1239262-52-2

Basic information

• Product Name: N-Hydroxy-4-[(1,2,3,4-tetrahydro-2-methyl-5H-pyrido[4,3-b]indol-5-yl)methyl]benzamide 2,2,2-Trifluoroacetate
• Synonyms: Tubastatin A Trifluoroacetate;Tubastatin A;TubaststinA HCl;Tubastatin A_HCl;Tubastatin A Trifluoroacetic Acid Salt;N-Hydroxy-4-((2-Methyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)Methyl)benzaMide 2,2,2-trifluoroacetate;Tubastatin A TFA;Tubastain A
• CAS NO: 1239262-52-2
• Molecular Formula: C₂HF₃O₂*C₂₀H₂₁N₃O₂
• Molecular Weight: 431.4077096
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 1239262-52-2.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: N-Hydroxy-4-[(1,2,3,4-tetrahydro-2-methyl-5H-pyrido[4,3-b]indol-5-yl)methyl]benzamide 2,2,2-Trifluoroacetate(CAS DataBase Reference)
• NIST Chemistry Reference: N-Hydroxy-4-[(1,2,3,4-tetrahydro-2-methyl-5H-pyrido[4,3-b]indol-5-yl)methyl]benzamide 2,2,2-Trifluoroacetate(1239262-52-2)
• EPA Substance Registry System: N-Hydroxy-4-[(1,2,3,4-tetrahydro-2-methyl-5H-pyrido[4,3-b]indol-5-yl)methyl]benzamide 2,2,2-Trifluoroacetate(1239262-52-2)

Safety Data

• Hazardous Substances Data: 1239262-52-2(Hazardous Substances Data)

Usage

Description

N-Hydroxy-4-[(1,2,3,4-tetrahydro-2-methyl-5H-pyrido[4,3-b]indol-5-yl)methyl]benzamide 2,2,2-Trifluoroacetate is a complex organic compound with a unique molecular structure. It is characterized by its benzamide backbone, which is modified with a tetrahydro-2-methyl-5H-pyrido[4,3-b]indol-5-ylmethyl group, and further functionalized with a 2,2,2-trifluoroacetate moiety. N-Hydroxy-4-[(1,2,3,4-tetrahydro-2-methyl-5H-pyrido[4,3-b]indol-5-yl)methyl]benzamide 2,2,2-Trifluoroacetate has been identified for its potential as a neuroprotective agent, specifically as an HDAC6 inhibitor.

Uses

Used in Pharmaceutical Industry:
N-Hydroxy-4-[(1,2,3,4-tetrahydro-2-methyl-5H-pyrido[4,3-b]indol-5-yl)methyl]benzamide 2,2,2-Trifluoroacetate is used as a neuroprotective agent for the treatment of neurodegenerative diseases. Its application is based on its ability to inhibit Histone deacetylase 6 (HDAC6), a protein known to play a role in the regulation of cellular processes and implicated in various neurological disorders.
Used in Research Applications:
In the field of research, N-Hydroxy-4-[(1,2,3,4-tetrahydro-2-methyl-5H-pyrido[4,3-b]indol-5-yl)methyl]benzamide 2,2,2-Trifluoroacetate serves as a potent HDAC inhibitor. It is utilized in studies aimed at understanding the role of HDAC6 in neurodegenerative processes and for the development of novel therapeutic strategies targeting this enzyme.
Used in Drug Development:
N-Hydroxy-4-[(1,2,3,4-tetrahydro-2-methyl-5H-pyrido[4,3-b]indol-5-yl)methyl]benzamide 2,2,2-Trifluoroacetate is also used in drug development for the creation of new pharmaceuticals targeting HDAC6. Its potent inhibitory activity makes it a valuable candidate for the design of drugs that could potentially treat a range of neurological conditions by modulating the activity of this enzyme.

Synthetic route

4-(2-methyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-ylmethyl)benzoic acid methyl ester (1239034-70-8) + trifluoroacetic acid (76-05-1) → N-hydroxy-4-(2-methyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-ylmethyl)benzamide trifluoroacetic acid salt (1239262-52-2)

Conditions	Yield
Stage #1: 4-(2-methyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-ylmethyl)benzoic acid methyl ester With hydroxylamine hydrochloride; sodium methylate In methanol at 20℃; for 24h; Inert atmosphere; Stage #2: trifluoroacetic acid In water HPLC column;	31%

tubastatin A (1252003-15-8) + trifluoroacetic acid (76-05-1) → N-hydroxy-4-(2-methyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-ylmethyl)benzamide trifluoroacetic acid salt (1239262-52-2)

1-Methyl-4-piperidone (1445-73-4) → N-hydroxy-4-(2-methyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-ylmethyl)benzamide trifluoroacetic acid salt (1239262-52-2)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sulfuric acid / 1,4-dioxane / 0 - 60 °C 1.2: pH 12 2.1: potassium tert-butylate / N,N-dimethyl-formamide / 0.25 h / 20 °C / Inert atmosphere 2.2: 2 h / 80 °C / Inert atmosphere 3.1: hydroxylamine hydrochloride; sodium methylate / methanol / 24 h / 20 °C / Inert atmosphere 3.2: HPLC column View Scheme

phenylhydrazine (100-63-0) → N-hydroxy-4-(2-methyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-ylmethyl)benzamide trifluoroacetic acid salt (1239262-52-2)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sulfuric acid / 1,4-dioxane / 0 - 60 °C 1.2: pH 12 2.1: potassium tert-butylate / N,N-dimethyl-formamide / 0.25 h / 20 °C / Inert atmosphere 2.2: 2 h / 80 °C / Inert atmosphere 3.1: hydroxylamine hydrochloride; sodium methylate / methanol / 24 h / 20 °C / Inert atmosphere 3.2: HPLC column View Scheme

2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (5094-12-2) → N-hydroxy-4-(2-methyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-ylmethyl)benzamide trifluoroacetic acid salt (1239262-52-2)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium tert-butylate / N,N-dimethyl-formamide / 0.25 h / 20 °C / Inert atmosphere 1.2: 2 h / 80 °C / Inert atmosphere 2.1: hydroxylamine hydrochloride; sodium methylate / methanol / 24 h / 20 °C / Inert atmosphere 2.2: HPLC column View Scheme

Upstream product

• 5094-12-2 2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole 
• 100-63-0 phenylhydrazine 
• 1445-73-4 1-Methyl-4-piperidone 
• 1239034-70-8 4-(2-methyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-ylmethyl)benzoic acid methyl ester 
• 76-05-1 trifluoroacetic acid 
• 1252003-15-8 tubastatin A 

Relevant articles and documents

HDAC INHIBITORS AND THERAPEUTIC METHODS USING THE SAME

Histone deacetylases inhibitors (HDACIs) and compositions containing the same are disclosed. Methods of treating diseases and conditions wherein inhibition of HDAC provides a benefit, like a cancer, a neurodegenerative disorder, a neurological disease, traumatic brain injury, stroke, malaria, an autoimmune disease, autism, and inflammation, also are disclosed.