Tubastatin-A

Base Information

• Chemical Name: Tubastatin-A
• CAS No.: 1252003-15-8
• Molecular Formula: C20H21N3O2
• Molecular Weight: 335.406
• Mol file: 1252003-15-8.mol

Synonyms:N-Hydroxy-4-[(1,2,3,4-tetrahydro-2-methyl-5H-pyrido[4,3-b]indol-5-yl)methyl]benzamide;N-hydroxy-4-((2-methyl-2,3,4,5-tetrahydro-1H-indeno[1,2-c]pyridin-5-yl)methyl)benzamide;N-Hydroxy-4-[(1,2,3,4-tetrahydro-2-methyl-5H-pyrido[4,3-b]indol-5-yl)methyl]benzamide Tubastatin A;Tubastatin A BASE;Tubastatin A(free base);N-hydroxy-4-((2-methyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)methyl)benzamide

Chemical Property of Tubastatin-A

Chemical Property:

• PKA: 8.95±0.10(Predicted)
• PSA: 57.50000
• Density: 1.28±0.1 g/cm3(Predicted)
• LogP: 3.12530
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Solubility.: insoluble in EtOH; insoluble in H2O; ≥10.75 mg/mL in DMSO

Purity/Quality:

99% ^*data from raw suppliers

TubastatinA >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Tubastatin-A

There total 3 articles about Tubastatin-A 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:

4-(2-methyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-ylmethyl)benzoic acid methyl ester (1239034-70-8) → tubastatin A (1252003-15-8)

Guidance literature:

With hydroxylamine hydrochloride; sodium methylate; In methanol; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1021/ja102758v

Reference yield:

1-Methyl-4-piperidone (1445-73-4) → tubastatin A (1252003-15-8)

Guidance literature:

Multi-step reaction with 3 steps

1: sulfuric acid / 1,4-dioxane / 1 h / 60 °C / Cooling with ice

2: potassium tert-butylate / N,N-dimethyl-formamide

3: hydroxylamine

With sulfuric acid; potassium tert-butylate; hydroxylamine; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1016/j.bbadis.2020.165903

Reference yield:

phenylhydrazine (100-63-0) → tubastatin A (1252003-15-8)

Guidance literature:

Multi-step reaction with 3 steps

1: sulfuric acid / 1,4-dioxane / 1 h / 60 °C / Cooling with ice

2: potassium tert-butylate / N,N-dimethyl-formamide

3: hydroxylamine

With sulfuric acid; potassium tert-butylate; hydroxylamine; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1016/j.bbadis.2020.165903

upstream raw materials:

4-(2-methyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-ylmethyl)benzoic acid methyl ester

phenylhydrazine

1-Methyl-4-piperidone

Downstream raw materials:

N-hydroxy-4-(2-methyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-ylmethyl)benzamide trifluoroacetic acid salt

Refernces

• 1、 Butler, Kyle V.,Kalin, Jay,Brochier, Camille,Vistoli, Guilio,Langley, Brett,Kozikowski, Alan P.. "Rational design and simple chemistry yield a superior, neuroprotective HDAC6 inhibitor, tubastatin A". supporting information; experimental part. p. 10842 - 10846. Retrieved 2010/09/16.