34611-43-3Relevant academic research and scientific papers
Synthesis and crystal structure of bis-chalcone-derived fused-ring pyrazoline having an unusual substitution pattern
Ashraf, Shumaila,Hameed, Shahid,Tahir, Muhammad Nawaz,Naseer, Muhammad Moazzam
, p. 1871 - 1875 (2017)
Abstract: Pyrazolines are an important class of heterocyclic compounds with diverse applications. A novel bis-chalcone-derived fused ring pyrazoline has been obtained by the reaction of bis-chalcone with hydrazine hydrate in acetic acid solvent having a catalytic amount of HCl and characterized by IR, 1H and 13C NMR, GC–MS, and finally by X-ray single crystal analysis. Interestingly, the in situ post-cyclization substitution pattern on pyrazoline ring nitrogen is entirely different from the previously reported related pyrazoline derivatives. The new compound crystallizes out from its ethanolic solution, which has monoclinic crystal lattice with P21/c space group, a?=?6.1001(4)??, b?=?38.602(2)??, c?=?7.7332(5)??, α?=?90°, β?=?113.039(3)°, γ?=?90°, V?=?1675.73(19)??3, Z?=?4, crystal size?=?0.38?×?0.30?×?0.18?mm3, and Rint?=?0.043. Graphical abstract: [Figure not available: see fulltext.].
PEG-400 assisted Kr?hnke synthesis of 2-(2-hydroxyphenyl)-4-arylpyridines annulated by C5-C6 cycles with substituted benzylidene group
Batalin, Sergey,Golikova, Margarita,Khrustaleva, Alexandra,Pchelintseva, Nina
, p. 659 - 668 (2020)
A simple and efficient method has been developed for the synthesis 2-(2-hydroxyphenyl)-4-arylpyridines annulated by C5-C6 cycles with substituted benzylidene group is achieved by multi-component Kr?hnke-type reaction with moderate to
Application of monocarbonyl curcumin compound in preparation of medicine for preventing and treating periodontitis
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Paragraph 0024-0026, (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.
Activated charcoal-mediated synthesis of chalcones catalyzed by NaOH in water
Tanemura, Kiyoshi,Rohand, Taoufik
, (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.
Corrosion study of copper in aqueous sulfuric acid solution in the presence of (2E,5E)-2,5-dibenzylidenecyclopentanone and (2E,5E)-bis[(4-dimethylamino)benzylidene]cyclopentanone: Experimental and theoretical study
Tha?i, Veprim,Hoti, Ramiz,Berisha, Avni,Bogdanov, Jane
, p. 1412 - 1420 (2020/12/23)
The corrosion behavior of copper in 0.1 M aqueous sulfuric acid medium has been studied using potentiodynamic polarization measurements, quantum chemical calculations, and molecular dynamic simulations in the presence and absence of (2E,5E)-2,5-dibenzylidenecyclopentanone (M1) and (2E,5E)-bis[(4-dimethylamino)benzylidene]cyclopentanone (M2). The compounds were freshly prepared in high yields via the Claisen-Schmidt reaction between the cyclopentanone and the corresponding aryl aldehyde. The results from the potentiodynamic measurements imply that M1 and M2 act as mixed inhibitors due to their adsorption on the copper surface. The more pronounced corrosion inhibition performance of the M2 molecule in comparison to M1 was related to the fact that this molecule contains two basic nitrogen atoms (in 4-dimethylamino group).
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.
Synthesis, structure, electrochemistry, and photophysics of 2,5-dibenzylidenecyclopentanones containing in benzene rings substituents different in polarity
Vatsadze,Gavrilova,Zyuz’kevich,Nuriev,Krut’ko,Moiseeva,Shumyantsev,Vedernikov,Churakov,Kuz’mina,Howard,Gromov
, p. 1761 - 1772 (2017/03/22)
A series of cross-conjugated dienones was synthesized to study the dependence of physicochemical characteristics on the nature of substituents in the aromatic groups of symmetric cyclopentanone dibenzylidene derivatives. The structure of compounds was established by electronic, IR, and NMR spectroscopy and X-ray diffraction study. All the compounds obtained possess the E,E-geometry. In the crystalline state, the arrangement of the dienone molecules is unfavorable for the intermolecular [2+2] photocycloaddition to take place. The low-temperature phases transition for unsubstituted diphenyl derivative of cyclopentanone was detected using variable-temperature X-ray diffraction and differential scanning calorimetry. Oxidation and reduction potentials of the dienones were measured by cyclic voltammetry. Their dependence on the nature and placement of substituents in the benzene rings was demonstrated. A linear correlation (R = 0.9343) between the difference of electrochemical oxidation and reduction potentials and the energy of the long-wavelength absorption maximum was found, that allows us to recommend the use of the data obtained in the correlation analysis of other compounds of this class.
Potent and Selective Inhibitors of Trypanosoma cruzi Triosephosphate Isomerase with Concomitant Inhibition of Cruzipain: Inhibition of Parasite Growth through Multitarget Activity
Aguilera, Elena,Varela, Javier,Birriel, Estefanía,Serna, Elva,Torres, Susana,Yaluff, Gloria,de Bilbao, Ninfa Vera,Aguirre-López, Beatriz,Cabrera, Nallely,Díaz Mazariegos, Selma,de Gómez-Puyou, Marieta Tuena,Gómez-Puyou, Armando,Pérez-Montfort, Ruy,Minini, Lucia,Merlino, Alicia,Cerecetto, Hugo,González, Mercedes,Alvarez, Guzmán
supporting information, p. 1328 - 1338 (2016/07/20)
Triosephosphate isomerase (TIM) is an essential Trypanosoma cruzi enzyme and one of the few validated drug targets for Chagas disease. The known inhibitors of this enzyme behave poorly or have low activity in the parasite. In this work, we used symmetrical diarylideneketones derived from structures with trypanosomicidal activity. We obtained an enzymatic inhibitor with an IC50value of 86 nm without inhibition effects on the mammalian enzyme. These molecules also affected cruzipain, another essential proteolytic enzyme of the parasite. This dual activity is important to avoid resistance problems. The compounds were studied in vitro against the epimastigote form of the parasite, and nonspecific toxicity to mammalian cells was also evaluated. As a proof of concept, three of the best derivatives were also assayed in vivo. Some of these derivatives showed higher in vitro trypanosomicidal activity than the reference drugs and were effective in protecting infected mice. In addition, these molecules could be obtained by a simple and economic green synthetic route, which is an important feature in the research and development of future drugs for neglected diseases.
Nano titania-supported sulfonic acid catalyzed synthesis of α,α'-bis(substituted-benzylidene)cycloalkanones and of their xanthene derivatives under solvent-free conditions
Amoozadeh, Ali,Tabrizian, Elham,Rahmani, Salman
, p. 848 - 857 (2015/08/06)
An efficient, rapid and green synthesis of α,α'-bis(substituted-benzylidene)cycloalkanones and their xanthene derivatives is reported under solvent-free conditions using nano titania-supported sulfonic acid (n-TSA) as a reusable catalyst. This method offers many advantages, such as environmental friendliness reaction conditions, simplicity, short reaction times, easy work-up, reusability of catalyst, and high yields of products. Eight new compounds are reported too.
Efficient method for the synthesis of, ′-bis(arylmethylidene) cycloalkanones catalyzed by bromodimethylsulfonium bromide
Zhao, Cong-Ying,Liu, Ju-Yan,Wang, Ying,Zhao, Xiao-Jun,Yuan, Bin,Yue, Min-Min
, p. 827 - 835 (2014/03/21)
Bromodimethylsulfonium bromide (BDMS)-catalyzed crossed aldol condensation between aromatic aldehydes and ketones is reported to access ′-bis(arylmethylidene) cycloalkanones at room temperature in good yields within 3-10 min. The salient features of this method are the simplicity of the procedure, the ready accessibility of the catalyst, and greater yields in relatively short reaction times. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]
