2-(3,4-Dichloro-benzylamino)-7-(4-morpholin-4-yl-butyl)-1,7-dihydro-purin-6-one

ID: ALA180999

PubChem CID: 135486101

Max Phase: Preclinical

Molecular Formula: C20H24Cl2N6O2

Molecular Weight: 451.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Oc1nc(NCc2ccc(Cl)c(Cl)c2)nc2ncn(CCCCN3CCOCC3)c12

Standard InChI:  InChI=1S/C20H24Cl2N6O2/c21-15-4-3-14(11-16(15)22)12-23-20-25-18-17(19(29)26-20)28(13-24-18)6-2-1-5-27-7-9-30-10-8-27/h3-4,11,13H,1-2,5-10,12H2,(H2,23,25,26,29)

Standard InChI Key:  HVUNHTWEGZXFIG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
    0.4875    0.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2208    0.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2000    0.0458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2208   -0.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4875   -1.2000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3167    1.2625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2000   -0.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8375    0.5958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5000    1.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5792   -0.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9167   -1.2000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9375   -1.2000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3625    1.2833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9875   -1.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7542   -0.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9833    0.9458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5792   -1.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3542   -1.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9875    0.2458    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.6250   -0.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8167   -1.2000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.7542   -1.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6375    0.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5458    1.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9208    1.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6125    0.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7208    1.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4208    0.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1833    1.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0000    0.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  2  2  0
  5  7  2  0
  6  1  1  0
  7  3  1  0
  8  2  1  0
  9  6  2  0
 10 15  2  0
 11  7  1  0
 12  4  1  0
 13 24  1  0
 14 17  2  0
 15 18  1  0
 16 28  1  0
 17 22  1  0
 18 20  1  0
 19 10  1  0
 20 11  1  0
 21 14  1  0
 22 18  2  0
 23  8  1  0
 24 30  1  0
 25 13  1  0
 26 13  1  0
 27 25  1  0
 28 26  1  0
 29 23  1  0
 30 29  1  0
  9  8  1  0
  5  4  1  0
 14 10  1  0
 16 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA180999

   ---

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: 451.36

Molecular Weight (Monoisotopic): 450.1338

AlogP: 3.56

#Rotatable Bonds: 8

Polar Surface Area: 88.33

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.33

CX Basic pKa: 7.62

CX LogP: 3.64

CX LogD: 3.21

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.51

Np Likeness Score: -1.68

References

1. Wright GE, Brown NC, Xu WC, Long ZY, Zhi C, Gambino JJ, Barnes MH, Butler MM..  (2005)  Active site directed inhibitors of replication-specific bacterial DNA polymerases.,  15  (3): [PMID:15664846] [10.1016/j.bmcl.2004.11.016]

2. Xu WC, Wright GE, Brown NC, Long ZY, Zhi CX, Dvoskin S, Gambino JJ, Barnes MH, Butler MM..  (2011)  7-Alkyl-N(2)-substituted-3-deazaguanines. Synthesis, DNA polymerase III inhibition and antibacterial activity.,  21  (14): [PMID:21684746] [10.1016/j.bmcl.2011.05.093]

Source

Source(1):

• Scientific Literature