N-(2-Chlorobenzyl)-2-[(3-phenyl-2-oxo-2H-[1,2,4]triazino[2,3-c]quinazoline-6-yl)thio]acetamide

ID: ALA2299063

PubChem CID: 47082779

Max Phase: Preclinical

Molecular Formula: C25H18ClN5O2S

Molecular Weight: 487.97

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CSc1nc2ccccc2c2nc(=O)c(-c3ccccc3)nn12)NCc1ccccc1Cl

Standard InChI:  InChI=1S/C25H18ClN5O2S/c26-19-12-6-4-10-17(19)14-27-21(32)15-34-25-28-20-13-7-5-11-18(20)23-29-24(33)22(30-31(23)25)16-8-2-1-3-9-16/h1-13H,14-15H2,(H,27,32)

Standard InChI Key:  DAVVMDOBWUPOLG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 38  0  0  0  0  0  0  0  0999 V2000
    9.7447  -13.8170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7434  -14.6443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4583  -15.0573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4565  -13.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1719  -13.8134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1707  -14.6418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6036  -13.8154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8861  -13.3978    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3191  -13.4046    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.0325  -13.8188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7480  -13.4080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4615  -13.8222    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7500  -12.5830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1770  -13.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6024  -14.6438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8840  -15.0545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8804  -15.8775    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5936  -16.2961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3121  -15.8854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3174  -15.0561    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5889  -17.1211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0244  -16.3017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8905  -13.8257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8831  -14.6514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5957  -15.0655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3122  -14.6547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3115  -13.8255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5984  -13.4150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5969  -12.5900    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.0182  -17.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7297  -17.5426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4473  -17.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4490  -16.3046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7369  -15.8921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5  8  1  0
  6 16  1  0
 15  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 12 14  1  0
 15 16  1  0
 15 20  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 18 21  2  0
 19 22  1  0
 14 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 28 29  1  0
 22 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2299063

   N-[(2-chlorophenyl)methyl]-2-[(2-oxo-3-phenyl-[1,2,4]triazino[2,3-c]quinazolin-6-yl)sulfanyl]acetamide

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: 487.97

Molecular Weight (Monoisotopic): 487.0870

AlogP: 4.37

#Rotatable Bonds: 6

Polar Surface Area: 89.25

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.85

CX LogP: 4.78

CX LogD: 4.78

Aromatic Rings: 5

Heavy Atoms: 34

QED Weighted: 0.22

Np Likeness Score: -2.01

References

1. Kovalenko SI, Nosulenko IS, Voskoboynik AY, Berest GG, Antipenko LN, Antipenko AN, Katsev AM.  (2013)  Novel N-aryl(alkaryl)-2-[(3-R-2-oxo-2H-[1,2,4]triazino[2,3-c]quinazoline-6-yl)thio]acetamides: synthesis, cytotoxicity, anticancer activity, COMPARE analysis and docking,  22  (6): [10.1007/s00044-012-0257-x]

Source

Source(1):

• Scientific Literature