4-(6,7-Dimethoxy-quinazolin-4-yl)-piperazine-1-carboxylic acid (thiophen-3-ylmethyl)-amide

ID: ALA140457

PubChem CID: 11026060

Max Phase: Preclinical

Molecular Formula: C20H23N5O3S

Molecular Weight: 413.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2ncnc(N3CCN(C(=O)NCc4ccsc4)CC3)c2cc1OC

Standard InChI:  InChI=1S/C20H23N5O3S/c1-27-17-9-15-16(10-18(17)28-2)22-13-23-19(15)24-4-6-25(7-5-24)20(26)21-11-14-3-8-29-12-14/h3,8-10,12-13H,4-7,11H2,1-2H3,(H,21,26)

Standard InChI Key:  CTSUBXDMAKHRNI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    1.7667   -4.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4792   -3.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -0.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -3.0917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -1.4500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7667   -5.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0542   -3.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1917   -4.3292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0542   -5.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6167   -0.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3417   -4.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3417   -5.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1875   -0.2125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4875   -5.5750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9167    0.0708    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.2000   -5.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3625   -0.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7625   -2.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1917   -2.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1917   -1.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7625   -1.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7542   -0.2125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6917    0.6083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5125    0.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9042   -0.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708   -3.9292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3750   -5.5792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0875   -5.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1250   -4.3042    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 20  1  0
  6  1  1  0
  7  1  2  0
  8  2  2  0
  9  6  2  0
 10 25  1  0
 11  7  1  0
 12 11  2  0
 13  3  1  0
 14  6  1  0
 15 17  1  0
 16 14  2  0
 17 10  2  0
 18  4  1  0
 19  4  1  0
 20 19  1  0
 21 18  1  0
 22  3  2  0
 23 10  1  0
 24 23  2  0
 25 13  1  0
 26 11  1  0
 27 12  1  0
 28 27  1  0
 29 26  1  0
 12  9  1  0
  8 16  1  0
  5 21  1  0
 24 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA140457

   4-(6,7-Dimethoxy-quinazolin-4-yl)-piperazine-1-carboxylic acid (thiophen-3-ylmethyl)-amide

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: 413.50

Molecular Weight (Monoisotopic): 413.1522

AlogP: 2.74

#Rotatable Bonds: 5

Polar Surface Area: 79.82

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.37

CX LogP: 2.28

CX LogD: 2.28

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.69

Np Likeness Score: -2.01

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