N-(4-(1H-benzo[d]imidazol-2-yl)phenyl)thiophene-2-carboxamide

ID: ALA1277660

Cas Number: 330635-70-6

PubChem CID: 684639

Max Phase: Preclinical

Molecular Formula: C18H13N3OS

Molecular Weight: 319.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(-c2nc3ccccc3[nH]2)cc1)c1cccs1

Standard InChI:  InChI=1S/C18H13N3OS/c22-18(16-6-3-11-23-16)19-13-9-7-12(8-10-13)17-20-14-4-1-2-5-15(14)21-17/h1-11H,(H,19,22)(H,20,21)

Standard InChI Key:  ULVMGOVEIWGGKV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
    4.6770  -18.4514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6759  -19.2787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3906  -19.6915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3888  -18.0387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1041  -18.4478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1089  -19.2741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8963  -19.5249    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3781  -18.8535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8885  -18.1879    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2010  -18.8481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6170  -19.5617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4411  -19.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8501  -18.8398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4291  -18.1256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6064  -18.1336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6750  -18.8339    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0927  -19.5453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9174  -19.5393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6853  -20.2626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4059  -20.2005    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.1886  -19.9400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1826  -19.1150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3963  -18.8659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
  8 10  1  0
  5  4  2  0
 13 16  1  0
  6  7  1  0
 16 17  1  0
  7  8  1  0
 17 18  1  0
  8  9  2  0
 17 19  2  0
 18 20  1  0
  9  5  1  0
  4  1  1  0
  5  6  1  0
 10 11  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 18  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1277660

   N-[4-(1H-benzimidazol-2-yl)phenyl]thiophene-2-carboxamide

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: 319.39

Molecular Weight (Monoisotopic): 319.0779

AlogP: 4.54

#Rotatable Bonds: 3

Polar Surface Area: 57.78

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.52

CX Basic pKa: 5.16

CX LogP: 4.29

CX LogD: 4.29

Aromatic Rings: 4

Heavy Atoms: 23

QED Weighted: 0.58

Np Likeness Score: -2.02

References

1. Keurulainen L, Salin O, Siiskonen A, Kern JM, Alvesalo J, Kiuru P, Maass M, Yli-Kauhaluoma J, Vuorela P..  (2010)  Design and synthesis of 2-arylbenzimidazoles and evaluation of their inhibitory effect against Chlamydia pneumoniae.,  53  (21): [PMID:20932010] [10.1021/jm1008083]

2. Keurulainen L, Siiskonen A, Nasereddin A, Kopelyanskiy D, Sacerdoti-Sierra N, Leino TO, Tammela P, Yli-Kauhaluoma J, Jaffe CL, Kiuru P..  (2015)  Synthesis and biological evaluation of 2-arylbenzimidazoles targeting Leishmania donovani.,  25  (9): [PMID:25827525] [10.1016/j.bmcl.2015.03.027]

3. L'abbate FP, Müller R, Openshaw R, Combrinck JM, de Villiers KA, Hunter R, Egan TJ..  (2018)  Hemozoin inhibiting 2-phenylbenzimidazoles active against malaria parasites.,  159  [PMID:30296683] [10.1016/j.ejmech.2018.09.060]

Source

Source(1):

• Scientific Literature