6-(Benzyloxy)-2-((4-(4-methylpiperazin-1-yl)phenyl)diazenyl)-9Hpurine

ID: ALA2312287

PubChem CID: 71562694

Max Phase: Preclinical

Molecular Formula: C23H24N8O

Molecular Weight: 428.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CCN(c2ccc(/N=N/c3nc(OCc4ccccc4)c4nc[nH]c4n3)cc2)CC1

Standard InChI:  InChI=1S/C23H24N8O/c1-30-11-13-31(14-12-30)19-9-7-18(8-10-19)28-29-23-26-21-20(24-16-25-21)22(27-23)32-15-17-5-3-2-4-6-17/h2-10,16H,11-15H2,1H3,(H,24,25,26,27)/b29-28+

Standard InChI Key:  XCYCLMGBKCGPNT-ZQHSETAFSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
   16.3465   -2.4515    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3454   -3.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0534   -3.6800    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.0516   -2.0427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5441   -2.1963    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7603   -2.4479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7585   -3.2718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5421   -3.5268    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0255   -2.8596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0492   -1.2255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3403   -0.8190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6338   -1.2297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9286   -0.8224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2226   -1.2324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2246   -2.0505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9385   -2.4568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6416   -2.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6374   -3.6791    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9300   -3.2700    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2219   -3.6780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5153   -3.2666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8078   -3.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8067   -4.4921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5190   -4.9011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2237   -4.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0992   -4.9010    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3913   -4.4928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0996   -5.7182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6838   -4.9018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3921   -6.1272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6842   -5.7190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9767   -6.1280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  7  2  0
  6  4  2  0
  4  1  1  0
  6  7  1  0
  5  6  1  0
  7  8  1  0
  8  9  1  0
  9  5  2  0
  4 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 17  2  0
 17 12  1  0
  2 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 23 26  1  0
 26 27  1  0
 26 28  1  0
 27 29  1  0
 28 30  1  0
 30 31  1  0
 29 31  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2312287

   [4-(4-methylpiperazin-1-yl)phenyl]-(6-phenylmethoxy-7H-purin-2-yl)diazene

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: 428.50

Molecular Weight (Monoisotopic): 428.2073

AlogP: 4.10

#Rotatable Bonds: 6

Polar Surface Area: 94.89

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.76

CX Basic pKa: 7.69

CX LogP: 4.65

CX LogD: 4.39

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.46

Np Likeness Score: -1.02

References

1. Zhu R, Baumann RP, Penketh PG, Shyam K, Sartorelli AC..  (2013)  Hypoxia-selective O6-alkylguanine-DNA alkyltransferase inhibitors: design, synthesis, and evaluation of 6-(benzyloxy)-2-(aryldiazenyl)-9H-purines as prodrugs of O6-benzylguanine.,  56  (3): [PMID:23311288] [10.1021/jm301804p]

Source

Source(1):

• Scientific Literature