N-{5-[2-(N,N-Dimethylsulfamoyl)-4,5-dimethoxy-benzyl]-1,3,4-thiadiazol-2-yl}-N-(p-chlorophenyl)amine

ID: ALA2270955

PubChem CID: 46177118

Max Phase: Preclinical

Molecular Formula: C19H21ClN4O4S2

Molecular Weight: 468.99

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(Cc2nnc(Nc3ccc(Cl)cc3)s2)c(S(=O)(=O)N(C)C)cc1OC

Standard InChI:  InChI=1S/C19H21ClN4O4S2/c1-24(2)30(25,26)17-11-16(28-4)15(27-3)9-12(17)10-18-22-23-19(29-18)21-14-7-5-13(20)6-8-14/h5-9,11H,10H2,1-4H3,(H,21,23)

Standard InChI Key:  WVAVWECPYOIWOD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
   10.8237   -5.7417    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.6409   -5.7404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2312   -5.0333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6988   -4.5151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6976   -5.3347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4057   -5.7437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1153   -5.3342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1125   -4.5116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4039   -4.1063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9896   -5.7427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2822   -5.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9910   -4.1067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9908   -3.2895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8250   -6.5589    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8187   -4.1003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7975   -3.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4459   -2.7832    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.1735   -2.0128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3565   -2.0338    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1242   -2.8173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6320   -1.3374    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4491   -1.3281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8599   -2.0315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6710   -2.0191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0765   -1.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6538   -0.6026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8431   -0.6178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1179   -6.9686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5333   -6.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8936   -1.3006    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  1  3  2  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  5 10  1  0
 10 11  1  0
  4 12  1  0
 12 13  1  0
  7  1  1  0
  1 14  1  0
  8 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 16  2  0
 18 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 14 28  1  0
 14 29  1  0
 25 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2270955

   2-[[5-(4-chloroanilino)-1,3,4-thiadiazol-2-yl]methyl]-4,5-dimethoxy-N,N-dimethylbenzenesulfonamide

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: 468.99

Molecular Weight (Monoisotopic): 468.0693

AlogP: 3.79

#Rotatable Bonds: 8

Polar Surface Area: 93.65

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.45

CX Basic pKa: 0.59

CX LogP: 3.17

CX LogD: 3.17

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.54

Np Likeness Score: -1.83

References

1. Camoutsis C, Geronikaki A, Ciric A, Soković M, Zoumpoulakis P, Zervou M..  (2010)  Sulfonamide-1,2,4-thiadiazole derivatives as antifungal and antibacterial agents: synthesis, biological evaluation, lipophilicity, and conformational studies.,  58  (2): [PMID:20118573] [10.1248/cpb.58.160]

Source

Source(1):

• Scientific Literature