methyl (1S,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: 161243
• 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-IERDGZPVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (1S,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 (1S,3R)-1-(2H-1,3-benzodioxol-5-yl)-2-(2-chloroacetyl)-1H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylate
• Synonyms: (1S,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

Database IDs

• CAS Number: 629652-42-2
• PubChem SID: 162255378
• PubChem CID: 10906056

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:Methanol Mixtu; Dimethyl Sulfoxide
• Apperance: Pale Yellow Solid

Safety Information

• Storage Condition: Room Temp

DETAILS

Toronto Research Chemicals - B200005

Tadalafil (T004500) derivative.

REFERENCES

• Beghyn, T. et al.: Bioorgan. Med. Chem. Lett. 17, 789(2007)