1-(2,4-dichlorobenzoyl)-1H-1,2,3-benzotriazole

• ChemBase ID: 153870
• Molecular Formular: C13H7Cl2N3O
• Molecular Mass: 292.12018
• Monoisotopic Mass: 290.99661722
• SMILES: c1ccc2c(c1)nnn2C(=O)c1ccc(cc1Cl)Cl
• Canonical SMILES: Clc1ccc(c(c1)Cl)C(=O)n1nnc2c1cccc2
• InChI: InChI=1S/C13H7Cl2N3O/c14-8-5-6-9(10(15)7-8)13(19)18-12-4-2-1-3-11(12)16-17-18/h1-7H
• InChIKey: UVNLAUGZMOPBPR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(2,4-dichlorobenzoyl)-1H-1,2,3-benzotriazole
• IUPAC Traditional name: 1-(2,4-dichlorobenzoyl)-1,2,3-benzotriazole
• Synonyms: 1-(2,4-Dichlorobenzoyl)-1H-benzotriazole; Inhibitor-1 of Trichostatin A; N-(1H-Benzotriazol-1-yl)-2,4-dichlorobenzamide; ITSA-1

Database IDs

• CAS Number: 200626-61-5
• MDL Number: MFCD00195103
• PubChem SID: 162248009; 24724515
• PubChem CID: 771910

CALCULATED PROPERTIES

• H Donor: 0
• LogD (pH = 5.5): 3.6833549
• LogD (pH = 7.4): 3.683355
• Log P: 3.683355
• Molar Refractivity: 73.6085 cm^3
• Polarizability: 29.021029 Å^3
• Polar Surface Area: 47.78 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true
• H Acceptors: 3

PROPERTIES

Physical Property

• Solubility: DMSO: ~28 mg/mL
• Apperance: solid

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C13H7Cl2N3O

DETAILS

Sigma Aldrich - I4159

Biochem/physiol Actions
ITSA-1 is a suppressor of Trichostatin A (TSA) and a molecular tool for dissecting gene regulation by distinct aceytlation events (histone and tubulin). ITSA-1 is membrane permeable and specifically suppresses TSA inhibition of HDAC (histone deacetylase), but not other HDAC inhibitors. ITSA-1 rreverses TSA induced histone acetylation, overall deacetylation. ITSA-1 also reverses TSA induced cell cycle arrest and apoptosis. Effective range 50 μM.