(5Z)-2-Amino-5-[(4-hydroxy-3,5-ditert-butyl-phenyl)methylidene]-1,3-thiazol-4-one

(5Z)-2-Amino-5-[(4-hydroxy-3,5-ditert-butyl-phenyl)methylidene]-1,3-thiazol-4-one

(5Z)-2-Amino-5-[(4-hydroxy-3,5-ditert-butyl-phenyl)methylidene]-1,3-thiazol-4-one

CAS: 139226-28-1

Molecular Formula: C18H24N2O2S

(5Z)-2-Amino-5-[(4-hydroxy-3,5-ditert-butyl-phenyl)methylidene]-1,3-thiazol-4-one - Names and Identifiers

Name	(5Z)-2-Amino-5-[(4-hydroxy-3,5-ditert-butyl-phenyl)methylidene]-1,3-thiazol-4-one
Synonyms	CS-490 darbufelone (5Z)-2-Amino-5-[(4-hydroxy-3,5-ditert-butyl-phenyl)methylide... (Z)-2-AMino-5-(3,5-di-tert-butyl-4-hydroxybenzylidene)thiazol-4(5H)-one 5-((z)-3,5-di-tert-butyl-4-hydroxybenzylidene)-2-imino-4-thiazolidinone (5Z)-2-amino-5-[(3,5-ditert-butyl-4-hydroxyphenyl)methylidene]-1,3-thiazol-4-one (5z)-2-amino-5-[(4-hydroxy-3,5-ditert-butyl-phenyl)methylidene]-1,3-thiazol-4-one (5Z)-2-Amino-5-[(4-hydroxy-3,5-ditert-butyl-phenyl)methylidene]-1,3-thiazol-4-one (5Z)-2-amino-5-[(3,5-di-tert-butyl-4-hydroxyphenyl)methylidene]-1,3-thiazol-4(5H)-one 4(5H)-Thiazolone, 2-amino-5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-, (5Z)-
CAS	139226-28-1
EINECS	1312995-182-4
InChI	InChI=1/C18H24N2O2S/c1-17(2,3)11-7-10(8-12(14(11)21)18(4,5)6)9-13-15(22)20-16(19)23-13/h7-9,21H,1-6H3,(H2,19,20,22)/b13-9-

(5Z)-2-Amino-5-[(4-hydroxy-3,5-ditert-butyl-phenyl)methylidene]-1,3-thiazol-4-one - Physico-chemical Properties

Molecular Formula	C18H24N2O2S
Molar Mass	332.46
Density	1.18g/cm³
Boling Point	448.6°C at 760 mmHg
Flash Point	225.1°C
Vapor Presure	1.16E-08mmHg at 25°C
Refractive Index	1.589
In vitro study	Darbufelone is a noncompetitive inhibitor of PGHS-2 (K i =10±5 μM). Darbufelone quenches the fluorescence of PGHS-2 at 325 nm (lambda(ex)=280 nm) with K d =0.98±0.03 μM.To test the putative anti-proliferative effect of Darbufelone, A549, H520 and H460 cell lines are used, which are established from three distinct pathological subtypes of NSCLC (adenocarcinoma, squamous and large cell lung cancer respectively). Increasing concentrations of Darbufelone, ranging from 5 to 60 μM, are tested for 72 h. The cell growth inhibition of these three cell lines gradually increases with higher drug concentration. The IC 50 of A549 and H520 are 20±3.6 and 21±1.8 μM, respectively, while the H460 has much lower IC 50 (15±2.7 μM).
In vivo study	Darbufelone is a dual inhibitor of cellular PGF2R and LTB4 production. Darbufelone is orally active and nonulcerogenic in animal models of inflammation and arthritis. When mice are treated with Darbufelone at dosage of 80 mg/kg/day, the tumor volumes decrease in a time-dependent manner. In contrast, lower dose of Darbufelone (20 or 40 mg/kg/day) dos not show any significant inhibition of tumor weight. At necropsy, the tumor weight in mice treated with Darbufelone (80 mg/kg/day) is reduced by 30.2% in comparison with control group.

(5Z)-2-Amino-5-[(4-hydroxy-3,5-ditert-butyl-phenyl)methylidene]-1,3-thiazol-4-one - Reference Information

biological activity	Darbufelone is a dual inhibitor of cellular PGF2α and LTB4 production. Darbufelone inhibited effectively by PGHS-2 (IC50=0.19 μm), but was much less potent against PGHS-1 (IC50=20 μm).
Target	IC50: 0.19 μm (PGHS-2), 20 μm (PGHS-1)

Last Update：2024-04-09 20:45:29

(5Z)-2-Amino-5-[(4-hydroxy-3,5-ditert-butyl-phenyl)methylidene]-1,3-thiazol-4-one

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(5Z)-2-Amino-5-[(4-hydroxy-3,5-ditert-butyl-phenyl)methylidene]-1,3-thiazol-4-one

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