4-(1-benzyl-2-(ethylthio)-1H-imidazol-5-yl)-6-(4-bromophenyl)-2-imino-1,2-dihydropyridine-3-carbonitrile

ID: ALA3946861

PubChem CID: 134147445

Max Phase: Preclinical

Molecular Formula: C24H20BrN5S

Molecular Weight: 490.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCSc1ncc(-c2cc(-c3ccc(Br)cc3)[nH]c(=N)c2C#N)n1Cc1ccccc1

Standard InChI:  InChI=1S/C24H20BrN5S/c1-2-31-24-28-14-22(30(24)15-16-6-4-3-5-7-16)19-12-21(29-23(27)20(19)13-26)17-8-10-18(25)11-9-17/h3-12,14H,2,15H2,1H3,(H2,27,29)

Standard InChI Key:  ZPUHISLIAUSNQH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   11.6910   -9.3770    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6899  -10.1966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3979  -10.6055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1076  -10.1961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1048   -9.3734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3961   -8.9682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9818  -10.6046    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3977  -11.4227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3975  -12.2399    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8159  -10.6036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9032  -11.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7028  -11.5824    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1103  -10.8740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5624  -10.2677    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9229  -10.7872    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.4043  -11.4475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2169  -11.3608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7301   -9.4678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5065   -9.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1131   -9.7606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8890   -9.5064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0572   -8.7059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4435   -8.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6700   -8.4170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3937   -8.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0990   -7.7437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0969   -6.9273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3874   -6.5200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6786   -6.9351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6842   -7.7502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3839   -5.7028    0.0000 Br  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  1  1  0
  2  7  2  0
  3  8  1  0
  8  9  3  0
  4 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 10  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 14 18  1  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 19  1  0
  6 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 28 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3946861

   ---

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: 490.43

Molecular Weight (Monoisotopic): 489.0623

AlogP: 5.82

#Rotatable Bonds: 6

Polar Surface Area: 81.25

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.50

CX Basic pKa: 8.46

CX LogP: 4.66

CX LogD: 3.78

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.33

Np Likeness Score: -1.48

References

1. Akhtar J, Khan AA, Ali Z, Haider R, Shahar Yar M..  (2017)  Structure-activity relationship (SAR) study and design strategies of nitrogen-containing heterocyclic moieties for their anticancer activities.,  125  [PMID:27662031] [10.1016/j.ejmech.2016.09.023]

2. Peng T, Gong J, Jin Y, Zhou Y, Tong R, Wei X, Bai L, Shi J..  (2018)  Inhibitors of phosphodiesterase as cancer therapeutics.,  150  [PMID:29574203] [10.1016/j.ejmech.2018.03.046]

Source

Source(1):

• Scientific Literature