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

ID: ALA4103700

PubChem CID: 132576469

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)c1ccc(/C=C/c2ccccc2)cc1

Standard InChI:  InChI=1S/C27H22F3N3O/c28-27(29,30)24-14-12-22(13-15-24)25(33-17-16-31-19-33)18-32-26(34)23-10-8-21(9-11-23)7-6-20-4-2-1-3-5-20/h1-17,19,25H,18H2,(H,32,34)/b7-6+

Standard InChI Key:  HIXLSOVLCVJNQN-VOTSOKGWSA-N

Molfile:  

     RDKit          2D

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    7.2462   -7.3490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2462   -8.1662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5371   -8.5748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.9512   -6.1232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6602   -7.3490    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1189   -8.5748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4140   -8.1662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7049   -8.5748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7049   -9.3920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9999   -9.8006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.4829   -9.4236    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6657   -9.4236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4152   -8.6463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0743   -8.1662    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7834   -6.9404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7834   -6.1232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4925   -5.7146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1974   -6.1232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1974   -6.9404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4925   -7.3490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9065   -5.7146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6139   -6.1238    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.9072   -4.8974    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.6116   -5.2994    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  3  4  2  0
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  5 10  1  0
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 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
 28 31  1  0
 19 25  1  0
  9 18  1  0
 31 32  1  0
 31 33  1  0
 31 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4103700

   ---

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: -1.11

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