4-((5-(2,6-dibromo-4-methylphenoxy)-2-nitropyridin-3-yl)amino)benzonitrile

ID: ALA4203523

PubChem CID: 145976524

Max Phase: Preclinical

Molecular Formula: C19H12Br2N4O3

Molecular Weight: 504.14

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(Br)c(Oc2cnc([N+](=O)[O-])c(Nc3ccc(C#N)cc3)c2)c(Br)c1

Standard InChI:  InChI=1S/C19H12Br2N4O3/c1-11-6-15(20)18(16(21)7-11)28-14-8-17(19(23-10-14)25(26)27)24-13-4-2-12(9-22)3-5-13/h2-8,10,24H,1H3

Standard InChI Key:  FMPTURNLDBWWEA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   22.2989   -6.2596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0107   -6.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0063   -7.4879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7173   -7.9007    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.4302   -7.4881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4277   -6.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7163   -6.2575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1382   -6.2516    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.5870   -6.6680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8787   -6.2562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1714   -6.6639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1707   -7.4861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8833   -7.8988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5918   -7.4846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1355   -5.4303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8420   -5.0192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8397   -4.1987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1301   -3.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4173   -4.2069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4231   -5.0261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1460   -7.8986    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.8533   -7.4851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1469   -8.7199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1278   -2.9745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1240   -2.1532    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4626   -7.8939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8802   -5.4390    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   22.3019   -7.8892    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  6  8  1  0
  1  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  8 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 21 22  2  0
 21 23  1  0
  5 21  1  0
 24 25  3  0
 18 24  1  0
 12 26  1  0
 10 27  1  0
 14 28  1  0
M  CHG  2  21   1  23  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4203523

   ---

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: 504.14

Molecular Weight (Monoisotopic): 501.9276

AlogP: 6.23

#Rotatable Bonds: 5

Polar Surface Area: 101.08

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.92

CX Basic pKa: ┄

CX LogP: 7.44

CX LogD: 7.44

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.33

Np Likeness Score: -1.31

References

1. Liu Z, Tian Y, Liu J, Huang B, Kang D, De Clercq E, Daelemans D, Pannecouque C, Zhan P, Liu X..  (2017)  Design, synthesis and anti-HIV evaluation of novel diarylpyridine derivatives as potent HIV-1 NNRTIs.,  140  [PMID:28987601] [10.1016/j.ejmech.2017.07.012]

Source

Source(1):

• Scientific Literature