2-amino-6-methyl-5-(pyridin-4-ylsulfanyl)-3,4-dihydroquinazolin-4-one

• ChemBase ID: 175548
• Molecular Formular: C14H12N4OS
• Molecular Mass: 284.33628
• Monoisotopic Mass: 284.07318202
• SMILES: [nH]1c(nc2c(c1=O)c(c(cc2)C)Sc1ccncc1)N
• Canonical SMILES: Cc1ccc2c(c1Sc1ccncc1)c(=O)[nH]c(n2)N
• InChI: InChI=1S/C14H12N4OS/c1-8-2-3-10-11(13(19)18-14(15)17-10)12(8)20-9-4-6-16-7-5-9/h2-7H,1H3,(H3,15,17,18,19)
• InChIKey: XHWRWCSCBDLOLM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-6-methyl-5-(pyridin-4-ylsulfanyl)-3,4-dihydroquinazolin-4-one
• IUPAC Traditional name: 2-amino-6-methyl-5-(pyridin-4-ylsulfanyl)-3H-quinazolin-4-one
• Synonyms: 2-Amino-6-methyl-5-(4-pyridinylthio)-4(1H)-quinazolinone Hydrochloride; AG 337; Thymitaq; Nolatrexed Dihydrochloride

Database IDs

• CAS Number: 152946-68-4
• PubChem SID: 164231458
• PubChem CID: 108189

CALCULATED PROPERTIES

• Acid pKa: 11.233831
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.9167137
• LogD (pH = 7.4): 1.9806715
• Log P: 1.9815601
• Molar Refractivity: 81.7571 cm^3
• Polarizability: 29.620365 Å^3
• Polar Surface Area: 80.37 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: >270°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Storage Warning: Hygroscopic

DETAILS

Toronto Research Chemicals - N635800

Antifolate thymidylate synthase inhibitor. Antineoplastic.

REFERENCES

• Webber, S.E., et al.: J. Med. Chem., 36, 733 (1993)
• Rafi, I., et al.: Clin. Cancer Res., 1, 1275 (1993)
• Dash, A.K., et al.: J. Pharm. Sci., 85, 1123 (1993)
• Webber, S., et al.: Cancer Chemother. Pharmacol., 37, 509 (1993)
• Stuart, K., et al.: Cancer, 86