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

Uses

Different sources of media describe the Uses of 1239262-52-2 differently. You can refer to the following data:
1. Neuroprotective HDAC6 inhibitor.
2. Neuroprotective HDAC6 inhibitor. Potent Histone deacetylase inhibitor.

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.