9-(4-Methoxybenzyl)-N2,N2-dimethyl-9H-pyrido[2,3-b]indole-2,4-diamine

ID: ALA561790

PubChem CID: 45269146

Max Phase: Preclinical

Molecular Formula: C21H22N4O

Molecular Weight: 346.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(Cn2c3ccccc3c3c(N)cc(N(C)C)nc32)cc1

Standard InChI:  InChI=1S/C21H22N4O/c1-24(2)19-12-17(22)20-16-6-4-5-7-18(16)25(21(20)23-19)13-14-8-10-15(26-3)11-9-14/h4-12H,13H2,1-3H3,(H2,22,23)

Standard InChI Key:  UOJCHWLFWLUAPU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    1.7868   -2.3254    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1993   -3.5949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4543   -2.8103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2612   -2.6388    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8133   -3.2519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5583   -4.0365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7514   -4.2080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1194   -2.8103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3743   -3.5949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8223   -4.2080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0153   -4.0365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3124   -2.6388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2396   -3.2519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4964   -4.9926    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6202   -3.0803    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1723   -3.6934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8752   -2.2957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7868   -1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5013   -1.0879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5013   -0.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2158    0.1496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9302   -0.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9302   -1.0879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2158   -1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6447    0.1496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6447    0.9746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  2  0
  1  3  1  0
 12 13  2  0
  5  6  1  0
  7 14  1  0
  5 15  1  0
  6  7  2  0
 15 16  1  0
  7  2  1  0
 15 17  1  0
  2  3  2  0
  1 18  1  0
  2  9  1  0
 18 19  1  0
  8  9  2  0
 19 20  2  0
  3  4  1  0
 20 21  1  0
  9 10  1  0
 21 22  2  0
  8  1  1  0
 22 23  1  0
 10 11  2  0
 23 24  2  0
 24 19  1  0
 11 13  1  0
 22 25  1  0
 12  8  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA561790

   9-[(4-methoxyphenyl)methyl]-2-N,2-N-dimethylpyrido[2,3-b]indole-2,4-diamine

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: 346.43

Molecular Weight (Monoisotopic): 346.1794

AlogP: 3.89

#Rotatable Bonds: 4

Polar Surface Area: 56.31

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.22

CX LogP: 3.90

CX LogD: 3.69

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.61

Np Likeness Score: -0.98

References

1. Willemann C, Grünert R, Bednarski PJ, Troschütz R..  (2009)  Synthesis and cytotoxic activity of 5,6-heteroaromatically annulated pyridine-2,4-diamines.,  17  (13): [PMID:19481463] [10.1016/j.bmc.2009.05.016]

Source

Source(1):

• Scientific Literature