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6-METHOXY-4-OXO-4H-CHROMENE-3-CARBALDEHYDE is a chemical with a specific purpose. Lookchem provides you with multiple data and supplier information of this chemical.

42059-79-0

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42059-79-0 Usage

Synthesis Reference(s)

Tetrahedron, 30, p. 3553, 1974 DOI: 10.1016/S0040-4020(01)97034-6

Check Digit Verification of cas no

The CAS Registry Mumber 42059-79-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 4,2,0,5 and 9 respectively; the second part has 2 digits, 7 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 42059-79:
(7*4)+(6*2)+(5*0)+(4*5)+(3*9)+(2*7)+(1*9)=110
110 % 10 = 0
So 42059-79-0 is a valid CAS Registry Number.
InChI:InChI=1/C11H8O4/c1-14-8-2-3-10-9(4-8)11(13)7(5-12)6-15-10/h2-6H,1H3

42059-79-0 Well-known Company Product Price

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  • Aldrich

  • (732931)  6-Methoxychromone-3-carboxaldehyde  

  • 42059-79-0

  • 732931-250MG

  • 1,585.35CNY

  • Detail

42059-79-0Relevant academic research and scientific papers

Design and synthesis of chromone-nitrogen mustard derivatives and evaluation of anti-breast cancer activity

Sun, Jianan,Mu, Jiahui,Wang, Shenglin,Jia, Cai,Li, Dahong,Hua, Huiming,Cao, Hao

, p. 431 - 444 (2022/01/04)

Chromone has emerged as one of the most important synthetic scaffolds for antitumor activity, which promotes the development of candidate drugs with better activity. In this study, a series of nitrogen mustard derivatives of chromone were designed and syn

Synthesis and biological evaluation of 3-styrylchromone derivatives as selective monoamine oxidase B inhibitors

Takao, Koichi,Takemura, Yuri,Nagai, Junko,Kamauchi, Hitoshi,Hoshi, Kaori,Mabashi, Ryo,Uesawa, Yoshihiro,Sugita, Yoshiaki

, (2021/06/15)

A series of 3-styrylchromone derivatives was synthesized and evaluated for monoamine oxidase (MAO) A and B inhibitory activities. Most of all derivatives inhibited MAO-B selectively, except compound 21. Compound 19, which had a methoxy group at R2 on the chromone ring and chlorine at R4 on phenyl ring, potently inhibited MAO-B, with an IC50 value of 2.2 nM. Compound 1 showed the highest MAO-B selectivity, with a selectivity index of >3700. Further analysis of these compounds indicated that compounds 1 and 19 were reversible and mixed-type MAO-B inhibitors, suggesting that their mode of action may be through tight-binding inhibition to MAO-B. Quantitative structure–activity relationship (QSAR) analyses of the 3-styrylchromone derivatives were conducted using their pIC50 values, through Molecular Operating Environment (MOE) and Dragon. There were 1796 descriptors of MAO-B inhibitory activity, which showed significant correlations (P 50 value index exhibited a determination coefficients (R2) of 0.972 and a Leave-One-Out cross-validated determination coefficients (Q2) of 0.914. These data suggest that the 3-styrylchromone derivatives assessed herein may be suitable for the design and development of novel MAO inhibitors.

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.

Novel p-functionalized chromen-4-on-3-yl chalcones bearing astonishing boronic acid moiety as MDM2 inhibitor: Synthesis, cytotoxic evaluation and simulation studies

Bhatia, Richa Kaur,Coutinho, Evans C.,Garg, Ruchika,Kancherla, Satyavathi,Kaur, Maninder,Madan, Jitender,Pissurlenkar, Raghuvir R. S.,Singh, Lakhwinder,Yadav, Manmohan

, p. 212 - 228 (2020/03/10)

Background: Novel 4-[3-(6/7/8-Substituted 4-Oxo-4H-chromen-3-yl)acryloyl]phenyl-boronic acid derivatives (5a-h) as well as other 6/7/8-substituted-3-(3-oxo-3-(4-substituted-phenyl)prop-1-enyl)-4H-chromen-4-one derivatives (3a-u) have been designed as p53-MDM2 pathway inhibitors and reported to possess significant cytotoxic properties against several cancer cell lines. Objectives: The current project aims to frame the structure-anticancer activity relationship of chromen-4-on-3-yl chalcones (3a-u/5a-h). In addition, docking studies were performed on these chromeno-chalcones in order to have an insight into their interaction possibilities with MDM2 pro-tein. Methods: Twenty-nine chromen-4-on-3-yl chalcone derivatives (3a-u/5a-h) were prepared by utilizing silica supported-HClO4 (green route with magnificent yield) and tested against four cancer cell lines (HCT116, MCF-7, THP-1, NCIH322). Results: Among the series 3a-u, compound 3b exhibited the highest anticancer activity (with IC50 values ranging from 8.6 to 28.4 μM) overall against tested cancer cell lines. Interestingly, para-Boronic acid derivative (5b) showed selective inhibition against colon cancer cell line, HCT-116 with an IC50 value of 2.35 μM. Besides the emblematic hydrophobic interactions of MDM2 inhibi-tors, derivative 5b was found to exhibit extra hydrogen bonding with GLN59 and GLN72 residues of MDM2 in molecular dynamics (MD) simulation. All the compounds were virtually nontoxic against normal fibroblast cells. Conclusion: Novel compounds were obtained with good anticancer activity especially 6-Chlorochromen-4-one substituted boronic acid derivative 5b. The molecular docking study proposed good activity as a MDM-2 inhibitor suggesting hydrophobic as well as hydrogen bonding interactions with MDM2.

Synthesis and biological evaluation of chromone-3-carboxamides

Gordon, Allen T.,Ramaite, Isaiah D.I.,Mnyakeni-Moleele, Simon S.

, p. 148 - 160 (2021/01/20)

The aim of our study was to synthesize novel chromone-3-carboxamides and to conduct biological evaluations in search for lead compounds for the treatment of a range of debilitating disease states. Corresponding 2-hydroxyacetophenones were subjected to Vilsmeier-Haack formylation to give chromone-3-carbaldehydes, which were subsequently oxidised to give chromone-3-carboxylic acids. Treatment of the carboxylic acids with thionyl chloride resulted in the in situ formation of the corresponding acid chlorides, which were reacted with various amines in the presence of triethylamine to give the corresponding novel chromone-3-carboxamides in good yields. Selected chromone derivatives were then evaluated for their anti-inflammatory, anti-tryponosomal and cytotoxic properties.

Antiproliferative chromone derivatives induce K562 cell death through endogenous and exogenous pathways

Cao, Hao,Hua, Huiming,Huang, Xiaofang,Jiao, Runwei,Li, Dahong,Li, Haonan,Li, Zhanlin,Liu, Weiwei,Xu, Fanxing,Zang, Linghe

, p. 759 - 772 (2020/04/01)

A series of furoxan derivatives of chromone were prepared. The antiproliferative activities were tested against five cancer cell lines HepG2, MCF-7, HCT-116, B16, and K562, and two normal human cell lines L-02 and PBMCs. Among them, compound 15a exhibited the most potent antiproliferative activity. It was also found 15a produced more than 8 μM of NO at the peak time of 45 min by Griess assay. Generally, antiproliferative activity is positively related to NO release to some extent. Further in-depth studies on apoptosis-related mechanisms showed that 15a caused S-phase cell cycle arrest in a concentration-dependent manner and induced apoptosis significantly through mitochondria-related pathways. Human apoptosis protein array assay also demonstrated 15a increased the expression levels of pro-apoptotic Bax, Bad, HtrA2 and Trail R2/DR5. The expression of catalase and cell cycle blocker claspin were similarly up-regulated. In balance, 15a induced K562 cells death through both endogenous and exogenous pathways.

Chromone and donepezil hybrids as new multipotent cholinesterase and monoamine oxidase inhibitors for the potential treatment of Alzheimer's disease

Huang, Ming,Jiang, Neng,Kong, Ling-Yi,Lan, Jin-Shuai,Wang, Xiao-Bing,Yin, Fu-Cheng

, p. 225 - 233 (2020/04/22)

A series of chromone and donepezil hybrids were designed, synthesized, and evaluated as multipotent cholinesterase (ChE) and monoamine oxidase (MAO) inhibitors for the potential therapy of Alzheimer's disease (AD). In vitro studies showed that the great majority of these compounds exhibited potent inhibitory activity toward BuChE and AChE and clearly selective inhibition for hMAO-B. In particular, compound 5c presented the most balanced potential for ChE inhibition (BuChE: IC50 = 5.24 μM; AChE: IC50 = 0.37 μM) and hMAO-B selectivity (IC50 = 0.272 μM, SI = 247). Molecular modeling and kinetic studies suggested that 5c was a mixed-type inhibitor, binding simultaneously to peripheral and active sites of AChE. It was also a competitive inhibitor, which occupied the substrate and entrance cavities of MAO-B. Moreover, compound 5c could penetrate the blood-brain barrier (BBB) and showed low toxicity to rat pheochromocytoma (PC12) cells. Altogether, these results indicated that compound 5c might be a hopeful multitarget drug candidate with possible impact on Alzheimer's disease therapy.

Organocatalytic [10+4] cycloadditions for the synthesis of functionalised benzo[a]azulenes

Giardinetti, Maxime,Jessen, Nicolaj Inunnguaq,Christensen, Mette Louise,J?rgensen, Karl Anker

supporting information, p. 202 - 205 (2019/01/04)

A direct and mild strategy for the synthesis of benzo[a]azulenes based on an organocatalytic [10+4] cycloaddition reaction is described. The strategy enables a diversity-oriented approach for the synthesis of various poly-functionalised azulenes from easily accessible starting materials.

One pot and metal-free approach to 3-(2-Hydroxybenzoyl)-1-aza-anthraquinones

Yuan, Jiaqi,He, Qian,Song, Shanshan,Zhang, Xiaofei,Miao, Zehong,Yang, Chunhao

supporting information, (2019/08/30)

Herein, a direct strategy to synthesize 3-(2-hydroxybenzoyl)-1-aza-anthraquinones with excellent efficiency,mild conditions, and benign functional group compatibilitywas reported. Avariety of 3-formylchromone compounds were employed as compatible substrates and this protocol gave the 3-(2-hydroxybenzoyl)-1-aza-anthraquinone derivatives in good to excellent yields without inert gas and expensive transition metal catalysts. Some compounds displayed good anti-proliferative activities.

Coumarin versus Chromone Monoamine Oxidase B Inhibitors: Quo Vadis?

Fonseca, André,Reis, Joana,Silva, Tiago,Matos, Maria Jo?o,Bagetta, Donatella,Ortuso, Francesco,Alcaro, Stefano,Uriarte, Eugenio,Borges, Fernanda

supporting information, p. 7206 - 7212 (2017/09/07)

Because of the lack of significant disease-modifying drugs for neurodegenerative disorders, a pressing need for new chemical entities endowed with IMAO-B still exists. Within this framework, and for the first time, a study was performed to compare coumari

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