6051-86-1Relevant 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
, (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.
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.
Rhodium/chiral diene-catalyzed asymmetric 1,4-addition of arylboronic acids to chromones: A highly enantioselective pathway for accessing chiral flavanones
He, Qijie,Wang, Jun,So, Chau Ming,Hayashi, Tamio,Bian, Zhaoxiang
, p. 540 - 543 (2015/05/05)
Chromone has been noted to be one of the most challenging substrates in the asymmetric 1,4-addi-tion of α,β-unsaturated carbonyl compounds. By employing the rhodium complex associated with a chiral diene ligand, (R,R)-Ph-bod, the 1,4-addition of a variety of aryl-boronic acids was realized to give high yields of the corresponding flavanones with excellent enantioselectivities (≥97% ee, 99% ee for most substrates). Ring-opening side products, which would lead to erosion of product enantioselectivity, were not observed under the stated reaction conditions.
Iodine catalyzed one-pot synthesis of flavanone and tetrahydropyrimidine derivatives via Mannich type reaction
Kavala, Veerababurao,Lin, Chunchi,Kuo, Chun-Wei,Fang, Hulin,Yao, Ching-Fa
experimental part, p. 1321 - 1329 (2012/02/13)
A variety of functionalized flavanone derivatives and tetrahydropyrimidine derivatives were achieved under remarkably mild conditions. The combination of good to excellent yields, a simple work-up, and the high compatibility of functional groups makes this an attractive synthetic approach to access flavanone and tetrahydropyrimidine derivatives.
Lead optimization of 4-imidazolylflavans: New promising aromatase inhibitors
Yahiaoui, Samir,Pouget, Christelle,Buxeraud, Jacques,Chulia, Albert José,Fagnère, Catherine
, p. 2541 - 2545 (2011/06/22)
Our previous studies have shown that several 7-substituted-4- imidazolylflavans are potent inhibitors of aromatase. These compounds were designed considering the anti-aromatase effect of some natural flavonoids and the importance of an azole ring for synthetic inhibitors such as letrozole or anastrozole towards binding to the heme iron of aromatase. In this study, we report the optimization of these lead compounds by the modulation of flavan A ring. The resulting 7,8-benzo-4-imidazolylflavans were tested in order to assess their ability to inhibit aromatase. Biological data concerning enantiomers obtained from the chiral separation of the racemate compound 4-imidazolyl-7-methoxyflavan are also presented.
New 7,8-benzoflavanones as potent aromatase inhibitors: Synthesis and biological evaluation
Yahiaoui, Samir,Fagnere, Catherine,Pouget, Christelle,Buxeraud, Jacques,Chulia, Albert-Jose
, p. 1474 - 1480 (2008/09/19)
Some natural compounds such as flavonoids are known to possess a moderate inhibitory activity against aromatase, this enzyme being an interesting target for hormone-dependent breast cancer treatment. It has been demonstrated that the modulation of flavonoid skeleton could increase anti-aromatase effect. Therefore, new 7,8-benzoflavanones were synthesized and tested for their activity toward aromatase inhibition. It was observed that the introduction of a benzo ring at position C-7 and C-8 on flavanone skeleton led to new potent aromatase inhibitors, the resulting 7,8-benzoflavanones being until nine times more potent than aminogluthetimide (the first aromatase inhibitor used clinically).
Tandem Fries Reaction-Conjugate Addition under Microwave Irradiation in Dry Media; One-pot Synthesis of Flavanones
Moghaddam, Firouz Matloubi,Ghaffarzadeh, Mohammad,Abdi-Oskoui, Seyed Hossein
, p. 574 - 575 (2007/10/03)
An AlCl3-ZnCl2 mixture supported on silica gel is found to be an efficient medium for the Fries rearrangement of acyloxybenzene or naphthalene derivatives in solvent-free conditions under microwave irradiation.
A New Chromone and Flavone Synthesis and Its Utilization for the Sythesis of Potentially Antitumorigenic Polycyclic Chromones and Flavones
Harvey, Ronald G.,Hahn, Jung-Tai,Bukowska, Maria,Jackson, Henry
, p. 6161 - 6166 (2007/10/02)
A new synthesis of chromones and flavones based on the ortho-directed metalation of methoxymethyl aryl ethers with alkyllithium reagents is described.It entails reaction of the ortho-lithiated intermediates with a conjugated unsaturated aldehyde followed by oxidation of the allylic alcohol product with "periodinane" to yield an ortho-allylic ketone.The latter on heating in acetic acid undergoes loss of the methoxymethyl protecting group and cyclization to a chromanone (or flavanone, if a β-phenyl substituent is present).Dehydrogenation by treatment with pyrrolidinehydrotribromide (PHT) in dimethyl sulfoxide yields the corresponding chromones (or flavones).This synthetic approach appears general in its applicability.It has been applied to the synthesis of a series of polycyclic chromone and flavone compounds containing the naphthalene and pyrene ring systems that hold promise as agents for the chemoprevention of cancer.
