4-(6,7-Dimethoxy-quinazolin-4-yl)-piperazine-1-carboxylic acid 4-propyl-benzylamide

ID: ALA435627

PubChem CID: 10863287

Max Phase: Preclinical

Molecular Formula: C25H31N5O3

Molecular Weight: 449.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCc1ccc(CNC(=O)N2CCN(c3ncnc4cc(OC)c(OC)cc34)CC2)cc1

Standard InChI:  InChI=1S/C25H31N5O3/c1-4-5-18-6-8-19(9-7-18)16-26-25(31)30-12-10-29(11-13-30)24-20-14-22(32-2)23(33-3)15-21(20)27-17-28-24/h6-9,14-15,17H,4-5,10-13,16H2,1-3H3,(H,26,31)

Standard InChI Key:  WXPLMRQBFSXQNM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    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
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    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
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    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
    3.1375   -5.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    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
    5.9792    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
    4.5417    0.3958    0.0000 C   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
    6.6917    0.8083    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
    7.4042    0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1167    0.8125    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 17  1  0
  6  1  1  0
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 32 29  1  0
 33 32  1  0
 11  9  1  0
  8 14  1  0
  5 18  1  0
 24 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA435627

   4-(6,7-Dimethoxy-quinazolin-4-yl)-piperazine-1-carboxylic acid 4-propyl-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: 449.56

Molecular Weight (Monoisotopic): 449.2427

AlogP: 3.63

#Rotatable Bonds: 7

Polar Surface Area: 79.82

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.37

CX LogP: 3.90

CX LogD: 3.90

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.59

Np Likeness Score: -1.26

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