BMS 833923
- Product Name
- BMS 833923
- CAS No.
- 1059734-66-5
- Chemical Name
- BMS 833923
- Synonyms
- XL139;CS-944;XL-139;XL 139;BMS 833923;BMS-833923 ，S7138;BMS-833923 (XL-139);BMS 833923 USP/EP/BP;BMS-833923, 10 mM in DMSO;BMS-833923, smoothened antagonist
- CBNumber
- CB42658184
- Molecular Formula
- C30H27N5O
- Formula Weight
- 473.57
- MOL File
- 1059734-66-5.mol
BMS 833923 Property
- Density
- 1.252±0.06 g/cm3(Predicted)
- storage temp.
- Store at -20°C
- solubility
- ≥47.4 mg/mL in DMSO; insoluble in H2O; ≥5.14 mg/mL in EtOH with gentle warming and ultrasonic
- form
- solid
- pka
- 13.42±0.70(Predicted)
- color
- Light yellow to yellow
- InChIKey
- KLRRGBHZCJLIEL-UHFFFAOYSA-N
- SMILES
- C(NC1=CC(CNC)=CC=C1C)(=O)C1=CC=C(NC2=NC(C3=CC=CC=C3)=C3C(=N2)C=CC=C3)C=C1
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
- Precautionary statements
-
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P332+P313IF SKIN irritation occurs: Get medical advice/attention.
P337+P313IF eye irritation persists: Get medical advice/attention.
N-Bromosuccinimide Price
- Product number
- 16240
- Product name
- BMS 833923
- Purity
- ≥98%
- Packaging
- 5mg
- Price
- $62
- Updated
- 2024/03/01
- Product number
- 16240
- Product name
- BMS 833923
- Purity
- ≥98%
- Packaging
- 10mg
- Price
- $109
- Updated
- 2024/03/01
- Product number
- 16240
- Product name
- BMS 833923
- Purity
- ≥98%
- Packaging
- 25mg
- Price
- $194
- Updated
- 2024/03/01
- Product number
- 16240
- Product name
- BMS 833923
- Purity
- ≥98%
- Packaging
- 50mg
- Price
- $317
- Updated
- 2024/03/01
- Product number
- B596320
- Product name
- BMS833923
- Packaging
- 100mg
- Price
- $395
- Updated
- 2021/12/16
BMS 833923 Chemical Properties,Usage,Production
Description
Smoothened (Smo) is a cell surface receptor that, with Patched, mediates sonic hedgehog (Shh) signaling to regulate gene expression through the Gli transcription factors. BMS 833923 is an orally bioavailable inhibitor of Smo. It blocks binding of BODIPY cyclopamine (IC50 = 21 nM) and inhibits Gli activation in cell lines that express wild-type Smo or activated mutant forms of Smo (IC50s = 6-35 nM). BMS 833923 robustly inhibits Shh pathway activity and prevents tumor growth in medulloblastoma and pancreatic carcinoma xenograft models.
Uses
BMS 833923 is an antagonist of smoothened, a key hedgehog (Hh) pathway regulator.
Synthesis
1059735-25-9
74-89-5
1059734-66-5
GENERAL STEPS: To a stirred suspension of 4-(4-phenylquinazolin-2-ylamino)benzoic acid (1.19 g, 3.49 mmol) prepared as described in Example 10 in dichloromethane (50 mL) was added catalytic amounts of dimethylformamide (100 μL) and thionyl chloride (1.50 mL, 20.6 mmol), and the resulting mixture was stirred at room temperature overnight. The solid was filtered, washed with hexane and dried under reduced pressure (high vacuum) to afford 4-(4-phenylquinazolin-2-ylamino)benzoyl chloride as a yellow solid (1.21 g, 97%). This was then added batchwise to a solution of commercially available 3-amino-4-methylbenzenemethanol (600 mg, 4.37 mmol) and triethylamine (1.0 mL, 7.2 mmol) in dichloromethane (50 mL), which had been cooled to 0 °C. The mixture was then cooled to 0 °C and the solution was mixed to a temperature of 0 °C. The mixture was warmed to room temperature overnight, then the solid was collected by filtration, washed with saturated sodium bicarbonate and water and dried under reduced pressure to afford N-(5-hydroxymethyl-2-methylphenyl)-4-(4-phenylquinazolin-2-ylamino)benzamide as a pure yellow solid (1.33 g, 86%). To a dichloromethane (50 mL) suspension of N-(5-hydroxymethyl-2-methylphenyl)-4-(4-phenylquinazolin-2-ylamino)benzamide (1.88 g, 4.08 mmol) which was cooled to 0 °C was slowly added thionyl chloride (475 μL, 6.54 mmol) and the mixture was stirred at 0 °C for 2 hours. Excess thionyl chloride and dichloromethane were removed on a rotary evaporator. The residue was stirred with ether, filtered, washed with ether and dried to give N-(5-chloromethyl-2-methylphenyl)-4-(4-phenylquinazolin-2-ylamino)benzamide as a yellow solid (2.15 g, 100%). This was then added to a tetrahydrofuran solution (20 mL, 32 mmol) of 1.6 M methylamine which was cooled to 0 °C in an ice bath. The stirred mixture was warmed to room temperature overnight and then concentrated on a rotary evaporator. The residue was redissolved in dichloromethane, washed with saturated sodium bicarbonate and dried over sodium sulfate. The solvent was then removed on a rotary evaporator and the residue was purified by fast column chromatography to afford N-(2-methyl-5-((methylamino)methyl)phenyl)-4-((4-phenylquinazolin-2- yl)amino)benzamide (1.12 g, 57%) as a yellow solid.1H NMR (400 MHz, DMSO-d6): δ 10.33 (s, 1H) 9.71 (s, 1H), 8.17 (d, 2H), 8.00 (d, 2H), 7.89-7.79 (m, 5H), 7.65 (m, 3H), 7.42 (m, 1H), 7.34 (s, 1H), 7.21 (d, 1H), 7.12 (d, 1H), 3.65 (s, 2H), 2.28 (s, 3H), 2.23 (s, 3H).MS (EI) for C30H27N5O: 474.2 (MH+).
in vivo
BMS-833923 (15 mg/kg, oral gavage, daily) alone or together with Selumetinib (HY-50706) (10 mg/kg, oral gavage, daily) reduces tumor metastasis and the post-extravasation tumor growth in orthotopic mouse model of pancreatic cancer metastasis[4].
BMS-833923 (30 mg/kg, p.o., seven consecutive days) alone or together with Gemcitabine (HY-17026) (40 mg/kg, i.p., at the 1st, 4th and 7th day) reduces tumor volume (to 60% and 32% respectively) in a nu/nu mice xenograft model of cholangiocarcinoma[5].
References
[1] Patent: WO2008/112913, 2008, A1. Location in patent: Page/Page column 174-175
BMS 833923 Preparation Products And Raw materials
Raw materials
Preparation Products
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