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Home > Products > Pharmaceutical R&D Materials > Functional Building Blocks > (5Z)-5-[[3-(Trifluoromethyl)phenyl]methylene]-2,4-thiazolidinedione
(5Z)-5-[[3-(Trifluoromethyl)phenyl]methylene]-2,4-thiazolidinedione structure, CAS 438190-29-5

(5Z)-5-[[3-(Trifluoromethyl)phenyl]methylene]-2,4-thiazolidinedione

CAS Number438190-29-5

Synonyms2,4-Thiazolidinedione (5-[[3-(trifluoromethyl)phenyl]methylene]; HMS3244E20; HMS3244E19; (5Z)-5-[3-(Trifluoromethyl)benzylidene]-1,3-thiazolidine-2,4-dione; SMI-4a; (Z)-SMI-4a

Molecular FormulaC11H6F3NO2S

Molecular Weight273.231

Purity98%%

Density1.5±0.1 g/cm3

Boiling Point

Melting Point

Flash Point

Appearancewhite to beige

EINECS

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Cat. No.: 2A-1170968 Purity: 98%%
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Quality Control of [ 438190-29-5 ] Purity: 98%% SDS Specification MoL

COA NMR CNMR HPLC LC-MS
Chemical & Physical Properties
CAS Number438190-29-5
Catalog No.2A-1170968
Chinese Name(Z)-SMI-4A
Synonyms2,4-Thiazolidinedione (5-[[3-(trifluoromethyl)phenyl]methylene]; HMS3244E20; HMS3244E19; (5Z)-5-[3-(Trifluoromethyl)benzylidene]-1,3-thiazolidine-2,4-dione; SMI-4a; (Z)-SMI-4a
Molecular FormulaC11H6F3NO2S
Molecular Weight273.231
Purity98%
Density1.5±0.1 g/cm3
Appearancewhite to beige
Water SolubilityDMSO: >10mg/mL
Storage ConditionDesiccate at +4°C
Application(Z)-SMI-4a is an ATP-competitive Pim kinase inhibitor with IC50s of 21nM and 100nM for Pim-1 and Pim-2 respectively, and has almost no activity against 50 other kinases.
PubChem ID16733554
SMILESO=C1NC(=O)C(=Cc2cccc(C(F)(F)F)c2)S1
InChIInChI=1S/C11H6F3NO2S/c12-11(13,14)7-3-1-2-6(4-7)5-8-9(16)15-10(17)18-8/h1-5H,(H,15,16,17)/b8-5-
InChI KeyNGJLOFCOEOHFKQ-YVMONPNESA-N
Hazard Symbolstransportation
MSDSmsds/171150_2_438190_29_5.pdf
Bioactivity(Z)-SMI-4a is a selective ATP-competitive Pim-1 kinase inhibitor with an IC50 of 21 nM for Pim-1 compared to an IC50 of 100 nM for Pim-2 and with little or no activity against a panel of 50 other kinases tested.IC50 value: 21 nM (Pim1); 100 nM (Pim2) [1]Target: Pim-1in vitro: Incubation of pre-T-LBL cells with (Z)-SMI-4a induced G1 phase cell-cycle arrest secondary to a dose-dependent induction of p27(Kip1), apoptosis through the mitochondrial pathway, and inhibition of the mammalian target of rapamycin C1 (mTORC1) pathway based on decreases in phospho-p70 S6K and phospho-4E-BP1, 2 substrates of this enzyme. In addition, treatment of these cells with (Z)-SMI-4a was found to induce phosphorylation of extracellular signal-related kinase1/2 (ERK1/2), and the combination of (Z)-SMI-4a and a mitogen-activated protein kinase kinase 1/2 (MEK1/2) inhibitor was highly synergistic in killing pre-T-LBL cells [1]. Ectopic expression of phosphomimetic mutants of eIF4B conferred resistance to apoptosis by the Pim kinase inhibitor (Z)-SMI-4a in Abl-transformed cells [2].in vivo: In immunodeficient mice carrying subcutaneous pre-T-LBL tumors, treatment twice daily with (Z)-SMI-4a caused a significant delay in the tumor growth without any change in the weight, blood counts, or chemistries [1]. Related Catalog Signaling Pathways >> JAK/STAT Signaling >> Pim Research Areas >> Cancer References [1]. Lin YW, et al. A small molecule inhibitor of Pim protein kinases blocks the growth of precursor T-cell lymphoblastic leukemia/lymphoma. Blood. 2010 ;115(4):824-33. [2]. Yang J, et al. eIF4B phosphorylation by pim kinases plays a critical role in cellular transformation by Abl oncogenes. Cancer Res. 2013 Aug 1;73(15):4898-908. Chemical & Physical Properties Density 1.5±0.1 g/cm3 Molecular Formula C11H6F3NO2S Molecular Weight 273.231 Exact Mass 273.007141 PSA 74.96000 LogP 2.30 Appearance of Characters white to beige Index of Refraction 1.602 InChIKey NGJLOFCOEOHFKQ-YVMONPNESA-N SMILES O=C1NC(=O)C(=Cc2cccc(C(F)(F)F)c2)S1 Storage condition Desiccate at +4°C Water Solubility DMSO: >10mg/mL
Use ofProperties Name 5-[[3-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Synonym More Synonyms SMI-4a Biological Activity Related Catalog Signaling Pathways >> JAK/STAT Signaling >> Pim Research Areas >> Cancer References [1]. Lin YW, et al. A small molecule inhibitor of Pim protein kinases blocks the growth of precursor T-cell lymphoblastic leukemia/lymphoma. Blood. 2010 ;115(4):824-33. [2]. Yang J, et al. eIF4B phosphorylation by pim kinases plays a critical role in cellular transformation by Abl oncogenes. Cancer Res. 2013 Aug 1;73(15):4898-908. Chemical & Physical Properties Molecular Formula C11H6F3NO2S Exact Mass 273.007141 PSA 74.96000 Appearance of Characters white to beige Index of Refraction 1.602 InChIKey NGJLOFCOEOHFKQ-YVMONPNESA-N
Transport InfoShipping Name: UN
MSDS Transport InfoModule 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available
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