59887-88-6Relevant articles and documents
Synthesis of (±)-3,3′-bis(4-hydroxy-2H-benzopyran): A literature correction
Hong, Ran,Feng, Jun,Hoen, Rob,Lin, Guo-Qiang
, p. 8685 - 8689 (2001)
The synthesis of bisbenzopyran-4-ol (1) was performed through the key steps of iodination, nickel(0)-modified Ullmann-type reaction, hydrogen-transfer hydrogenation and diastereoselective reduction. The X-ray diffraction experiment of compound 9 confirmed that the reported structure in the literature was not the real natural product.
Asymmetric Synthesis of Sakuranetin-Relevant Flavanones for the Identification of New Chiral Antifungal Leads
Kong, Wenlong,Lai, Jixing,Li, Shengkun,Yang, Juan
, (2022/03/31)
Discovery and efficient synthesis of new promising leads have a central role in agrochemical science. Reported herein is the sakuranetin-directed synergistic exploration of an asymmetric synthesis and an antifungal evaluation of chiral flavanones. A new palladium catalytic system with CarOx-type ligands was successfully identified for the highly enantioselective addition of arylboronic acids to chromones. This enabled the facile and programmable construction of a constellation of chiral flavanones (up to 98% yield and 97% ee), in which (R)-pinostrobin was efficiently constructed without laborious protecting/deprotecting operations. Its good performance in asymmetric induction and functional tolerance expanded the chemical space of pharmaceutically important flavanones. The chiral differentiation of flavanones based on antifungal activity and a concise structure-activity relationship model was disclosed and summarized. This synergistic project culminated with acquisition of the naturally unprecedented flavanones with better antifungal potentials than sakuranetin, in which the R-enantiomer of flavanone 54 (EC50 = 0.8 μM) demonstrated better performance than boscalid against Rhizoctonia solani. The novel scaffold and predicted new target compared with the commercial fungicides in the FRAC reinforce the value of further exploration.
The study on structure-activity relationship between chromone derivatives and inhibition of superoxide anion generating from human neutrophils
Chang, Yi-Han,Shu-Yen, Fang,Lai, Hsuan-Yu,Hwang, Tsong-Long,Hung, Hsin-Yi
supporting information, (2021/02/09)
Over activation of neutrophils has been linked to many inflammatory diseases; one of critical pathologic mechanisms is that generation and exocellular release of superoxide anion from neutrophils results in peripheral tissues damage. Besides, in this study, 2-(3,5-dimethoxyphenoxy)-5,7-dimethoxy-chromen-4-one (4), a 2-phexnoychromone from our compound bank, was demonstrated to have the moderate inhibitory effect on superoxide anion generating. Therefore, serial chromones substituted with phenols or 3-flourothiophenol were designed, synthesized, and examined for suppression of superoxide anion generation. In accordance with the results, the methoxy group at 7 position (R3) of the chromone, as well as a hydrogen bond donor at a meta site of the phenyl ring greatly impacted on the activity. 2-(3-fluorophenyl)sulfanyl-7-methoxy-chromen-4-one (16), a successful example of bioisosteres from a phenol to a thiophenol, exhibited prominent anti-inflammatory effects with the IC50 value against superoxide anion generation of 5.0 ± 1.4 μM.
Direct Enantio- and Diastereoselective Vinylogous Addition of Butenolides to Chromones Catalyzed by Zn-ProPhenol
Trost, Barry M.,Gnanamani, Elumalai,Kalnmals, Christopher A.,Hung, Chao-I Joey,Tracy, Jacob S.
supporting information, p. 1489 - 1493 (2019/01/30)
We report the first enantio- and diastereoselective 1,4-addition of butenolides to chromones. Both α,β- and β,γ-butenolide nucleophiles are compatible with the Zn-ProPhenol catalyst, and preactivation as the siloxyfurans is not required. The scope of electrophiles includes a variety of substituted chromones, as well as a thiochromone and a quinolone, and the resulting vinylogous addition products are generated in good yield (31 to 98%), diastereo- (3:1 to >30:1), and enantioselectivity (90:10 to 99:1 er). These Michael adducts allow rapid access to several natural product analogs, and can be easily transformed into a variety of other interesting scaffolds as well.
Substituent-Oriented Synthesis of Substituted Pyrazoles/Chromeno[3,2- c]pyrazoles via Sequential Reactions of Chromones/3-Chlorochromones and Tosylhydrazones
Dai, Tianzi,Li, Qunyi,Zhang, Xiaofei,Yang, Chunhao
, p. 5913 - 5921 (2019/05/10)
A facile and efficient synthetic strategy for the chemoselective synthesis of monocyclic/tricyclic-fused pyrazoles was developed, and it was oriented by different 3-position substituents (H or Cl) on the chromones. The reaction proceeded in a one-pot sequential way with a broad substrate scope and moderate to excellent yields.
Iron-Catalyzed Regioselective Decarboxylative Alkylation of Coumarins and Chromones with Alkyl Diacyl Peroxides
Jin, Can,Sun, Bin,Xu, Tengwei,Yan, Zhiyang,Zhang, Xun
supporting information, p. 1585 - 1591 (2019/08/07)
A facile iron-catalyzed decarboxylative radical coupling of alkyl diacyl peroxides with coumarins or chromones has been developed, affording a highly efficient approach to synthesize a variety of α-alkylated coumarins and β-alkylated chromones. The reaction proceeded smoothly without adding any ligand or additive and provided the corresponding products containing a wide scope of functional groups in moderate to excellent yields. This protocol was highlighted by its high regioselectivity, readily available starting materials, and operational simplicity.
An Efficient Microwave-Assisted Propylphosphonic Anhydride (T3P )-Mediated One-Pot Chromone Synthesis via Enaminones
Balakrishna,Kandula, Venu,Gudipati, Ramakrishna,Yennam, Satyanarayana,Devi, P. Uma,Behera, Manoranjan
supporting information, p. 1087 - 1091 (2018/04/30)
An efficient synthesis of 4 H -chromene-4-ones via enamino ketones, with cyclization by using T3P under microwave heating is described. This is the first report for the synthesis of chromones by using T3P . Significant features of this method include short reaction times and high-purity products.
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
supporting information, 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.
Synthesis, antiproliferative, and c-Src kinase inhibitory activities of 4-oxo-4H-1-benzopyran derivatives
Chand, Karam,Tiwari, Rakesh K.,Kumar, Sumit,Shirazi, Amir Nasrolahi,Sharma, Sweta,Van Der Eycken, Erik V.,Parmar, Virinder S.,Parang, Keykavous,Sharma, Sunil K.
, p. 562 - 572 (2015/03/30)
A new class of 4-oxo-4H-1-benzopyran derivatives were synthesized and their antiproliferative activity examined against a panel of three human cancer cell lines, that is, breast carcinoma (MDA-MB-468), ovarian adenocarcinoma (SK-OV-3), and colorectal adenocarcinoma (HT-29). Two compounds, that is, 3-hexyl-7,8-dihydroxy-4-oxo-4H-1-benzopyran and (E)-ethyl 3-(7-methoxy-4-oxo-4H-1-benzopyran-3-yl)acrylate were found to be potent against all three cancer cell lines studied at 50 μM concentration. Also, the inhibitory potency of the compounds was evaluated against active Src kinase. A few of these compounds exhibited modest Src kinase inhibitory activity (IC50 = 52-57 μM). Structure-activity relationship studies with respect to the nature and position of substituents on the lead compounds could be further exploited for the design and development of more potent antiproliferative agents and/or Src kinase inhibitors.
2,3-Unsubstituted chromones and their enaminone precursors as versatile reagents for the synthesis of fused pyridines
Iaroshenko, Viktor O.,Mkrtchyan, Satenik,Gevorgyan, Ashot,Miliutina, Mariia,Villinger, Alexander,Volochnyuk, Dmytro,Sosnovskikh, Vyacheslav Ya.,Langer, Peter
supporting information; experimental part, p. 890 - 894 (2012/02/02)
A divergent and regioselective approach to fused pyridines was developed through formal [3 + 3] cyclocondensations from simple 2,3-unsubstituted chromones or their enaminone precursors.
