41255-15-6Relevant academic research and scientific papers
Convenient synthesis of flavanone derivatives via oxa-Michael addition using catalytic amount of aqueous cesium fluoride
Miura, Motofumi,Shigematsu, Karin,Toriyama, Masaharu,Motohashi, Shigeyasu
supporting information, (2021/10/25)
A total of 36 flavanones, which included polycyclic aromatic and heterocyclic rings, were readily synthesized via oxa-Michael addition from the corresponding hydroxychalcones with a catalytic amount of aqueous cesium fluoride solution under mild conditions. This method could be applied to the scalable synthesis of eriodictyol as a known potent inhibitor of the SARS-CoV-2 spike protein.
Synthesis of 3-HCF2S-Chromones through Tandem Oxa-Michael Addition and Oxidative Difluoromethylthiolation
Zhang, Pingshun,Chen, Wanzhi,Liu, Miaochang,Wu, Huayue
supporting information, p. 9326 - 9329 (2019/12/24)
A simple protocol for the synthesis of difluoromethylthiolated chromen-4-ones using elemental sulfur and ClCF2CO2Na as the difluoromethylthiolating agent is described. Three-component reactions of 2′-hydroxychalcones, ClCF2CO2Na, and sulfur under basic conditions using TEMPO as the oxidant afforded HCF2S-containing 4H-chromen-4-one and 9H-thieno[3,2-b]chromen-9-one derivatives in good yield. The protocol is practical and efficient, and the starting materials are cheap and readily available.
From Carbamate to Chalcone: Consecutive Anionic Fries Rearrangement, Anionic Si → C Alkyl Rearrangement, and Claisen-Schmidt Condensation
Kumar, Singam Naveen,Bavikar, Suhas Ravindra,Pavan Kumar, Chebolu Naga Sesha Sai,Yu, Isaac Furay,Chein, Rong-Jie
, p. 5362 - 5366 (2018/09/12)
A highly efficient one-pot procedure was developed for the synthesis of various 2′-hydroxychalcones from phenyl diethylcarbamate, featuring consecutive Snieckus-Fries rearrangement, anionic Si a?' C alkyl rearrangement, and Claisen-Schmidt condensation in a single operation. The applicability of this protocol was demonstrated by the highly efficient synthesis of the anti-inflammatory natural product lonchocarpin. The mechanism insight is also provided.
Coumarin based novel ligands in the Suzuki–Miyaura and Mizoroki–Heck cross-couplings under aqueous medium
Waheed, Mohammed,Ahmed, Naseem
supporting information, p. 3785 - 3789 (2016/07/26)
Coumarin-based novel ligands (benzylidine-bis-(4-hydroxycoumarin)-diethylamines) were easily synthesized using 4-hydroxycoumarin, aromatic aldehydes, and diethylamine. The ionic ligand structure was established by X-ray study. They are air and moisture stable ligands and have shown highly efficient catalytic activity with Pd(OAc)2(0.1 mol % loading) in the Suzuki–Miyaura and (0.3 mol % loading) in the Mizoroki–Heck cross-coupling reactions in water or water/ethanol mixture. Pd-catalyst was reused efficiently without affecting variety of functional groups in the reaction.
Extended Aromatic and Heteroaromatic Ring Systems in the Chalcone-Flavanone Molecular Switch Scaffold
Muller, Brian M.,Litberg, Theodore J.,Yocum, Reid A.,Pniewski, Chanté A.,Adler, Marc J.
, p. 5775 - 5781 (2016/07/13)
Previous work on the o-hydroxychalcone/flavanone molecular switching scaffold showed that simple substitutions alter the pH range in which rapid interconversion occurs. Herein, more impactful structural modifications were performed via alteration of the characteristic phenyl rings to alternative aromatic systems. It was determined that the scaffold was still viable after these changes and that the range of accessible midpoint pH values was markedly increased. To further explore the switch's scope, scaffolds able to have multiple switching events were also investigated.
Inhibitory activity of prostaglandin E2 production by the synthetic 2′-hydroxychalcone analogues: Synthesis and SAR study
Tran, Thanh-Dao,Park, Haeil,Kim, Hyun Pyo,Ecker, Gerhard F.,Thai, Khac-Minh
experimental part, p. 1650 - 1653 (2009/11/30)
A series of 2′-hydroxychalcones has been synthesized and screened for their in vitro inhibitory activities of cyclooxygenase-2 catalyzed prostaglandin production from lipopolysaccharide-treated RAW 264.7 cells. Structure-activity relationship study suggested that inhibitory activity against prostaglandin E2 production was governed to a greater extent by the substituent on B ring of the chalcone, and most of the active compounds have at least two methoxy or benzyloxy groups on B ring. The relationship between chalcone structures and their PGE2 inhibitory activities was also interpreted by docking study on cyclooxygenase-2.
Synthesis and characterization of some substituted chromones as an anti-infective and antioxidant agents
Rode, Milind,Gupta,Karale,Rindhe
scheme or table, p. 1597 - 1602 (2009/06/28)
(Chemical Equation Presented) A series of substituted chromones were synthesized and characterized by spectral data. Some of the synthesized compounds were tested for in-vitro antibacterial, antifungal and antioxidant activity. Two compounds have shown ve
Design and synthesis of novel diphenacoum-derived, conformation-restricted vitamin K 2,3-epoxide reductase inhibitors
Chen, Ding-Uei,Kuo, Pei-Yu,Yang, Ding-Yah
, p. 2665 - 2668 (2007/10/03)
Two novel diphenacoum-derived analogues 5 and 6 are designed, synthesized and tested as potential vitamin K 2,3-epoxide reductase (VKOR) inhibitors. The inhibition studies indicated that 5 is a potent VKOR inhibitor, which confirmed that the replacement of the tetrahydronaphthalene on diphenacoum to a chroman functionality does not have a major impact on inhibition potency. The conformation-restricted compound 6 is a moderate inhibitor which may serve as a lead compound for further study of the mode of action of coumarin-type anticoagulants at the molecular level.
The Direct Preparation of Flavones from 2'-Hydroxychalcones Using Disulfides
Hoshino, Yukio,Oohinata, Toshinori,Takeno, Noboru
, p. 2351 - 2352 (2007/10/02)
Flavone was obtained by a reaction of 2'-hydroxychalcone with disulfides in good yield.Among several disulfides, diphenyl disulfide gave the best result.Under the same conditions, some flavones were obtained from the corresponding 2'-hydroxychalcones in satisfactory yields.
