1635-31-0Relevant articles and documents
Synthesis of 3-aminocoumarin-N-benzylpyridinium conjugates with nanomolar inhibitory activity against acetylcholinesterase
Khunnawutmanotham, Nisachon,Laongthipparos, Cherdchai,Saparpakorn, Patchreenart,Chimnoi, Nitirat,Techasakul, Supanna
, p. 2545 - 2552 (2018)
A series of 3-amino-6,7-dimethoxycoumarins conjugated with the N-benzylpyridinium moiety through an amide-bond linkage was synthesized and evaluated for their acetylcholinesterase inhibitory activity. A number of the benzylpyridinium derivatives exhibited potent activities with inhibitory concentration (IC50) values in the nanomolar concentration range. Among them, the 2,3-difluo-robenzylpyridinium-containing compound was the most potent inhibitor with an IC50 value of 1.53 ± 0.01 nM. Docking studies revealed that the synthesized compounds inhibit the target enzyme by a dual binding site mechanism whereby the coumarin portion binds with the peripheral anionic site while the N-benzylpyridinium residue binds with the catalytic anionic site of the enzyme.
Tyrosine-like condensed derivatives as tyrosinase inhibitors
Matos, Maria Joao,Santana, Lourdes,Uriarte, Eugenio,Serra, Silvia,Corda, Marcella,Fadda, Maria Benedetta,Era, Benedetta,Fais, Antonella
, p. 742 - 746 (2012)
Objectives We report the pharmacological evaluation of a new series of 3-aminocoumarins differently substituted with hydroxyl groups, which have been synthesized because they include in their structures the tyrosine fragment (tyrosine-like compounds), with the aim of discovering structural features necessary for tyrosinase inhibitory activity. Methods The synthesized compounds 4 and 7-9 were evaluated in vitro as mushroom tyrosinase inhibitors. Key findings Two of the described compounds showed lower IC50 (concentration giving 50% inhibition of tyrosinase activity) than umbelliferone, used as a reference compound. Conclusions Compound 7 (IC50 = 53 μm) was the best tyrosinase inhibitor of this small series, having an IC50 value 10-fold lower than umbelliferone. Compound 7 (3-amino-7-hydroxycoumarin) had amino and hydroxyl groups precisely mimicking the same positions that both groups occupy on the tyrosine molecule. 2012 The Authors. JPP
An efficient and facile synthesis of substituted 3-aminocoumarins under mw irradiation in dry media
Valizadeh, Hassan,Shockravi, Abbas
, p. 475 - 478 (2004)
A variety of 3-aminocoumarins were prepared by reaction of salicylaldehyde derivatives with benzoylglycine catalyzed by piperidine under microwave irradiation (MWI) and subsequent acid hydrolysis. The structure of products was proven by elemental analysis, IR, NMR and Mass spectra. These investigations will contribute to development of environmentally friendly and inexpensive processes in organic synthesis.
Design and synthesis of aminocoumarin derivatives as DPP-IV inhibitors and anticancer agents
Soni, Rina,Soman, Shubhangi S.
, p. 277 - 284 (2018)
DPP-IV “a moonlighting protein” has immerged as promising pathway to control Type 2 diabetes as well as found to play key role in earlier stages of cancer. Here we have reported design, synthesis and applications of aminocoumarin derivatives as DPP-IV inhibitors. Compounds have been synthesized and studied for their DPP-IV inhibition activity. Three compounds have shown moderate inhibition at 100 μM concentration. All compounds were also screened for their anticancer activity against A549 (Lung cancer cell line), MCF-7 (Breast cancer cell line) using MTT assay. One of the compounds has shown very good anticancer activity with IC50 value 24 ± 0.1 nM against A549 cell line.
Design, synthesis and biological evaluation of amino organophosphorus imidazoles as a new type of potential antimicrobial agents
Gao, Wei-Wei,Rasheed, Syed,Tangadanchu, VijaiKumarReddy,Sun, Yi,Peng, Xin-Mei,Cheng, Yu,Zhang, Feng-Xiu,Lin, Jian-Mei,Zhou, Cheng-He
, p. 769 - 785 (2017)
A series of amino organophosphorus imidazoles were designed and synthesized as a novel structural type of antimicrobial agents. Bioactive evaluation in vitro showed that compound 3f exhibited equipotent or superior anti-methicillin-resistant Staphylococcus aureus (anti-MRSA) and anti-S. cerevisiae efficiencies (minimal inhibitory concentration (MIC)=2 μg/mL) to clinical drugs, and the combinations with antibacterial or antifungal drugs enhanced the antimicrobial efficiency. Highly active molecule 3f showed low propensity for bacteria to develop resistance, and the preliminary action mechanism studies demonstrated that 3f was membrane-active, but had no significant intercalation towards MRSA DNA. The computational study on 3f reasonably explained its high antimicrobial activity. Experimental data revealed that ground-state 3f-HSA complexes were formed mainly through hydrophobic interactions and hydrogen bonds with a spontaneous process, and the non-radioactive energy transfer from HSA to 3f occurred beyond F?rster resonance energy transfer theory. The participation of metal ions in 3f-HSA supramolucular system could increase the concentration of free compound 3f, and shorten its storage time and half-life in the blood to improve the maximum antimicrobial efficacy.
A novel class of human 15-LOX-1 inhibitors based on 3-hydroxycoumarin
Alavi, Seyed Jamal,Sadeghian, Hamid,Seyedi, Seyed Mohammad,Salimi, Alireza,Eshghi, Hossein
, p. 1125 - 1132 (2018)
Inflammations, sensitivities, and some cancers in mammals are intimately linked to the activity of lipo-oxygenase enzymes. Owing to the importance of these enzymes, mechanistic studies, product analysis, and synthesis of inhibitors have expanded. In this study, a series of hydroxycoumarins, methoxy-3-hydroxy coumarins, and 7-alkoxy-3-hydroxy coumarins were synthesized and evaluated as potential inhibitors of human 15-LOX-1. Among the synthetic coumarins, 7-methoxy-3-hydroxycoumarin derivative demonstrated potent inhibitory activity and the compound, 5f, showed the best result. Radical scavenging assessment, IC50, HNMR, and DPPH bleaching results indicate that the electronic properties are the major factors for the lipo-oxygenase inhibition potency of the synthetic coumarins. Based on the theoretical studies, it was suggested that the mesomeric effect of the substituent at the seventh position of the benzene ring is one of the major factors in the stability of the oxy-radical intermediate.
Synthesis of new 2H,4H-benzopyrano[3,4-b]pyridine-1,3,5-trione derivatives via carbon suboxide
Bonsignore, Leonardo,Loy, Giuseppe
, p. 117 - 119 (1998)
The new 2H,4H-[1]benzopyrano[3,4-b]pyridine-1,3,5-trione derivatives 10a-f were prepared in the following three steps; the first preparation of new N-(tert-butoxycarbonyl)-3-amino-2H-1-benzopyran-2-one derivatives 5a-f by reaction of coumarin-3-carboxylic acids and diphenylphosphorlyazide, then hydrolysis of 5a-f with gaseous hydrogen chloride to give the corresponding amines 7a-f, and finally the preparation of 10a-f by reaction of 7a-f and carbon suboxide in the presence of a Lewis acid.
Mild and highly efficient deacetylation of acetamido and acetoxy coumarins: A convenient and expeditious synthesis of substituted 3-aminocoumarins
Krajňáková, Jana,Joniak, Jakub,Putala, Martin,Górová, Renáta,Jurdáková, Helena,Stankovi?ová, Henrieta
supporting information, p. 3277 - 3291 (2021/09/02)
A convenient protocol for efficient and cost-effective method for synthesis of substituted 3-aminocoumarins has been developed. The synthetic route involves expeditious and fast quantitative deacetylation of readily available acetamido derivative under anhydrous acidic conditions, employing thionyl chloride in methanol, without formation of undesired substituted 3-hydroxycoumarins. The method is suitable for derivatives bearing electron-donating as well as electron-withdrawing groups at position 7 of the coumarin scaffold. Under these conditions, a series of acetoxy substituted 3-dialkylaminocoumarins has been also successfully deacetylated to afford easily isolable corresponding hydroxy derivatives in high yields.
Rational design, synthesis and biological evaluation of novel multitargeting anti-AD iron chelators with potent MAO-B inhibitory and antioxidant activity
Bai, Renren,Gu, Jinping,Guo, Jianan,Jiang, Xiaoying,Lv, Yangjing,Mi, Zhisheng,Shi, Yuan,Xie, Yuanyuan,Yao, Chuansheng,Zhang, Changjun,Zhou, Tao
, (2020/05/22)
A series of (3-hydroxypyridin-4-one)-coumarin hybrids were developed and investigated as potential multitargeting candidates for the treatment of Alzheimer's disease (AD) through the incorporation of iron-chelating and monoamine oxidase B (MAO-B) inhibition. This combination endowed the hybrids with good capacity to inhibit MAO-B as well as excellent iron-chelating effects. The pFe3+ values of the compounds were ranging from 16.91 to 20.16, comparable to more potent than the reference drug deferiprone (DFP). Among them, compound 18d exhibited the most promising activity against MAO-B, with an IC50 value of 87.9 nM. Moreover, compound 18d exerted favorable antioxidant activity, significantly reversed the amyloid-β1-42 (Aβ1-42) induced PC12 cell damage. More importantly, 18d remarkably ameliorated the cognitive dysfunction in a scopolamine-induced mice AD model. In brief, a series of hybrids with potential anti-AD effect were successfully obtained, indicating that the design of iron chelators with MAO-B inhibitory and antioxidant activities is an attractive strategy against AD progression.
