5-(naphthalen-2-yl)-1-(3,4,5-trimethoxyphenyl)-1H-imidazole

ID: ALA221473

Cas Number: 915954-53-9

PubChem CID: 24205849

Max Phase: Preclinical

Molecular Formula: C22H20N2O3

Molecular Weight: 360.41

Molecule Type: Small molecule

Names and Identifiers

Synonyms: NSC-736992 | 915954-53-9|NSC-736992|5-(naphthalen-2-yl)-1-(3,4,5-trimethoxyphenyl)-1H-imidazole|CHEMBL221473|DTXSID90639843|NSC736992|5-(naphthalen-2-yl)-1-(3,5-trimethoxyphenyl)-1H-imidazole

Canonical SMILES:  COc1cc(-n2cncc2-c2ccc3ccccc3c2)cc(OC)c1OC

Standard InChI:  InChI=1S/C22H20N2O3/c1-25-20-11-18(12-21(26-2)22(20)27-3)24-14-23-13-19(24)17-9-8-15-6-4-5-7-16(15)10-17/h4-14H,1-3H3

Standard InChI Key:  VQIFHAGEERVOKJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
    9.3155   -1.0702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9660   -1.5771    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6500   -1.1156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4203   -0.3206    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5965   -0.2967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9387   -2.3989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2091   -2.7865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1811   -3.6102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8818   -4.0474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6122   -3.6548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6367   -2.8323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3140   -4.0886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0405   -3.6978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8551   -4.8720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5559   -5.3073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4529   -3.9981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5907   -1.4565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5626   -2.2776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1600   -1.4039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8899   -1.0190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8372   -2.6660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1356   -2.2282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4077   -2.6168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3802   -3.4431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0866   -3.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8116   -3.4881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4248   -4.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  9 14  1  0
  6  7  2  0
 14 15  1  0
  8 16  1  0
  7  8  1  0
 17 20  2  0
 19 22  2  0
  2  3  1  0
 21 18  2  0
 18 17  1  0
  1 17  1  0
  8  9  2  0
  3  4  2  0
 19 20  1  0
  9 10  1  0
  4  5  1  0
 21 22  1  0
 10 11  2  0
 22 23  1  0
 11  6  1  0
 23 24  2  0
  2  6  1  0
 24 25  1  0
  5  1  2  0
 25 26  2  0
 26 21  1  0
 10 12  1  0
 16 27  1  0
  1  2  1  0
 12 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA221473

   5-(naphthalen-2-yl)-1-(3,4,5-trimethoxyphenyl)-1H-imidazole

2. Alternative Forms:

   

   ALA221473

   5-Naphthalen-2-yl-1-(3,4,5-trimethoxyphenyl)imidazole;hydrochloride

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: 360.41

Molecular Weight (Monoisotopic): 360.1474

AlogP: 4.72

#Rotatable Bonds: 5

Polar Surface Area: 45.51

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.76

CX LogP: 3.82

CX LogD: 3.81

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.52

Np Likeness Score: -0.50

References

1. Bellina F, Cauteruccio S, Monti S, Rossi R..  (2006)  Novel imidazole-based combretastatin A-4 analogues: evaluation of their in vitro antitumor activity and molecular modeling study of their binding to the colchicine site of tubulin.,  16  (22): [PMID:16950621] [10.1016/j.bmcl.2006.08.087]

2. Bonezzi K, Taraboletti G, Borsotti P, Bellina F, Rossi R, Giavazzi R..  (2009)  Vascular disrupting activity of tubulin-binding 1,5-diaryl-1H-imidazoles.,  52  (23): [PMID:19954252] [10.1021/jm900968s]

3. Ramajayam R..  (2019)  Medicinal chemistry of vicinal diaryl scaffold: A mini review.,  162  [PMID:30396033] [10.1016/j.ejmech.2018.10.054]

Source

Source(1):

• Scientific Literature