2-(2-Bromo-5,6-dichloro-benzoimidazol-1-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol

ID: ALA473894

Cas Number: 142356-43-2

PubChem CID: 465094

Max Phase: Preclinical

Molecular Formula: C12H11BrCl2N2O4

Molecular Weight: 398.04

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@H]1O[C@@H](n2c(Br)nc3cc(Cl)c(Cl)cc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C12H11BrCl2N2O4/c13-12-16-6-1-4(14)5(15)2-7(6)17(12)11-10(20)9(19)8(3-18)21-11/h1-2,8-11,18-20H,3H2/t8-,9-,10-,11-/m1/s1

Standard InChI Key:  NMAMPJIAXSGTLN-GWOFURMSSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    4.6408  -22.3984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6408  -23.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3549  -23.6360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0691  -23.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0691  -22.3984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3549  -21.9859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9549  -23.5862    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3418  -22.8110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8544  -22.1431    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1097  -24.2641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6269  -24.9274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1097  -25.5999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8951  -25.3400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8951  -24.5149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8547  -26.3845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0477  -26.5560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5638  -25.8231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5613  -24.0282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1640  -22.7420    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.9262  -21.9860    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.9262  -23.6359    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  4  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
 10  7  1  1
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 10  1  0
 12 15  1  1
  1  2  2  0
 15 16  1  0
  2  3  1  0
 13 17  1  6
  3  4  2  0
 14 18  1  6
  4  5  1  0
  8 19  1  0
  5  6  2  0
  1 20  1  0
  6  1  1  0
  2 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA473894

   (2R,3R,4S,5R)-2-(2-bromo-5,6-dichloro-benzimidazol-1-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

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: 398.04

Molecular Weight (Monoisotopic): 395.9279

AlogP: 1.72

#Rotatable Bonds: 2

Polar Surface Area: 87.74

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.45

CX Basic pKa: 3.04

CX LogP: 1.97

CX LogD: 1.97

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.72

Np Likeness Score: 0.41

References

1. Gudmundsson KS, Tidwell J, Lippa N, Koszalka GW, van Draanen N, Ptak RG, Drach JC, Townsend LB..  (2000)  Synthesis and antiviral evaluation of halogenated beta-D- and -L-erythrofuranosylbenzimidazoles.,  43  (12): [PMID:10882374] [10.1021/jm990195p]

2. Gudmundsson KS, Freeman GA, Drach JC, Townsend LB..  (2000)  Synthesis of fluorosugar analogues of 2,5,6-trichloro-1-(beta-D-ribofuranosyl)benzimidazole as antivirals with potentially increased glycosidic bond stability.,  43  (12): [PMID:10882375] [10.1021/jm990219s]

3. Williams JD, Chen JJ, Drach JC, Townsend LB..  (2004)  Synthesis and antiviral activity of 3-formyl- and 3-cyano-2,5,6-trichloroindole nucleoside derivatives.,  47  (23): [PMID:15509175] [10.1021/jm040032n]

4. Williams JD, Chen JJ, Drach JC, Townsend LB..  (2004)  Design, synthesis, and antiviral activity of certain 3-substituted 2,5,6-trichloroindole nucleosides.,  47  (23): [PMID:15509174] [10.1021/jm0400146]

5. Chien TC, Saluja SS, Drach JC, Townsend LB..  (2004)  Synthesis and antiviral evaluation of polyhalogenated imidazole nucleosides: dimensional analogues of 2,5,6-trichloro-1-(beta-D-ribofuranosyl)benzimidazole.,  47  (23): [PMID:15509173] [10.1021/jm040016q]

6. Williams JD, Ptak RG, Drach JC, Townsend LB..  (2004)  Synthesis, antiviral activity, and mode of action of some 3-substituted 2,5,6-trichloroindole 2'- and 5'-deoxyribonucleosides.,  47  (23): [PMID:15509176] [10.1021/jm0400606]

7. Prado-Prado FJ, Martinez de la Vega O, Uriarte E, Ubeira FM, Chou KC, González-Díaz H..  (2009)  Unified QSAR approach to antimicrobials. 4. Multi-target QSAR modeling and comparative multi-distance study of the giant components of antiviral drug-drug complex networks.,  17  (2): [PMID:19112024] [10.1016/j.bmc.2008.11.075]

8. Hwang JS, Schilf R, Drach JC, Townsend LB, Bogner E..  (2009)  Susceptibilities of human cytomegalovirus clinical isolates and other herpesviruses to new acetylated, tetrahalogenated benzimidazole D-ribonucleosides.,  53  (12): [PMID:19786605] [10.1128/aac.00809-09]

Source

Source(1):

• Scientific Literature