(5Z)-5-[3-(trifluoromethyl)benzylidene]-1,3-thiazolidine-2,4-dione

Base Information

• Chemical Name: (5Z)-5-[3-(trifluoromethyl)benzylidene]-1,3-thiazolidine-2,4-dione
• CAS No.: 438190-29-5
• Molecular Formula: C11H6F3NO2S
• Molecular Weight: 273.235
• European Community (EC) Number: 803-742-0
• Nikkaji Number: J2.989.178H,J3.561.866J
• Wikidata: Q27451064
• Pharos Ligand ID: HX998FFQD3UR
• ChEMBL ID: CHEMBL183906
• Mol file: 438190-29-5.mol

Synonyms:SMI-4a;438190-29-5;SMI 4a;TCS PIM-1 4a;(Z)-SMI-4a;(5Z)-5-[3-(trifluoromethyl)benzylidene]-1,3-thiazolidine-2,4-dione;CHEMBL183906;(Z)-5-(3-(trifluoromethyl)benzylidene)thiazolidine-2,4-dione;(Z)-5-(3-(Trifluoromethyl)benzylidene)-thiazolidine-2,4-dione;(5Z)-5-[[3-(TRIFLUOROMETHYL)PHENYL]METHYLENE]-2,4-THIAZOLIDINEDIONE;(5Z)-5-[[3-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione;(5Z)-5-{[3-(trifluoromethyl)phenyl]methylidene}-1,3-thiazolidine-2,4-dione;5-(3-(Trifluoromethyl)benzylidene)thiazolidine-2,4-dione;Pim inhibitor 4a;3vc4;5-[3-(Trifluoromethyl)benzylidene]thiazolidine-2,4-dione;thiazolidine-2,4-dione, 4a;SCHEMBL2541382;SCHEMBL2541388;BDBM26626;EX-A111;BDBM138364;HMS3229J21;HY-16576A;MFCD01152003;s8005;AKOS001314163;SMI-4a, >=98% (HPLC);CCG-265027;NCGC00345836-02;NCGC00345836-14;AC-32861;HY-15474;EC-000.2291;EN300-55235;J3.561.866J;A11945;EN300-6743263;US8877795, 12;Q27451064;Z2312387408;5-[[3-(trifluoromethyl)phenyl]methylene]-2,4-thiazolidinedione;(5Z)-5-[[3-(Trifluoromethyl)phenyl]methylene]-2,4-thiazolidinedione thiazolidine-2,4-dione, 4a;0FS

Chemical Property of (5Z)-5-[3-(trifluoromethyl)benzylidene]-1,3-thiazolidine-2,4-dione

Chemical Property:

• PSA: 74.96000
• LogP: 3.30520
• Storage Temp.: Desiccate at +4°C
• Solubility.: DMSO: >10mg/mL
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 273.00713409
• Heavy Atom Count: 18
• Complexity: 406

Purity/Quality:

99%, ^*data from raw suppliers

SMI-4a ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36-43
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC(=C1)C(F)(F)F)C=C2C(=O)NC(=O)S2
• Isomeric SMILES: C1=CC(=CC(=C1)C(F)(F)F)/C=C\2/C(=O)NC(=O)S2
• Description: SMI-4a (438190-29-5) is a selective, ATP-competitive inhibitor of the Pim protein kinases (IC50 = 24 and 100 nM for Pim-1 and Pim-2 respectively). Selective over a panel of ~50 other kinases.1?Induces cell cycle arrest in leukemia and prostate cancer cells.2?Blocks the growth of a wide range of myeloid and lymphoid cell lines with precursor T-cell lymphoblastic leukemia/lymphoma (pre-T-LBL/T-ALL) being highly sensitive.3?SMI-4a is a useful tool for exploring the involvement of Pim in cellular signaling.4?Cell permeable.
• Uses: SMI-4a is an aldose reductase inhibitor as well as a COX-2 inhibitor, a potential agent in the inhibition and treatment of cancer and cancer cell lines.

Technology Process of (5Z)-5-[3-(trifluoromethyl)benzylidene]-1,3-thiazolidine-2,4-dione

There total 1 articles about (5Z)-5-[3-(trifluoromethyl)benzylidene]-1,3-thiazolidine-2,4-dione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 57.0%

thiazoline-2,4-dione (2295-31-0) + 3-Trifluoromethylbenzaldehyde (454-89-7) → (Z)-5-(3-trifluoromethylbenzylidene)thiazolidine-2,4-dione (438190-29-5)

Guidance literature:

With piperidine; In ethanol; Heating;

DOI:10.1016/S0968-0896(01)00366-2

Reference yield: 88.0%

bromoacetic acid methyl ester (96-32-2) + (Z)-5-(3-trifluoromethylbenzylidene)thiazolidine-2,4-dione (438190-29-5) → {2,4-Dioxo-5-[1-(3-trifluoromethyl-phenyl)-meth-(Z)-ylidene]-thiazolidin-3-yl}-acetic acid methyl ester (438190-38-6)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; Heating;

DOI:10.1016/S0968-0896(01)00366-2

Reference yield:

(Z)-5-(3-trifluoromethylbenzylidene)thiazolidine-2,4-dione (438190-29-5) → {2,4-Dioxo-5-[1-(3-trifluoromethyl-phenyl)-meth-(Z)-ylidene]-thiazolidin-3-yl}-acetic acid

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / NaH / dimethylformamide / Heating

2: 98 percent / aq. HCl / acetic acid / 4 h / Heating

With hydrogenchloride; sodium hydride; In acetic acid; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(01)00366-2

upstream raw materials:

thiazoline-2,4-dione

3-Trifluoromethylbenzaldehyde

Downstream raw materials:

{2,4-Dioxo-5-[1-(3-trifluoromethyl-phenyl)-meth-(Z)-ylidene]-thiazolidin-3-yl}-acetic acid methyl ester

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