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

ID: ALA3246662

PubChem CID: 86220238

Max Phase: Preclinical

Molecular Formula: C14H11BrN4S

Molecular Weight: 347.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N)c2cc(Sc3ccc(Br)cc3)ccc2n1

Standard InChI:  InChI=1S/C14H11BrN4S/c15-8-1-3-9(4-2-8)20-10-5-6-12-11(7-10)13(16)19-14(17)18-12/h1-7H,(H4,16,17,18,19)

Standard InChI Key:  ZVRAALLIIFQTIW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
   16.8432  -17.3756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8432  -18.1928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5485  -18.5973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5485  -16.9629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2538  -17.3756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2548  -18.1928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9591  -18.5983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6669  -18.1910    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.6659  -17.3738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9571  -16.9639    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3735  -16.9650    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9590  -19.4155    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1361  -18.6024    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.4278  -18.1949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4255  -17.3787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7180  -16.9712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0140  -17.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0184  -18.2023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7218  -18.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3045  -16.9754    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  2  0
  2  3  2  0
  3  6  1  0
  5  4  1  0
  5  6  2  0
  5 10  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  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
M  END

Alternative Forms

1. Parent:

   

   ALA3246662

   6-(4-Bromophenyl)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: 347.24

Molecular Weight (Monoisotopic): 345.9888

AlogP: 3.71

#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: 4.00

CX LogD: 3.88

Aromatic Rings: 3

Heavy Atoms: 20

QED Weighted: 0.74

Np Likeness Score: -1.06

References

1. Elslager EF, Hutt MP, Jacob P, Johnson J, Temporelli B, Werbel LM, Worth DF, Rane L..  (1979)  Folate antagonists. 15. 2,3-Diamino-6-(2-naphthylsulfonyl)quinazoline and related 2,4-diamino-6-[(phenyl and naphthyl)sulfinyl and sulfonyl]quinazolines, a potent new class of antimetabolites with phenomenal antimalarial activity.,  22  (10): [PMID:117107] [10.1021/jm00196a019]

2. 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