4-({4-[(2,4,6-trimethylphenyl)amino]pyrimidin-2-yl}amino)benzonitrile

• ChemBase ID: 6243
• Molecular Formular: C20H19N5
• Molecular Mass: 329.39836
• Monoisotopic Mass: 329.16404563
• SMILES: c1(Nc2nc(Nc3ccc(cc3)C#N)ncc2)c(C)cc(cc1C)C
• Canonical SMILES: N#Cc1ccc(cc1)Nc1nccc(n1)Nc1c(C)cc(cc1C)C
• InChI: InChI=1S/C20H19N5/c1-13-10-14(2)19(15(3)11-13)24-18-8-9-22-20(25-18)23-17-6-4-16(12-21)5-7-17/h4-11H,1-3H3,(H2,22,23,24,25)
• InChIKey: ILAYIAGXTHKHNT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-({4-[(2,4,6-trimethylphenyl)amino]pyrimidin-2-yl}amino)benzonitrile
• IUPAC Traditional name: 4-({4-[(2,4,6-trimethylphenyl)amino]pyrimidin-2-yl}amino)benzonitrile
• Synonyms: 4-[4-(2,4,6-TRIMETHYL-PHENYLAMINO)-PYRIMIDIN-2-YLAMINO]-BENZONITRILE; 4-[[4-[(2,4,6-Trimethylphenyl)amino]-2-pyrimidinyl]amino]benzonitrile; R 147681; TMC 120; TMC 120R147681; Dapivirine; TMC120

Database IDs

• CAS Number: 244767-67-7
• PubChem SID: 160969668; 99445110
• PubChem CID: 214347

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.926171
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 5.4419494
• LogD (pH = 7.4): 5.5967746
• Log P: 5.5991907
• Molar Refractivity: 100.7994 cm^3
• Polarizability: 37.1268 Å^3
• Polar Surface Area: 73.63 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 4.12
• LOG S: -4.29
• Solubility (Water): 1.70e-02 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Light Beige Solid
• Melting Point: 219-221°C

Safety Information

• Storage Condition: Refrigerator

Pharmacology Properties

• Target: Reverse Transcriptase

Product Information

• Salt Data: Free Base

DETAILS

DrugBank - DB08639

Drug information: experimental

Toronto Research Chemicals - D185500

Non-nucleoside Reverse Transcriptase inhibitor. An antiviral agent.

REFERENCES

• Qin, B., et al.: J. Med. Chem., 53, 4906 (2010)
• Woolfson, A., et al.: Int. J. Pharm., 388, 136 (2010)
• Johnson, T., et al.: Eur. J. Pharm. Sci., 39, 203 (2010)