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

ID: ALA3272716

PubChem CID: 622601

Max Phase: Preclinical

Molecular Formula: C14H12N4S

Molecular Weight: 268.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N)c2cc(Sc3ccccc3)ccc2n1

Standard InChI:  InChI=1S/C14H12N4S/c15-13-11-8-10(19-9-4-2-1-3-5-9)6-7-12(11)17-14(16)18-13/h1-8H,(H4,15,16,17,18)

Standard InChI Key:  ZPCHLRLETWGWJB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
   11.4186  -14.6558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4175  -15.4753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1255  -15.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1237  -14.2469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8324  -14.6522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8331  -15.4712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5417  -15.8782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2499  -15.4674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2452  -14.6453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5361  -14.2419    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9504  -14.2324    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5433  -16.6954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7094  -15.8833    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.0021  -15.4742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0072  -14.6571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3007  -14.2480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5917  -14.6561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5937  -15.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3008  -15.8829    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
M  END

Alternative Forms

1. Parent:

   

   ALA3272716

   2,4-Diamino-6-phenylthioquinazoline

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: 268.35

Molecular Weight (Monoisotopic): 268.0783

AlogP: 2.95

#Rotatable Bonds: 2

Polar Surface Area: 77.82

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.91

CX LogP: 3.23

CX LogD: 3.11

Aromatic Rings: 3

Heavy Atoms: 19

QED Weighted: 0.75

Np Likeness Score: -1.03

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