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

ID: ALA455012

PubChem CID: 44569106

Max Phase: Preclinical

Molecular Formula: C23H25N5

Molecular Weight: 371.49

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C23H25N5/c1-2-3-12-28(15-16-8-9-17-6-4-5-7-18(17)13-16)19-10-11-21-20(14-19)22(24)27-23(25)26-21/h4-11,13-14H,2-3,12,15H2,1H3,(H4,24,25,26,27)

Standard InChI Key:  XROWQZMGTMLPOY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   -3.5977   -5.4089    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5988   -6.2364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8839   -6.6493    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8857   -4.9961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1703   -5.4053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1696   -6.2322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4542   -6.6433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7390   -6.2284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7438   -5.3983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4598   -4.9911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8882   -4.1710    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3137   -6.6484    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0318   -4.9815    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6853   -5.3896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3974   -4.9728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1122   -5.3844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0970   -3.7342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3884   -4.1528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0368   -4.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7538   -3.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8190   -4.1422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8209   -4.9672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5323   -5.3757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2464   -4.9640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2446   -4.1390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5286   -3.7258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7589   -2.9231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4759   -2.5149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
  5  6  1  0
 20 27  1  0
  9 13  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA455012

   2,4-Diamino-6-[N-(beta-naphthyl)-N-cyclopropyl methylamino]-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: 371.49

Molecular Weight (Monoisotopic): 371.2110

AlogP: 4.75

#Rotatable Bonds: 6

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: 5.19

CX LogD: 4.89

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.51

Np Likeness Score: -1.03

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