1-benzyl-2-phenyl-1H-benzo[d]imidazole

ID: ALA1922082

Cas Number: 739-88-8

PubChem CID: 1221687

Max Phase: Preclinical

Molecular Formula: C20H16N2

Molecular Weight: 284.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  c1ccc(Cn2c(-c3ccccc3)nc3ccccc32)cc1

Standard InChI:  InChI=1S/C20H16N2/c1-3-9-16(10-4-1)15-22-19-14-8-7-13-18(19)21-20(22)17-11-5-2-6-12-17/h1-14H,15H2

Standard InChI Key:  LCFXRSKBJWQHON-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
   -4.9999    2.8390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0010    2.0113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2858    1.5981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2876    3.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5719    2.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5717    2.0112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7812    1.7532    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2922    2.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7812    3.0998    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4668    2.4276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0577    1.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2330    1.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1803    2.4282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2371    3.1452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0604    3.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7844    0.9326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0640    0.5296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0546   -0.2943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3350   -0.6972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6248   -0.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6387    0.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3588    0.9540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
 10 11  2  0
 11 12  1  0
  2  3  1  0
 12 13  2  0
  3  6  2  0
 13 14  1  0
  1  2  2  0
 14 15  2  0
 15 10  1  0
  5  4  2  0
  7 16  1  0
  6  7  1  0
 16 17  1  0
  7  8  1  0
 17 18  2  0
  8  9  2  0
 18 19  1  0
  9  5  1  0
 19 20  2  0
  4  1  1  0
 20 21  1  0
  8 10  1  0
 21 22  2  0
 22 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1922082

   1-Benzyl-2-phenyl-1H-benzoimidazole

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: 284.36

Molecular Weight (Monoisotopic): 284.1313

AlogP: 4.75

#Rotatable Bonds: 3

Polar Surface Area: 17.82

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.71

CX LogP: 5.23

CX LogD: 5.23

Aromatic Rings: 4

Heavy Atoms: 22

QED Weighted: 0.53

Np Likeness Score: -1.22

References

1. Bandyopadhyay P, Sathe M, Ponmariappan S, Sharma A, Sharma P, Srivastava AK, Kaushik MP..  (2011)  Exploration of in vitro time point quantitative evaluation of newly synthesized benzimidazole and benzothiazole derivatives as potential antibacterial agents.,  21  (24): [PMID:22047695] [10.1016/j.bmcl.2011.10.034]

2. Zimmermann G, Schultz-Fademrecht C, Küchler P, Murarka S, Ismail S, Triola G, Nussbaumer P, Wittinghofer A, Waldmann H..  (2014)  Structure guided design and kinetic analysis of highly potent benzimidazole inhibitors targeting the PDEδ prenyl binding site.,  57  (12): [PMID:24884780] [10.1021/jm500632s]

3. Tonelli M, Novelli F, Tasso B, Vazzana I, Sparatore A, Boido V, Sparatore F, La Colla P, Sanna G, Giliberti G, Busonera B, Farci P, Ibba C, Loddo R..  (2014)  Antiviral activity of benzimidazole derivatives. III. Novel anti-CVB-5, anti-RSV and anti-Sb-1 agents.,  22  (17): [PMID:25082514] [10.1016/j.bmc.2014.06.043]

4. Zhang C, Zhong B, Yang S, Pan L, Yu S, Li Z, Li S, Su B, Meng X..  (2015)  Synthesis and biological evaluation of thiabendazole derivatives as anti-angiogenesis and vascular disrupting agents.,  23  (13): [PMID:25936258] [10.1016/j.bmc.2015.03.085]

5. Chen L, Zhuang C, Lu J, Jiang Y, Sheng C..  (2018)  Discovery of Novel KRAS-PDEδ Inhibitors by Fragment-Based Drug Design.,  61  (6): [PMID:29510040] [10.1021/acs.jmedchem.8b00057]

6. Dokla EME,Abutaleb NS,Milik SN,Li D,El-Baz K,Shalaby MW,Al-Karaki R,Nasr M,Klein CD,Abouzid KAM,Seleem MN.  (2020)  Development of benzimidazole-based derivatives as antimicrobial agents and their synergistic effect with colistin against gram-negative bacteria.,  186  [PMID:31735572] [10.1016/j.ejmech.2019.111850]

Source

Source(1):

• Scientific Literature