2-[(E)-3,4-dimethoxy-benzenesulfonylimino]-imidazolidine-1-carbodithioic acid 3-thioxo-5,6-dihydro-imidazo[2,1-c][1,2,4]thiadiazol-7-yl ester

ID: ALA384448

PubChem CID: 24205515

Max Phase: Preclinical

Molecular Formula: C16H18N6O4S5

Molecular Weight: 518.69

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(S(=O)(=O)NC2=NCCN2C(=S)SN2CCn3c2nsc3=S)cc1OC

Standard InChI:  InChI=1S/C16H18N6O4S5/c1-25-11-4-3-10(9-12(11)26-2)31(23,24)19-13-17-5-6-20(13)16(28)30-22-8-7-21-14(22)18-29-15(21)27/h3-4,9H,5-8H2,1-2H3,(H,17,19)

Standard InChI Key:  ZQRYRWIRCZCNTF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   11.0075   -5.5826    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7802   -5.8796    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.2995   -5.2386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0530   -4.7614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8516   -4.5454    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8932   -3.7202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1205   -3.4234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6012   -4.0682    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1246   -5.2801    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.7800   -4.0228    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.3647   -3.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5418   -3.3094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7800   -2.5959    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.0554   -2.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2701   -2.8979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2701   -3.7208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0554   -3.9758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3104   -4.7610    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7238   -5.3476    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.3104   -5.9303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1411   -4.7610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1411   -5.9303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3484   -5.7155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7660   -6.2974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9791   -7.0944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7799   -7.3063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3589   -6.7228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3981   -7.6770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6120   -8.4715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9957   -8.1003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7912   -8.3104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  4  1  0
  3  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  2  0
 19 22  1  0
 22 23  2  0
  1  2  1  0
 23 24  1  0
  2  3  1  0
 24 25  2  0
  3  5  1  0
 25 26  1  0
  4  1  2  0
 26 27  2  0
 27 22  1  0
  4  5  1  0
 25 28  1  0
  5  6  1  0
 28 29  1  0
  6  7  1  0
 26 30  1  0
  7  8  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA384448

   (3-Sulfanylidene-5,6-dihydroimidazo[2,1-c][1,2,4]thiadiazol-7-yl) 2-[(3,4-dimethoxyphenyl)sulfonylamino]-4,5-dihydroimidazole-1-carbodithioate

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: 518.69

Molecular Weight (Monoisotopic): 517.9993

AlogP: 2.09

#Rotatable Bonds: 5

Polar Surface Area: 101.29

Molecular Species: NEUTRAL

HBA: 12

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.85

CX Basic pKa: 1.49

CX LogP: 3.45

CX LogD: 3.45

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.47

Np Likeness Score: -1.40

References

1. Saczewski J, Brzozowski Z, Saczewski F, Bednarski PJ, Liebeke M, Gdaniec M..  (2006)  Synthesis and in vitro anti-tumor activity of N-{1-[(3-thioxo-5,6-dihydroimidazo[2,1-c][1,2,4]thiadiazol-7-ylthio)thiocarbonyl]-2-imidazolidene}arylsulfonamides.,  16  (14): [PMID:16682194] [10.1016/j.bmcl.2006.04.067]

Source

Source(1):

• Scientific Literature