29974-49-0Relevant academic research and scientific papers
Synthesis, crystal structures, spectroscopic, and cytotoxicity study of Cu(II), Co(II), Ni(II) and Pd(II) complexes with 2-anilinomethylidene-5,5-dimethylcyclohexane-1,3-dione
Eremina, Julia A.,Lider, Elizaveta V.,Sukhikh, Taisiya S.,Eltsov, Ilia V.,Kuratieva, Natalia V.,Zakharov, Boris A.,Sheludyakova, Liliya A.,Klyushova, Lyubov S.,Ermakova, Ekaterina A.,Dotsenko, Victor V.
, (2020)
The coordination compounds of Cu(II), Co(II), Ni(II) and Pd(II) with 2-anilinomethylidene-5,5-dimethylcyclohexane-1,3-dione (HL) of the composition [ML2(C2H5OH)2]·nH2O (M = Co (n = 1), Ni (n = 0)) and
Ultrasound assisted regioselective synthesis, photophysical and structural studies of 1-substituted indazol-4(5H)-ones and enaminodiketones of dimedone
Chaudhary, R. P.,Gautam, Deepika,Gautam, Poonam,Mittal, Isha
, (2020/12/23)
Enaminodiketone, obtained from reaction of dimedone with DMF-DMA, on reaction with nucleophiles such as amines, guanidine hydrochloride and substituted aromatic hydrazines furnished enaminodiketones, quinazolines and indazole derivatives respectively. The
Uses of dimedone to synthesis pyrazole, isoxazole and thiophene derivatives with antiproliferative, tyrosine kinase and Pim-1 kinase inhibitions
Abdelwahab, Amal,Mahmoud, Mahmoud Ali Abdelaziz,Manhi, Fatma Mohamed,Mohareb, Rafat Milad
, (2020/06/30)
We are aiming in this work to synthesize target molecules not only possess antitumor activities but also kinase inhibitors. The target molecules were obtained from dimedone, which reacted with triethoxymethane to produce a product that is capable for many heterocyclization reactions to give fused pyrazole, thiophene and isoxazole derivatives. Compounds 7b, 7c, 7d, 9b, 11, 12c, 12d, 14b, 16b, 17c, 17d, 18c, 18d, and 18e were the most cytotoxic compounds, their further tests toward the five tyrosine kinases c-Kit, Flt-3, VEGFR-2, EGFR, and PDGFR and Pim-1 kinase showed that compounds 7b, 7d, 11, 12c, 14b, 16b, 17d, 18d, and 18e were the most potent of the tested compounds toward the five tyrosine kinases and compounds 7b, 7d, 14b, 16b, and 18e were of the highest inhibitions toward Pim-1 kinase. PAINS the most cytotoxic compounds showed zero PAINS alert, therefore, these compounds can be used as useful drugs in the future.
The synthesis, biological evaluation and structure-activity relationship of 2-phenylaminomethylene-cyclohexane-1,3-diones as specific anti-tuberculosis agents
Rather, Muzafar Ahmad,Lone, Ali Mohd,Teli, Bisma,Bhat, Zubair Shanib,Singh, Paramjeet,Maqbool, Mubashir,Shairgojray, Bashir Ahmad,Dar, Mohd Jamal,Amin, Shajrul,Yousuf, Syed Khalid,Bhat, Bilal A.,Ahmad, Zahoor
supporting information, p. 2133 - 2141 (2017/11/22)
The present study utilised whole cell based phenotypic screening of thousands of diverse small molecules against Mycobacterium tuberculosis H37Rv (M. tuberculosis) and identified the cyclohexane-1,3-dione-based structures 5 and 6 as hits. The selected hit molecules were used for further synthesis and a library of 37 compounds under four families was synthesized for lead generation. Evaluation of the library against M. tuberculosis lead to the identification of three lead antituberculosis agents (37, 39 and 41). The most potential compound, 2-(((2-hydroxyphenyl)amino)methylene)-5,5-dimethylcyclohexane-1,3-dione (39) showed an MIC of 2.5 μg mL-1, which falls in the range of MICs values found for the known antituberculosis drugs ethambutol, streptomycin and levofloxacin. Additionally, this compound proved to be non-toxic (20% inhibition at 50 μM concentration) against four human cell lines. Like first line antituberculosis drugs (isoniazid, rifampicin and pyrazinamide) this compound lacks activity against general Gram positive and Gram negative bacteria and even against M. smegmatis; thereby reflecting its highly specific antituberculosis activity.
Development of Inhibitors of Salicylic Acid Signaling
Jiang, Kai,Kurimoto, Tetsuya,Seo, Eun-Kyung,Miyazaki, Sho,Nakajima, Masatoshi,Nakamura, Hidemitsu,Asami, Tadao
, p. 7124 - 7133 (2015/09/01)
Salicylic acid (SA) plays important roles in the induction of systemic acquired resistance (SAR) in plants. Determining the mechanism of SAR will extend our understanding of plant defenses against pathogens. We recently reported that PAMD is an inhibitor of SA signaling, which suppresses the expression of the pathogenesis-related PR genes and is expected to facilitate the understanding of SA signaling. However, PAMD strongly inhibits plant growth. To minimize the side effects of PAMD, we synthesized a number of PAMD derivatives, and identified compound 4 that strongly suppresses the expression of the PR genes with fewer adverse effects on plant growth than PAMD. We further showed that the adverse effects on plant growth were partially caused the stabilization of DELLA, which is also related to the pathogen responses. These results indicate that compound 4 would facilitate our understanding of SA signaling and its cross talk with other plant hormones.
Anilinomethylidene derivatives of cyclic 1,3-dicarbonyl compounds in the synthesis of new sulfur-containing pyridines and quinolines
Dotsenko,Krivokolysko,Chernega,Litvinov
, p. 1556 - 1561 (2007/10/03)
Simple methods for the synthesis of previously unknown sulfur-containing pyridin-2-ones and 5,6,7,8-tetrahydroquinolines from cyanothioacetamide and anilinomethylidene derivatives of cyclic 1,3-dicarbonyl compounds were developed. Structures and chemical transformations of compounds obtained were studied.
Photobleaching Activity of 2-(Phenylamino)methylidenecyclohexane-1,3-diones in Tobacco (Nicotiana tabacum) Cultured Cells
Wang, Jing-Ming,Asami, Tadao,Che, Fan-Sik,Murofushi, Noboru,Yoshida, Shigeo
, p. 2728 - 2734 (2007/10/03)
A series of phenylalkylidenecyclohexane-1,3-dione derivatives were designed and synthesized as vinylogous analogs of phthalimides, which are known photobleaching herbicides. The bleaching activity of synthesized compounds was assayed with photomixotrophic tobacco cultured cells under either light or dark conditions. Both the chlorophyll and the carotenoid contents of the cells treated with the cyclic diones decreased to almost zero within 24 h under the light condition but not under the dark condition. This rapid emergence of bleaching activity with light is one of the most distinctive actions of Protox-inhibiting herbicides; however, the cyclic dione did not inhibit protoporphyrinogen oxidase in vitro. Thus, we concluded that the cyclic diones possessed a different herbicidal mode of action from Protox-inhibiting herbicide.
ACETALS OF LACTAMS AND ACID AMIDES. 48. REACTION OF ENAMINO DIKETONES WITH AMIDE ACETALS. SYNTHESIS OF DERIVATIVES OF COUMARIN AND CARBOSTYRIL
Grannik, V. G.,Shanazarov, A. K.,Solov'eva, N. P.,Chistyakov, V. V.,Persianova, I. V.,Sheinker, Yu. N.
, p. 1171 - 1177 (2007/10/02)
It was established that the reaction of derivatives of 2-aminomethylenecyclohexane-1,3-dione with N,N-dimethyl-diethylacetal gives dienediamines, heating of which in aqueous hydrochloric acid leads, depending on the structure, to derivatives of carbostyri
Kinetics of the Three Components Condensation of Triethoxymethane, Aniline and CH2-Acidic Compounds Forming Arylaminomethylene Compounds
Uray, Georg,Wolfbeis, Otto S.
, p. 627 - 642 (2007/10/02)
Condensation of triethoxymethane and aniline with dimedone gives 2-anilinomethylene dimedone as the main product.An 1H-NMR-spectroscopic investigation of the kinetics in chloroform-d1 and methanol-d4 shows different rate determining steps in these solvents.There are two predominant rate determining steps in a complicated multistep reaction sequence.The initial one involves condensation of aniline with triethoxymethane to form diphenyl formamidine via ethyl phenyl formimidate.The second step involves reaction of the intermediate diphenyl formamidine with dimedone.The rates are strongly dependent upon the nature of the solvent and the concentration of catalytic acid.In methanol the reaction of dimedone with the intermediate diphenyl formamidine is rate determining.For preparative purposes the isolation of the intermediate diphenyl formamidine and the subsequent use of less polar solvents offer an advantage, because the second step is found to be accelerated. - Keywords: Enaminones; Formimidate; Formamidine
