449-81-0Relevant articles and documents
Zeolite (Y-H)-based green synthesis, antimicrobial activity, and molecular docking studies of imidazole bearing oxydibenzene hybrid molecules
Ahmad, Iqrar,Desai, Nisheeth C.,Jethawa, Aratiba M.,Maheta, Abhay S.,Pandit, Unnat P.,Patel, Harun
supporting information, (2021/12/23)
In this green synthesis, zeolite (Y-H) appears to be an intriguing choice for obtaining a high yield with a shorter reaction time. In addition, we have synthesized N-aryl-(4-benzylidene-5-oxo-2-phenyl-4,5-dihydro-1H-imidazol-1-yl)-3-phenoxybenzamides (4a-i), which will be proved to be potent antimicrobial agents. The title compounds were tested against Gram-positive, Gram-negative, and fungal strains using the Mueller–Hinton Broth technique. N-(4-benzylidene-5-oxo-2-phenyl-4,5-dihydro-1H-imidazol-1-yl)-3-phenoxybenzamide (4a) (minimum inhibitory concentration [MIC]?=?25 μg/mL, S. pyogenes) and N-(4-[4-fluorobenzylidene]-5-oxo-2-phenyl-4,5-dihydro-1H-imidazol-1-yl)-3-phenoxybenzamide (4f) (MIC?=?100 μg/mL, C. albicans, A. niger, A. clavatus) were the most effective against Gram-positive and Gram-negative bacteria as well as fungal strains. To understand the mechanism of action of synthesized compounds, molecular docking experiments were performed against S. aureus tyrosyl-tRNA synthetase and C. albicans sterol 14-α demethylase.
Novel Approach to the Synthesis of 3-amino-4-arylpyridin-2(1H)-one Derivatives
Chernenko, Sergei А.,Dmitriev, Maksim V.,Fisyuk, Alexander S.,Samsonenko, Anna L.,Shatsauskas, Anton L.,Shuvalov, Vladislav Yu.
, p. 764 - 771 (2021/10/04)
[Figure not available: see fulltext.] The reaction of 4-arylidene-2-phenyloxazol-5(4H)-ones with enamines of ethyl acetoacetate gave 4-aryl-2-methyl-6-oxo-5-[(phenylcarbonyl)amino]-1,4,5,6-tetrahydropyridine-3-carboxylic acid esters, which, when heated with phosphorus oxychloride, were converted into esters of 7-aryl-5-methyl-2-phenyloxazolo[5,4-b]pyridine-6-carboxylic acids. Alkaline hydrolysis of these compounds gave 4-aryl-2-methyl-6-oxo-5-[(phenylcarbonyl)amino]-1,6-dihydropyridine-3-carboxylic acid esters.
Base Induced Condensation of Malononitrile with Erlenmeyer Azlactones: An Unexpected Synthesis of Multi-Substituted Δ2-Pyrrolines and Their Cytotoxicity
Anil, Seegehalli M.,Kiran, Kuppalli R.,Rajeev, Narasimhamurthy,Sadashiva, Maralinganadoddi P.,Shobith, Rangappa,Sudhanva, Muddenahalli S.,Swaroop, Toreshettahally R.,Vinayaka, Ajjampura C.
, (2020/04/29)
An efficient, metal free approach to synthesize multi-substituted Δ2-pyrroline derivatives by mild base catalyzed cyclocondensation of malononitrile with Erlenmeyer azlactones via 1,2 addition was developed. The modularity of this reaction was used to assemble a range of poly-substituted pyrrolines. Further, synthesized products were screened for cytotoxic properties on different cancer cell lines such as A549 (Human lung adenocarcinoma cells), HeLa (Human cervical adenocarcinoma cells), Jurkat (Human chronic myeloid leukemia cells) and K562 (Human leukemic T cell Lymphoblast cells). Among the synthesized library of compounds, 6f and 6q displayed potent cytotoxic activity.
Synthesis, biological evaluation and in silico studies with 4-benzylidene-2-phenyl-5(4H)-imidazolone-based benzenesulfonamides as novel selective carbonic anhydrase IX inhibitors endowed with anticancer activity
Eldehna, Wagdy M.,Abdelrahman, Mohamed A.,Nocentini, Alessio,Bua, Silvia,Al-Rashood, Sara T.,Hassan, Ghada S.,Bonardi, Alessandro,Almehizia, Abdulrahman A.,Alkahtani, Hamad M.,Alharbi, Amal,Gratteri, Paola,Supuran, Claudiu T.
, (2019/07/12)
In the presented work, we report the synthesis of a series of 4-benzylidene-2-phenyl-5(4H)-imidazolone-based benzenesulfonamides 7a-f via the Erlenmeyer–Pl?chl reaction. All the prepared imidazolones 7a-f were evaluated as inhibitors of human (h) carbonic anhydrases (CA, EC 4.2.1.1) cytosolic isoforms hCA I and II, as well as transmembrane tumor-associated isoforms hCA IX and XII. All the tested hCA isoforms were inhibited by the prepared imidazolones 7a-f in variable degrees with the following KIs ranges: 673.2–8169 nM for hCA I, 61.2–592.1 nM for hCA II, 23–155.4 nM for hCA XI, and 21.8–179.6 nM for hCA XII. In particular, imidazolones 7a, 7e, and 7f exhibited good selectivity towards the tumor-associated isoforms (CAs IX and XII) over the off-target cytosolic (CAs I and II) with selectivity index (SI) in the range of 6.2–19.4 and 3.3–8, respectively. Moreover, imidazolones 7a-f were screened for their anticancer activity in one dose (10?5 M) assay against a panel of 60 cancer cell lines according to US-NCI protocol. Furthermore, 7a, 7e and 7f were evaluated for their anti-proliferative activity against colorectal cancer HCT-116 and breast cancer MCF-7 cell lines. Furthermore, 7e and 7f were screened for cell cycle disturbance and apoptosis induction in HCT-116 cells. Finally, a molecular docking study was carried out to rationalize the obtained results.
Benzothiazol clubbed imidazol-4-ones as anti-fungal, anti-tubercular and anti-HIV-1 agents: Their synthesis and molecular docking study
Patel, Navin B.,Shaikh, Asif R.,Patel, Vatsal M.,Lara-Ramirez, Edgar E.,Rivera, Gildardo
, p. 382 - 391 (2019/06/18)
Background: The present work describes antimicrobial, antimycobacterium and anti HIV-1 evaluation of newly synthesized 5-(4-Substituted-benzylidene)-3-[4-(5-methyl-benzothiazol2-yl)-phenyl]-2-phenyl-3,5-dihydro-imidazol-4-one (4a-o). The docking studies were performed in order to predict the potential binding affinities. Objective: The major aim of this study is to develop the new class of bezylidine candidate clubbed with benzothiazole with less toxicity and improved potency as antimicrobial, antitubercular and anti HIV-1. Methods: The titled compounds were characterized by spectral studies (IR, 1H NMR, 13C NMR and Mass). In vitro antimycobacterium activity was carried out using Lowenstein-Jensen medium method and antimicrobial activity using the broth microdilution method. The anti HIV-1 reverse transcriptase activity was determined by the colorimetric MTT method and inhibition of virusinduced cytopathogenicity in MT-4 cells. Results: Compound 4i (50 μM) showed better antifungal activity against A. clavatus. Compound 4g (50 μM) with 95% inhibition demonstrated good activity against M. tuberculosis H37Rv. Compound 4k showed CC50 (50 μM) against MT-4 (CD4+ Human T-cells containing an integrated HTLV-1 genome) cells by 50%, while 16 μM concentration value EC50 from the HIV-1 induced cytopathogenicity. Molecular docking study suggested that 4k interacted with the target with binding energy by Vina score (-10.3 Kcal/mol) Conclusion: The preliminary in vitro evaluation results revealed that some of the compounds have promising antimicrobial activities as well as antitubercular potency. Among the various substituents on benzylidene, the nitro group was the most beneficial for improving the anti-HIV-1 activity. Docking result suggested that 4k compound could be acting as a non-competitive or weak inhibitor of Reverse Transcriptase (RT).
An ionic liquid gel: A heterogeneous catalyst for Erlenmeyer-Plochl and Henry reactions
Jagadale, Megha,Naikwade, Altafhusen,Salunkhe, Rajashri,Rajmane, Mohan,Rashinkar, Gajanan
, p. 10993 - 11005 (2018/07/06)
An ionic liquid gel has been prepared by entrapping 1-butyl-3-methylimidazolium hydroxide ([Bmim]OH) in an aqueous agar gel. The ionic liquid gel has been characterized by Fourier transform infrared (FT-IR), Fourier transform Raman (FT-Raman) spectroscopy, scanning electron microscopy (SEM), thermogravimetric analysis (TGA) and energy dispersive X-ray analysis (EDX). The ionic liquid gel has been successfully employed as a heterogeneous catalyst in the Erlenmeyer-Plochl reaction involving aldehydes, hippuric acid and acetic anhydride as well as in the Henry reaction between aldehydes and nitromethane in ethanol at room temperature. The heterogeneity of the ionic liquid gel has been confirmed by conducting hot filtration tests and leaching studies. Additionally, the ionic liquid gel could be easily recovered by simple filtration and reused five times without significant loss in catalytic activity.
Stereoselective Intermolecular [2 + 2] Cycloadditions of Erlenmeyer-Pl?chl Azlactones Using Visible Light Photoredox Catalysis
Marra, Isabellar F. S.,De Almeida, Angelina M.,Silva, Larissa P.,De Castro, Pedro P.,Corrêa, Charlane C.,Amarante, Giovanni Wilson
, p. 15144 - 15154 (2018/12/14)
The first report of the preparation of symmetric and nonsymmetric diaminotruxinic derivatives through the photoredox [2 + 2] cycloadditions of Erlenmeyer azlactones is described, affording the desired compounds in high regio- and diastereocontrol (only head-to-head coupling). Mechanistic studies by DFT suggest that the reaction proceeds through a neutral photocatalytic pathway.
Synthesis and cytotoxicity of novel dispiro derivatives of 5-arylidenoxazolones, potential inhibitors of p53—MDM2 protein-protein interaction
Beloglazkina,Skvortsov,Tafeenko,Majouga,Zyk,Beloglazkina
, p. 562 - 569 (2018/07/06)
Regioselective synthesis of new dispiro indolinones combining both an indolinone and an oxazolone fragment in their structure comprised the 1,3-dipolar cycloaddition of azomethine ylides, generated in situ from isatin and sarcosine, at 2-aryl-5-arylmethylidene-substituted 1,3-oxazol-5(4H)-ones. When ortho and para halogen atoms were present in the aromatic substituents of the starting oxazolones, complex mixtures containing large amounts of oxazoline ring opening products and their dispiro derivatives were formed. The cytotoxicity of compounds was tested by MTT on LNCaP, PC3, HCT116, MCF7, A549, HEK, and VA13 cell lines. The compound possessing the best cytotoxicity revealed the IC50 = 1.08±0.96 μM towards the p53- expressing LNCaP cells and lower activity (IC50 = 3.21±1.45 μM) towards the non-expressing p53 protein PC3 cells, however, it has proved inactive towards the HCT cells, both expressing (HCТ+/+) and non-expressing (HCT–/–) p53.
Triphenylphosphine (PPh3) Catalyzed Erlenmeyer Reaction for Azlactones under Solvent-free Conditions
Punna Rao, Alapati Mohan Lakshmi,Sridhar Rao, Abburi,Saratchandra Babu, Mukkamala,Krishnaji Rao
supporting information, p. 429 - 435 (2017/02/03)
This study presents triphenylphosphine catalyzed process for the synthesis of azlactones and their derivatives using hippuric and substituted aromatic aldehydes. The methodology also found to be effective for the synthesis of azlactones from 5-(2,6-dichlorophenyl)-3-methyl-1,2-oxazol-4-yl carbonyl amino acetic acid and offers several advantages such as solvent-free conditions, excellent yields, simple procedure, mild conditions, and reduced environmental consequences.
Alpha-amino acrylate microbicide and preparation method and application thereof
-
Paragraph 0079, (2017/10/13)
The invention provides an alpha-amino acrylate microbicide and a preparation method and application thereof. The alpha-amino acrylate microbicide has a specific chemical structure formula shown as a formula I, and the formula I is shown in the description. The alpha-amino acrylate microbicide has the advantages that by utilizing the design principle of pesticide molecules, a medical leading compound with anti-coronavirus activity is performed with structure modification of agricultural plant virus-resisting activity, a series of alpha-amino acrylate derivatives is designed and synthesized, and particularly, the alpha-amino acrylate derivative containing piperidine ring is synthesized; the known compound is used as a positive reference compound to systematically screen the biology activity; a plurality of high-efficiency anti-virus leading molecules are provided for the developing of new pesticides, and the positive meaning is realized for the reduction application of the pesticide and the protection of environment ecology.
