4-(6,7-Dimethoxy-quinazolin-4-yl)-piperazine-1-carbothioic acid 4-chloro-benzylamide

ID: ALA140972

PubChem CID: 10863443

Max Phase: Preclinical

Molecular Formula: C22H24ClN5O2S

Molecular Weight: 457.99

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H24ClN5O2S/c1-29-19-11-17-18(12-20(19)30-2)25-14-26-21(17)27-7-9-28(10-8-27)22(31)24-13-15-3-5-16(23)6-4-15/h3-6,11-12,14H,7-10,13H2,1-2H3,(H,24,31)

Standard InChI Key:  KVSCJEFMRSEDOZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    1.7042   -4.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4167   -4.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4125   -0.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4125   -3.3167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4125   -1.6667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7042   -5.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9917   -4.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1292   -4.5500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9917   -5.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2792   -4.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2792   -5.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1250   -0.4292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4250   -5.7917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6917   -0.4292    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.1375   -5.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7000   -2.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1292   -2.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1292   -2.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7000   -2.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8417   -0.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9792    0.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5542   -0.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4333   -4.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4375   -5.8000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6917    0.8083    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.2542    0.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9792   -0.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5417    0.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2667   -0.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1500   -5.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1875   -4.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  5  1  0
  4  2  1  0
  5 18  1  0
  6  1  1  0
  7  1  2  0
  8  2  2  0
  9  6  2  0
 10  7  1  0
 11 10  2  0
 12  3  2  0
 13  6  1  0
 14  3  1  0
 15 13  2  0
 16  4  1  0
 17  4  1  0
 18 17  1  0
 19 16  1  0
 20 12  1  0
 21 27  2  0
 22 20  1  0
 23 10  1  0
 24 11  1  0
 25 21  1  0
 26 28  2  0
 27 29  1  0
 28 22  1  0
 29 22  2  0
 30 24  1  0
 31 23  1  0
 11  9  1  0
  8 15  1  0
  5 19  1  0
 26 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA140972

   4-(6,7-Dimethoxy-quinazolin-4-yl)-piperazine-1-carbothioic acid 4-chloro-benzylamide

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: 457.99

Molecular Weight (Monoisotopic): 457.1339

AlogP: 3.91

#Rotatable Bonds: 5

Polar Surface Area: 63.08

Molecular Species: ZWITTERION

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 0.89

CX Basic pKa: 13.61

CX LogP: 5.23

CX LogD: 5.22

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.36

Np Likeness Score: -1.08

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