2199-86-2

Usage

Uses

Used in Pharmaceutical Industry:
6,8-DICHLORO-2-OXO-2H-CHROMENE-3-CARBOXYLIC ACID is used as an intermediate in the synthesis and production of various pharmaceuticals. Its chemical structure allows it to be a key component in the development of new drugs with potential therapeutic applications.
Used in Agricultural Chemicals:
In the agricultural sector, 6,8-DICHLORO-2-OXO-2H-CHROMENE-3-CARBOXYLIC ACID is used in the synthesis of herbicides and fungicides. Its ability to inhibit the growth of unwanted plants and fungi makes it a valuable compound for crop protection and management.
Used as an Antibacterial Agent:
6,8-DICHLORO-2-OXO-2H-CHROMENE-3-CARBOXYLIC ACID exhibits antibacterial properties, making it a potential candidate for the development of new antimicrobial agents. Its ability to combat bacterial infections can contribute to the advancement of treatments for various diseases.
Used as an Antifungal Agent:
Similarly, 6,8-DICHLORO-2-OXO-2H-CHROMENE-3-CARBOXYLIC ACID also possesses antifungal properties, which can be harnessed in the development of new antifungal agents. This can be particularly useful in treating fungal infections and controlling the spread of fungal diseases.
Used in Anti-inflammatory and Analgesic Applications:
6,8-DICHLORO-2-OXO-2H-CHROMENE-3-CARBOXYLIC ACID has been investigated for its potential anti-inflammatory and analgesic properties. Its ability to reduce inflammation and alleviate pain makes it a compound of interest for the development of new medications in the pharmaceutical industry.

InChI:InChI=1/C10H4Cl2O4/c11-5-1-4-2-6(9(13)14)10(15)16-8(4)7(12)3-5/h1-3H,(H,13,14)

Upstream product

• 2199-88-4 6,8-dichloro-2-oxo-2H-1-benzopyran-3-carboxylic acid ethyl ester 
• 2033-24-1 cycl-isopropylidene malonate 
• 320-72-9 3,5-dichlorosalicylic acid 
• 90-60-8 3,5-dichlorosalicyclaldehyde 
• 120-83-2 2,4-dichlorophenol 

Downstream Products

• 491870-39-4 6,8-dichloro-N-(2-morpholinoethyl)-2-oxo-2H-1-benzopyran-3-carboxamide 

Relevant academic research and scientific papers

Synthesis and characterisation of some new hybrid molecules containing thiophene, triazole and coumarin rings under microwave conditions

In this work, a new series of N′-([4-amino-5-oxo-3-(thiophen-2-yl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetyl)-2-oxo-2H-1-benzopyran-3-carbohydrazides (thiophene–triazole–coumarin hybrid molecules) was synthesised from the reaction of 2-[4-amino-5-oxo-3-(thiophen-2-yl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetohydrazide and 3-(1H-benzotriazol-1-ylcarbonyl)-2H-chromen-2-ones by using microwave irradiation and conventional heating procedures and their results were compared. The reaction was performed using a very small amount of organic solvent and without using a catalyst.

Synthesis and biological evaluation of some 1,3-benzoxazol-2(3H)-one hybrid molecules as potential antioxidant and urease inhibitors

A new series of 1,3-benzoxazol-2(3H)-one hybrid compounds, including coumarin, isatin 1,3,4-triazole and 1,3,4-thiadiazole moieties, were synthesized and biologically evaluated for their antioxidant capacities and anti-urease properties. The synthesized benzoxazole-coumarin (6a–e) and benzoxazole-isatin (10a–c) hybrids showed remarkable urease inhibitory activities with IC50 (μM), ranging from 0.0306 ± 0.0030 to 0.0402 ± 0.0030, while IC50 of standard thiourea is 0.5027 ± 0.0293. The synthesized benzoxazole-triazole (8a–c) and benzoxazole-thiadiazole (9a–c) hybrids showed similar urease inhibitory activities with IC50 (μM), ranging from 0.3861 ± 0.0379 to 0.5126 ± 0.0345. The antioxidant activity of the synthesized compounds was evaluated for their antioxidant activities, such as reducing power and ABTS (2,2′-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) diammonium salt) radical scavenging. The results of ABTS radical scavenging activities of some of the synthesized molecules showed higher activities than standard Trolox, SC50 (μM) = 213.04 ± 18.12. One benzoxazole-coumarin (6f), two benzoxazole-isothiocyanate (7b, 7c), and two benzoxazole-triazole (8b, 8c) derivatives showed higher activities (SC50 (μM) values, 82.07 ± 10.34, 120.19 ± 7.30, 104.58 ± 10.55, 153.26 ± 7.14, and 144.82 ± 10.68, respectively) than standard Trolox, (SC50 (μM) = 213.04 ± 18.12).

Ultrasound-assisted sequential multicomponent strategy for the combinatorial synthesis of novel coumarin hybrids

The present investigation reports an easy access to a library of novel spiro-oxindole-pyrrolizine or pyrrolo[1,2-c]thiazole fused coumarin hybrid heterocycles through a one-pot sequential four-component reactions of 2,2-dimethyl-1,3-dioxane-4,6-dione, salicylaldehydes, isatins, and cyclic α-amino acids under ultrasound irradiation.

Design, Synthesis, and Biological Evaluation of Coumarin–Triazole Hybrid Molecules as Potential Antitumor and Pancreatic Lipase Agents

The design, synthesis, and investigation of antitumor and anti-lipase activities of some coumarin–triazole hybrid molecules are reported. The synthesis of these hybrid molecules was performed under microwave irradiation and conventional heating procedures

Monoamine oxidase A and B inhibitory activities of 3,5-diphenyl-1,2,4-triazole substituted [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole derivatives

Monoamine oxidase (EC 1.4.3.4, MAO) is a flavin adenine dinucleotide-containing flavoenzyme located on the outer mitochondrial membrane and catalyzes the oxidative deamination of monoaminergic neurotransmitters and dietary amines. MAO exists in humans as two isoenzymes, hMAO-A and hMAO-B, which are distinguished by their tertiary structures, preferred substrates and inhibitors, and selective inhibition of these isoenzymes are used in the treatment of different diseases such as Alzheimer's, Parkinson's and depression. In the present study, we report the design, synthesis and characterization of 3,5-diphenyl-1,2,4-triazole substituted [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole derivatives as novel and selective inhibitors of hMAO-B. Twenty one compounds (38, 39a-h, 41a-d, 42a-h) were screened for their inhibitory activity against hMAO-A and hMAO-B by using in vitro Amplex Red reagent based fluorometric method and all compounds were found to be as selective h-MAO-B inhibitors to a different degree. The compound 42e and 42h displayed the highest inhibitory activity against hMAO-B with IC50 values of 2.51 and 2.81 μM, respectively, and more than 25-fold selectivity towards inhibition of hMAO-B. A further kinetic evaluation of the most potent derivative (42e) was also performed and a mixed mode of inhibition of hMAO-B by the compound 42e was determined (Ki = 0,26 μM). According to our findings the [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole emerged as a promising scaffold for the development of novel and selective hMAO-B inhibitors.

Synthesis and antioxidant activity of conjugates of hydroxytyrosol and coumarin

Antioxidants have been the subject of intense research interest due to their numerous health benefits. In this work, a series of new conjugates of hydroxytyrosol and coumarin were synthesized and evaluated for their free radical scavenging, toxicity and antioxidant mechanism in vitro. The all target compounds 14a–t exhibited better radical scavenging activity than BHT, hydroxytyrosol, and coumarin in both DPPH radical and ABTS+ radical cation scavenging assays. The structure-activity relationships study indicated that the number and position of hydroxyl groups on the coumarin ring were vital to a good antioxidant capacity. Furthermore, the most promising compound 14q showed less toxicity in hemolysis assay and weaker antiproliferative effects than BHT against normal WI-38 and GES cells, and enhanced viability of H2O2-induced HepG2 cells. Additionally, 14q decreased the apoptotic percentage of HepG2 cells, reduced the ROS produce and LDH release, and improved GSH and SOD levels in H2O2-treated HepG2 cells. Lastly, 14q exhibited more stability than hydroxytyrosol in methanol solution. These results revealed that conjugations of hydroxytyrosol and coumarin show better antioxidant capacity, and are the efficacious approach to finding novel potential antioxidant.

Design, synthesis and biological evaluation of coumarin-based N-hydroxycinnamamide derivatives as novel histone deacetylase inhibitors with anticancer activities

A series of novel coumarin-based N-hydroxycinnamamide derivatives were designed and synthesized as histone deacetylase (HDAC) inhibitors. Most of the synthesized compounds showed potent HDAC inhibitory activity and significant antiproliferative activity a

Synthesis and Biological Evaluation of Some Succinimide Hybrid Molecules

In this study, a new series of succinimide hybrid molecules containing isothiocyanate, coumarin, isatin, and furan moieties was synthesized and screened for α-glucosidase and antioxidant activities. Preliminary results revealed that all molecules showed good α-glucosidase inhibition effectiveness. Antioxidant activities of the hybrid molecules were determined using cupric reducing antioxidant capacity (CUPRAC) and ferric reducing antioxidant power (FRAP) assays. Also, the radical scavenging activities of the synthesized compounds were assayed by using ABTS?+?and DPPH??methods. The results showed that all compounds exhibited moderated to high scavenging activity.

3-substituted coumarin derivative and application and GPR35 receptor agonist

The invention discloses a 3-substituted coumarin derivative and a pharmaceutically acceptable salt, a solvate, a hydrate or a crystal form. The compound of the invention generally exhibits high agonistic activity against human G protein-coupled receptor 35 (GPR35) and is specific agonists of the human GPR35 receptor. The compound provided by the invention is an active ligand of the novel GPR35 receptor, and the compound and the pharmaceutically acceptable salt, the solvate, the hydrate or the crystal form thereof generally exhibit higher activity and good selectivity to the human GPR35. The 3-substituted coumarin derivative is the specific agonist of the GPR35 receptor and can be used in the preparation of a medicament for treating, preventing and inhibiting a disease mediated by the GPR35receptor.

Design and synthesis of novel Vitamin D-coumarin hybrids using microwave irradiation

A series of novel vitamin D-coumarin hybrids were synthesised by esterification of the corresponding coumarin-3-carboxylic acids and vitamin D or vitamin D CD-ring alcohol in CH2Cl2 under microwave irradiation. They were obtained in higher yields (from 64-81% up to 79-87%) and shorter reaction time (from 3 h down to 15 min), compared with earlier conventional methodologies. The structures of all the target compounds were confirmed by 1H NMR, 13C NMR and HRMS. This provides an attractive and alternative method for the preparation of high-value vitamin D-coumarin hybrids.