395-12-0Relevant articles and documents
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.
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.
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.
