4-(2-Phenyl-quinazolin-4-ylamino)-benzoic acid methyl ester

ID: ALA120099

PubChem CID: 1183964

Max Phase: Preclinical

Molecular Formula: C22H17N3O2

Molecular Weight: 355.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1ccc(Nc2nc(-c3ccccc3)nc3ccccc23)cc1

Standard InChI:  InChI=1S/C22H17N3O2/c1-27-22(26)16-11-13-17(14-12-16)23-21-18-9-5-6-10-19(18)24-20(25-21)15-7-3-2-4-8-15/h2-14H,1H3,(H,23,24,25)

Standard InChI Key:  YNJLEXNLBZQNTP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   -0.5500   -2.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0333   -2.4292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0333   -3.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5500   -3.3375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0708   -2.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0708   -3.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5583   -1.5292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5167   -0.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0000   -0.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917   -3.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5125    0.2750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0333   -1.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0042   -1.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4750   -0.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0375   -0.6167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0458   -0.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4792   -1.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5833   -2.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5833   -3.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917   -3.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0042   -3.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0417   -1.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1083   -2.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1083   -3.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0125   -4.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5292   -3.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5292   -3.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  6  1  0
  5  1  1  0
  6  5  1  0
  7  1  1  0
  8  9  1  0
  9 13  2  0
 10  3  1  0
 11  8  2  0
 12  7  1  0
 13 17  1  0
 14 16  2  0
 15  8  1  0
 16 12  1  0
 17 12  2  0
 18  5  2  0
 19  6  2  0
 20 10  2  0
 21 10  1  0
 22 15  1  0
 23 18  1  0
 24 23  2  0
 25 20  1  0
 26 21  2  0
 27 26  1  0
  4  3  2  0
 14  9  1  0
 19 24  1  0
 25 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA120099

   4-(2-Phenyl-quinazolin-4-ylamino)-benzoic acid methyl ester

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: 355.40

Molecular Weight (Monoisotopic): 355.1321

AlogP: 4.83

#Rotatable Bonds: 4

Polar Surface Area: 64.11

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.18

CX LogP: 5.77

CX LogD: 5.77

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.53

Np Likeness Score: -1.23

References

1. Lee SJ, Konishi Y, Yu DT, Miskowski TA, Riviello CM, Macina OT, Frierson MR, Kondo K, Sugitani M, Sircar JC..  (1995)  Discovery of potent cyclic GMP phosphodiesterase inhibitors. 2-Pyridyl- and 2-imidazolylquinazolines possessing cyclic GMP phosphodiesterase and thromboxane synthesis inhibitory activities.,  38  (18): [PMID:7658441] [10.1021/jm00018a014]

2. Krapf MK, Wiese M..  (2016)  Synthesis and Biological Evaluation of 4-Anilino-quinazolines and -quinolines as Inhibitors of Breast Cancer Resistance Protein (ABCG2).,  59  (11): [PMID:27148793] [10.1021/acs.jmedchem.6b00330]

Source

Source(1):

• Scientific Literature