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

ID: ALA207001

PubChem CID: 24205509

Max Phase: Preclinical

Molecular Formula: C14H13BrN6O2S5

Molecular Weight: 537.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=S(=O)(NC1=NCCN1C(=S)SN1CCn2c1nsc2=S)c1ccc(Br)cc1

Standard InChI:  InChI=1S/C14H13BrN6O2S5/c15-9-1-3-10(4-2-9)28(22,23)18-11-16-5-6-19(11)14(25)27-21-8-7-20-12(21)17-26-13(20)24/h1-4H,5-8H2,(H,16,18)

Standard InChI Key:  OPHLBAWCOGSTNY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    0.9550  -19.4286    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7274  -19.7255    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.2467  -19.0846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0003  -18.6075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7989  -18.3915    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8404  -17.5665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0678  -17.2695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5486  -17.9143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0717  -19.1262    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2725  -17.8689    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6877  -17.1556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5104  -17.1556    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2725  -16.4423    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9969  -16.4892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7821  -16.7442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7821  -17.5669    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9969  -17.8220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7419  -18.6071    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3284  -19.1936    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7419  -19.7763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9111  -18.6071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9111  -19.7763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7036  -19.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2860  -20.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0729  -20.9402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2722  -21.1519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6933  -20.5686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6539  -21.5227    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
  6  7  1  0
  7  8  1  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
M  END

Alternative Forms

1. Parent:

   

   ALA207001

   2-(4-Bromo-benzenesulfonylimino)-imidazolidine-1-car bodithioic acid 3-thioxo-5,1-c][1,2, 4]thiadiazol-7-yl ester

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: 537.54

Molecular Weight (Monoisotopic): 535.8887

AlogP: 2.84

#Rotatable Bonds: 3

Polar Surface Area: 82.83

Molecular Species: NEUTRAL

HBA: 10

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.20

CX Basic pKa: 1.64

CX LogP: 4.53

CX LogD: 4.53

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.47

Np Likeness Score: -1.60

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