7-(5-(1,5-dichloropentan-3-yl)-1-Methyl-1H-benzo[d]iMidazol-2-yl)-N-hydroxyheptanaMide

Base Information

• Chemical Name: 7-(5-(1,5-dichloropentan-3-yl)-1-Methyl-1H-benzo[d]iMidazol-2-yl)-N-hydroxyheptanaMide
• CAS No.: 1236199-60-2
• Molecular Formula: C₁₉H₂₈Cl₂N₄O₂
• Molecular Weight: 415.363
• Mol file: 1236199-60-2.mol

Synonyms:7‐[5‐[bis(2-chloroethyl)amino]‐1‐methyl-1H-benzimidazole-2-yl]-N-hydroxyheptanamide

Chemical Property of 7-(5-(1,5-dichloropentan-3-yl)-1-Methyl-1H-benzo[d]iMidazol-2-yl)-N-hydroxyheptanaMide

Chemical Property:

• PKA: 9.48±0.20(Predicted)
• Density: 1.27±0.1 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C

Purity/Quality:

99%, ^*data from raw suppliers

Tinostamustine(EDO-S101) >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: EDO-S101 is a fusion molecule composed of the DNA alkylating agent bendamustine and the histone deacetylase (HDAC) inhibitor SAHA that inhibits class I and II HDACs (IC50s = 9-107 nM for HDAC1-3, 6, 8, and 10). It inhibits HDAC activity in rat peripheral blood mononuclear cells (PBMCs) ex vivo by 90% following a single dose of 10 mg/kg. EDO-S101 also induces formation of DNA crosslinks and double-strand breaks in HL-60 cells. It reduces growth of multiple myeloma (MM) cell lines irrespective of p53 mutational status or established resistance to DNA alkylating agents (IC50s = 1.6-4.8 μM). EDO-S101 also induces MM cell death ex vivo in bone marrow samples isolated from patients with early- and late-stage MM. In vivo, EDO-S101 (60 mg/kg per week) reduces tumor growth and prolongs survival in an MM1S end-stage mouse xenograft model. It also prolongs survival in a multidrug resistant Vk12653 mouse transplant model of refractory MM.

Technology Process of 7-(5-(1,5-dichloropentan-3-yl)-1-Methyl-1H-benzo[d]iMidazol-2-yl)-N-hydroxyheptanaMide

There total 12 articles about 7-(5-(1,5-dichloropentan-3-yl)-1-Methyl-1H-benzo[d]iMidazol-2-yl)-N-hydroxyheptanaMide 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: 88.5%

[1-methyl-2-(7'-heptanoate)-5-Ν,Ν-bis(2'-chloroethyl)]-1H-benzimidazole → 7‐[5‐[bis(2-chloroethyl)amino]‐1‐methyl-1H-benzimidazole-2-yl]-N-hydroxyheptanamide (1236199-60-2)

Guidance literature:

With hydroxylamine hydrochloride; potassium hydroxide; In methanol; at 20 ℃; for 3h; Time;

Reference yield:

C19H27Cl2N3O2 → 7‐[5‐[bis(2-chloroethyl)amino]‐1‐methyl-1H-benzimidazole-2-yl]-N-hydroxyheptanamide (1236199-60-2)

Guidance literature:

C₁₉H₂₇Cl₂N₃O₂; With 4-methyl-morpholine; chloroformic acid ethyl ester; In diethyl ether; at 0 ℃; for 0.166667h;

With hydroxylamine; In methanol; at 20 ℃; for 0.25h;

Reference yield:

C15H21N3O5 (1236199-92-0) → 7‐[5‐[bis(2-chloroethyl)amino]‐1‐methyl-1H-benzimidazole-2-yl]-N-hydroxyheptanamide (1236199-60-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: hydrogen / palladium on activated charcoal / ethanol / 4 h / 20 °C / Inert atmosphere

2.1: sodium acetate; acetic acid / water / 10 - 20 °C

3.1: thionyl chloride / chloroform / 5 h / 20 °C / Cooling with ice bath

4.1: 4-methyl-morpholine; chloroformic acid ethyl ester / diethyl ether / 0.17 h / 0 °C

4.2: 0.25 h / 20 °C

With 4-methyl-morpholine; thionyl chloride; hydrogen; sodium acetate; chloroformic acid ethyl ester; acetic acid; palladium on activated charcoal; In diethyl ether; ethanol; chloroform; water;

upstream raw materials:

methyl 8-chloro-8-oxooctanoate

2,4-Dinitroanilin

C₁₅H₂₁N₃O₅

N-methyl-2,4-dinitroaniline

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