2,4-diamino-6-[(3,4-di-chlorobenzyl)nitrosamino]quinazoline acetate

ID: ALA3272735

PubChem CID: 90677671

Max Phase: Preclinical

Molecular Formula: C17H16Cl2N6O3

Molecular Weight: 363.21

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)O.Nc1nc(N)c2cc(N(Cc3ccc(Cl)c(Cl)c3)N=O)ccc2n1

Standard InChI:  InChI=1S/C15H12Cl2N6O.C2H4O2/c16-11-3-1-8(5-12(11)17)7-23(22-24)9-2-4-13-10(6-9)14(18)21-15(19)20-13;1-2(3)4/h1-6H,7H2,(H4,18,19,20,21);1H3,(H,3,4)

Standard InChI Key:  CRQQJZKCLNMADH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
   22.6367   -5.9998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3512   -5.5873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0657   -5.9998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3512   -4.7623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4854   -2.7498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4843   -3.5772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1990   -3.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1972   -2.3371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9127   -2.7462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9134   -3.5730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6287   -3.9840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3437   -3.5693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.3389   -2.7393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6231   -2.3321    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.0508   -2.3225    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.6304   -4.8090    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.7696   -3.9891    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0554   -3.5760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3406   -3.9880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6273   -3.5727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9130   -3.9840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9119   -4.8099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6310   -5.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3424   -4.8092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1995   -5.2206    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   16.6333   -6.0435    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   18.7689   -4.8141    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0541   -5.2260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  5  6  2  0
  6  7  1  0
  7 10  2  0
  9  8  2  0
  8  5  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
 13 15  1  0
 11 16  1  0
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 22 25  1  0
 23 26  1  0
 17 27  1  0
 27 28  2  0
M  END

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: 363.21

Molecular Weight (Monoisotopic): 362.0450

AlogP: 3.79

#Rotatable Bonds: 4

Polar Surface Area: 110.49

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.87

CX LogP: 3.70

CX LogD: 3.59

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.54

Np Likeness Score: -1.22

References

1. Elslager EF, Jacob P, Johnson J, Werbel LM, Worth DF, Rane L..  (1978)  Folate antagonists. 13. 2,4-Diamino-6-](alpha,alpha,alpha-trifluoro-m-tolyl)thio]quinazoline and related 2,4-diamino-6-[(phenyl- and naphthyl)thio]quinazolines, a unique class of antimetabolites with extraordinary antimalarial and antibacterial effects.,  21  (10): [PMID:102792] [10.1021/jm00208a010]

Source

Source(1):

• Scientific Literature