6-Chloro-N-[4-({[7-methyl-2-(methylamino)-quinazolin-4-yl]amino}methyl)phenyl]nicotinamide

ID: ALA583242

PubChem CID: 44818493

Max Phase: Preclinical

Molecular Formula: C23H21ClN6O

Molecular Weight: 432.92

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNc1nc(NCc2ccc(NC(=O)c3ccc(Cl)nc3)cc2)c2ccc(C)cc2n1

Standard InChI:  InChI=1S/C23H21ClN6O/c1-14-3-9-18-19(11-14)29-23(25-2)30-21(18)27-12-15-4-7-17(8-5-15)28-22(31)16-6-10-20(24)26-13-16/h3-11,13H,12H2,1-2H3,(H,28,31)(H2,25,27,29,30)

Standard InChI Key:  GXJWTRQQFNHPOC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    3.7961  -23.1444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7961  -22.3194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0844  -21.9069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0844  -21.0819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7961  -20.6694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5120  -21.0819    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5120  -21.9069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5120  -23.5569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0844  -23.5569    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3686  -23.1444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6569  -23.5569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9410  -23.1444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9410  -22.3194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6569  -21.9069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3686  -22.3194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2251  -21.9069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4907  -22.3194    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6300  -21.0819    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9183  -20.6694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2024  -21.0819    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2024  -21.9069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9183  -22.3194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9183  -23.1444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6300  -23.5569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3459  -23.1444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3459  -22.3194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6300  -21.9069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9183  -19.8444    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6300  -19.4319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0617  -23.5569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7961  -19.8444    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  2  7  2  0
  1  8  2  0
  1  9  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 10 15  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 18 27  2  0
 22 27  1  0
 28 29  1  0
 19 28  1  0
 25 30  1  0
 17 21  1  0
 16 17  1  0
 13 16  1  0
  9 10  1  0
  5 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA583242

   6-chloro-N-[4-[[[7-methyl-2-(methylamino)quinazolin-4-yl]amino]methyl]phenyl]pyridine-3-carboxamide

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: 432.92

Molecular Weight (Monoisotopic): 432.1465

AlogP: 4.89

#Rotatable Bonds: 6

Polar Surface Area: 91.83

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.17

CX LogP: 4.58

CX LogD: 4.38

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.38

Np Likeness Score: -1.75

References

1. Dehnhardt CM, Venkatesan AM, Chen Z, Ayral-Kaloustian S, Dos Santos O, Delos Santos E, Curran K, Follettie MT, Diesl V, Lucas J, Geng Y, Dejoy SQ, Petersen R, Chaudhary I, Brooijmans N, Mansour TS, Arndt K, Chen L..  (2010)  Design and synthesis of novel diaminoquinazolines with in vivo efficacy for beta-catenin/T-cell transcriptional factor 4 pathway inhibition.,  53  (2): [PMID:20025292] [10.1021/jm901370m]

2.  (2009)  Amino-substituted quinazoline derivatives as inhibitors of Beta-catenin/TCF-4 pathway and cancer treatment agents, 

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data