3034-09-1Relevant academic research and scientific papers
An efficient synthesis of flavanones and their docking studies with aldose reductase
Kondhare,Gyananath,Tamboli, Yasinalli,Kumbhar, Santosh S.,Choudhari, Prafulla B.,Bhatia, Manish S.,Zubaidha
, p. 987 - 998 (2017/04/14)
A series of flavanone derivatives have been synthesized from 2-hydroxy acetophenone and benzaldehyde using fused calcium chloride in good to moderate yields, and their in vitro aldose reductase inhibitory activity has been tested on aldose reductase purified enzyme from Bovine lens. Most of the synthesized compounds exhibited potent aldose reductase inhibitory activity, and the obtained results are supported by the docking studies. Among the tested derivatives, 2, 3, 4-methoxy derivative 19 (IC50 5.88 ± 0.03 μM) exhibited the highest inhibitory activity whereas 2-methoxy derivative 12 showed the lowest, and the remaining compounds exhibited moderate activity with IC50 in the range of 6.09–7.89 μM. The spatial configuration of the most active derivative 19 was compared with pharmacophore requirements of the aldose reductase inhibitor site using a molecular modeling system.
Guanidino-graphene catalysed synthesis of flavones via Aldol-Michael-oxidation
Mishra, Sweta,Arora, Smriti,Nagpal, Ritika,Chauhan, Shive Murat Singh
, p. 2525 - 2530 (2017/03/09)
Guanidino-graphene has been synthesized by the reaction of bromoamine with reduced graphene oxide and characterized by FT-IR, Raman, TGA, powder XRD, TEM, SEM, and zeta potential. It is a cheap, heterogeneous and environmentally benign solid base catalyst used for cascade Aldol-Michael-oxidation in the synthesis of chalcone, flavonoids.
SAR studies of o-hydroxychalcones and their cyclized analogs and study them as novel inhibitors of cathepsin B and cathepsin H
Raghav,Garg
, p. 55 - 63 (2014/06/10)
Cathepsins have emerged as a potential target for anti-cancer drug development. In the present study, we have synthesized three structurally related series of flavanoids i.e., 2′-hydroxychalcones, flavanones and flavones and assayed in vitro to study their inhibitory potency against cathepsin B and H, promising drug candidate for cancer therapy. Enzyme kinetics studies were carried out in presence of these compounds after preliminary proteolytic studies on endogenous protein substrates. SAR studies suggested that open chain flavanoids were better inhibitors as compared to their cyclized analogs. The most potent inhibitors among the three series were nitro substituted compounds 1g, 2g and 3g with Ki values of ～6.18 × 10-8 M, 4.8 × 10-7 M and 7.85 × 10-7 M for cathepsin B and Ki values of ～2.8 × 10-7 M, 31.8 × 10-6 M and 33.7 × 10 -6 M for cathepsin H, respectively. The relationship between chalcone, flavanones and flavone structures interpreted by docking studies on cathepsin B and H also provided useful insights.
Applications of caged-designed proton sponges in base-catalyzed transformations Dedicated to Professor Milan Kratochvíl for his 90th birthday anniversary.
Galeta, Juraj,Potá?ek, Milan
, p. 87 - 92 (2014/11/08)
Superbasic properties of caged proton sponges (PSs) - substituted diazatetracyclo[4.4.0.13,10.15,8]dodecanes (DTDs) - were utilized in Knoevenagel and Claisen-Schmidt condensations, the Pudovik reaction, and Michael addition. This investigation covers the influence of the solvent, reaction temperature, catalyst loadings as well as the electronic properties of substituents upon the reaction. Moreover, we provided an activity comparison between our new base and a well-known and commercially available proton sponge (DMAN). The basicity (in MeCN) of our chosen DTD (pKBH+=21.7±0.1) exceeded the prototypal PS - 1,8-bis(dimethylamino)naphthalene (DMAN, pKBH+=18.6), by three orders of magnitude. We proved that DTDs are reasonably active species in monitored reactions, which is a consequence of a hydrogen bridge angle (～130°) between the two nitrogen atoms and the captured proton. We present here syntheses of aminoindolizine, substituted 4H-chromene, and flavanones, and the unexpected formation of a bis-addition product formed after Michael addition, all under mild conditions.
Fe(HSO4)3/SiO2: An efficient and heterogeneous catalyst for one-pot synthesis of 2-aryl-chromene-4-ones (flavanones)
Eshghi, Hossein,Rahimizadeh, Mohammad,Mousavi, Seyed Mohsen
supporting information, p. 438 - 443 (2014/04/17)
Silica ferric hydrogensulphate is an efficient heterogeneous catalyst for cyclisation of 2-hydroxychalcones to their corresponding flavanones (chromanone). This intramolecular oxa-Michael reaction was carried out in high yields in the presence of electron donating and electron withdrawing groups in the chalcone structure. Also, we found that aniline can act as an organic co-catalyst in direct synthesis of flavanones from 2-hydroxyacethophenone and aldehydes in the presence of Fe(HSO4)3/SiO2. Flavanones were prepared in high yields in a new catalytic system with similar substituted effect in the indirect cyclisation method. The catalyst in all the above reactions is reusable without significant decreases in its activity after four times of recycling.
Hydromagnesite as an efficient recyclable heterogeneous solid base catalyst for the synthesis of flavanones, flavonols and 1,4-dihydropyridines in water
Rajesh, U. Chinna,Manohar, Sunny,Rawat, Diwan S.
, p. 3170 - 3178 (2013/12/04)
A form of hydromagnesite (HM) with flower-like thin-sheet morphology was synthesized by an environmentally benign approach using simple conventional heating at moderate temperature without using any template in water as medium. The versatility of this HM catalyst was studied in the synthesis of flavanones, flavonols and the multicomponent synthesis of 1,4-dihydropyridines in water. The recyclability of catalyst was studied for six times and there was no appreciable loss in its catalytic activity. Copyright
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.
Synthetic approach to flavanones and flavones via ligand-free palladium(ii)-catalyzed conjugate addition of arylboronic acids to chromones
Kim, Donghee,Ham, Kyungrok,Hong, Sungwoo
experimental part, p. 7305 - 7312 (2012/09/22)
The remarkable catalytic effects of Fe(OTf)3 in the context of the Pd(ii)-catalyzed conjugate addition of arylboronic acids to chromones were observed to yield a variety of flavanones under mild conditions. The addition of catalytic amounts of DDQ and KNO2 to the reactions exclusively yielded flavone analogs. The reaction scope for the transformation was fairly broad, affording good yields of a wide range of flavanones and flavones, which are privileged structures in many biologically active compounds.
Synthesis of flavanones, azaflavanones, and thioflavanones catalyzed by PMA-SiO2 as a mild, efficient, and reusable catalyst
Sakirolla, Raghavendra,Yaeghoobi, Marzieh,Rahman, Noorsaadah Abd.
experimental part, p. 797 - 800 (2012/09/07)
Cyclization of a variety of chalcones to flavanones catalyzed by 1 mol% phosphomolybdic acid (PMA) supported on silica as a mild, efficient, and reusable catalyst was carried out in high yields. PMA-SiO2 is an efficient, inexpensive, and green catalyst which gave high conversion yields and could be recycled up to three times without significant loss in activity. Springer-Verlag 2011.
Environmentally benign syntheses of flavanones
Chen, Po-Yuan,Wang, Tzu-Pin,Chiang, Michael Y.,Huang, Keng-Shian,Tzeng, Cherng-Chyi,Chen, Yi-Long,Wang, Eng-Chi
, p. 4155 - 4160 (2011/06/26)
Mild and environmentally benign methods for the syntheses of flavanones are described. The reaction of o-hydroxyacetophenones (1) and benzaldehydes (2) in water in the presence of DABCO at room temperature gave 3-hydroxy-1-(2- hydroxylphenyl)-3-arylpropan-1-ones (3a-i) as intermediates. Followed by an intramolecular dehydration of the 3a-i with the modified Mitsunobu's reaction, the target flavanones (4a-i) were obtained. Moreover, the reaction of 1 and 2 at the same conditions but at reflux gave flavanones in one pot with good yields.
