BI 2536

Base Information

• Chemical Name: BI 2536
• CAS No.: 755038-02-9
• Molecular Formula: C28H39N7O3
• Molecular Weight: 521.663
• Mol file: 755038-02-9.mol

Synonyms:(R)-4-[(8-Cyclopentyl-7-ethyl-5,6,7,8-tetrahydro-5-methyl-6-oxo-2-pteridinyl)amino]-3-methoxy-N-(1-methyl-4-piperidinyl)benzamide;

Chemical Property of BI 2536

Chemical Property:

• PKA: 14.09±0.20(Predicted)
• PSA: 102.93000
• Density: 1.28 g/cm³
• LogP: 4.08860
• Storage Temp.: Keep in dark place,Sealed in dry,Store in freezer, under -20°C
• Solubility.: Soluble in DMSO (up to 20 mg/ml) or in Ethanol (up to 25 mg/ml)

Purity/Quality:

99% ^*data from raw suppliers

BI2536 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: BI 2536 (755038-02-9) was originally reported as a potent (IC50’s Plk1 = 0.83nM, Plk2 = 3.5nM and Plk3 = 9.0nM)1?and selective2?Polo-like kinase inhibitor?that caused mitotic arrest and apoptosis induction in various human cancer cell lines.1?It was later found to be a potent inhibitor (IC50?= 100nM) of BET family member BRD4 and able to potently suppress c-Myc expression in MM.1S multiple myeloma cells.3?BI 2536 destabilizes N-Myc by inhibiting the deactivation of the ubiquitin E3 ligase Fbw7 by Plk1.4
• Uses: BI 2536 is a PLK1 inhibitor, inducing apoptosis together with micro-tubule-destabilizing drugs in preclinical rhabdomyosarcoma models. Anti-cancer and potent PLK1 inhibitor.

Technology Process of BI 2536

There total 10 articles about BI 2536 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: 61.0%

4-Amino-1-methylpiperidine (41838-46-4) + (R)-4-((8-cyclopentyl-7-ethyl-5-methyl-6-oxo-5,6,7,8-tetrahydropteridin-2-yl)amino)-3-methoxybenzoic acid (755039-56-6) → 4-[[(7R)-8-cyclopentyl-7-ethyl-5,6,7,8-tetrahydro-5-methyl-6-oxo-2-pteridinyl]amino]-3-methoxy-N-(1-methyl-4-piperidinyl)benzamide (755038-02-9)

Guidance literature:

(R)-4-((8-cyclopentyl-7-ethyl-5-methyl-6-oxo-5,6,7,8-tetrahydropteridin-2-yl)amino)-3-methoxybenzoic acid; With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h; Inert atmosphere;

4-Amino-1-methylpiperidine; In N,N-dimethyl-formamide; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1002/anie.201103273

Reference yield: 40.0%

(R)-2-chloro-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one (755039-55-5) + 4-amino-3-methoxy-N-(1-methylpiperidin-4-yl)benzamide (876126-60-2) → 4-[[(7R)-8-cyclopentyl-7-ethyl-5,6,7,8-tetrahydro-5-methyl-6-oxo-2-pteridinyl]amino]-3-methoxy-N-(1-methyl-4-piperidinyl)benzamide (755038-02-9)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; ethanol; water; Inert atmosphere; Reflux;

DOI:10.1021/acsmedchemlett.5b00084

Reference yield:

4-Amino-1-methylpiperidine (41838-46-4) → 4-[[(7R)-8-cyclopentyl-7-ethyl-5,6,7,8-tetrahydro-5-methyl-6-oxo-2-pteridinyl]amino]-3-methoxy-N-(1-methyl-4-piperidinyl)benzamide (755038-02-9)

Guidance literature:

(R)-4-((8-cyclopentyl-7-ethyl-5-methyl-6-oxo-5,6,7,8-tetrahydropteridin-2-yl)amino)-3-methoxybenzoic acid; With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 25 ℃; for 0.5h;

4-Amino-1-methylpiperidine; In dichloromethane; at 25 ℃; for 2.5h;

upstream raw materials:

4-Amino-1-methylpiperidine

(R)-2-chloro-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one

4-amino-3-methoxy-N-(1-methylpiperidin-4-yl)benzamide

(R)-4-((8-cyclopentyl-7-ethyl-5-methyl-6-oxo-5,6,7,8-tetrahydropteridin-2-yl)amino)-3-methoxybenzoic acid

Downstream raw materials:

4-[[(7R)-8-cyclopentyl-7-ethyl-5,6,7,8-tetrahydro-5-methyl-6-oxo-2-pteridinyl]amino]-3-methoxy-N-(1-methyl-4-piperidinyl)-benzamide; monohydrate

Refernces

• 1、 Chen, Lijia,Yap, Jeremy L.,Yoshioka, Makoto,Lanning, Maryanna E.,Fountain, Rachel N.,Raje, Mithun,Scheenstra, Jacob A.,Strovel, Jeffrey W.,Fletcher, Steven. "BRD4 Structure-Activity Relationships of Dual PLK1 Kinase/BRD4 Bromodomain Inhibitor BI-2536". . p. 764 - 769. Retrieved 2015/08/06.
• 2、 -. "SULFONYL AMIDE DERIVATIVES FOR THE TREATMENT OF ABNORMAL CELL GROWTH". Page/Page column 53; 130. . Retrieved 2009/04/24.