315702-99-9

Basic information

• Product Name: STF-62247
• Synonyms: STF-62247;N-(3-Methylphenyl)-4-(4-pyridinyl)-1,3-thiazol-2-amine;N-(3-Methylphenyl)-4-(4-pyridinyl)-2-thiazolaMine;4-(pyridin-4-yl)-N-m-tolylthiazol-2-amine;Autophagy Inducer, STF-62247;N-(3-methylphenyl)-4-pyridin-4-yl-1,3-thiazol-2-amine
• CAS NO: 315702-99-9
• Molecular Formula: C₁₅H₁₃N₃S
• Molecular Weight: 267.34882
• EINECS: -0
• Product Categories: Inhibitors
• Mol File: 315702-99-9.mol
• Article Data: 2

Chemical Properties

• Melting Point: 158-160℃
• Boiling Point: 444.8°C at 760 mmHg
• Flash Point: 222.8°C
• Appearance: /
• Density: 1.255
• Vapor Pressure: 4.15E-08mmHg at 25°C
• Refractive Index: 1.67
• Storage Temp.: room temp
• Solubility: DMSO: soluble26mg/mL
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.
• CAS DataBase Reference: STF-62247(CAS DataBase Reference)
• NIST Chemistry Reference: STF-62247(315702-99-9)
• EPA Substance Registry System: STF-62247(315702-99-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26-39
• WGK Germany: 2
• Hazardous Substances Data: 315702-99-9(Hazardous Substances Data)

Usage

Description

STF-62247 is a compound that specifically induces autophagic cell death in VHL (von Hippel-Lindau)-deficient renal carcinoma cells, both in vitro and in vivo. It has an IC50 value of 625 nM and can radiosensitize renal cell carcinoma cell lines by inducing autophagy.

Uses

Used in Oncology:
STF-62247 is used as an autophagy inducer for selectively killing renal cell carcinoma (RCC) cells that have lost VHL tumor suppressor activity. This selective targeting makes it a potential therapeutic agent for treating RCC patients with VHL deficiency.
Used in Radiosensitization:
STF-62247 is used to radiosensitize renal cell carcinoma cell lines by inducing autophagy. This property can enhance the effectiveness of radiation therapy in treating RCC, particularly in cases where the tumor cells have lost VHL activity.

in vitro

in vitro study demonstrated that stf-62247 exhibited selectively cytotoxicity and tumor growth inhibitory activity towards wild-type vhl and vhl-deficient renal cell carcinoma (rcc) in a hif-independent manner with ic50 of 16 μm and 0.625 μm, respectively. in addion, stf-62247 also resulted in cell apoptosis by inducing acidification and increasing autophagy in vhl-deficient cells. [1]

in vivo

animal experiments for stf-62247 activity were performed according to institutional and national guidelines and approved by stanford university's administrative panel on laboratory animal care. based on an in vivo mouse model, it was found that intraperitoneal injection of stf-62247 at a dose of 8 mg/kg significantly inhibited tumor growth of vhl-deficient sn12c tumor cells. [1]

IC 50

stf-62247 inhibits tumor growth in wild-type vhl and vhl-deficient renal cell carcinoma (rcc) in a hif-independent manner with ic50 of 16 μm and 0.625 μm, respectively.

References

1) Turcotte et al. (2008), Targeted therapy for the loss of von Hippel-Lindau in renal cell carcinoma: a novel molecule that induces autophagic cell death; Autophagy, 4 944 2) Chan et al. (2008), Targeting cancer cells by synthetic lethality: autophagy and VHL in cancer therapeutics; Cell Cycle, 7 2987 3) Anbalagan et al. (2012), Radiosensitization of renal cell carcinoma in vitro through the induction of autophagy; Radiother. Oncol., 103 388

InChI:InChI=1/C15H13N3S/c1-11-3-2-4-13(9-11)17-15-18-14(10-19-15)12-5-7-16-8-6-12/h2-10H,1H3,(H,17,18)

Upstream product

• 621-40-9 (3-methylphenyl)thiourea 
• 5349-17-7 4-bromoacetylpyridine hydrobromide 
• 1122-54-9 methyl (4-pyridyl) ketone 
• 108-44-1 1-amino-3-methylbenzene 

Downstream Products

• 1187669-19-7 N-methyl-N-(3-methylphenyl)-4-(4-pyridinyl)-1,3-thiazol-2-amine 
• 1187669-20-0 N-ethyl-N-(3-methylphenyl)-4-(4-pyridinyl)-1,3-thiazol-2-amine 
• 1187668-87-6 [2-[(3-methylphenyl)amino]-4-(4-pyridinyl)-1,3-thiazol-5-yl]methanol 
• 1187669-21-1 2-{3-methyl[4-(4-pyridinyl)-1,3-thiazol-2-yl]anilino}ethanol 
• 1187669-65-3 N-(3-methylphenyl)-4-(1-oxido-4-pyridinyl)-1,3-thiazol-2-amine 
• 1187668-90-1 2-[(3-methylphenyl)amino]-4-(4-pyridinyl)-1,3-thiazole-5-carbaldehyde 
• 1187669-02-8 5-[(dimethylamino)methyl]-N-(3-methylphenyl)-4-(4-pyridinyl)-1,3-thiazol-2-amine 
• 1187668-92-3 methyl (2E)-3-[2-[(3-methylphenyl)amino]-4-(4-pyridinyl)-1,3-thiazol-5-yl]-2-propenoate 
• 1187668-94-5 methyl 3-[2-[(3-methylphenyl)amino]-4-(4-pyridinyl)-1,3-thiazol-5-yl]propanoate 
• 1187668-96-7 3-[2-[(3-methylphenyl)amino]-4-(4-pyridinyl)-1,3-thiazol-5-yl]-1-propanol 
• 1187669-04-0 5-[(diethylamino)methyl]-N-(3-methylphenyl)-4-(4-pyridinyl)-1,3-thiazol-2-amine 
• 1187668-99-0 3-[2-[(3-methylphenyl)amino]-4-(4-pyridinyl)-1,3-thiazol-5-yl]propanoic acid 
• 1187669-07-3 N-(3-methylphenyl)-5-(1-piperidinylmethyl)-4-(4-pyridinyl)-1,3-thiazol-2-amine 
• 1187669-09-5 N-(3-methylphenyl)-5-(4-morpholinylmethyl)-4-(4-pyridinyl)-1,3-thiazol-2-amine 

Relevant articles and documents

4-Pyridylanilinothiazoles that selectively target von Hippel - Lindau deficient renal cell carcinoma cells by inducing autophagic cell death

Renal cell carcinomas (RCC) are refractory to standard therapy with advanced RCC having a poor prognosis; consequently treatment of advanced RCC represents an unmet clinical need. The von Hippel-Lindau (VHL) tumor suppressor gene is mutated or inactivated in a majority of RCCs. We recently identified a 4-pyridyl-2-anilinothiazole (PAT) with selective cytotoxicity against VHL-deficient renal cells mediated by induction of autophagy and increased acidification of autolysosomes. We report exploration of structure-activity relationships (SAR) around this PAT lead. Analogues with substituents on each of the three rings, and various linkers between rings, were synthesized and tested in vitro using paired RCC4 cell lines. A contour map describing the relative spatial contributions of different chemical features to potency illustrates a region, adjacent to the pyridyl ring, with potential for further development. Examples probing this domain validated this approach and may provide the opportunity to develop this novel chemotype as a targeted approach to the treatment of RCC. 2009 American Chemical Society.