41295-51-6

Usage

Uses

Used in Pharmaceutical Industry:
4-CHLOROMETHYL-7-METHYL-CHROMEN-2-ONE is used as a pharmaceutical agent for its potential anti-inflammatory and anti-cancer properties. It is being studied for its potential use in the treatment of various diseases and conditions, due to its ability to interact with specific cellular targets.
Used in Research and Development:
4-CHLOROMETHYL-7-METHYL-CHROMEN-2-ONE is used as a research compound for exploring its unique structure and properties. Its potential biological activities and therapeutic applications make it a valuable compound for further research and development in the field of medicine and pharmaceuticals.

InChI:InChI=1/C11H9ClO2/c1-7-2-3-9-8(6-12)5-11(13)14-10(9)4-7/h2-5H,6H2,1H3

Upstream product

• 50402-83-0 7-methylcoumarin-4-acetic acid 
• 84097-07-4 4-Hydroxymethyl-7-methylcoumarin 
• 638-07-3 ethyl (2-chloroaceto)acetate 
• 108-39-4 3-methyl-phenol 
• 14002-90-5 4,7-dimethyl-coumarin 
• 84096-83-3 7-methyl benzopyran-2-one-4-carboxaldehyde 

Downstream Products

• 84097-09-6 4-Piperidinomethyl-7-methylcoumarin 
• 79344-57-3 4-Anilinomethyl-7-methylcoumarin 
• 845651-57-2 4-(azepan-1-ylmethyl)-7-methylchromen-2-one 
• 1246656-08-5 N-benzyloxycarbonyl-L-phenylalanine (7-methylcoumarin-4-yl)methyl ester 

Relevant academic research and scientific papers

Synthesis of C4-substituted coumarins via Pechmann condensation catalyzed by sulfamic acid. Insights into the reaction mechanism by HRMS analysis

A series of functionalized C4-substituted coumarins were synthesized by exploring the reaction of activated and non-activated phenols and β-ketoesters under solvent-free conditions in the presence of sulfamic acid as a Br?nsted acid catalyst. Fifteen exam

Design, synthesis, and antifungal evaluation of novel coumarin-pyrrole hybrids

A series of coumarin derivatives bearing a pyrrole scaffold were designed, prepared, and assessed for their in vitro antifungal activities against six phytopathogenic fungi. The antifungal activity screening results suggest that some synthesized hybrids exhibited potential fungicidal activities against the tested fungi. In particular, compounds 6j, 6k, 6o, 6p, and 6r displayed significant antifungal effects against Rhizoctorzia solani, and possessed EC50 values of 3.94, 7.75, 6.38, 6.25, and 7.67 μg/ mL, respectively. The above activities are more potent than the commercialized fungicide Boscalid (11.52 μg/mL) and Osthole (9.79 μg/mL). These results provide a significant reference for further rational design of coumarin-based fungicides.

Design and synthesis of pyrimidine-5-carbonitrile hybrids as COX-2 inhibitors: Anti-inflammatory activity, ulcerogenic liability, histopathological and docking studies

Two new series of 1,3,4-oxadiazole and coumarin derivatives based on pyrimidine-5-carbonitrile scaffold have been synthesized and evaluated for their COX-1/COX-2 inhibitory activity. Compounds 10c, 10e, 10h-j, 14e-f, 14i and 16 were found to be the most potent and selective inhibitors of COX-2 (IC50 0.041–0.081 μM, SI 139.74–321.95). Eight compounds were further investigated for their in vivo anti-inflammatory activity. The most active derivatives 10c, 10j and 14e displayed superior in vivo anti-inflammatory activity (% edema inhibition 39.3–48.3, 1 h; 58.4–60.5, 2 h; 70.8–83.2, 3 h; 78.9–89.5, 4 h) to the reference drug celecoxib (% edema inhibition 38.0, 1 h; 48.8, 2 h; 58.4, 3 h; 65.4, 4 h). These derivatives were also tested for their ulcerogenic liability, compound 10j showed better safety profile with reference to celecoxib while 10c and 14e exhibited mild lesions. Molecular docking studies of 10c, 10j, and 14e in the COX-2 active site revealed similar orientation and binding interactions as selective COX-2 inhibitors with a higher liability to access the selectivity side pocket.

Synthesis of Coumarin-4-Ylmethyl Phosphonic Acids

New coumarin-4-ylmethylphosphonates and coumarin-4-ylmethylphosphonic acids were synthesized and tested for antiviral activity.

Design, synthesis, and mechanism of dihydroartemisinin-coumarin hybrids as potential anti-neuroinflammatory agents

Cancer patients frequently suffer from cancer-related fatigue (CRF), which is a complex syndrome associated with weakness and depressed mood. Neuroinflammation is one of the major inducers of CRF. The aim of this study is to find a potential agent not only on the treatment of cancer, but also for reducing CRF level of cancer patients. In this study, total-thirty new Dihydroartemisinin-Coumarin hybrids (DCH) were designed and synthesized. The in vitro cytotoxicity against cancer cell lines (HT-29, MDA-MB-231, HCT-116, and A549) was evaluated. Simultaneously, we also tested the anti-neuroinflammatory activity of DCH. DCH could inhibit the activated microglia N9 release of NO, TNF-α, and IL-6. The docking analysis was shown that MD-2, the coreceptor of TLR4, might be one of the targets of DCH.

1,2,3-Triazole pharmacophore-based benzofused nitrogen/sulfur heterocycles with potential anti-Moraxella catarrhalis activity

Versatile 1,2,3-triazole pharmacophore-based benzofused heterocycles containing halogen-substituted aromatic (9-17 and 25-28), 7-substituted coumarin (18-23 and 29-30) or penciclovir-like subunit (31a,b-38a) were designed and synthesized to evaluate their

Synthesis and biological evaluation of coumarin-1,2,3-triazole- dithiocarbamate hybrids as potent LSD1 inhibitors

Two series of coumarin-1,2,3-triazole-dithiocarbamate hybrids were designed, synthesized and evaluated for their inhibitory activity towards lysine specific demethylase 1 (LSD1). Compounds 8a, 8d-8f, 8i-8l presented potent activity against lysine specific demethylase 1. Among them, compound 8k showed potent and reversible inhibition against lysine specific demethylase 1 with an IC50 value of 0.39 μM, which was 74-fold more potent than that of tranylcypromine (2-PCPA). Besides, compound 8k displayed excellent selectivity against lysine specific demethylase 1 without inhibition against monoamine oxidases (MAOs) A and B. Further investigation revealed that compound 8k was active at both recombinant and cell levels by upregulating the expression of H3K4me1, H3K4me2 and H3K9me2. This journal is the Partner Organisations 2014.

Light-induced cleavage of model phenylalanine conjugates based on coumarins and quinolones

In order to evaluate the application of quinolone as a new photocleavable protecting group, in comparison with coumarin, a series of model phenylalanine conjugates were prepared by reaction with chloromethylated O and N heterocycles. The photophysical pro

Synthesis of meso-coumarin-conjugated porphyrins and investigation of their luminescence properties

A series of meso-coumarin-conjugated porphyrins 1a-e were designed and synthesized. Condensation of 4-chloroacetoacetate ethyl ester with m-cresol or resorcin afforded 4-chloromethylcoumarins, which were then hydrolyzed to give coumarin alcohols, followed by oxidation to provide coumarin aldehydes. The reaction of coumarin aldehydes with pyrrole under Adler or Lindsey conditions afforded the meso-coumarin-conjugated porphyrins 1a-e. Their UV/Vis absorption spectra and photoluminescent spectra were recorded both in dilute THF solution and as solid films. Analysis of the luminescence spectra indicate that the energy transfer from the coumarin substituents to the porphyrin core for 1a-e is more efficient in solid film than in solution, and the energy transfer from the coumarin substituent to the porphyrin core for 1d and 1e is more efficient than that of 1a, 1b and 1c in solid film. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Synthesis of 4-Substituted Coumarins, 3a,8a-Dihydrofurobenzofuran-2(3H)-ones and 2,3,3a,8a-Tetrahydrobenzofuropyrrol-2(1H)-ones

Oxidation of methylcoumarins (I) with SeO2 shows that the methyl group in position-4 is selectively oxidised to CHO but methyl groups in other positions remain unaffected.However, a bulky substituent in position-3 hampers oxidation of CH3 in position-4.A large number of derivatives (III to XIV) of II have been prepared by making use of the reactivity of CHO function. 3a,8a-Dihydrofurobenzofuran-2(3H)-ones (XVa-c) and 2,3,3a,8a-tetrahydrobenzofuropyrrol-2(1H)-ones (XVIa-c) have been synthesised by the action of zinc and acetic acid on II and III, respectively.