3722-45-0

Usage

Chemical class

Chromene derivatives

Structure

Tetrahydro derivative of chromen-6-one

Functional groups

Two hydroxyl groups at positions 1 and 3

Pharmacological properties

a. Anti-inflammatory
b. Antioxidant
c. Anticancer

Potential applications

a. Treatment of neurodegenerative diseases
b. Therapeutic agent for cardiovascular conditions

Research significance

Interesting candidate for further research and development in medicinal chemistry and drug discovery

Upstream product

• 108-73-6 3,5-dihydroxyphenol 
• 1655-07-8 ethyl 2-oxocyclohexane carboxylate 
• 141-97-9 ethyl acetoacetate 
• 911217-74-8 C₁₅H₁₃F₁₃O₃ 
• 108-46-3 recorcinol 

Relevant academic research and scientific papers

1-Nicotinoylbenzotriazole: A Convenient Tool for Site-Selective Protection of 5,7-Dihydroxycoumarins

1-Nicotinoylbenzotriazole (NicBt) was uncovered as an efficient protecting agent for the site-selective acylation of resorcinol-type phenolic groups with almost equal reactivity. The use of NicBt allows selective protection of the 7-OH group in 5,7-dihydr

Derivatives of Natural Product Agrimophol as Disruptors of Intrabacterial pH Homeostasis in Mycobacterium tuberculosis

This article reports the rational medicinal chemistry of a natural product, agrimophol (1), as a new disruptor of intrabacterial pH (pHIB) homeostasis in Mycobacterium tuberculosis (Mtb). Through the systematic investigation of the structure-activity relationship of 1, scaffold-hopping of the diphenylmethane scaffold, pharmacophore displacement strategies, and studies of the structure-metabolism relationship, a new derivative 5a was achieved. Compound 5a showed 100-fold increased potency in the ability to reduce pHIB to pH 6.0 and similarly improved mycobactericidal activity compared with 1 against both Mycobacterium bovis-BCG and Mtb. Compound 5a possessed improved metabolic stability in human liver microsomes and hepatocytes, lower cytotoxicity, higher selectivity index, and similar pKa value to natural 1. This study introduces a novel scaffold to an old drug, resulting in improved mycobactericidal activity through decreasing pHIB, and may contribute to the critical search for new agents to overcome drug resistance and persistence in the treatment of tuberculosis.

Novel diphenylmethyl compounds having mycobacterium tuberculosis inhibitory activity

The invention relates to novel diphenylmethyl derivatives having mycobacterium tuberculosis inhibitory activity and a preparation method thereof and particularly relates novel diphenylmethyl derivatives having activity for inhibiting replicative and non-replicating mycobacterium tuberculosis and a preparation method thereof. In particular, the invention relates to compounds shown in the formula (I) or all possible isomers, prodrugs, pharmaceutically acceptable salts, solvates or hydrates thereof, wherein the variables are as described in the specification. The invention also relates to the preparation method of the compounds and their pharmaceutical compositions and a use of the compounds in preparation of drugs for treating mycobacterium tuberculosis infection-caused diseases.

An environmentally friendly, chemoselective, and efficient protocol for the preparation of coumarin derivatives by Pechman condensation reaction using new and reusable heterogeneous Lewis acid catalyst polystyrene-supported GaCl 3

An environmentally benign Pechman protocol for the one-pot synthesis of 4-substituted coumarins through the condensation reactions of phenol substrates with β-ketoesters using polystyrene-supported GaCl3 (PS-GaCl3) as a highly active and reusable solid Lewis acid catalyst under mild and heterogeneous conditions in good to excellent yields is described. This new protocol is easy, simple, cost-effective, chemoselective, and in addition has the advantages of easy availability, stability, reusability and eco-friendly character of the catalyst, high to excellent yields, simple experimental and work-up procedure.

PEG-SO3H: A mild and efficient recyclable catalyst for the synthesis of coumarin derivatives

A simple and efficient synthesis of coumarin derivatives through condensation reaction of substituted phenols and dicarbonyl compounds using PEG-SO3H as a recyclable catalyst under solvent-free conditions is described.

TETRIACYCLODIPYRANYL COUMARINS AND THE ANTI-HIV AND ANTI-TUBERCULOSIS USES THEREOF

The present invention relates to tctracyclodipyrano-coumarin compounds of general formula (I), wherein the substituents are defined herein. These compounds exihibit dual biological activities of anti human immunodeficiency virus type 1 (HIV-1) infection a

Microwave-promoted automated synthesis of a coumarin library

A 30-membered library of coumarins has been synthesized in a microwave-assisted Pechmann reaction using neat trifluoroacetic acid both as an acidic reagent and a reaction medium. Alternatively, polymer-supported sulfonic acid Amberlyst-15 could also be employed to facilitate the formation of coumarins. The use of a specially-built microwave synthesizer with liquid handling tools rendered the automated synthesis of a coumarin library feasible.

Ultrasound-assisted Pechmann condensation of phenols with β-ketoesters to form coumarins, in the presence of bismuth(III) chloride catalyst

Ultrasound was found to synergistically accelerate the condensation of phenol with β-ketoesters in the presence of BiCl3. In the absence of ultrasound, under the same conditions, the reaction was found to be slow. Thus, the reaction can be carried out in the presence of ultrasound at room temperature (28-30°C), with a considerable reduction of reaction time, with high yield and high purity of coumarins. Copyright Taylor & Francis Group, LLC.

Selectfluor: A simple and efficient catalyst for the synthesis of substituted coumarins under solvent-free conditions

Selectfluor is used as an alternative catalyst to conventional catalysts for the synthesis of substituted coumarins via Pechmann condensation of phenols with β-ketoesters under solvent-free conditions at 120 °C. This method of synthesis is simple, cost-effective, requires short reaction time, solvent-free and gives good yields.

Vanadium(III) chloride as an effective catalyst for the Pechmann reaction

Good yields of substituted coumarins were obtained by a synthetic method involving the Pechmann reaction using vanadium(III)chloride (VCl3) reagent to effect this condensation under solvent-free conditions. 2006 Springer Science+Business Media, Inc.