methyl (1R,3R)-1-(2H-1,3-benzodioxol-5-yl)-2-(2-chloroacetyl)-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylate

• ChemBase ID: 161242
• Molecular Formular: C22H19ClN2O5
• Molecular Mass: 426.84966
• Monoisotopic Mass: 426.0982494
• SMILES: c1ccc2c(c1)c1c([nH]2)[C@H](N([C@H](C1)C(=O)OC)C(=O)CCl)c1cc2c(cc1)OCO2
• Canonical SMILES: ClCC(=O)N1[C@H](Cc2c([C@H]1c1ccc3c(c1)OCO3)[nH]c1c2cccc1)C(=O)OC
• InChI: InChI=1S/C22H19ClN2O5/c1-28-22(27)16-9-14-13-4-2-3-5-15(13)24-20(14)21(25(16)19(26)10-23)12-6-7-17-18(8-12)30-11-29-17/h2-8,16,21,24H,9-11H2,1H3/t16-,21-/m1/s1
• InChIKey: JUKHNCNDFOAFLT-IIBYNOLFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (1R,3R)-1-(2H-1,3-benzodioxol-5-yl)-2-(2-chloroacetyl)-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylate
• IUPAC Traditional name: methyl (1R,3R)-1-(2H-1,3-benzodioxol-5-yl)-2-(2-chloroacetyl)-1H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylate
• Synonyms: (1R,3S)-1-(1,3-Benzodioxol-5-yl)-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic Acid Methyl Ester; (1R,3R)-1-(1,3-Benzodioxol-5-yl)-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic Acid Methyl Ester; (1R,3R)-Methyl-1,2,3,4-tetrahydro-2-chloroacetyl-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate (Chloropretadalafil)

Database IDs

• CAS Number: 171489-59-1; 629652-44-4
• PubChem SID: 162255377
• PubChem CID: 10873617

CALCULATED PROPERTIES

• Acid pKa: 15.169558
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.9808397
• LogD (pH = 7.4): 2.9808397
• Log P: 2.9808397
• Molar Refractivity: 108.5474 cm^3
• Polarizability: 43.557854 Å^3
• Polar Surface Area: 80.86 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Chloroform:Methanol Mixture; Dimethyl Sulfoxide; DMSO; Ethyl Acetate; Methanol
• Apperance: Brown Solid; Pale Yellow to Pale Orange Solid
• Melting Point: 215-218°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere; Room Temp

DETAILS

Toronto Research Chemicals - M330125

An intermediate in the synthesis of Tadalafil (T004500), which is used for the treatment of erectile dysfunction. A phosphodiesterase 5 inhibitor.

Toronto Research Chemicals - B200000

Tadalafil (T004500) derivative.

REFERENCES

• Carrier, S., et al.: Can. J. Urol., 10(1)
• 12 (1)
• Beghyn, T. et al.: Bioorgan. Med. Chem. Lett. 17, 789(2007)