4-((6-(Benzyloxy)-9H-purin-2-yl)diazenyl)-N,N-dimethylaniline

ID: ALA2312288

PubChem CID: 71562692

Max Phase: Preclinical

Molecular Formula: C20H19N7O

Molecular Weight: 373.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)c1ccc(/N=N/c2nc(OCc3ccccc3)c3nc[nH]c3n2)cc1

Standard InChI:  InChI=1S/C20H19N7O/c1-27(2)16-10-8-15(9-11-16)25-26-20-23-18-17(21-13-22-18)19(24-20)28-12-14-6-4-3-5-7-14/h3-11,13H,12H2,1-2H3,(H,21,22,23,24)/b26-25+

Standard InChI Key:  NLCHIPOIIKLKKA-OCEACIFDSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    5.8510   -2.6166    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8498   -3.4362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5579   -3.8451    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5561   -2.2078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0485   -2.3614    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2647   -2.6130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2629   -3.4369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0466   -3.6919    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5300   -3.0247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5537   -1.3906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8447   -0.9841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1383   -1.3948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4331   -0.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7271   -1.3975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7291   -2.2156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4430   -2.6219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1461   -2.2095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1418   -3.8442    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4344   -3.4350    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7264   -3.8431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0198   -3.4317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3122   -3.8391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3111   -4.6572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0235   -5.0662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7281   -4.6564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6036   -5.0661    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8957   -4.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6041   -5.8833    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
M  END

Alternative Forms

1. Parent:

   

   ALA2312288

   N,N-dimethyl-4-[(6-phenylmethoxy-7H-purin-2-yl)diazenyl]aniline

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: 373.42

Molecular Weight (Monoisotopic): 373.1651

AlogP: 4.41

#Rotatable Bonds: 6

Polar Surface Area: 91.65

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.72

CX Basic pKa: 3.51

CX LogP: 5.06

CX LogD: 5.04

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.51

Np Likeness Score: -0.89

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