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

ID: ALA4076840

PubChem CID: 137651189

Max Phase: Preclinical

Molecular Formula: C28H27N3O

Molecular Weight: 421.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(C(CNC(=O)c2ccc(/C=C/c3ccccc3)cc2)n2ccnc2)cc1C

Standard InChI:  InChI=1S/C28H27N3O/c1-21-8-13-26(18-22(21)2)27(31-17-16-29-20-31)19-30-28(32)25-14-11-24(12-15-25)10-9-23-6-4-3-5-7-23/h3-18,20,27H,19H2,1-2H3,(H,30,32)/b10-9+

Standard InChI Key:  UCZSCRJCMATYOS-MDZDMXLPSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    8.3226   -4.0059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6176   -4.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6176   -5.2317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9086   -5.6403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1995   -5.2317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1995   -4.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9086   -4.0059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3226   -3.1888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0317   -4.4145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4904   -5.6403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7854   -5.2317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0763   -5.6403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0763   -6.4575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3714   -6.8661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6623   -6.4575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6623   -5.6403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3714   -5.2317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7367   -4.0059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4458   -4.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1090   -5.7119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8543   -6.4891    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0372   -6.4891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7866   -5.7119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4458   -5.2317    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1548   -4.0059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1548   -3.1888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8639   -2.7802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5689   -3.1888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5689   -4.0059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8639   -4.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2769   -2.7808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8650   -1.9630    0.0000 C   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
 28 31  1  0
 27 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4076840

   ---

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: 421.54

Molecular Weight (Monoisotopic): 421.2154

AlogP: 5.69

#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: 6.11

CX LogD: 6.05

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.39

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