2,4-Diamino-6-[N-(2,3,5-trichlorobenzyl)-N-ethylamino]quinazoline

ID: ALA522543

PubChem CID: 25132197

Max Phase: Preclinical

Molecular Formula: C17H16Cl3N5

Molecular Weight: 396.71

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(Cc1cc(Cl)cc(Cl)c1Cl)c1ccc2nc(N)nc(N)c2c1

Standard InChI:  InChI=1S/C17H16Cl3N5/c1-2-25(8-9-5-10(18)6-13(19)15(9)20)11-3-4-14-12(7-11)16(21)24-17(22)23-14/h3-7H,2,8H2,1H3,(H4,21,22,23,24)

Standard InChI Key:  LAQLUYMJSYVNIA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   -4.0889  -25.0041    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0901  -25.8315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3753  -26.2444    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3771  -24.5914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6617  -25.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6609  -25.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9456  -26.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2306  -25.8235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2354  -24.9936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9513  -24.5863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3795  -23.7664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8049  -26.2434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5234  -24.5767    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1935  -24.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9055  -24.5680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6202  -24.9796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3317  -24.5634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3271  -23.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6051  -23.3296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8966  -23.7481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5284  -23.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2454  -23.3436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6230  -25.8046    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0484  -24.9719    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.5972  -22.5047    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2 12  1  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
  7  8  2  0
 16 17  1  0
  5  4  2  0
 17 18  2  0
  8  9  1  0
 18 19  1  0
  4  1  1  0
 19 20  2  0
 20 15  1  0
  9 10  2  0
 13 21  1  0
 10  5  1  0
 21 22  1  0
 16 23  1  0
  4 11  1  0
 17 24  1  0
  2  3  1  0
 19 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA522543

   2,4-Diamino-6-[N-(2,3,5-trichlorobenzyl)-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: 396.71

Molecular Weight (Monoisotopic): 395.0471

AlogP: 4.78

#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: 5.04

CX LogD: 4.75

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.62

Np Likeness Score: -1.37

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