(E)-N-(2-(1H-Imidazol-1-yl)-2-(2-(trifluoromethyl)phenyl)ethyl)-4-styrylbenzamide

ID: ALA4079445

PubChem CID: 132576470

Max Phase: Preclinical

Molecular Formula: C27H22F3N3O

Molecular Weight: 461.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NCC(c1ccccc1C(F)(F)F)n1ccnc1)c1ccc(/C=C/c2ccccc2)cc1

Standard InChI:  InChI=1S/C27H22F3N3O/c28-27(29,30)24-9-5-4-8-23(24)25(33-17-16-31-19-33)18-32-26(34)22-14-12-21(13-15-22)11-10-20-6-2-1-3-7-20/h1-17,19,25H,18H2,(H,32,34)/b11-10+

Standard InChI Key:  JKWJGXHSEICGCI-ZHACJKMWSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
    7.2991  -11.2740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5941  -11.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5941  -12.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8850  -12.9084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1759  -12.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1759  -11.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8850  -11.2740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2991  -10.4568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0081  -11.6826    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4668  -12.9084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7619  -12.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0528  -12.9084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0528  -13.7256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3478  -14.1342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6387  -13.7256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6387  -12.9084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3478  -12.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7131  -11.2740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4222  -11.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0855  -12.9799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8308  -13.7571    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0136  -13.7571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7631  -12.9799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4222  -12.4998    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1313  -11.2740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1313  -10.4568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8404  -10.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5453  -10.4568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5453  -11.2740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8404  -11.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4238  -10.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4241   -9.2307    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.7159  -10.4562    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.7126   -9.6371    0.0000 F   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  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 12 17  2  0
  5 10  1  0
 18 19  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 20 24  1  0
 19 24  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 25 30  2  0
 19 25  1  0
  9 18  1  0
 26 31  1  0
 31 32  1  0
 31 33  1  0
 31 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4079445

   ---

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: 461.49

Molecular Weight (Monoisotopic): 461.1715

AlogP: 6.09

#Rotatable Bonds: 7

Polar Surface Area: 46.92

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 6.71

CX LogP: 5.96

CX LogD: 5.90

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.34

Np Likeness Score: -1.05

References

1. Taban IM, Zhu J, DeLuca HF, Simons C..  (2017)  Synthesis, molecular modelling and CYP24A1 inhibitory activity of novel of (E)-N-(2-(1H-imidazol-1-yl)-2-(phenylethyl)-3/4-styrylbenzamides.,  25  (15): [PMID:28601511] [10.1016/j.bmc.2017.05.055]

2. Bruno, Robert D RD and Njar, Vincent C O VC.  2007-08-01  Targeting cytochrome P450 enzymes: a new approach in anti-cancer drug development.  [PMID:17544277]

3. Taban, Ismail M IM, Zhu, Jinge J, DeLuca, Hector F HF and Simons, Claire C.  2017-08-01  Synthesis, molecular modelling and CYP24A1 inhibitory activity of novel of (E)-N-(2-(1H-imidazol-1-yl)-2-(phenylethyl)-3/4-styrylbenzamides.  [PMID:28601511]

Source

Source(1):

• Scientific Literature