6-(4-methoxyphenylthio)quinazoline-2,4-diamine

ID: ALA3272726

PubChem CID: 86220118

Max Phase: Preclinical

Molecular Formula: C15H14N4OS

Molecular Weight: 298.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(Sc2ccc3nc(N)nc(N)c3c2)cc1

Standard InChI:  InChI=1S/C15H14N4OS/c1-20-9-2-4-10(5-3-9)21-11-6-7-13-12(8-11)14(16)19-15(17)18-13/h2-8H,1H3,(H4,16,17,18,19)

Standard InChI Key:  VNLVZGRBERBUNJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   13.5235  -28.6140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5224  -29.4336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2304  -29.8425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2286  -28.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9372  -28.6104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9380  -29.4295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6465  -29.8365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3548  -29.4257    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3501  -28.6036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6410  -28.2002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.0553  -28.1907    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6482  -30.6537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8143  -29.8416    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.1070  -29.4325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1121  -28.6154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4056  -28.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6966  -28.6144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6986  -29.4358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4057  -29.8412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9886  -28.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2812  -28.6152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  9 11  1  0
  7 12  1  0
  2 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 17 20  1  0
 20 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3272726

   6-(4-Methoxyphenyl)sulfanylquinazoline-2,4-diamine

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: 298.37

Molecular Weight (Monoisotopic): 298.0888

AlogP: 2.95

#Rotatable Bonds: 3

Polar Surface Area: 87.05

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.91

CX LogP: 3.07

CX LogD: 2.95

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.77

Np Likeness Score: -0.88

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