simple aliphatic alcohols (R = Me, Et) under microwave irradiation (MWI) at 100 °C obtain respective ester 2a–b; (2) resulting mixture ʟ-tryptophanates 2a–b carbon disulfide (E)-chalcone 3a–b MWI 50 during 60 min, followed by purification through classical column chromatography (55–76% yields). products obtained as mixtures (S,R) (S,S) diastereoisomers. An LC-DAD-MS analysis allowed us establish ratio these diastereoisomers, subsequent DFT/B3LYP-based computational calculations NMR 1H chemical shifts suggested that major diastereoisomer involved an absolute configuration, comprising more than 60% mixture. subjected test F. using amended medium-based assay. Compound series 1 showed inhibition percentages 80% first concentration IC50 values between 0.33 5.71 mM, demonstrating greater potential agents compared other ʟ-tryptophan derivatives like (2S)-3-(1H-indol-3-yl)-2-{[(1Z)-3-oxobut-1-en-1-yl]amino}propanoate, presented lower percentages. In summary, phytoalexin derived from (E)-chalcones significantly inhibited mycelial growth oxysporum, indicating effective agents.

Язык: Английский

Процитировано

0