2-(4-Dimethylamino-phenyl)-3-hexyl-3H-quinazolin-4-one

ID: ALA152046

PubChem CID: 44369232

Max Phase: Preclinical

Molecular Formula: C22H27N3O

Molecular Weight: 349.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCn1c(-c2ccc(N(C)C)cc2)nc2ccccc2c1=O

Standard InChI:  InChI=1S/C22H27N3O/c1-4-5-6-9-16-25-21(17-12-14-18(15-13-17)24(2)3)23-20-11-8-7-10-19(20)22(25)26/h7-8,10-15H,4-6,9,16H2,1-3H3

Standard InChI Key:  XMOVBXFEJGGQKY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    6.3750   -7.4167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3792   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6542   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6667   -8.6667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   -7.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   -8.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0917   -8.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6542   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5167   -9.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2292   -9.9042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0917   -9.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8042   -8.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5167   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8000   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0875   -7.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2292   -7.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2292   -8.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2250  -10.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9417   -9.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8042   -7.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5167   -7.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9417   -6.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2292   -7.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5167   -6.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5167   -8.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6542   -7.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  2  2  0
  5  3  1  0
  6  5  1  0
  7  2  1  0
  8  3  2  0
  9 13  1  0
 10  9  1  0
 11  7  2  0
 12  7  1  0
 13 12  2  0
 14 11  1  0
 15  1  1  0
 16  5  2  0
 17  6  2  0
 18 10  1  0
 19 10  1  0
 20 15  1  0
 21 16  1  0
 22 23  1  0
 23 24  1  0
 24 20  1  0
 25 21  2  0
 26 22  1  0
  4  6  1  0
 14  9  2  0
 25 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA152046

   2-(4-Dimethylamino-phenyl)-3-hexyl-3H-quinazolin-4-one

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: 349.48

Molecular Weight (Monoisotopic): 349.2154

AlogP: 4.71

#Rotatable Bonds: 7

Polar Surface Area: 38.13

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.06

CX LogP: 5.17

CX LogD: 5.17

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.58

Np Likeness Score: -1.12

References

1. Wang S, Ryder H, Pretswell I, Depledge P, Milton J, Hancox TC, Dale I, Dangerfield W, Charlton P, Faint R, Dodd R, Hassan S..  (2002)  Studies on quinazolinones as dual inhibitors of Pgp and MRP1 in multidrug resistance.,  12  (4): [PMID:11844674] [10.1016/s0960-894x(01)00804-6]

2. Brown CE, Kong T, Bordón C, Yolken R, Jones-Brando L, McNulty J..  (2018)  One-pot, multicomponent synthesis of 2,3-disubstituted quinazolin-ones with potent and selective activity against Toxoplasma gondii.,  28  (9): [PMID:29598911] [10.1016/j.bmcl.2018.03.036]

Source

Source(1):

• Scientific Literature