Highly efficient approach to the total synthesis of flavoxate hydrochloride

Sheelam, Kalidasu; Chidara, Sridhar; Vinnakota, Srilalitha; Polothi, Ravikumar

doi:10.1016/j.cdc.2021.100694

Cited by 4 publications

(2 citation statements)

References 4 publications

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“…The coupling of carboxylic acid 70 with piperidine ethanol yields flavoxate hydrochloride 23 (Figure 17). 202 The synthesis of cromolyn sodium 24 (Figure 18 The alkaline hydrolysis of ethyl ester 74 forms cromolyn sodium 24. 203 The synthesis of amlexanox ( 25) is described in Figure 19.…”

Section: Synthetic Approaches For the Construction Of Benzopyronesmentioning

confidence: 99%

Benzopyrone, a privileged scaffold in drug discovery: An overview of FDA‐approved drugs and clinical candidates

Sharma,

Wadje

et al. 2024

Medicinal Research Reviews

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Natural products have always served as an important source of drugs for treating various diseases. Among various privileged natural product scaffolds, the benzopyrone class of compounds has a substantial presence among biologically active compounds. One of the pioneering anticoagulant drugs, warfarin approved in 1954 bears a benzo‐α‐pyrone (coumarin) nucleus. The widely investigated psoriasis drugs, methoxsalen, and trioxsalen, also contain a benzo‐α‐pyrone nucleus. Benzo‐γ‐pyrone (chromone) containing drugs, cromoglic acid, and pranlukast were approved as treatments for asthma in 1982 and 2007, respectively. Numerous other small molecules with a benzopyrone core are under clinical investigation. The present review discusses the discovery, absorption, distribution, metabolism, excretion properties, and synthetic approaches for the Food and Drug Administration‐approved and clinical‐stage benzopyrone class of compounds. The role of the pyrone core in biological activity has also been discussed. The present review unravels the potential of benzopyrone core in medicinal chemistry and drug development.

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Section: Synthetic Approaches For the Construction Of Benzopyronesmentioning

confidence: 99%

Benzopyrone, a privileged scaffold in drug discovery: An overview of FDA‐approved drugs and clinical candidates

Sharma,

Wadje

et al. 2024

Medicinal Research Reviews

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“…9 Flavoxate was employed as an anticholinergic agent for its antimuscarinic effect. 10 Given our interest in the development of new synthetic methodologies utilizing chromone-3-carboxylic acids as starting materials, 11 it was envisioned that they should be able to participate in the cross-couplings reaction with aziridines leading to C-3substituted chromen-4-ones, thus resulting in the unique C(sp 2 )-C(sp 3 ) bond forming process. Devised reactivity can be considered as a formal alkenylation of aziridines providing access to homoallylic amines.…”

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confidence: 99%

Stereoretentive Decarboxylative C-3 Func-tionalization of Chromone-3-carboxylic Acids via Visible Light Irradiation

Monirialamdari,

Kowalska,

Sieroń

et al. 2023

Preprint

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Herein, we report a stereoretentive and decar-boxylative C-3 functionalization of chromone-3-carboxylic acids with optically active aziridines via visible light irradia-tion. This metal-free and operationally simple protocol utilizes a simple combination of stable and inexpensive tetrabu-tylammonium iodide and visible light irradiation. It enables a facile and direct access to chiral 3-substituted chromenones with maintaining the optical purity of starting aziri-dines.Cross-coupling reactions allowing for efficient carbon–carbon as well as carbon–heteroatom bond formations are of crucial importance in the modern organic chemistry.1 Among them transition-metal-catalyzed decarboxylative cross-couplings utilizing carboxylic acids as substrates occupy a prominent position.2 They offer several distinctive advantages related to availability and price of carboxylic acid derivatives, their stability and handling as well as generation of less-toxic carbon dioxide as the by-product that reduces the waste treatment costs. While these methods have proven particularly useful for C(sp2)-C(sp2) bond formations and were applied for the synthesis of numerous relevant products ranging from pharmaceuticals to organic materials, their application in the C(sp2)-C(sp3) remains limited. Consequently, there is a need for the development of alternative, transition-metal-free cross-coupling reactions allowing for C(sp2)-C(sp3) bond formations.

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Solid-liquid equilibrium solubility, thermodynamic properties, and solvent effect of flavoxate hydrochloride in twelve pure solvents ranged from 278.15 K to 323.15 K

Fan

Cao

Liu

et al. 2023

The Journal of Chemical Thermodynamics

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Highly efficient approach to the total synthesis of flavoxate hydrochloride

Cited by 4 publications

References 4 publications

Benzopyrone, a privileged scaffold in drug discovery: An overview of FDA‐approved drugs and clinical candidates

Benzopyrone, a privileged scaffold in drug discovery: An overview of FDA‐approved drugs and clinical candidates

Stereoretentive Decarboxylative C-3 Func-tionalization of Chromone-3-carboxylic Acids via Visible Light Irradiation

Solid-liquid equilibrium solubility, thermodynamic properties, and solvent effect of flavoxate hydrochloride in twelve pure solvents ranged from 278.15 K to 323.15 K

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