ChemicalBook > CAS DataBase List > BMS 833923

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

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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

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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.

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N-Bromosuccinimide Price

Cayman Chemical

Product number: 16240
Product name: BMS 833923
Purity: ≥98%
Packaging: 5mg
Price: $62
Updated: 2024/03/01

Cayman Chemical

Product number: 16240
Product name: BMS 833923
Purity: ≥98%
Packaging: 10mg
Price: $109
Updated: 2024/03/01

Cayman Chemical

Product number: 16240
Product name: BMS 833923
Purity: ≥98%
Packaging: 25mg
Price: $194
Updated: 2024/03/01

Cayman Chemical

Product number: 16240
Product name: BMS 833923
Purity: ≥98%
Packaging: 50mg
Price: $317
Updated: 2024/03/01

TRC

Product number: B596320
Product name: BMS833923
Packaging: 100mg
Price: $395
Updated: 2021/12/16

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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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1059734-66-5, BMS 833923Related Search:

XL019 XL147 Y16 TENOVIN-1 LY 303511 (hydrochloride) PFK-015 CCT 137690 CTS-1027 TG101209 BIX 02189 MS436 CNX-1351 Mutant IDH1 inhibitor Glasdegib LDE225 (NVP-LDE225,Erismodegib) Vismodegib (GDC-0449) ABT 737 Sunitinib Malate

BMS 833923

XL 139

XL139

XL-139

BMS-833923 (XL-139)

N-[2-Methyl-5-[(methylamino)methyl]phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide

Benzamide, N-[2-methyl-5-[(methylamino)methyl]phenyl]-4-[(4-phenyl-2-quinazolinyl)amino]-

BMS 833923 N-[2-Methyl-5-[(methylamino)methyl]phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide

N-[2-Methyl-5-[(methylamino)methyl]phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide BMS-833923

BMS 833923; BMS833923; XL-139; XL139; XL 139

CS-944

BMS 833923 USP/EP/BP

BMS-833923, smoothened antagonist

BMS-833923, 10 mM in DMSO

BMS-833923 ，S7138

1059734-66-5

Inhibitors