(E)-2-((7-Amino-2-phenylimidazo[1,2-a]pyrimidin-3-yl)methylene)hydrazine-1-carboximidamide Hydrochloride

ID: ALA4474200

PubChem CID: 155536968

Max Phase: Preclinical

Molecular Formula: C14H15ClN8

Molecular Weight: 294.32

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cl.N=C(N)N/N=C/c1c(-c2ccccc2)nc2nc(N)ccn12

Standard InChI:  InChI=1S/C14H14N8.ClH/c15-11-6-7-22-10(8-18-21-13(16)17)12(20-14(22)19-11)9-4-2-1-3-5-9;/h1-8H,(H2,15,19,20)(H4,16,17,21);1H/b18-8+;

Standard InChI Key:  GLPZGZFKMARTJI-JUIXXEQESA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    8.6259   -7.6065    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.0971   -5.3695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0971   -6.1867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8065   -6.5912    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8065   -4.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2899   -6.4406    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7710   -5.7787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2900   -5.1168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5118   -6.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5119   -5.3685    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5872   -5.7786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9951   -6.4879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8116   -6.4883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2210   -5.7800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8080   -5.0700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9929   -5.0731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5389   -4.3397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3383   -4.1703    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5954   -3.3933    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3900   -6.5963    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3957   -3.2277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6524   -2.4519    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9392   -3.8380    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  2  5  2  0
  3  4  2  0
  4  9  1  0
 10  5  1  0
  9  6  2  0
  6  7  1  0
  7  8  2  0
  8 10  1  0
  9 10  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  7 11  1  0
  8 17  1  0
 17 18  2  0
 18 19  1  0
  3 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 294.32

Molecular Weight (Monoisotopic): 294.1341

AlogP: 0.80

#Rotatable Bonds: 3

Polar Surface Area: 130.47

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 7.28

CX LogP: 0.52

CX LogD: 0.28

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.32

Np Likeness Score: -1.07

References

1. Amato J, Miglietta G, Morigi R, Iaccarino N, Locatelli A, Leoni A, Novellino E, Pagano B, Capranico G, Randazzo A..  (2020)  Monohydrazone Based G-Quadruplex Selective Ligands Induce DNA Damage and Genome Instability in Human Cancer Cells.,  63  (6): [PMID:32142285] [10.1021/acs.jmedchem.9b01866]

Source

Source(1):

• Scientific Literature