methyl 2-(2-chloroacetyl)-1-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-1-carboxylate

• ChemBase ID: 155038
• Molecular Formular: C16H17ClN2O3
• Molecular Mass: 320.77078
• Monoisotopic Mass: 320.09277009
• SMILES: CC1(c2c(c3ccccc3[nH]2)CCN1C(=O)CCl)C(=O)OC
• Canonical SMILES: ClCC(=O)N1CCc2c(C1(C)C(=O)OC)[nH]c1c2cccc1
• InChI: InChI=1S/C16H17ClN2O3/c1-16(15(21)22-2)14-11(7-8-19(16)13(20)9-17)10-5-3-4-6-12(10)18-14/h3-6,18H,7-9H2,1-2H3
• InChIKey: BCSIRYFYAKLJDK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 2-(2-chloroacetyl)-1-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-1-carboxylate
• IUPAC Traditional name: methyl 2-(2-chloroacetyl)-1-methyl-3H,4H,9H-pyrido[3,4-b]indole-1-carboxylate
• Synonyms: 2-(2-Chloroacetyl)-2,3,4,9-tetrahydro-1-methyl-1H-pyrido[3,4-b]indole-1-carboxylic acid methyl ester; Methyl 2-(2-chloroacetyl)-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-carboxylate; PDI inhibitor 16F16

Database IDs

• CAS Number: 922507-80-0
• MDL Number: MFCD20134198
• PubChem SID: 162249176
• PubChem CID: 4555562

CALCULATED PROPERTIES

• Acid pKa: 14.979968
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.006132
• LogD (pH = 7.4): 2.006132
• Log P: 2.006132
• Molar Refractivity: 83.211 cm^3
• Polarizability: 33.32899 Å^3
• Polar Surface Area: 62.4 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥12 mg/mL
• Apperance: white to tan powder

Safety Information

• German water hazard class: 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C16H17ClN2O3

DETAILS

Sigma Aldrich - SML0021

Biochem/physiol Actions
16F16 is a protein disulfide isomerase (PDI) inhibitor, first identified in a screen for compounds that prevent apoptosis induced by mutant huntingtin protein. 16F16 not only suppressed apoptosis induced by the misfolded protein mutant hungtingtin, it also protected rat neurons from cell death triggered by Aβ peptide. The actions of this inhibitor helped to identify a new mechanism in which a cell death pathway is regulated by protein misfolding via PDI upregulation.