13565-38-3Relevant academic research and scientific papers
Chalcone-Supported Cardiac Mesoderm Induction in Human Pluripotent Stem Cells for Heart Muscle Engineering
Raad, Farah S.,Khan, Taukeer A.,Esser, Tilman U.,Hudson, James E.,Seth, Bhakti Irene,Fujita, Buntaro,Gandamala, Ravi,Tietze, Lutz F.,Zimmermann, Wolfram
supporting information, p. 3300 - 3305 (2021/09/02)
Human pluripotent stem cells (hPSCs) hold great promise for applications in cell therapy and drug screening in the cardiovascular field. Bone morphogenetic protein 4 (BMP4) is key for early cardiac mesoderm induction in hPSC and subsequent cardiomyocyte derivation. Small-molecular BMP4 mimetics may help to standardize cardiomyocyte derivation from hPSCs. Based on observations that chalcones can stimulate BMP4 signaling pathways, we hypothesized their utility in cardiac mesoderm induction. To test this, we set up a two-tiered screening strategy, (1) for directed differentiation of hPSCs with commercially available chalcones (4’-hydroxychalcone [4’HC] and Isoliquiritigen) and 24 newly synthesized chalcone derivatives, and (2) a functional screen to assess the propensity of the obtained cardiomyocytes to self-organize into contractile engineered human myocardium (EHM). We identified 4’HC, 4-fluoro-4’-methoxychalcone, and 4-fluoro-4’-hydroxychalcone as similarly effective in cardiac mesoderm induction, but only 4’HC as an effective replacement for BMP4 in the derivation of contractile EHM-forming cardiomyocytes.
Fluorine as a robust balancer for tuning the reactivity of topo-photoreactions of chalcones and the photomechanical effects of molecular crystals
Gao, Hongqiang,Lu, Ran,Shu, Yuanhong,Sun, Jingbo,Wang, Haoran,Yang, Xiqiao,Ye, Kaiqi,Yue, Yuan,Zhong, Jiangbin
, p. 5856 - 5868 (2021/09/08)
Fluorine-free chalcones and chalcones bearing different numbers of fluorine atoms have been synthesized. It is found that fluorine can tune the reactivity of photo-induced [2 + 2] cycloaddition reactions in crystals. The higher the number of fluorine atom
N-Heterocyclic Carbene Catalyzed Synthesis of Trisubstituted Epoxides via Tandem Amidation/Epoxidation Sequence
Devi, E. Sankari,Pavithra, Thangavel,Tamilselvi,Nagarajan, Subbiah,Sridharan, Vellaisamy,Maheswari, C. Uma
supporting information, p. 3576 - 3580 (2020/04/20)
A tandem amidation/epoxidation sequence between various substituted chalcones and N,N-dimethylformamide (DMF) for the synthesis of trisubstituted epoxides employing N-heterocyclic carbene catalysis was developed. This reaction was performed under metal-free conditions in the presence of tert-butyl hydroperoxide (TBHP) as the oxidant. Trisubstituted epoxides bearing a ketone and an amide functionality (N,N-dimethyl formyl group) were synthesized starting from a wide range of chalcones in moderate to good yields with excellent diastereoselectivity.
Cu/TEMPO catalyzed dehydrogenative 1,3-dipolar cycloaddition in the synthesis of spirooxindoles as potential antidiabetic agents
Babu, Spoorthy N.,Daniel, J. Arul,Devi, S. Asha,Nawaz Khan, Fazlur Rahman,Noor, Ayesha,Teja, Chitrala
, p. 12262 - 12271 (2020/04/20)
A series of spiro-[indoline-3,3′-pyrrolizin/pyrrolidin]-2-ones, 4, 5 and 6 were synthesized in a sequential manner from Cu-TEMPO catalyzed dehydrogenation of alkylated ketones, 1 followed by 1,3-dipolar cycloaddition of azomethine ylides via decarboxylative condensation of isatin, 2 and l-proline/sarcosine, 3 in high regioselectivities and yields. The detailed mechanistic studies were performed to identify the reaction intermediates, which revealed that the reaction proceeds via dehydrogenative cycloaddition. Additionally, the regio and stereochemistry of the synthesized derivatives were affirmed by 2D NMR spectroscopic studies. The synthesized derivatives were explored further with molecular docking, in vitro antioxidant, and anti-diabetic activities.
Three Step Synthesis of Fully and Differently Arylated Pyridines
Arita, Mao,Yokoyama, Soichi,Asahara, Haruyasu,Nishiwaki, Nagatoshi
, p. 466 - 474 (2020/01/25)
Condensation of β-(2-pyridyl)enamine and α,β-unsaturated ketone in the presence of FeCl3 under air afforded highly substituted pyridines. In this transformation, FeCl3 acted as not only an acid catalyst but also an oxidant for the in
Naphtho[2,3-: B] furan-4,9-dione synthesis via palladium-catalyzed reverse hydrogenolysis
Li, Jimei,Zhang, Jie,Li, Mingfei,Zhang, Chenyang,Yuan, Yongkun,Liu, Renhua
supporting information, p. 2348 - 2351 (2019/02/27)
A reverse hydrogenolysis process has been developed for two-site coupling of 2-hydroxy-1,4-naphthoquinones with olefins to produce naphtha[2,3-b]furan-4,9-diones and hydrogen (H2). The reaction is catalyzed by commercially available Pd/C without oxidants and hydrogen acceptors, thereby providing an intrinsically waste-free approach for the synthesis of functionalized and potentially biologically relevant naphtha[2,3-b]furan-4,9-diones.
Synthesis of stable benzimidazole derivatives bearing pyrazole as anticancer and EGFR receptor inhibitors
Akhtar, Md. Jawaid,Khan, Ahsan Ahmed,Ali, Zulphikar,Dewangan, Rikeshwer Prasad,Rafi, Md.,Hassan, Md. Quamrul,Akhtar, Md. Sayeed,Siddiqui, Anees Ahmad,Partap, Sangh,Pasha, Santosh,Yar, M. Shahar
, p. 158 - 169 (2018/03/24)
A new series of benzimidazole linked pyrazole derivatives were synthesized by cyclocondensation reaction through one-pot multicomponent reaction in absolute ethanol. All the synthesized compounds were tested for their in vitro anticancer activities on fiv
Visible Light Activated Radical Denitrative Benzoylation of β-Nitrostyrenes: A Photocatalytic Approach to Chalcones
Tripathi, Shubhangi,Kapoor, Ritu,Yadav, Lal Dhar S.
supporting information, p. 1407 - 1413 (2018/04/10)
A metal-free, convenient photocatalytic approach to chalcones from β-nitrostyrenes and benzaldehydes via a radical denitrative benzoylation pathway is reported. The salient features of the protocol include the utilization of visible light as an inexpensive and ecosustainable energy source, N-hydroxyphthalimide (NHPI) as a reusable organophotocatalyst and acetonitrile as an acceptable green solvent to afford chalcones in excellent yields at room temperature in a one-pot procedure. Notably, this is the first application of β-nitrostyrenes as readily available substrates for chalcone synthesis and the first example of photocatalysis in this field. (Figure presented.).
Revisiting the Juliá-Colonna enantioselective epoxidation: Supramolecular catalysis in water
Bérubé, Christopher,Barbeau, Xavier,Lagüe, Patrick,Voyer, Normand
supporting information, p. 5099 - 5102 (2017/07/12)
We describe an efficient epoxidation process leading to chiral epoxyketones using the reusable homo-oligopeptide poly-l-leucine (PLL) in pure water, without any organic co-solvent. A range of substituted epoxyketones can be accessed with good conversions and high enantioselectivities. Based on the experimental results and computational studies, we propose a mechanism that demonstrates the importance of both the α-helical structure and the presence of a hydrophobic groove of the homo-oligopeptide catalyst for reactivity and selectivity.
Through scaffold modification to 3,5-diaryl-4,5-dihydroisoxazoles: new potent and selective inhibitors of monoamine oxidase B
Meleddu, Rita,Distinto, Simona,Cirilli, Roberto,Alcaro, Stefano,Yanez, Matilde,Sanna, Maria Luisa,Corona, Angela,Melis, Claudia,Bianco, Giulia,Matyus, Peter,Cottiglia, Filippo,Maccioni, Elias
, p. 264 - 270 (2017/11/10)
3,5-Diaryl-4,5-dihydroisoxazoles were synthesized and evaluated as monoamine oxidase (MAO) enzyme inhibitors and iron chelators. All compounds exhibited selective inhibitory activity towards the B isoform of MAO in the nanomolar concentration range. The b
