1-(3,4-dichlorobenzyl)-5,6-dimethyl-1H-benzo[d]imidazole

ID: ALA1945507

Chembl Id: CHEMBL1945507

PubChem CID: 2949939

Max Phase: Preclinical

Molecular Formula: C16H14Cl2N2

Molecular Weight: 305.21

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc2ncn(Cc3ccc(Cl)c(Cl)c3)c2cc1C

Standard InChI:  InChI=1S/C16H14Cl2N2/c1-10-5-15-16(6-11(10)2)20(9-19-15)8-12-3-4-13(17)14(18)7-12/h3-7,9H,8H2,1-2H3

Standard InChI Key:  PCJBTWVYIQBUCM-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA1945507

   1-(3,4-dichlorobenzyl)-5,6-dimethyl-1H-benzimidazole

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: 305.21

Molecular Weight (Monoisotopic): 304.0534

AlogP: 5.01

#Rotatable Bonds: 2

Polar Surface Area: 17.82

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 5.93

CX LogP: 5.44

CX LogD: 5.43

Aromatic Rings: 3

Heavy Atoms: 20

QED Weighted: 0.65

Np Likeness Score: -1.72

References

1. Hevener KE, Mehboob S, Su PC, Truong K, Boci T, Deng J, Ghassemi M, Cook JL, Johnson ME..  (2012)  Discovery of a novel and potent class of F. tularensis enoyl-reductase (FabI) inhibitors by molecular shape and electrostatic matching.,  55  (1): [PMID:22098466] [10.1021/jm201168g]

2. Mehboob S, Hevener KE, Truong K, Boci T, Santarsiero BD, Johnson ME..  (2012)  Structural and enzymatic analyses reveal the binding mode of a novel series of Francisella tularensis enoyl reductase (FabI) inhibitors.,  55  (12): [PMID:22642319] [10.1021/jm300489v]

3. Wilkinson C, McPhillie MJ, Zhou Y, Woods S, Afanador GA, Rawson S, Khaliq F, Prigge ST, Roberts CW, Rice DW, McLeod R, Fishwick CW, Muench SP..  (2014)  The benzimidazole based drugs show good activity against T. gondii but poor activity against its proposed enoyl reductase enzyme target.,  24  (3): [PMID:24398298] [10.1016/j.bmcl.2013.12.066]

4. Mehboob S, Song J, Hevener KE, Su PC, Boci T, Brubaker L, Truong L, Mistry T, Deng J, Cook JL, Santarsiero BD, Ghosh AK, Johnson ME..  (2015)  Structural and biological evaluation of a novel series of benzimidazole inhibitors of Francisella tularensis enoyl-ACP reductase (FabI).,  25  (6): [PMID:25677657] [10.1016/j.bmcl.2015.01.048]

5. Štular T,Lešnik S,Rožman K,Schink J,Zdouc M,Ghysels A,Liu F,Aldrich CC,Haupt VJ,Salentin S,Daminelli S,Schroeder M,Langer T,Gobec S,Janežič D,Konc J.  (2016)  Discovery of Mycobacterium tuberculosis InhA Inhibitors by Binding Sites Comparison and Ligands Prediction.,  59  (24.0): [PMID:27936766] [10.1021/acs.jmedchem.6b01277]

Source

Source(1):

• Scientific Literature