622-21-9Relevant academic research and scientific papers
Pyrrolidine catalyzed novel domino reaction for the synthesis of polysubstituted 4-oxocyclohexanecarbaldehyde derivatives
Bao, Feng-Zu,Wang, Xiao-Bing,Kong, Ling-Yi
, p. 1405 - 1408 (2013)
A novel domino reaction catalyzed by an organic molecule based on α,β-unsaturated aromatic aldehydes and methylethylketones has been developed. The progress allows one-pot and efficient synthesis of polysubstituted 4-oxocyclohexanecarbaldehyde derivatives via pyrrolidine mediated under mild conditions. The reaction consists of three consecutive reactions: an aldol condensation reaction and a tandem inter-Michael-intra- Michael addition reaction. Copyright
Synthesis and conformational studies of newly synthesized cis-2r,6c-distyryltetrahydro thiopyran-4-one and its oxime: Comparison of experimental and theoretical NMR spectral data
Vimalraj,Vijayalakshmi,Umayaparvathi
, p. 8 - 13 (2013)
The cis-2r,6c-distyryltetrahydro thiopyran-4-one (4) was synthesized by the reaction of dicinnamylacetone with hydrogen sulphide. cis-2r,6c- distyryltetrahydro thiopyran-4-one oxime (5) was synthesized via oximination of 4. The synthesized compounds were
Palladium-Catalyzed Aminomethylation of Nitrodienes and Dienones via Double C—N Bond Activation
Yu, Bangkui,Gao, Bao,Zhang, Xuexia,Zhang, Haocheng,Huang, Hanmin
supporting information, p. 566 - 570 (2021/02/01)
A new strategy for the generation of the active Pd-alkyl species from aminal via C—N bond activation has been established, in which the formation of zwitterionic intermediate through aza-Michael addition of aminal to nitrodienes or dienones is identified as a key step for the activation of the C—N bond. The efficient strategy has enabled a new palladium-catalyzed α-aminomethylation of nitrodienes and dienones via double C—N bond activation. The scope and versatility of the reaction were demonstrated and a broad range of substrates bearing electron-donating and -withdrawing groups on the aromatic rings were all compatible with this reaction to furnish the desired α-aminomethylated products in moderate to good yields with excellent regioselectivities and E/Z selectivities.
A Broad-Spectrum Synthesis of Tetravinylethylenes
Horvath, Kelsey L.,Newton, Christopher G.,Roper, Kimberley A.,Ward, Jas S.,Sherburn, Michael S.
, p. 4072 - 4076 (2019/03/22)
The first general synthesis of compounds of the tetravinylethylene (TVE) family is reported. Ramirez-type dibromo-olefination of readily accessible penta-1,4-dien-3-ones generates 3,3-dibromo[3]dendralenes, which undergo twofold Negishi, Suzuki–Miyaura or Mizoroki–Heck reactions with a wide variety of olefinic coupling partners. This route delivers a broad range of unsymmetrically substituted tetravinylethylenes with up to three different alkenyl substituents attached to the central C=C bond. The extensive scope of the approach is demonstrated by the preparation of the first higher order oligo-alkenic through-conjugated/cross-conjugated hybrid compounds. An unsymmetrically substituted TVE is shown to undergo a domino electrocyclization–cycloaddition with high site-selectivity and diastereoselectivity, thereby demonstrating the substantial synthetic potential of substituted TVEs for controlled, rapid structural complexity generation.
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.
Intermolecular Multiple Dehydrogenative Cross-Couplings of Ketones with Boronic Acids and Amines via Copper Catalysis
Wang, Tianzhang,Chen, Guowei,Lu, Yu-Jing,Chen, Qian,Huo, Yanping,Li, Xianwei
supporting information, p. 3886 - 3892 (2019/07/19)
An efficient and versatile oxidative coupling reaction was developed for the synthesis of valuable β-functionalized unsaturated ketones and meta-substituted phenols. In the case of intramolecular reactions, achieving rapid molecular complexity through multiple dehydrogenative couplings is already a well-established strategy. Herein, we report an intermolecular multiple dehydrogenative coupling between ketones and nucleophilic amines or boronic acids using inexpensive copper(I) oxide as a catalyst. This method provides a facile access to highly desirable chemical products such as α,β-unsaturated ketones, enaminones, and synthetically relevant meta-substituted phenols. (Figure presented.).
Synthesis of Asymmetrical 2,6-Diarylpyridines from Linear α,β,γ,δ-Unsaturated Ketones by Addition of Ammonium Formate Followed by Annulation
Chen, Rener,Gao, Yejun,Ma, Yongmin
, p. 3875 - 3882 (2019/10/11)
A simple and efficient method has been established for the synthesis of asymmetrical 2,6-diarylpyridines by cyclization of α,β,γ,δ-unsaturated ketones with ammonium formate under air atmosphere. The reaction is metal-free and operationally convenient from readily available starting materials. Thirty-three examples have been presented, most of which show good yields.
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.
Chemoselective biohydrogenation of α,β- and α,β,γ,δ-unsaturated ketones by the marine-derived fungus Penicillium citrinum CBMAI 1186 in a biphasic system
Ferreira, Irlon M.,Meira, Eloá B.,Rosset, Isac G.,Porto, André L.M.
, p. 59 - 65 (2015/05/27)
To broaden the range of applicability of a reduction reaction mediated by the marine fungal strain Penicillium citrinum CBMAI 1186 to organic chemical processes, the ability of whole mycelia to grow in biphasic mixtures with organic solvents was tested with acetone, ethyl acetate, n-butanol, dichloromethane, n-hexane and toluene. n-Hexane was the least toxic solvent according to the amount of mycelial mass grown in an artificial sea water medium mixed with each solvent. Therefore, whole hyphae of P. citrinum CBMAI 1186 were used as biocatalysts in the chemoselective biotransformation of the carbon-carbon double bond in α,β-, di-α,β-, and mono-α,β,γ,δ-unsaturated ketones (3a, 3c-f) in a biphasic system of phosphate buffer and n-hexane (9:1). Only the di-α,β,γ,δ-unsaturated ketone (3b) was not biocatalyzed under these conditions. In general, there were good conversions of saturated ketones by the enoate reductase enzymes of P. citrinum CBMAI 1186.
New spiro (thio) barbiturates based on cyclohexanone and bicyclo [3.1.1]heptan-6-one by nonconcerted [1+5] cyclo addition reaction and their conformational structures
Pesyan, Nader Noroozi,Noori, Sirons,Poorhassan, Soodabeh,ahin, Ertan
, p. 423 - 440 (2015/02/02)
Crossed-aldol condensation reaction of aromatic aldehydes with ketones such as; acetone and cyclohexanone leads to the efficient formation of cross conjugated α,β-unsaturated ketones in excellent yield. The intermolecular and then intramolecular Michael addition reaction of α,β-unsaturated ketones derived from acetone and cyclohexanone with (thio)barbituric acids lead to synthesis new type of 7,11-diaryl-2,4-diazaspiro[5.5]undecane-1,3,5,9-tetraone and 2,4-diaryl-1'H-spiro[bicyclo[3.3.l]nonane-3,5'-pyrimidine]-2',4',6',9(3'H)-tetraone, respectively in good yield. Structure elucidation is carried out by 1H NMR, 13C NMR, FT-IR, UV-Visible, mass spectroscopy and X-ray crystallography techniques. A possible mechanism of the formation is discussed. The structural conformation also demonstrated by coupling constants derived from dihedral angles between vicinal and geminal protons. The 1H NMR spectra of NH protons of spiro compounds derived from barbituric acid show a broad singlet peak instead, these protons in the spiro compounds derived from thiobarbituric acid show two distinct peaks.
