LMK-235

Base Information

• Chemical Name: LMK-235
• CAS No.: 1418033-25-6
• Molecular Formula: C₁₅H₂₂N₂O₄
• Molecular Weight: 294.351
• Mol file: 1418033-25-6.mol

Synonyms:LMK235

Chemical Property of LMK-235

Chemical Property:

• Melting Point: 135-138°C
• PKA: 9.46±0.20(Predicted)
• Density: 1.155±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble20mg/mL, clear

Purity/Quality:

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

LMK 235 ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Description: Histone deacetylases (HDACs) catalyze the hydrolytic removal of acetyl groups from histone lysine residues, which commonly results in chromatin condensation and transcriptional repression. LMK 235 is an HDAC inhibitor that selectively targets HDACs 4 and 5 (IC50s = 12 and 4 nM, respectively) over other HDACs (IC50s = 56, 320, 850, 880, and 1,280 for HDACs 6, 1, 11, 2, and 8, respectively). It displays enhanced cytotoxic effects against human cancer cell lines, compared to SAHA or trichostatin A . LMK 235 and derivatives inhibit the growth of the malarial parasite P. falciparum at multiple life cycle stages at nanomolar concentrations.
• Uses: LMK 235 is a histone deacetylase (HDAC)4 and HDAC5 inhibitor and has shown to have enhanced cytotoxic effects against the human cancer cell lines A2780, Cal27, Kyse510, and MDA-MB231.

Technology Process of LMK-235

There total 4 articles about LMK-235 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: 58.0%

N-((6-((benzyloxy)amino)-6-oxohexyl)oxy)-3,5-dimethylbenzamide (1418033-00-7) → LMK235 (1418033-25-6)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; at 20 ℃; for 4h; under 750.075 Torr;

DOI:10.1021/jm301254q

Reference yield:

6-(1,3-dioxo-1,3-dihydroisoindol-2-yloxy)hexanoic acid (1101114-27-5) → LMK235 (1418033-25-6)

Guidance literature:

Multi-step reaction with 5 steps

1: thionyl chloride / dichloromethane / 2 h / Reflux

2: pyridine / dichloromethane / 18 h / 20 °C

3: methylhydrazine / dichloromethane / 2 h / -10 °C

4: 1,2-dichloro-ethane; dmap / dichloromethane / 24 h / 20 °C

5: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 4 h / 20 °C / 750.08 Torr

With pyridine; dmap; thionyl chloride; palladium 10% on activated carbon; hydrogen; 1,2-dichloro-ethane; methylhydrazine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm301254q

Reference yield:

benzyl 6-(1,3-dioxoisoindolin-2-yloxy)hexanoate (1418032-61-7) → LMK235 (1418033-25-6)

Guidance literature:

Multi-step reaction with 6 steps

1: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 2 h / 20 °C / 750.08 Torr

2: thionyl chloride / dichloromethane / 2 h / Reflux

3: pyridine / dichloromethane / 18 h / 20 °C

4: methylhydrazine / dichloromethane / 2 h / -10 °C

5: 1,2-dichloro-ethane; dmap / dichloromethane / 24 h / 20 °C

6: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 4 h / 20 °C / 750.08 Torr

With pyridine; dmap; thionyl chloride; palladium 10% on activated carbon; hydrogen; 1,2-dichloro-ethane; methylhydrazine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm301254q

upstream raw materials:

6-(1,3-dioxo-1,3-dihydroisoindol-2-yloxy)hexanoic acid

benzyl 6-(1,3-dioxoisoindolin-2-yloxy)hexanoate

N-((6-((benzyloxy)amino)-6-oxohexyl)oxy)-3,5-dimethylbenzamide

benzyl 6-bromohexanoate

Refernces