42059-58-5Relevant academic research and scientific papers
Discovery of Novel Chromone Derivatives Containing a Sulfonamide Moiety as Anti-ToCV Agents through the Tomato Chlorosis Virus Coat Protein-Oriented Screening Method
Jiang, Donghao,Chen, Jixiang,Zan, Ningning,Li, Chunyi,Hu, Deyu,Song, Baoan
, p. 12126 - 12134 (2021/10/26)
A number of novel chromone derivatives containing sulfonamide moieties were designed and synthesized, and the activity of compounds against tomato chlorosis virus (ToCV) was assessed using the ToCVCP-oriented screening method. Comparative molecular field analysis (CoMFA) and comparative molecular similarity index analysis (CoMSIA) models were established based on the dissociation constant (Kd) values of the target compounds, and compound 35 was designed and synthesized with the aid of CoMFA and CoMSIA models. The study of affinity interaction indicated that compound 35 exhibited excellent affinity with ToCVCP with a Kd value of 0.11 μM, which was better than that of the positive control agents xiangcaoliusuobingmi (0.44 μM) and ningnanmycin (0.79 μM). In addition, the in vivo inhibitory effect of compound 35 on the ToCVCP gene was evaluated by the quantitative real-time polymerase chain reaction. ToCVCP gene expression levels of the compound 35 treatment group were reduced by 67.2%, which was better than that of the positive control agent ningnanmycin (59.5%). Therefore, compound 35 can be used as a potential anti-ToCV drug in the future.
Discovery and Optimization of Chromone Derivatives as Novel Selective Phosphodiesterase 10 Inhibitors
Gao, Yuqi,Guo, Lei,Huang, Yi-You,Lai, Zengwei,Li, Xiangmin,Li, Zhe,Luo, Hai-Bin,Wu, Deyan,Wu, Yinuo,Yu, Yan-Fa,Zhang, Chen,Zhang, Sirui,Zhou, Qian
, (2020/03/24)
Phosphodiesterase 10 (PDE10) inhibitors have received much attention as promising therapeutic agents for central nervous system (CNS) disorders such as schizophrenia and Huntington's disease. Recently, a hit compound 1 with a novel chromone scaffold has shown moderate inhibitory activity against PDE10A (IC50 = 500 nM). Hit-to-lead optimization has resulted in compound 3e with an improved inhibitory activity (IC50 = 6.5 nM), remarkable selectivity (>95-fold over other PDEs), and good metabolic stability (RLM t1/2 = 105 min) by using an integrated strategy (molecular modeling, chemical synthesis, bioassay, and cocrystal structure). The cocrystal structural information provides insights into the binding pattern of 3e in the PDE10A catalytic domain to highlight the key role of the halogen and hydrogen bonds toward Tyr524 and Tyr693, respectively, thereby resulting in high selectivity against other PDEs. These new observations are of benefit for the rational design of the next generation PDE10 inhibitors for CNS disorders.
Discovery of New Chemical Entities for Old Targets: Insights on the Lead Optimization of Chromone-Based Monoamine Oxidase B (MAO-B) Inhibitors
Reis, Joana,Cagide, Fernando,Chavarria, Daniel,Silva, Tiago,Fernandes, Carlos,Gaspar, Alexandra,Uriarte, Eugenio,Remi?o, Fernando,Alcaro, Stefano,Ortuso, Francesco,Borges, Fernanda
, p. 5879 - 5893 (2016/07/06)
The discovery of new chemical entities endowed with potent, selective, and reversible monoamine oxidase B inhibitory activity is a clinically relevant subject. Therefore, a small library of chromone derivatives was synthesized and screened toward human monoamine oxidase isoforms (hMAO-A and hMAO-B). The structure-activity relationships studies strengthen the importance of the amide spacer and the direct linkage of carbonyl group to the γ-pyrone ring, along with the presence of meta and para substituents in the exocyclic ring. The most potent MAO-B inhibitors were N-(3′-chlorophenyl)-4-oxo-4H-chromene-3-carboxamide (20) (IC50 = 403 pM) and N-(3′,4′-dimethylphenyl)-4-oxo-4H-chromene-3-carboxamide (27) (IC50 = 669 pM), acting as competitive and noncompetitive reversible inhibitors, respectively. Computational docking studies provided insights into enzyme-inhibitor interactions and a rationale for the observed selectivity and potency. Compound 27 stands out due to its favorable toxicological profile and physicochemical properties, which pointed toward blood-brain barrier permeability, thus being a valid candidate for subsequent animal studies.
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.
A Mild and Efficient Route to 3-Vinylchromones in Aqueous Micellar Media
Kumar, Vikash,Chatterjee, Amrita,Banerjee, Mainak
supporting information, p. 2364 - 2377 (2015/10/12)
A simple, mild, and ecofriendly method has been developed for the synthesis of 3-vinylchromones from 4-oxo-4H-1-benzopyran-3-carboxaldehyde (3-formylchromone) by simple Knoevenagel condensation with various active methylene compounds (AMC) in aqueous mice
A study of the reactions of 2-aryl-4-hydroxy-6H-1,3-thiazin-6-ones with chromone-3-carboxaldehydes
Shutov, Roman V.,Kuklina, Elizaveta V.,Ivin, Boris A.
experimental part, p. 266 - 269 (2011/02/26)
Reaction of 3-formylchromones with 2-aryl-4-hydroxy-6H-1,3-thiazin-6-ones in the presence of pyridine leads to formation of a mixture of novel N-thioaroyl-5-hydroxy-2H,5H-pyrano[3,2-]chromen-2-one-3-carboxamides and 2-aryl-5-(4′-oxochromen-3′-yl)-6,7-dihy
Alum [KA1(S04)2. 12H20]: An efficient, novel, clean, catalyst for Doebner Knoevenagel reaction for the efficient production of αβ-unsaturated acids
Suresh, Dhruva Kumar,Sandhu, Jagir S.
experimental part, p. 1479 - 1483 (2011/12/02)
Alum mediated solvent free, microwave enhanced, clean process for the production of -unsaturated acids 3, 5 and 7 is described. Only 10 mole % of alum is enough in this protocol to achieve optimal yields and this protocol is fairly general and applicable to heterocyclic aldehydes and benzopyran 3-aldehydes.
Development of practical methodologies for the synthesis of novel 3(4-oxo-4H-chromen-3-yl)acrylic acid hydrazides
Joshi, Ratnadeep S.,Mandhane, Priyanka G.,Badadhe, Pravin V.,Gill, Charansingh H.
experimental part, p. 735 - 738 (2012/02/05)
We report a new environmentally-benign, convenient and facile methodology for the synthesis of new series of 3(4-oxo-4H-chromen-3-yl)acrylic acid hydrazides derivatives designed by exploring the molecular hybridization approach between isoniazide and 3(4-
Facile route to 2,3-disubstituted chromanones via chromone-3-carboxaldehyde activated by silylation
Iwasaki, Hideharu,Kume, Takashi,Yamamoto, Yohsuke,Akiba, Kin-ya
, p. 1599 - 1602 (2007/10/02)
Aldol type condensation of chromone-3-carboxaldehyde (1) with active methylenes in the presence of t-butyldimethylsilyl triflate afforded silylated aldol adducts (4), which were further converted to 2,3-disubstituted chromanones by reaction with enol silyl ethers via the corresponding 4-siloxypyrylium salts.
