N2-(4-bromophenyl)-N4-(furan-2-ylmethyl)quinazoline-2,4-diamine

ID: ALA379386

PubChem CID: 1316842

Max Phase: Preclinical

Molecular Formula: C19H15BrN4O

Molecular Weight: 395.26

Molecule Type: Small molecule

Names and Identifiers

Synonyms: GNF-Pf-2722 | GNF-PF-2722|CHEMBL379386|ChemDiv1_009584|Neuro1_000225|Oprea1_457098|Oprea1_788431|HMS614D14|BDBM50187063|AKOS022095522|EU-0044608|N2-(4-bromophenyl)-N4-(furan-2-ylmethyl)quinazoline-2,4-diamine

Canonical SMILES:  Brc1ccc(Nc2nc(NCc3ccco3)c3ccccc3n2)cc1

Standard InChI:  InChI=1S/C19H15BrN4O/c20-13-7-9-14(10-8-13)22-19-23-17-6-2-1-5-16(17)18(24-19)21-12-15-4-3-11-25-15/h1-11H,12H2,(H2,21,22,23,24)

Standard InChI Key:  WYDGHRZFSRBHSA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   -2.1144   -4.2765    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.1144   -3.4515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8288   -3.0390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8288   -2.2140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1144   -1.8015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1144   -0.9765    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3999   -0.5640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3999    0.2610    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6854    0.6735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6854    1.4985    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3999    1.9110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3999    2.7360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0673    3.2209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8124    4.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9874    4.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7325    3.2209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0290    0.2610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7435    0.6735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4580    0.2610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4580   -0.5640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7435   -0.9765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0290   -0.5640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6854   -0.9765    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3999   -2.2140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3999   -3.0390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 12  1  0
  9 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 17  1  0
 22 23  2  0
 23  7  1  0
  5 24  1  0
 24 25  2  0
 25  2  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA379386

   N2-(4-bromophenyl)-N4-(furan-2-ylmethyl)quinazoline-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: 395.26

Molecular Weight (Monoisotopic): 394.0429

AlogP: 5.34

#Rotatable Bonds: 5

Polar Surface Area: 62.98

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.56

CX Basic pKa: 4.88

CX LogP: 5.16

CX LogD: 5.16

Aromatic Rings: 4

Heavy Atoms: 25

QED Weighted: 0.48

Np Likeness Score: -1.71

References

1. Kim ND, Yoon J, Kim JH, Lee JT, Chon YS, Hwang MK, Ha I, Song WJ..  (2006)  Putative therapeutic agents for the learning and memory deficits of people with Down syndrome.,  16  (14): [PMID:16698266] [10.1016/j.bmcl.2006.04.042]

2. Plouffe D, Brinker A, McNamara C, Henson K, Kato N, Kuhen K, Nagle A, Adrián F, Matzen JT, Anderson P, Nam TG, Gray NS, Chatterjee A, Janes J, Yan SF, Trager R, Caldwell JS, Schultz PG, Zhou Y, Winzeler EA..  (2008)  In silico activity profiling reveals the mechanism of action of antimalarials discovered in a high-throughput screen.,  105  (26): [PMID:18579783] [10.1073/pnas.0802982105]

3. Meister S, Plouffe DM, Kuhen KL, Bonamy GM, Wu T, Barnes SW, Bopp SE, Borboa R, Bright AT, Che J, Cohen S, Dharia NV, Gagaring K, Gettayacamin M, Gordon P, Groessl T, Kato N, Lee MC, McNamara CW, Fidock DA, Nagle A, Nam TG, Richmond W, Roland J, Rottmann M, Zhou B, Froissard P, Glynne RJ, Mazier D, Sattabongkot J, Schultz PG, Tuntland T, Walker JR, Zhou Y, Chatterjee A, Diagana TT, Winzeler EA..  (2011)  Imaging of Plasmodium liver stages to drive next-generation antimalarial drug discovery.,  334  (6061): [PMID:22096101] [10.1126/science.1211936]

4. Gilson PR, Tan C, Jarman KE, Lowes KN, Curtis JM, Nguyen W, Di Rago AE, Bullen HE, Prinz B, Duffy S, Baell JB, Hutton CA, Jousset Subroux H, Crabb BS, Avery VM, Cowman AF, Sleebs BE..  (2017)  Optimization of 2-Anilino 4-Amino Substituted Quinazolines into Potent Antimalarial Agents with Oral in Vivo Activity.,  60  (3): [PMID:28080063] [10.1021/acs.jmedchem.6b01673]

5. Abbott JR, Patel PA, Howes JE, Akan DT, Kennedy JP, Burns MC, Browning CF, Sun Q, Rossanese OW, Phan J, Waterson AG, Fesik SW..  (2018)  Discovery of Quinazolines That Activate SOS1-Mediated Nucleotide Exchange on RAS.,  9  (9): [PMID:30258545] [10.1021/acsmedchemlett.8b00296]

Source

Source(2):

• Scientific Literature
• Novartis Malaria Screening