2,4-Diamino-6-[N-(beta-naphthyl)-N-ethylamino]quinazoline

ID: ALA522678

PubChem CID: 25132196

Max Phase: Preclinical

Molecular Formula: C21H21N5

Molecular Weight: 343.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(Cc1ccc2ccccc2c1)c1ccc2nc(N)nc(N)c2c1

Standard InChI:  InChI=1S/C21H21N5/c1-2-26(13-14-7-8-15-5-3-4-6-16(15)11-14)17-9-10-19-18(12-17)20(22)25-21(23)24-19/h3-12H,2,13H2,1H3,(H4,22,23,24,25)

Standard InChI Key:  SXZPDRHCLNZYOT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   -4.5984  -20.1673    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5995  -20.9948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8845  -21.4078    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8863  -19.7544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1708  -20.1636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1701  -20.9907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4546  -21.4017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7393  -20.9869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7441  -20.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4602  -19.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8888  -18.9292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3145  -21.4069    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0320  -19.7398    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3149  -20.1480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3973  -19.7311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1122  -20.1427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0971  -18.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3883  -18.9110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0370  -18.9146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7541  -18.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8191  -18.9004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8210  -19.7255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5325  -20.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2467  -19.7222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2449  -18.8972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5288  -18.4840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
  9 13  1  0
  3  6  2  0
 13 14  1  0
  6  7  1  0
 14 15  1  0
  1  2  2  0
 15 16  2  0
 16 22  1  0
  7  8  2  0
 21 17  1  0
  5  4  2  0
 17 18  2  0
 18 15  1  0
  8  9  1  0
 13 19  1  0
  4  1  1  0
 19 20  1  0
 21 22  2  0
  9 10  2  0
 10  5  1  0
  4 11  1  0
  2  3  1  0
  2 12  1  0
 21 26  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA522678

   2,4-Diamino-6-[N-(beta-naphthyl)-N-ethylamino]quinazoline

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: 343.43

Molecular Weight (Monoisotopic): 343.1797

AlogP: 3.97

#Rotatable Bonds: 4

Polar Surface Area: 81.06

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.40

CX LogP: 4.22

CX LogD: 3.92

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.59

Np Likeness Score: -1.09

References

1. Gangjee A, Adair OO, Pagley M, Queener SF..  (2008)  N9-substituted 2,4-diaminoquinazolines: synthesis and biological evaluation of lipophilic inhibitors of pneumocystis carinii and toxoplasma gondii dihydrofolate reductase.,  51  (19): [PMID:18771252] [10.1021/jm800694g]

Source

Source(1):

• Scientific Literature