(E)-N-(2-(4-Chlorophenyl)-2-(1H-imidazol-1-yl)ethyl)-4-styrylbenzamide

ID: ALA4087325

PubChem CID: 137642698

Max Phase: Preclinical

Molecular Formula: C26H22ClN3O

Molecular Weight: 427.94

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C26H22ClN3O/c27-24-14-12-22(13-15-24)25(30-17-16-28-19-30)18-29-26(31)23-10-8-21(9-11-23)7-6-20-4-2-1-3-5-20/h1-17,19,25H,18H2,(H,29,31)/b7-6+

Standard InChI Key:  HGUHQGFKVOCVHW-VOTSOKGWSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    8.5702   -7.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8653   -7.8112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8653   -8.6284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1562   -9.0370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4471   -8.6284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4471   -7.8112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1562   -7.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5702   -6.5855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2793   -7.8112    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7380   -9.0370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0331   -8.6284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3240   -9.0370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3240   -9.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6190  -10.2628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9099   -9.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9099   -9.0370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6190   -8.6284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9843   -7.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6934   -7.8112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3567   -9.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1020   -9.8858    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2848   -9.8858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0342   -9.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6934   -8.6284    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4025   -7.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4025   -6.5855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1116   -6.1769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8165   -6.5855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8165   -7.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1116   -7.8112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5256   -6.1769    0.0000 Cl  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
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  6  7  1  0
  2  7  2  0
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  1  9  1  0
 10 11  2  0
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 15 16  2  0
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 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
 28 31  1  0
 19 25  1  0
  9 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4087325

   ---

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: 427.94

Molecular Weight (Monoisotopic): 427.1451

AlogP: 5.73

#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: 5.68

CX LogD: 5.62

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.38

Np Likeness Score: -1.10

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