- Chromanone compound as well as preparation method and application thereof
-
The invention discloses a chromanone compound, a preparation method of the chromanone compound and application of the chromanone compound to preparation of medicines for treating or preventing infectious diseases caused by mycobacterium tuberculosis. Specifically, the present invention relates to a compound represented by formula (I), a pharmaceutically acceptable salt thereof, and a pharmaceutical composition containing the compound of the present invention, where X, Y, R1, R2, R3 and R4 are as described in the specification. The purpose of the present invention is to prepare a novel compound having anti-mycobacterium tuberculosis activity, which can be used as a potential novel drug for overcoming the problems associated with mycobacterium tuberculosis drug resistance.
- -
-
Paragraph 0106-0111
(2021/04/26)
-
- An efficient TBHP/TBAI-mediated protocol for the synthesis of 4H-chromen-4-ones from chroman-4-ones via oxidative C–C bond formation
-
Abstract: A transition metal-free and efficient TBHP/TBAI-mediated protocol has been developed for the synthesis of 4H-chromen-4-ones from chroman-4-ones via oxidative C–C bond formation. It proceeds in the presence of a catalytic amount of tetrabutylammonium iodide and oxidant tert-butyl hydroperoxide (TBHP, 5–6 M in decane) to afford the corresponding products in good to excellent yields. Furthermore, it has been observed that an increase in the concentration of TBHP to 30 mol % drastically increases the yield of 4H-chromen-4-ones, any further increase will lead to a decrease in percent yield. The mechanism of this reaction involves the generation of tertiary butoxide radical initially which by oxidative single-electron transformation is converted to iodochroman-4-one. Later the hydrogen iodide is removed from iodochroman-4-one to give the desired product, i.e. 4H-chromen-4-ones. Moreover, this is a rare example of the n-Bu4NI/TBHP-mediated C–C bond through dehydrogenative reaction. Graphic abstract: [Figure not available: see fulltext.]
- Agisho, Habtamu Abebe,Hairat, Suboot,Zaki, Mehvash
-
p. 599 - 603
(2020/05/04)
-
- Nitrogen-containing flavonoid and their analogs with diverse B-ring in acetylcholinesterase and butyrylcholinesterase inhibition
-
In this study, a series of new flavones (2-phenyl-chromone), 2-naphthyl chromone, 2-anthryl-chromone, or 2-biphenyl-chromone derivatives containing 6 or 7-substituted tertiary amine side chain were designed, synthesized, and evaluated in acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibition. The results indicated that the alteration of aromatic ring connecting to chromone scaffold brings about a significant impact on biological activity. Compared with flavones, the inhibitory activity of 2-naphthyl chromone, 2-anthryl-chromone derivatives against AChE significantly decreased, while that of 2-biphenyl chromone derivatives with 7-substituted tertiary amine side chain is better than relative flavones derivatives. For all new synthesized compounds, the position of tertiary amine side chain obviously influenced the activity of inhibiting AChE. The results above provide great worthy information for the further development of new AChE inhibitors. Among the newly synthesized compounds, compound 5a is potent in AChE inhibition (IC50 = 1.29 ± 0.10 μmol/L) with high selectivity for AChE over BChE (selectivity ratio: 27.96). An enzyme kinetic study of compound 5a suggests that it produces a mixed-type inhibitory effect against AChE.
- Lu, Qiao-Qiao,Chen, Ya-Ming,Liu, Hao-Ran,Yan, Jian-Ye,Cui, Pei-Wu,Zhang, Qian-Fan,Gao, Xiao-Hui,Feng, Xing,Liu, Ying-Zi
-
p. 1037 - 1047
(2020/08/06)
-
- Nickel-catalyzed removal of alkene protecting group of phenols, alcohols via chain walking process
-
An efficient nickel-catalyzed removal of alkene protection group under mild condition with high functional group tolerance through chain walking process has been established. Not only phenolic ethers, but also alcoholic ethers can be tolerated with the retention of stereocenter adjacent to hydroxyl group. The new reaction brings the homoallyl group into a start of new type of protecting group.
- Meng, Chenkai,Niu, Haolin,Ning, Juehan,Wu, Wengang,Yi, Jun
-
-
- Design, synthesis, and biological evaluation of novel 4H-chromen-4-one derivatives as antituberculosis agents against multidrug-resistant tuberculosis
-
A series of 4H-chromen-4-one derivatives obtained by scaffold morphing of the benzofuran compound, TAM16, were tested for antitubercular activity. Compound 8d was active against drug-sensitive and multidrug-resistant tuberculosis. A preliminary druggability evaluation showed that compound 8d displayed favorable mouse and human microsomal stability, low cytotoxicity, and acceptable oral bioavailability. An in vivo study indicated that compound 8d exhibited modest efficacy in an acute mouse model of TB after 3 weeks of treatment. Thus, 8d is a promising antituberculosis lead compound.
- Fu, Lei,Liu, Yuke,Lu, Yu,Sheng, Li,Wang, Bin,Zhang, Dongfeng,Zhao, Hongyi,Zhao, Wenting
-
-
- Synthesis of Phenols: Organophotoredox/Nickel Dual Catalytic Hydroxylation of Aryl Halides with Water
-
A highly effective hydroxylation reaction of aryl halides with water under synergistic organophotoredox and nickel catalysis is reported. The OH group of the resulting phenols originates from water, following deprotonation facilitated by an intramolecular base group on the ligand. Significantly, aryl bromides as well as less reactive aryl chlorides served as effective substrates to afford phenols with a wide range of functional groups. Without the need for a strong inorganic base or an expensive noble-metal catalyst, this process can be applied to the efficient preparation of diverse phenols and enables the hydroxylation of multifunctional pharmaceutically relevant aryl halides.
- Yang, Liu,Huang, Zhiyan,Li, Gang,Zhang, Wei,Cao, Rui,Wang, Chao,Xiao, Jianliang,Xue, Dong
-
supporting information
p. 1968 - 1972
(2018/02/06)
-
- An Efficient One-Pot Synthesis and Anticancer Activity of 4'-Substituted Flavonoids
-
A number of 4'-substituted (R = H, Me, Cl, F) flavone derivatives is synthesized from 2-hydroxyacetophenones using the modified Baker–Venkataraman reaction. Compound [3-(4-fluorobenzoyl)-5- hydroxy-4'-fluoroflavone] was synthesized for the first time with the yield of 12%. Antiproliferative assays indicate that the synthesized flavones with F substituent at the 4' position demonstrate higher activity than the other flavone derivatives, particularly against HeLa and MCF-7 with the IC50 9.5 and 2.7 μM, respectively.
- Wang,Liu,Zhang
-
p. 1036 - 1041
(2018/07/06)
-
- Ferrocenyl-appended aurone and flavone: Which possesses higher inhibitory effects on DNA oxidation and radicals?
-
The aim of the present work was to compare the antioxidative effect of the ferrocenyl-appended aurone with that of ferrocenyl-appended flavone; therefore, nine aurones together with the flavone-type analogues were synthesized by using chalcone as the reactant. The radical-scavenging property was evaluated by reacting with the 2,2β-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS+·), 2,2β-diphenyl-1-picrylhydrazyl radical (DPPH), and galvinoxyl radical, respectively. The cytotoxicity was estimated by inhibiting 2,2β-azobis(2-amidinopropane hydrochloride) (AAPH)-induced oxidation of DNA. It was found that the introduction of the ferrocenyl group remarkably increased the radical-scavenging activities of aurone and flavone. Especially, the ferrocenyl group in flavones can quench radicals even in the absence of the phenolic hydroxyl group, while ferrocenyl-appended aurones can efficiently protect DNA against AAPH-induced oxidation. Therefore, the antioxidative effect was generated by the ferrocenyl group and enhanced by the electron-donating group attaching to the para-position of the ferrocenyl group. Introducing the ferrocenyl group into natural compounds may be a useful strategy for increasing the antioxidative effectiveness.
- Chen, Jia-Feng,Liu, Zai-Qun
-
p. 451 - 459
(2015/03/30)
-
- Enantioselective conversion of certain derivatives of 6-hydroxyflavanone
-
In the culture of Aspergillus niger MB, three racemic flavonoid derivatives (6-acetoxy-, 6-propionoxy-, and 6-butyryloxyflavanone) undergo microbial transformations resulting in optically pure (-)-(S)-6,4′- dihydroxyflavanone formation. In turn, biotransf
- Kostrzewa-Suslow, Edyta,Dymarska, Monika,Bialonska, Agata,Janeczko, Tomasz
-
-
- Glucosylation of hydroxyflavones by glucosyltransferases from Phytolacca americana
-
Cell suspension cultures of Phytolacca americana can glucosylate 6- and 7-hydroxyflavone, but not 5-hydroxyflavone. In order to identify the enzymes responsible for these transformations, glucosyltransferases (GTs) from P. americana were overexpressed in Escherichia coli and purified. The purified PaGT3 enzyme could glucosylate 6- and 7-hydroxyflavone when incubated with UDP-glucose, a glucosyl donor molecule, but PaGT2 could conjugate a glucose moiety only to 6-hydroxyflavone. E. coli cells expressing PaGT2 and 3 could also be utilized for the glucosylation of hydroxyflavones. The glucoside products which had accumulated in the medium of overnight E. coli cell cultures were isolated using hydrophobic resins. This methodology might be suitable for the glucosylation of aglycones with important health-related properties.
- Iwakiri, Tomoya,Mase, Shogo,Murakami, Tomonori,Matsumoto, Masahiro,Hamada, Hiroki,Nakayama, Toru,Ozaki, Shin-Ichi
-
-
- COMPOUNDS THAT EXPAND HEMATOPOIETIC STEM CELLS
-
The present invention relates to compounds and compositions for expanding the number of CD34+ cells for transplantation. The invention further relates to a cell population comprising expanded hematopoietic stem cells (HSCs) and its use in autologous or allogeneic transplantation for the treatment of patients with inherited immunodeficient and autoimmune diseases and diverse hematopoietic disorders to reconstitute the hematopoietic cell lineages and immune system defense.
- -
-
Page/Page column 33; 35
(2012/08/08)
-
- An efficient one-pot synthesis of flavones
-
Flavones were prepared using a one-pot procedure starting from the corresponding 2′-hydroxyacetophenones. The latter were treated with 3 equiv of aroyl chloride in wet K2CO3/acetone (1% w/w water) to afford a good yield of flavone and a smaller amount of 3-aroylflavone. Evidence was obtained that the reaction proceeds via a triketone intermediate. When the reactants were heated in 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and pyridine, the 3-aroylflavone was obtained exclusively. Use of a stoichiometric amount of aroyl chloride afforded only the corresponding flavone.
- Chee, Chin Fei,Buckle, Michael J.C.,Rahman, Noorsaadah Abd.
-
supporting information; experimental part
p. 3120 - 3123
(2011/06/26)
-
- Squarylium compounds, and processes and intermediates for the synthesis of these compounds
-
Squarylium compounds of the formula: STR1 wherein Q1 and Q2 are each independently a pyrylium, thiopyrylium, selenopyrylium, benzpyrylium, benzthiopyrylium or benzselenopyrylium nucleus, and R1 and R2 are each independently an aliphatic or cycloaliphatic group, can be prepared by reacting a squaric acid derivative of the formula: STR2 with a compound of the formula Q2 CH2 R2 in the presence of a base.
- -
-
-
- Enzyme-catalyzed alcoholysis of flavone acetates in organic solvent
-
Pseudomonas sp. lipase suspended in tetrahydrofuran was used to deacylate flavone acetates. Regioselectivity of the reaction has been observed.
- Natoli, Mariapina,Nicolosi, Giovanni,Piattelli, Mario
-
p. 7371 - 7374
(2007/10/02)
-
- SYNTHESE DE DIHYDROXY PHENACYLIDENE TRIPHENYLPHOSPHORANES NOUVEAUX PRECURSEURS DE COMPOSES FLAVONOIDES : SYNTHESE D'HYDROXY-6 ET HYDROXY-7 CHROMONES.
-
The synthesis of two new dihydroxy phenacylidene triphenylphosphoranes from 2,4-dibenzoyloxy and 2,5-dibenzoyloxy acetophenones is described.By acylation of the hydroxyl groups of these ylides, intramolecular olefination of the ester carbonyl group and hydrolysis of the second ester group, some 6-hydroxy and 7-hydroxy chromones are prepared with good yields.
- Le Floc'H, Yves,Lefeuvre, Martine
-
p. 2751 - 2752
(2007/10/02)
-
- Sodium Hydrogen Telluride - A Mild Reagent for Deacylation of Aryl Acetates and Benzoates
-
Sodium hydrogen telluride is found to be a mild and effective reagent for the deacylation of aryl acetates and benzoates.
- Shobana, N.,Shanmugam, P.
-
-