30779-94-3Relevant academic research and scientific papers
Asymmetric Transfer Hydrogenation of Arylidene-Substituted Chromanones and Tetralones Catalyzed by Noyori-Ikariya Ru(II) Complexes: One-Pot Reduction of C═C and C═O bonds
Caleffi, Guilherme S.,Brum, Juliana De O. C.,Costa, Angela T.,Domingos, Jorge L. O.,Costa, Paulo R. R.
, p. 4849 - 4858 (2021/04/06)
3-Arylidenechroman-4-ones and 2-arylidene-1-tetralones are hydrogenated to cis-benzylic alcohols in dr's and er's up to 99:1 via a C═C and C═O one-pot reduction in the presence of 2-5 mol % Noyori-Ikariya-type RuII chiral complexes and HCO2Na as a hydroge
From Celecoxib to a Novel Class of Phosphodiesterase 5 Inhibitors: Trisubstituted Pyrazolines as Novel Phosphodiesterase 5 Inhibitors with Extremely High Potency and Phosphodiesterase Isozyme Selectivity
Abdel-Halim, Mohammad,Sigler, Sara,Racheed, Nora A. S.,Hefnawy, Amr,Fathalla, Reem K.,Hammam, Mennatallah A.,Maher, Ahmed,Maxuitenko, Yulia,Keeton, Adam B.,Hartmann, Rolf W.,Engel, Matthias,Piazza, Gary A.,Abadi, Ashraf H.
supporting information, p. 4462 - 4477 (2021/05/04)
A ligand-based approach involving systematic modifications of a trisubstituted pyrazoline scaffold derived from the COX2 inhibitor, celecoxib, was used to develop novel PDE5 inhibitors. Novel pyrazolines were identified with potent PDE5 inhibitory activit
Rhodium-Catalyzed Asymmetric Transfer Hydrogenation/Dynamic Kinetic Resolution of 3-Benzylidene-Chromanones
Molina Betancourt, Ricardo,Phansavath, Phannarath,Ratovelomanana-Vidal, Virginie
supporting information, p. 1621 - 1625 (2021/03/08)
Straightforward access to enantiomerically enriched cis-3-benzyl-chromanols from (E)-3-benzylidene-chromanones was developed through Rh-catalyzed asymmetric transfer hydrogenation. This transformation allowed the reduction of both the CaC and CaO bonds and the formation of two stereocenters in high yields with excellent levels of diastereo- A nd enantioselectivities (up to >99:1 dr, up to >99% ee) in a single step through a dynamic kinetic resolution process using a low catalyst loading and HCO2H/DABCO as the hydrogen source.
Tetralone derivatives are MIF tautomerase inhibitors and attenuate macrophage activation and amplify the hypothermic response in endotoxemic mice
?rfi, László,Bagóné Vántus, Viola,Garai, János,Garami, András,Jakus, Péter Balázs,Kéringer, Patrik,Kovács, Dominika,Krekó, Marcell,Lóránd, Tamás,Radnai, Balázs,Rumbus, Zoltán,Vámos, Eszter
, p. 1357 - 1369 (2021/07/22)
Macrophage migration inhibitory factor (MIF) is a pro-inflammatory cytokine playing crucial role in immunity. MIF exerts a unique tautomerase enzymatic activity that has relevance concerning its multiple functions and its small molecule inhibitors have been proven to block its pro-inflammatory effects. Here we demonstrate that some of the E-2-arylmethylene-1-tetralones and their heteroanalogues efficiently bind to MIF’s active site and inhibit MIF tautomeric (enolase, ketolase activity) functions. A small set of the synthesised derivatives, namely compounds (4), (23), (24), (26) and (32), reduced inflammatory macrophage activation. Two of the selected compounds (24) and (26), however, markedly inhibited ROS and nitrite production, NF-κB activation, TNF-α, IL-6 and CCL-2 cytokine expression. Pre-treatment of mice with compound (24) exaggerated the hypothermic response to high dose of bacterial endotoxin. Our experiments suggest that tetralones and their derivatives inhibit MIF’s tautomeric functions and regulate macrophage activation and thermal changes in severe forms of systemic inflammation.
Biological evaluation of 3-benzylidenechromanones and their spiropyrazolines-based analogues
Adamus-Grabicka, Angelika A.,Budzisz, Elzbieta,Cieslak, Marcin,Hikisz, Pawe?,Królewska-Golinska, Karolina,Kusz, Joachim,Ma?ecka, Magdalena,Markowicz-Piasecka, Magdalena
, (2020/04/10)
A series of 3-benzylidenechrmanones 1, 3, 5, 7, 9 and their spiropyrazoline analogues 2, 4, 6, 8, 10 were synthesized. X-ray analysis confirms that compounds 2 and 8 crystallize in a monoclinic system in P21/n space groups with one and three molecules in each asymmetric unit. The crystal lattice of the analyzed compounds is enhanced by hydrogen bonds. The primary aim of the study was to evaluate the anti-proliferative potential of 3-benzylidenechromanones and their spiropyrazoline analogues towards four cancer cell lines. Our results indicate that parent compounds 1 and 9 with a phenyl ring at C2 have lower cytotoxic activity against cancer cell lines than their spiropyrazolines analogues. Analysis of IC50 values showed that the compounds 3 and 7 exhibited higher cytotoxic activity against cancer cells, being more active than the reference compound (4-chromanone or quercetin). The results of this study indicate that the incorporation of a pyrazoline ring into the 3-arylideneflavanone results in an improvement of the compounds’ activity and therefore it may be of use in the search of new anticancer agents. Further analysis allowed us to demonstrate the compounds to have a strong inhibitory effect on the cell cycle. For instance, compounds 2, 10 induced 60% of HL-60 cells to be arrested in G2/M phase. Using a DNA-cleavage protection assay we also demonstrated that tested compounds interact with DNA. All compounds at the concentrations corresponding to cytotoxic properties are not toxic towards red blood cells, and do not contribute to hemolysis of RBCs.
The relationship between Hirshfeld potential and cytotoxic activity: A study along a series of flavonoid and chromanone derivatives
Adamus-Grabicka, Angelika,Budzisz, El?bieta,Eriksson, Lars,Kusz, Joachim,Ma?ecka, Magdalena
, p. 723 - 733 (2020/08/21)
The present study examines a series of six biologically-active flavonoid and chromanone derivatives by X-ray crystal structure analysis: (E)-3-benzyl-idene-2-phenyl-chroman-4-one, C 22 H 16 O 2, I, (E)-3-(4-methyl-benzyl-idene)-2-phenyl-chroman-4-one, C 23 H 18 O 2, II, (E)-3-(3-methyl-benzyl-idene)-2-phenyl-chroman-4-one, C 23 H 18 O 2, III, (E)-3-(4-meth-oxy-benzyl-idene)-2-phenyl-chroman-4-one, C 23 H 18 O 3, IV, (E)-3-benzyl-idenechroman-4-one, C 16 H 12 O 2, V, and (E)-3-(4-meth-oxy-benzyl-idene)chroman-4-one, C 17 H 14 O 3, VI. The cytotoxic activities of the presented crystal structures have been determined, together with their inter-molecular inter-action preferences and Hirshfeld surface characteristics. An inverse relationship was found between the contribution of C?C close contacts to the Hirshfeld surface and cytotoxic activity against the WM-115 cancer line. Dependence was also observed between the logP value and the percentage contribution of C?H contacts to the Hirshfeld surface.
Synthesis and biological evaluation of 3-benzylidene-4-chromanone derivatives as free radical scavengers and α-glucosidase inhibitors
Takao, Koichi,Yamashita, Marimo,Yashiro, Aruki,Sugita, Yoshiaki
, p. 1203 - 1207 (2016/08/11)
A series of 3-benzylidene-4-chromanone derivatives (3-20) were synthesized and the structure-activity relationships for antioxidant and α-glucosidase inhibitory activities were evaluated. Among synthesized compounds, compounds 5, 13, 18, which contain catechol moiety, showed the potent 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activity (5: EC50 13 μM; 13: EC50 14 μM; 18: EC50 13 μM). The compounds 12, 14, 18 showed higher α-glucosidase inhibitory activity (12: IC50 15 μM; 14: IC50 25 μM; 18: IC50 28 μM). The compound 18 showed both of potent DPPH radical scavenging and α-glucosidase inhibitory activities. These data suggest that 3-benzylidene-4-chromanone derivatives, such as compound 18, may serve as the lead compound for the development of novel α-glucosidase inhibitors with antioxidant activity.
Discovery of 3,3a,4,5-tetrahydro-2H-benzo[g]indazole containing quinoxaline derivatives as novel EGFR/HER-2 dual inhibitors
Zong, Xi,Cai, Jin,Chen, Junqing,Sun, Chunlong,Li, Lushen,Ji, Min
, p. 24814 - 24823 (2015/03/30)
In the present study, twenty-five pyrazole-quinoxaline derivatives (4a-4y) were designed and synthesized, and their biological activity as potential EGFR or HER-2 kinase inhibitors was evaluated. Among them, compound 4l displayed better antiproliferative
Substituted 3-E-styryl-2H-chromenes and 3-E-styryl-2 H-thiochromenes: Synthesis, photophysical studies, anticancer activity, and exploration to tricyclic benzopyran skeleton
Roy, Rimi,Rakshit, Soumyadipta,Bhowmik, Tanmoy,Khan, Sagar,Ghatak, Avishek,Bhar, Sanjay
, p. 6603 - 6614 (2014/08/05)
A series of densely substituted 2H-chromenes and 2H-thiochromenes were synthesized in good yield through cyanuric chloride-dimethylformamide mediated cleavage of different spiro-4-hydroxychroman-3,1′-cyclopropanes and similar thiochroman analogues. This p
Imidazolium ionic liquids as catalyst for synthesis of (E)-3- arylidene(thio)chroman-4-ones under microwave irradiation
Li, Hong-Ya,Li, Shu-Na,Wang, Quan,Wang, Shu-Xiang,Zhu, Bao-Cheng
, p. 635 - 637 (2013/02/23)
Use of imidazolium ionic liquids [Bmim][CF3COO] and [Bmim]OH as a catalyst for synthesis of 3-arylidene(thio)chroman- 4-ones by the condensation of (thio)chroman-4-ones and aromatic aldehydes under microwave irradiation conditions. A series of 3-arylidene(thio)chroman-4-ones were obtained as the only product and considerable increase of yield was founded within short time. The products 3-arylidene(thio)chromanones were assigned the (E)-configuration based on 1H NMR spectroscopic data.
