42052-61-9Relevant academic research and scientific papers
Syntheses and X-ray crystal structures combined with conformational and Hirshfeld analyses of chalcones based on a cyclohexanone scaffold
Lotfy,Said, Mohamed M.,El Ashry, El Sayed H.,El Tamany, El Sayed H.,Abdel Aziz, Yasmine M.,Soliman, Saied M.,Al-Majid, Abdullah Mohammed,Ghabbour, Hazem A.,Barakat
, (2019)
Four chalcone structures based on cyclohexanone cores were presented. The structures of bis-benzylidenecyclohexanone analogs 3a-d were elucidated using spectrophotometric and single-crystal X-ray techniques. Compounds 3a, 3b, and 3d crystalized in the monoclinic crystal system with the space group P21/c. However, 3c crystalized in the orthorhombic system with the space group Pna21. A set of computational studies related to the structures were carried out. Using the B3LYP method and the 6-31G(d,p) basis set, the molecular structures of the studied dienones were optimized, followed by the evaluation of their electronic properties and UV–vis spectra. The bond distances and angles well-correlated with the experimental data. All the dienones were stabilized by C–H?O intramolecular H-bonding interactions. The presence of two Cl atoms at the ortho-position of each phenyl ring in 3c caused steric hinderance with the cyclohexanone ring, leading to the weakest H?O interactions among the studied compounds. The TD-DFT method was used to assign and explain the origin of the electronic spectra of the studied dienones.
Synthesis of 3,7-disubstituted hexahydro- and tetrahydro-2H-indazoles from cross-conjugated dienones
Nuriev,Vatsadze,Sviridenkova,Vatsadze
, p. 389 - 396 (2016)
The oxidation of 3,7-disubstituted hexahydroindazoles with potassium hexacyanoferrate(III) afforded previously unknown tetrahydro-2H-indazole derivatives. A novel ring contraction reaction leading to 2,3-diazaspiro[4.4]non-3-en-1-one derivatives was discovered. The product structure was proved by NMR spectroscopy, mass spectrometry, and X-ray analysis.
Synthesis, characterization, molecular docking evaluation, antidepressant, and anti-Alzheimer effects of dibenzylidene ketone derivatives
Bashir, Muhammad Adnan,Khan, Arif-ullah,Badshah, Haroon,Rodrigues-Filho, Edson,Din, Zia Ud,Khan, Aslam
, p. 595 - 605 (2019)
Novel bioactive compounds as synthetic analogs of the potent herbal medicines can be optimized as potential drug candidates for various neurologic disorders. This study was performed to investigate the newly synthesized dibenzylidene ketone derivatives: (2E,6E)-2,6-dibenzylidene cyclohexanone (A1K1) and (1E,4E)-5-(2,3-dichlorophenyl)-1-(4-methoxyphenyl)-2-methylpenta-1,4-diene-3-one (A2K2) and evaluate its potential anti-Alzheimer's and anti-depressant properties. Both the derivatives are chemically characterized by using HNMR and CNMR techniques. Auto Dock Vina program was used to investigate ligand-protein affinity. Forced swim test, tail suspension test, open field test, Y-maze test, and Morris water maze test (MWM) models were employed to evaluate anti-depressant and anti-Alzheimer's activity of dibenzylidene ketone derivatives in mice. Both A1K1 and A2K2 showed high binding affinities against various proteins involved in depression and Alzheimer's mechanisms like monoamine oxidase B, acetylcholinesterase, norepinephrine transporter 2, serotonin transporter, dopamine receptor, serotonin receptor modulator, and beta-amyloid targets. A1K1 and A2K2 dose-dependently (0.1–1 mg/kg) decreased immobility time, while increased swimming and climbing time of mice in forced swim test (FST). A1K1 and A2K2 decreased animal immobility time in TST. In the open field test, both A1K1 and A2K2 increased the number of ambulations and rearings. A1K1 and A2K2 dose-dependently (0.5–1.0 mg/kg) increased spontaneous alternation behavior (%) and the number of entries of mice in Y-maze test. In the MWM test, A1K1 and A2K2 decreased escape latency time. Overall, both in-silico and in-vivo investigations of A1K1 and A2K2, report their therapeutic potential for antidepressant and anti-Alzheimer properties. Hence, these compounds possess potent neuroprotective properties and may be further evaluated for their therapeutic potential in various neurological disorders.
Synthesis of thiazolylidenethiazoloquinazolinone hybrids from monocarbonyl curcumin analogues. Characterization, bio-evaluation and DFT study
Benreka, Soufiane,Zradni, Fatima-Zohra,Madi, Fatiha,Kirsch, Gilbert,Kasmi-Mir, Souad
, p. 53 - 77 (2021/09/03)
Given the diverse pharmacological attributes possessed by the curcumin and its analogs, quinazolinethione 3, thiazoloquinazolinone 4, and thiazolylidene thiazoloquinazolinone hybrids D1-D12 were synthesized from α, α’ Bis(arylidene)Cyclohexanone (BAC) as starting material. The proposed structures of all synthesized compounds were confirmed by 1H, 13CNMR, and elemental analysis. The newly synthesized hybrids were screened in vitro for their antimicrobial and antioxidant activities. Preliminary studies showed that compounds D4, D5, D10, D11, and D12 exhibited superior inhibitory behaviors against some microorganisms in comparison with standard drugs. In addition, DPPH radical scavenging assay was used to evaluate their antioxidant property. Accordingly, compound D11 was found to be a more powerful antioxidant than the other compounds. Furthermore, the HOMO–LUMO energy values and some chemical parameters indicate that the synthesized hybrid D11 is more reactive than D7. These results were consistent with our experimental data on antioxidants. Moreover, molecular electrostatic potential (MEP) maps were computed in order to predict the reactive sites for nucleophilic and electrophilic attacks of the synthesized hybrids D7 and D11.
Activated charcoal-mediated synthesis of chalcones catalyzed by NaOH in water
Tanemura, Kiyoshi,Rohand, Taoufik
supporting information, (2021/02/27)
A variety of chalcones were synthesized in good yields by the activated charcoal-mediated aldol reactions between benzaldehydes and acetophenones catalyzed by NaOH in water. 2,6-Bis((E)-benzylidene)cyclohexan-1-ones were prepared by the aldol reactions between benzaldehydes and cyclohexanone. Activated charcoal could be recycled five times without the significant decrease of yields.
Application of monocarbonyl curcumin compound in preparation of medicine for preventing and treating periodontitis
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Paragraph 0024-0027, (2021/06/22)
The invention belongs to the technical field of medicines, and particularly relates to application of a specific monocarbonyl curcumin analogue in preparation of a medicine for preventing and treating periodontitis. Experiments prove that the monocarbonyl curcumin analogues not only can play a better anti-oxidation protection role by activating an Nrf2/HO-1 signal channel, but also can play an anti-inflammatory role by inhibiting release of inflammatory factors TNF alpha and IL1-beta, so that the monocarbonyl curcumin analogues have a remarkable prevention and treatment effect on rat periodontitis, have good potential value and significance for prevention and treatment of periodontitis, and have a good research and development prospect.
Antiparasitic activity of synthetic curcumin monocarbonyl analogues against Trichomonas vaginalis
Carapina da Silva, Caroline,Pacheco, Bruna Silveira,das Neves, Raquel Nascimento,Dié Alves, Mirna Samara,Sena-Lopes, ?ngela,Moura, Sidnei,Borsuk, Sibele,de Pereira, Claudio Martin Pereira
, p. 367 - 377 (2019/01/03)
Trichomoniasis is a parasitic infection caused by Trichomonas vaginalis and it is considered to be the most common non-viral sexually transmitted infection in the world. Since the 1960s, nitroimidazoles such as metronidazole are the drugs of choice for the treatment of trichomoniasis, but many adverse effects and allergic reactions may result from their use. Reports of metronidazole-resistant infections also highlight the importance for the search of new anti-T. vaginalis agents. Considering this, herein we report the anti-T. vaginalis evaluation of 21 synthetic monocarbonyl analogues of curcumin, which itself has been reported to possess antiparasitic potential. From the in vitro analysis of the synthetic molecules, untreated trophozoites, and metronidazole at 100 μM, it was observed that three curcumin analogues (3a, 3e, and 5e) exhibited anti-T. vaginalis activity comparable to metronidazole (no significant statistical difference). Optimal antiparasitic concentrations were determined to be 80 μM and 90 μM for propanone derivatives 3a and 3e, respectively, and 200 μM for cyclohexanone derivative 5e. Kinetic growth curves showed that, after 24 h, the trophozoites were completely inhibited. At the tested concentrations, natural curcumin did not significantly inhibit the growth of trophozoites, therefore demonstrating that the designed synthetic molecules not only have better chemical stability, but also higher anti-T. vaginalis potential. Cytotoxicity analysis, performed on VERO cells, demonstrated low, moderate and high cytotoxic effects for analogues 3e, 5e and 3a, respectively. This study suggests that these analogues possess chemical features of interest to be further explored as alternatives for the treatment of trichomoniasis.
Ag/P-Stereogenic Phosphine-Catalyzed Enantioselective 1,3-Dipolar Cycloadditions: A Method to Optically Active Pyrrolidines
Zhi, Mengna,Gan, Zhenjie,Ma, Rong,Cui, Hao,Li, Er-Qing,Duan, Zheng,Mathey, Fran?ois
supporting information, (2019/05/07)
A Ag/P-stereogenic phosphine-complex-catalyzed 1,3-dipolar cycloaddition of azomethine ylides with electron-deficient olefins is reported. In this reaction, highly functionalized pyrrolines with a spiro-quaternary stereogenic center were obtained in good yields (up to 99%) with excellent levels of diastereo-(up to >20:1 dr) and enantioselectivities (up to >99% ee). The chirality of adducts was controlled predominantly by the P-stereogenic phosphines.
Bovine serum albumin-catalysed cross aldol condensation: Influence of ketone structure
Ardanaz, Sebastián M.,Borucki, Estefanía L.,Velez Rueda, Ana J.,Parisi, Gustavo,Iribarren, Adolfo M.,Iglesias, Luis E.
, p. 50 - 57 (2019/08/26)
Bovine serum albumin (BSA) catalyses the cross aldol condensation and proved to be catalytically active at mild temperature and in ethanol, a cheap and green solvent, contrasting with the strong or expensive reaction media usually employed for this reaction. We herein report the reaction of a set of ketones (butanone, 3-pentanone, cyclopentanone and cyclohexanone) with benzaldehyde and p-nitrobenzaldehyde which provided high conversions (77–95%) of the corresponding enones (isolated in a range of yields from 19% to 74%). Parameters assayed to achieve these conversion values were solvent, ketone/aldehyde molar ratio and temperature. In this procedure only cyclohexanone gave the bis-enone, by-product of the conventional aldol condensation, in low amount even at high benzaldehyde/cyclohexanone molar excess. Under the assayed conditions null or low ketol amounts were observed, except for the reaction of cyclopentanone and p-nitrobenzaldehyde. Moreover, kinetic data of BSA-catalysed aldol condensation of cyclohexanone and p-nitrobenzaldehyde suggest an ordered bi bi mechanism for enone formation; an enamine mechanism involving residues of the catalytic cavity exhibiting abnormal pKa values is also proposed.
Symmetrical and unsymmetrical substituted 2,5-diarylidene cyclohexanones as anti-parasitic compounds
Din, Zia Ud,Trapp, Marilia Almeida,Soman de Medeiros, Lívia,Lazarin-Bidóia, Danielle,Garcia, Francielle Pelegrin,Peron, Francieli,Nakamura, Celso Vataru,Rodríguez, Ihosvany Camps,Wadood, Abdul,Rodrigues-Filho, Edson
, p. 596 - 608 (2018/06/20)
Symmetrical and unsymmetrical bis-aryl-α,β-unsaturated ketones were synthesized in moderate to excellent yield by treating cyclohexanone with various aldehydes. Dimethylammonium dimethylcarbamate (DIMCARB) was used as both catalyst and reaction medium for the synthesis of monoarylidenes cycloadduct intermediates, which was further used to produce diarylidene cyclohexanones. All the 34 compounds synthesized were evaluated for their anti-proliferative activity, particularly against promastigote of Leishmania amazonensis, epimastigoteand trypomastigoteof Trypanosoma cruzi. Eighteen compounds displayed anti-leishmanial activity against promastigotes of L. amazonensis with IC50 values ranging from 2.8 to 10 μM. In addition, two compounds exhibited significant antitrypanosomal activity against epimastigotes of T. cruzi with IC50 values of 5.2 ± 0.8 and 3.0 ± 0.0 μM, while five compounds exhibited activity from 15.0 ± 1.4 to 30.2 ± 1.8 μM against trypomastigote of T. cruzi. Moreover, all compounds were more selective against the parasites than the epithelial cells. The unsymmetrical compounds 16, 28, 30 and 33 can be considered as favorable anti-parasitic lead molecule having IC50 and EC50 values in the low-micromolar range, better than the reference drug benznidazole, and low cytotoxicity against Vero cells. The potent compounds were screened in silico against 17 enzymes of T. cruzi and best scoring were found against Dihydroorotate Dehydrogenase.
