(Z,E)-5-(4-ETHYLBENZYLIDINE)-2-THIOXOTHIAZOLIDIN-4-ONE

(Z,E)-5-(4-ETHYLBENZYLIDINE)-2-THIOXOTHIAZOLIDIN-4-ONE Basic information
Product Name:(Z,E)-5-(4-ETHYLBENZYLIDINE)-2-THIOXOTHIAZOLIDIN-4-ONE
Synonyms:(5E)-5-[(4-ethylphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one;c-Myc Inhibitor;ZINC01085340;CS-1512;(Z,E)-5-(4-ETHYLBENZYLIDINE)-2-THIOXOTHIAZOLIDIN-4-ONE;10058-F4;5-[(4-Ethylphenyl)methylene]-2-thioxo-4-thiazolidinone;(5E)-5-(4-ethylbenzylidene)-2-mercapto-1,3-thiazol-4(5H)-one
CAS:403811-55-2
MF:C12H11NOS2
MW:249.35
EINECS:
Product Categories:Inhibitors
Mol File:403811-55-2.mol
(Z,E)-5-(4-ETHYLBENZYLIDINE)-2-THIOXOTHIAZOLIDIN-4-ONE Structure
(Z,E)-5-(4-ETHYLBENZYLIDINE)-2-THIOXOTHIAZOLIDIN-4-ONE Chemical Properties
density 1.33±0.1 g/cm3(Predicted)
storage temp. 2-8°C
solubility DMSO: >10mg/mL
pka7.72±0.30(Predicted)
form Yellow solid
color yellow
Water Solubility Soluble in DMSO. Soluble in water at concentrations less than 2mg/ml
Stability:Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 1 month.
Safety Information
Hazard Codes Xi
Risk Statements 36-43
Safety Statements 26-36/37
WGK Germany 3
HazardClass IRRITANT
HS Code 2934100090
MSDS Information
(Z,E)-5-(4-ETHYLBENZYLIDINE)-2-THIOXOTHIAZOLIDIN-4-ONE Usage And Synthesis
Description10058-F4 (403811-55-2) effectively disables c-Myc by inhibiting the c-Myc-Max association and function.It prevents the growth of fibroblasts in a c-Myc-dependent manner. Downregulates human telomerase reverse transcriptase and enhances chemosensitivity in human hepatocellular carcinoma cells.10058-F4 induces cell cycle arrest, apoptosis and myeloid differentiation in human acute myeloid leukemia.Inhibits the MYCN/Max interaction leading to cell cycle arrest, apoptosis and neuronal differentiation in MYCN-amplified neuroblastoma cells.
UsesA c-Myc inhibitor that induces apoptosis
DefinitionChEBI: 10058-F4 is a member of the class of thiazolidinones that is 2-sulfanylidene-1,3-thiazolidin-4-one which is substituted at position 5 by a (4-ethylphenyl)methylidene group. It is a cell permeable inhibitor of c-Myc-Max dimerization and exhibits antitumour effects in vivo. It downregulates c-Myc expression and upregulates CDK inhibitors, p21 and p27 resulting in the inhibition of proliferation, induction of apoptosis and cell cycle arrest in G0/G1 phase. It has a role as an apoptosis inducer and an antineoplastic agent. It is a thiazolidinone and an olefinic compound.
Biochem/physiol Actions10058-F4 is a c-Myc inhibitor that induces cell-cycle arrest and apoptosis. 10058-F4 is a cell-permeable thiazolidinone that specificallly inhibits the c-Myc-Max interaction and prevents transactivation of c-Myc target gene expression. 10058-F4 inhibits tumor cell growth in a c-Myc-dependent manner both in vitro and in vivo (64 μM using c-Myc transfected Rat1a fibroblasts).
storageStore at +4°C
References1) Yin?et al. (2003),?Low molecular weight inhibitors of Myc-Max interaction and function; Oncogene,?22?6151 2) Lin?et al. (2007),?Small-molecule c-Myc inhibitor, 10058-F4, inhibits proliferation, downregulates human telomerase reverse transcriptase and enhances chemosensitivity in human hepatocellular carcinoma cells; Anti-Cancer Drugs,?18161 3) Huang?et al. (2006),?A small-molecule c-Myc inhibitor, 10058-F4, induces cell-cycle arrest, apoptosis, and myeloid differentiation of human acute myeloid leukemia; Exp. Hematol.,?34?1480 4) Zirath?et al. (2013),?MYC inhibition induces metabolic changes leading to accumulation of lipid droplets in tumor cells; Proc. Natl. Acad. Sci. USA,?110?10258
(Z,E)-5-(4-ETHYLBENZYLIDINE)-2-THIOXOTHIAZOLIDIN-4-ONE Preparation Products And Raw materials
PLX4032 Ibrutinib (E)-3-[[[3-[2-(7-CHLORO-2-QUINOLINYL)ETHENYL]PHENYL]-[[(3-DIMETHYLAMINO)-3-OXOPROPYL]THIO]METHYL]THIO]-PROPANOIC ACID, SODIUM SALT METHYLENECYCLOHEXANE Adapalene TYRPHOSTIN AG 1296 BKM120 (NVP-BKM120, Buparlisib) IWR-1-endo Geldanamycin Bortezomib 10058-F4 AKOS B018344 AKOS B018339 AKOS B018345

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