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

ID: ALA4087998

PubChem CID: 137642065

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)c1cccc(/C=C/c2ccccc2)c1

Standard InChI:  InChI=1S/C26H22ClN3O/c27-24-13-11-22(12-14-24)25(30-16-15-28-19-30)18-29-26(31)23-8-4-7-21(17-23)10-9-20-5-2-1-3-6-20/h1-17,19,25H,18H2,(H,29,31)/b10-9+

Standard InChI Key:  VXMNXDLERTXXCF-MDZDMXLPSA-N

Molfile:  

     RDKit          2D

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    7.9808  -11.3194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2718  -11.7280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5627  -11.3194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5627  -10.5022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2718  -10.0936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8536  -11.7280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1486  -11.3194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4395  -11.7280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4395  -12.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7346  -12.9538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0255  -12.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0255  -11.7280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7346  -11.3194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6884  -11.7283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3963  -11.3200    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6880  -12.5455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1038  -11.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.5192  -11.7295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8120  -10.5034    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4684  -10.0219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2162   -9.2446    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3990   -9.2442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1462  -10.0213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5160  -12.5437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2227  -12.9525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9316  -12.5442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9293  -11.7228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2220  -11.3176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6396  -12.9521    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
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  9 14  2  0
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 20 26  2  0
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 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 20  1  0
 28 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4087998

   ---

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: -1.06

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