127179-84-4Relevant articles and documents
STEREOELECTRONIC EFFECTS IN RING CLOSURE REACTIONS
Bradley, Jeremy P.,Jarvis, Terence C.,Johnson, David C.,McDonnell, Peter D.,Weatherstone, Timothy A. P.
, p. 2851 - 2854 (1983)
The mechanistic criterion of reversed substituent effects in reactions, formally classified as 5-endo-trig and 6-endo-trig, is examined.
Eco-friendly polyethylene glycol promoted Michael addition reactions of α,β-unsaturated carbonyl compounds
Kumar, Dalip,Patel, Gautam,Mishra, Braja G.,Varma, Rajender S.
, p. 6974 - 6976 (2008)
Intra- and inter-nucleophilic addition reactions of different α,β-unsaturated carbonyl compounds were found to be highly effective without any additives in PEG-400 as a recyclable reaction medium under neutral conditions.
Ionic liquid catalyzed expeditious synthesis of 2-aryl-2,3-dihydroquinolin- 4(1H)-ones and 2-aryl-2,3-dihydro-4H-chromen-4-ones under microwave irradiation
Kumar, Dalip,Patel, Gautam,Kumar, Anil,Roy, Ram K.
, p. 791 - 795 (2009)
(Chemical Equation Presented) A facile and convenient synthesis of 2-aryl-2,3-dihydroquinolin-4(1H)-one and 2-aryl-2,3-dihydro-4Hchromen-4-one has been described using ionic liquid catalyzed intramolecular cyclization of the corresponding 2′-aminochalcones and 2′-hydroxychalcones, respectively. The rapid and fairly general protocol affords product in good yield. Ionic liquid, 1-butyl-3-methylimidazolium tetrafluoroborate, was recovered and reused without loosing its efficiency.
Synthesis and kinetic study for the interconversion process of some 2'-hydroxychalcones to their corresponding flavanones
Majed, Zainab Waleed,Said, Said Abdelqader,Shareef, Omar Adil
, p. 4379 - 4386 (2020/12/09)
In this work, five substituted2'-Hydroxychalconeswere prepared using Claisen - Schmidt condensation and used as a synthone for substituted flavanones via base catalyzed isomerization process. The latter process has been studied kinetically using HPLC technique in (8:2) (CH3CN:CH3OH) medium at different temperatures (298 K - 318 K). The obtained results were inconsonance with a four-step mechanism which considered the existence of phenoxide ion as the key intermediate. The reaction was achieved as a pseudo first order reaction in which the rate of the studied compounds followed the sequence 1>2>3>4>5, and the activation energy had the same sequence for these compounds. The reaction rate was affected by the electronic behavior of the different substituents at ring B since they played an important role in the stability of the intermediate that led to the final product.
Organocatalytic Approach for Assembling Flavanones via a Cascade 1,4-Conjugate Addition/oxa-Michael Addition between Propargylamines with Water
He, Xinwei,He, Xinwei,Xie, Mengqing,Li, Ruxue,Choy, Pui Ying,Tang, Qiang,Shang, Yongjia,Kwong, Fuk Yee
, p. 4306 - 4310 (2020/06/05)
A DBU-catalyzed one-pot cascade reaction of propargylamines and water for the synthesis of flavanones has been developed. This process proceeds via a sequence of 1,4-conjugate addition of water to alkynyl o-quinone methide (o-AQM), followed by the alkyne-allene isomerization and subsequent intramolecular oxa-Michael addition. This strategy provides a convenient method for accessing a broad range of flavanones in good to excellent yields with good functional-group tolerance, in particular, the reactive halo functional groups.
Synthesis of Flavanones via Palladium(II)-Catalyzed One-Pot β-Arylation of Chromanones with Arylboronic Acids
Cho, Yang Yil,Jang, Hyu Jeong,Kim, Dong Hwan,Kim, Nam Yong,Kim, Nam-Jung,Kim, Young Min,Lee, Soo Jin,Lee, Yong Sup,Park, Boyoung Y.,Son, Seung Hwan,Yoo, Hyung-Seok
, p. 10012 - 10023 (2019/08/30)
A total of 47 flavanones were expediently synthesized via one-pot β-arylation of chromanones, a class of simple ketones possessing chemically unactivated β sites, with arylboronic acids via tandem palladium(II) catalysis. This reaction provides a novel route to various flavanones, including natural products such as naringenin trimethyl ether, in yields up to 92percent.
Discovery of a Prenylated Flavonol Derivative as a Pin1 Inhibitor to Suppress Hepatocellular Carcinoma by Modulating MicroRNA Biogenesis
Zheng, Yuanyuan,Pu, Wenchen,Li, Jiao,Shen, Xianyan,Zhou, Qiang,Fan, Xin,Yang, Sheng-Yong,Yu, Yamei,Chen, Qiang,Wang, Chun,Wu, Xin,Peng, Yong
supporting information, p. 130 - 134 (2018/11/30)
Peptidyl-prolyl cis-trans isomerase Pin1 plays a crucial role in the development of human cancers. Recently, we have disclosed that Pin1 regulates the biogenesis of miRNA, which is aberrantly expressed in HCC and promotes HCC progression, indicating the therapeutic role of Pin1 in HCC therapy. Here, 7-(benzyloxy)-3,5-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one (AF-39) was identified as a novel Pin1 inhibitor. Biochemical tests indicate that AF-39 potently inhibits Pin1 activity with an IC50 values of 1.008 μm, and also displays high selectivity for Pin1 among peptidyl prolyl isomerases. Furthermore, AF-39 significantly suppresses cell proliferation of HCC cells in a dose- and time-dependent manner. Mechanistically, AF-39 regulates the subcellular distribution of XPO5 and increases miRNAs biogenesis in HCC cells. This work provides a promising lead compound for HCC treatment, highlighting the therapeutic potential of miRNA-based therapy against human cancer.
Synthesis of pyrazole-substituted chromene analogues with selective anti-leukemic activity
Madhu,Sudhakar,Santosh Kumar,Rajashekher Reddy,Sravani,Ramakrishna,Prasad Rao, Ch.
, p. 2421 - 2428 (2017/11/24)
We report design and synthesis of a series of flavanone/chromene derivatives containing pyrazoles 6a–6h and 8a–8e with potent anti-leukemic activity. Anti-leukemic activity of novel flavanone derivatives was tested using the K562 cell line. The parental flavanone was selected as the reference compound in identification of analogues with superior anti-leukemic activity. More than two-thirds of the derivatives displayed higher activity than the initial flavanone. Positions of substituents that promoted anti-leukemic activity were identified on both the chromene and pyrazole fragments. Compounds 6b and 6c showed the highest activity against K562 cell line, with IC50 values 3.0 and 0.5 μM respectively. Notably, compounds 6b and 6c displayed very high selectivity in inhibition of leukemic cells (K562) but not of healthy HEK293 cells or solid cancer cell lines HeLa, MCF7 and BT474. Moreover, both the 6b and 6c compounds were predicted to have good ADME properties.
Palladium-Catalyzed [3+3] Annulation of Vinyl Chromium(0) Carbene Complexes through Carbene Migratory Insertion/Tsuji–Trost Reaction
Wang, Kang,Ping, Yifan,Chang, Taiwei,Wang, Jianbo
, p. 13140 - 13144 (2017/10/11)
Vinyl chromium(0) Fischer carbene complexes were employed as the source of π-allylic palladium species for catalytic [3+3] annulation under palladium catalysis. Mechanistically, this transformation is proposed to involve carbene migratory insertion and intramolecular Tsuji–Trost reaction as the key steps. Substituted six-membered heterocyclic flavonones and quinolines are obtained, depending on the nucleophilic functional group on the coupling partners.
A Borane-Catalyzed Metal-Free Hydrosilylation of Chromones and Flavones
Ren, Xiaoyu,Han, Caifang,Feng, Xiangqing,Du, Haifeng
, p. 2421 - 2424 (2017/11/04)
A Piers-type hydrosilylation of chromones and flavones has been successfully realized for the first time using 0.1 mol % of borane catalyst generated in situ by hydroboration of pentafluorostyrene with HB(C 6 F 5) 2 to afford a variety of chromanones and flavanones in 60-99% yields. An attempt for the asymmetric transformation with chiral diyne and HB(C 6 F 5) 2 gave chromanones and flavanones in high yields with up to 32% ee.
