(E)-N-(2-(1H-imidazol-1-yl)-2-(4-(trifluoromethyl)phenyl)ethyl)-3-styrylbenzamide

ID: ALA4066700

PubChem CID: 132576475

Max Phase: Preclinical

Molecular Formula: C27H22F3N3O

Molecular Weight: 461.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NCC(c1ccc(C(F)(F)F)cc1)n1ccnc1)c1cccc(/C=C/c2ccccc2)c1

Standard InChI:  InChI=1S/C27H22F3N3O/c28-27(29,30)24-13-11-22(12-14-24)25(33-16-15-31-19-33)18-32-26(34)23-8-4-7-21(17-23)10-9-20-5-2-1-3-6-20/h1-17,19,25H,18H2,(H,32,34)/b10-9+

Standard InChI Key:  CNOVPBCKUAHRKG-MDZDMXLPSA-N

Molfile:  

     RDKit          2D

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    8.5091  -10.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5091  -11.5051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8000  -11.9137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0909  -11.5051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0909  -10.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2628  -13.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5538  -12.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2628  -11.5051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2167  -11.9140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9245  -11.5057    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2163  -12.7312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   11.3403  -10.6891    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9967  -10.2076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7445   -9.4303    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9272   -9.4299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6745  -10.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0443  -12.7294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7510  -13.1383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4598  -12.7299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4576  -11.9085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7503  -11.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1679  -13.1379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1687  -13.9551    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.8753  -12.7286    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.8704  -13.5456    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
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  7  8  2  0
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  9 14  2  0
  4  7  1  0
  2 15  1  0
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 19 20  1  0
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 21 22  1  0
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 24 25  2  0
 25 21  1  0
 20 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 20  1  0
 28 31  1  0
 31 32  1  0
 31 33  1  0
 31 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4066700

   ---

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: -1.08

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