2-(4-(2,4-difluorobenzyloxy)phenyl)quinazolin-4(3H)-one

ID: ALA4084413

PubChem CID: 137645181

Max Phase: Preclinical

Molecular Formula: C21H14F2N2O2

Molecular Weight: 364.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1[nH]c(-c2ccc(OCc3ccc(F)cc3F)cc2)nc2ccccc12

Standard InChI:  InChI=1S/C21H14F2N2O2/c22-15-8-5-14(18(23)11-15)12-27-16-9-6-13(7-10-16)20-24-19-4-2-1-3-17(19)21(26)25-20/h1-11H,12H2,(H,24,25,26)

Standard InChI Key:  JHDBNFXRMWLNDK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   22.7918  -17.8156    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.5114  -17.4258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5349  -16.6077    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.8353  -16.1774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1158  -16.5673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4198  -16.1391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7002  -16.5290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6767  -17.3470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3727  -17.7752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0923  -17.3853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8567  -15.3628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9270  -17.4640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2074  -17.8539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1839  -18.6720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8800  -19.1001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5995  -18.7103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6230  -17.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2956  -19.1384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.2728  -19.9553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9688  -20.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9418  -21.1981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6371  -21.6261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3569  -21.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3771  -20.4162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6812  -19.9919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6996  -19.1749    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   29.0535  -21.6647    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  1 10  1  0
  5 10  2  0
  4 11  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 12 17  2  0
  2 13  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 25 26  1  0
 23 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4084413

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 364.35

Molecular Weight (Monoisotopic): 364.1023

AlogP: 4.45

#Rotatable Bonds: 4

Polar Surface Area: 54.98

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.12

CX Basic pKa: 4.66

CX LogP: 4.48

CX LogD: 4.42

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.58

Np Likeness Score: -1.38

References

1. Mohd Siddique MU, McCann GJ, Sonawane VR, Horley N, Gatchie L, Joshi P, Bharate SB, Jayaprakash V, Sinha BN, Chaudhuri B..  (2017)  Quinazoline derivatives as selective CYP1B1 inhibitors.,  130  [PMID:28259840] [10.1016/j.ejmech.2017.02.032]

2. Sonawane V, Mohd Siddique MU, Jadav SS, Sinha BN, Jayaprakash V, Chaudhuri B..  (2019)  Cink4T, a quinazolinone-based dual inhibitor of Cdk4 and tubulin polymerization, identified via ligand-based virtual screening, for efficient anticancer therapy.,  165  [PMID:30665142] [10.1016/j.ejmech.2019.01.011]

Source

Source(1):

• Scientific Literature