Last update 21 Nov 2024

Ethyl Biscoumacetate

Last update 21 Nov 2024

Overview

R&D Status

Clinical Result

Translational Medicine

Overview

Basic Info

Drug Type

Small molecule drug

Synonyms

Ethyl bis(4-hydroxy-2-oxo-2h-1-benzopyran-3-yl)acetate, Ethyl biscoumacetate (INN), Ethyldicoumarol

+ [1]

Target-

Mechanism

Vitamin K antagonists

Therapeutic Areas

Cardiovascular Diseases

Active Indication

Thrombosis

Inactive Indication-

Originator Organization-

Active Organization-

Inactive Organization-

Drug Highest PhaseApproved

First Approval Date-

Regulation-

Structure

Molecular FormulaC22H16O8

InChIKeyJCLHQFUTFHUXNN-UHFFFAOYSA-N

CAS Registry548-00-5

100 Clinical Results associated with Ethyl Biscoumacetate

100 Translational Medicine associated with Ethyl Biscoumacetate

100 Patents (Medical) associated with Ethyl Biscoumacetate

Literatures (Medical) associated with Ethyl Biscoumacetate

01 Jun 2020·DARU Journal of Pharmaceutical SciencesQ4 · MEDICINE

Benzoxazines as new human topoisomerase I inhibitors and potential poisons

Q4 · MEDICINE

Article

Author: Diril, Nuran ; Zilifdar, Fatma ; Akı-Yalçın, Esin ; Özen, Çigdem ; Foto, Egemen ; Yıldız, İlkay ; Tekiner-Gülbaş, Betül ; Yalçın, İsmail

BACKGROUNDThe numbers of topoisomerase I targeted drugs on the market are very limited although they are used clinically for treatment of solid tumors. Hence, studies about finding new chemical structures which specifically target topoisomerase I are still remarkable.OBJECTIVESIn this present study, we tested previously synthesized 3,4-dihydro-2H-1,4-benzoxazin-3-one derivatives to reveal their human DNA topoisomerase I inhibitory potentials.METHODSWe investigated inhibitory activities of 3,4-dihydro-2H-1,4-benzoxazin-3-one derivatives on human topoisomerase I by relaxation assay to clarify inhibition mechanisms of effective derivatives with EMSA and T4 DNA ligase based intercalation assay. With SAR study, it was tried to find out effective groups in the ring system.RESULTSWhile 10 compounds showed catalytic inhibitory activity, 8 compounds were found to be potential topoisomerase poisons. 4 of them also exhibited both activities. 2-hydroxy-3,4-dihydro-2H-1,4-benzoxazin-3-one (BONC-001) was the most effective catalytic inhibitor (IC₅₀:8.34 mM) and ethyl 6-chloro-4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-acetate (BONC-013) was the strongest potential poison (IC₅₀:0.0006 mM). BONC-013 was much more poisonous than camptothecin (IC₅₀:0.034 mM). Intercalation assay showed that BONC-013 was not an intercalator and BONC-001 most probably prevented enzyme-substrate binding in an unknown way. Another important result of this study was that OH group instead of ethoxycarbonylmethyl group at R position of benzoxazine ring was important for hTopo I catalytic inhibition while the attachment of a methyl group of R1 position at R₂ position were play a role for increasing of its poisonous effect.CONCLUSIONAs a result, we presented new DNA topoisomerase I inhibitors which might serve novel constructs for future anticancer agent designs. Graphical abstract.

01 Jun 2020·Chemistry & BiodiversityQ3 · CHEMISTRY

Benzopyran Derivatives and an Aliphatic Compound from a Mangrove Endophytic Fungus Penicillium citrinum QJF‐22

Q3 · CHEMISTRY

Article

Author: Yang, Wencong ; Cai, Runlin ; Chen, Yan ; Wang, Bo ; She, Zhigang ; Zou, Ge

AbstractTwo new benzopyran derivatives, (2R,4S)‐5‐methoxy‐2‐methyl‐3,4‐dihydro‐2H‐1‐benzopyran‐4‐ol and (2S,4R,2′S,4′R)‐4,4′‐oxybis(5‐methoxy‐2‐methyl‐3,4‐dihydro‐2H‐1‐benzopyran), and a new aliphatic compound, (3E,5Z,8S,10E)‐8‐hydroxytrideca‐3,5,10,12‐tetraen‐2‐one, together with three known benzopyran derivatives, were obtained from a mangrove endophytic fungus Penicillium citrinum QJF‐22 collected in Hainan island. Their structures were determined by analysis of spectroscopic data and the relative configuration of (2R,4S)‐5‐methoxy‐2‐methyl‐3,4‐dihydro‐2H‐1‐benzopyran‐4‐ol was also confirmed by single‐crystal X‐ray diffraction. The absolute configurations of four compounds were established by comparison of ECD spectra to calculations. The configuration of (3E,5Z,8S,10E)‐8‐hydroxytrideca‐3,5,10,12‐tetraen‐2‐one was confirmed by comparison of optical value to the similar compound. The configurations of the compounds (2S,4S)‐5‐methoxy‐2‐methyl‐3,4‐dihydro‐2H‐1‐benzopyran‐4‐ol and (2R,4R)‐5‐methoxy‐2‐methyl‐3,4‐dihydro‐2H‐1‐benzopyran‐4‐ol were first determined. (3R,4S)‐3,4,8‐Trihydroxy‐3,4‐dihydronaphthalen‐1(2H)‐one exhibited moderate inhibitory effects on LPS‐induced NO production in RAW264.7 cells with IC50 of 44.7 μM, and without cytotoxicity to RAW264.7 cells within 50 μM.

01 Apr 2018·Bioorganic ChemistryQ2 · CHEMISTRY

Design and synthesis of novel coumarin-pyridinium hybrids: In vitro cholinesterase inhibitory activity

Q2 · CHEMISTRY

Article

Author: Akbarzadeh, Tahmineh ; Vafadarnejad, Fahimeh ; Karimpour-Razkenari, Elahe ; Sameem, Bilqees ; Edraki, Najmeh ; Khanavi, Mahnaz ; Mahdavi, Mohammad ; Saeedi, Mina

A novel series of coumarin-pyridinium hybrids were synthesized and evaluated as inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) using Ellman's method. Among synthesized compounds, 1-(3-fluorobenzyl)-4-((2-oxo-2H-chromene-3-carboxamido)methyl)pyridinium bromide (7l) was found to be the most active compound toward AChE (IC₅₀ = 10.14 µM), 1-(3-chlorobenzyl)-3-((2-oxo-2H-chromene-3-carboxamido)methyl)pyridinium bromide (7g) and 1-(2,3-dichlorobenzyl)-3-((2-oxo-2H-chromene-3-carboxamido)methyl)pyridinium chloride (7h) depicted the best BChE inhibitory activity (IC₅₀s = 0.32 and 0.43 µM, respectively). Although most compounds showed moderate to good anti-AChE activity, their anti-BChE activity was more significant and compound 7g was found as the most selective BChE with SI of 101.18. Also, kinetic study of the compounds 7g and 7l displayed a mixed type inhibition for both AChE and BChE. Furthermore, they were evaluated against β-secretase; however, they showed low inhibitory activity.

100 Deals associated with Ethyl Biscoumacetate

External Link

KEGG	Wiki	ATC	Drug Bank
D07131	Ethyl Biscoumacetate	B01AA08	DB08794

R&D Status

10 top approved records.

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Indication	Country/Location	Organization	Date
Thrombosis	-	-	-

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