4-(6,7-Dimethoxy-quinazolin-4-yl)-piperazine-1-carbothioic acid cyclohexylmethyl-amide

ID: ALA341602

PubChem CID: 9804548

Max Phase: Preclinical

Molecular Formula: C23H24ClN7O2

Molecular Weight: 465.95

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2ncnc(N3CCN(/C(=N\Cc4ccc(Cl)cc4)NC#N)CC3)c2cc1OC

Standard InChI:  InChI=1S/C23H24ClN7O2/c1-32-20-11-18-19(12-21(20)33-2)28-15-29-22(18)30-7-9-31(10-8-30)23(27-14-25)26-13-16-3-5-17(24)6-4-16/h3-6,11-12,15H,7-10,13H2,1-2H3,(H,26,27)

Standard InChI Key:  SHSIPFRSMGKGSV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
    4.0917   -6.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7417   -5.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7417   -2.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0875   -2.5292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7417   -5.1792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7417   -3.6667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0917   -7.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4417   -5.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0875   -1.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4042   -6.3042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4417   -7.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0875   -1.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7875   -6.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7875   -7.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3917   -2.5292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7542   -7.4500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4042   -7.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0917   -4.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4000   -4.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4000   -4.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0917   -4.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0542   -2.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0167   -1.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7042   -2.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1292   -5.9417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1292   -7.4542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6792   -1.4000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.3625   -1.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0167   -2.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7042   -1.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3667   -2.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4417   -6.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4792   -7.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  6  1  0
  4  3  1  0
  5  2  1  0
  6 20  1  0
  7  1  1  0
  8  1  2  0
  9  4  1  0
 10  2  2  0
 11  7  2  0
 12  9  3  0
 13  8  1  0
 14 13  2  0
 15  3  2  0
 16  7  1  0
 17 16  2  0
 18  5  1  0
 19  5  1  0
 20 19  1  0
 21 18  1  0
 22 15  1  0
 23 29  2  0
 24 22  1  0
 25 13  1  0
 26 14  1  0
 27 23  1  0
 28 30  2  0
 29 31  1  0
 30 24  1  0
 31 24  2  0
 32 25  1  0
 33 26  1  0
 14 11  1  0
 10 17  1  0
 21  6  1  0
 23 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA341602

   N'-[(4-chlorophenyl)methyl]-N-cyano-4-(6,7-dimethoxyquinazolin-4-yl)piperazine-1-carboximidamide

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: 465.95

Molecular Weight (Monoisotopic): 465.1680

AlogP: 3.05

#Rotatable Bonds: 5

Polar Surface Area: 98.90

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.33

CX LogP: 3.58

CX LogD: 3.58

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.27

Np Likeness Score: -1.11

References

1. Matsuno K, Nakajima T, Ichimura M, Giese NA, Yu JC, Lokker NA, Ushiki J, Ide S, Oda S, Nomoto Y..  (2002)  Potent and selective inhibitors of PDGF receptor phosphorylation. 2. Synthesis, structure activity relationship, improvement of aqueous solubility, and biological effects of 4-[4-(N-substituted (thio)carbamoyl)-1-piperazinyl]-6,7-dimethoxyquinazoline derivatives.,  45  (20): [PMID:12238930] [10.1021/jm0201114]

Source

Source(1):

• Scientific Literature