LFM-A13

Base Information

• Chemical Name: LFM-A13
• CAS No.: 244240-24-2
• Molecular Formula: C11H8 Br2 N2 O2
• Molecular Weight: 360.005
• Mol file: 244240-24-2.mol

Synonyms:LFM-A 13

Chemical Property of LFM-A13

Chemical Property:

• PSA: 73.12000
• LogP: 3.57868
• Storage Temp.: −20°C
• Solubility.: DMSO: 15 mg/mL

Purity/Quality:

98%,99%, ^*data from raw suppliers

LFM-A13 ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Description: LFM-A13 (244240-24-2) is a selective inhibitor of Bruton’s tyrosine kinase (BTK) – IC50‘s = 2.5 μM (recombinant BTK) and 17.2 μM (human BTK).1,2 It has also been shown to inhibit Polo-like kinase (PLK) – IC50 = 61 μM for human PLK3.3 LFM-A13 displayed no activity (concentrations up to 278 μM) at JAK1, JAK3, HCK, EGFRK and IRK2 or CDK1-3, CHK1, IKK, MAPK1, SAPK2a and ten other tyrosine kinases.3
• Uses: LFM-A13 is a potent inhibitor of Polo-like kinase (PLK), used for anti-breast cancer activity. Also a specific Bruton’s tyrosine kinase inhibitor.

Technology Process of LFM-A13

There total 3 articles about LFM-A13 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: 79.0%

N-(2,5-dibromophenyl)-2-cyanoacetamide (63034-99-1) + acetic anhydride (108-24-7) → (2Z)-N-(2,5-dibromophenyl)-2-cyano-3-hydroxybut-2-enamide (244240-24-2,62004-35-7)

Guidance literature:

With sodium t-butanolate; In tetrahydrofuran; at 20 ℃;

Reference yield: 78.0%

N-(2,5-dibromophenyl)-2-cyanoacetamide (63034-99-1) + acetyl chloride (75-36-5) → (2Z)-N-(2,5-dibromophenyl)-2-cyano-3-hydroxybut-2-enamide (244240-24-2,62004-35-7)

Guidance literature:

N-(2,5-dibromophenyl)-2-cyanoacetamide; With sodium hydride; In tetrahydrofuran; at -0.15 ℃; for 1h;

acetyl chloride; In tetrahydrofuran; for 1h; room t.;

DOI:10.1107/S0108270199005727

Reference yield:

2,5-dibromoaniline (3638-73-1) → (2Z)-N-(2,5-dibromophenyl)-2-cyano-3-hydroxybut-2-enamide (244240-24-2,62004-35-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / 1,3-diisopropylcarbodiimide / ethyl acetate / 24 h / 20 °C

2: 79 percent / sodium tert-butoxide / tetrahydrofuran / 20 °C

With sodium t-butanolate; diisopropyl-carbodiimide; In tetrahydrofuran; ethyl acetate;

upstream raw materials:

N-(2,5-dibromophenyl)-2-cyanoacetamide

acetyl chloride

acetic anhydride

2,5-dibromoaniline

Refernces

• 1、 DuMez, Darin,Venkatachalam, Taracad K.,Uckun, Fatih M.. "Large-scale synthesis of GMP grade α-cyano-β-hydroxy-β- methyl-N-(2,5-dibromophenyl) propenamide (LFM-A13), a new anti-cancer drug candidate". . p. 155 - 163. Retrieved 2007/10/03.
• 2、 Tibbles, Heather E.,Samuel, Peter,Erbeck, Doug,Mahajan, Sandeep,Uckun, Fatih M.. "In vivo toxicity and antithrombotic profile of the oral formulation of the antileukemic agent, LFM-A13-F". . p. 330 - 339. Retrieved 2007/10/03.