301305-73-7

Basic information

• Product Name: TCS 359
• Synonyms: 2-(3,4-DIMETHOXY-BENZOYLAMINO)-4,5,6,7-T;TCS359;2-(3,4-Dimethoxy-benzoylamino)-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid amide;Flt-3 inhibitor;2-[(3,4-Dimethoxybenzoyl)amino]-4,5,6,7-benzo[b]thiophene-3-carboxamide;2-(3,4-diMethoxybenzaMido)- 4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxaMide;Benzo[b]thiophene-3-carboxaMide,2-[(3,4-diMethoxybenzoyl)aMino]-4,5,6,7-tetrahydro-;2-[(3,4-Dimethoxybenzoyl)amino]-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxamide
• CAS NO: 301305-73-7
• Molecular Formula: C18H20N2O4S
• Molecular Weight: 360.432
• Product Categories: API;Inhibitors
• Mol File: 301305-73-7.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 454.4°Cat760mmHg
• Flash Point: 228.6°C
• Appearance: white to off-white/
• Density: 1.328g/cm³
• Vapor Pressure: 1.91E-08mmHg at 25°C
• Refractive Index: 1.644
• Storage Temp.: −20°C
• Solubility: H2O:
• PKA: 12.43±0.20(Predicted)
• Sensitive: Light Sensitive
• CAS DataBase Reference: TCS 359(CAS DataBase Reference)
• NIST Chemistry Reference: TCS 359(301305-73-7)
• EPA Substance Registry System: TCS 359(301305-73-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 301305-73-7(Hazardous Substances Data)

Usage

Description

TCS 359 is a cell-permeable, ATP-competitive inhibitor of Fms-like tyrosine kinase (FLT3), a cell-surface receptor that plays a crucial role in stem cell development, hematopoiesis, and cancer. It selectively targets FLT3 over a panel of 22 other kinases, making it a promising pharmaceutical candidate for the treatment of leukemia.

Uses

Used in Oncology:
TCS 359 is used as a potent FLT3 inhibitor for the treatment of leukemia. It effectively blocks the proliferation of myelomonocytic leukemia MV4-11 cells, demonstrating an IC50 of 0.41 μM. Additionally, TCS 359 synergistically increases the cytotoxicity of an AF4-mimetic peptide against MV4-11 cells, enhancing its therapeutic efficacy in the treatment of leukemia.

Biological Activity

Potent inhibitor of FLT3 receptor tyrosine kinase (IC 50 = 42 nM) that displays selectivity over a range of other kinases. Exhibits antiproliferative effects on MV4-11 cells, a human acute myelogenous leukaemia cell line expressing a constitutively active mutant FLT3 (IC 50 = 340 nM).

references

[1]. trzci′nska-daneluti a.m., nguyen l., jiang c., et al. use of kinase inhibitors to correct δf508-cftr function. molecular & cellular proteomics, 2012, 11(9):745-757.[2]. patch r.j., baumann c.a., liu j., et al. identification of 2-acylaminothiophene-3-carboxamides as potent inhibitors of flt3. bioorganic & medicinal chemistry letters, 2006, 16: 3282-3286.[3]. kar r.k., suryadevara p., roushan r., et al. quantifying the structural requirements for designing newer flt3 inhibitors. medicinal chemistry, 2012, 8:913-927.[4]. nishijima c., kawamura k., okamoto n., et al. regulation of preimplantation embryo development in mice by fms-like tyrosine kinase 3 ligand. journal of mammalian ova research, 2014, 31(1):45-51.[5]. o'farrell a.m., yuen h.a., smolich b., et al. effects of su5416, a small molecule tyrosine kinase receptor inhibitor, on flt3 expression and phosphorylation in patients with refractory acute myeloid leukemia. leuk. res., 2004, 28(7):679-89.

InChI:InChI=1/C18H20N2O4S/c1-23-12-8-7-10(9-13(12)24-2)17(22)20-18-15(16(19)21)11-5-3-4-6-14(11)25-18/h7-9H,3-6H2,1-2H3,(H2,19,21)(H,20,22)