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

ID: ALA212324

PubChem CID: 24205514

Max Phase: Preclinical

Molecular Formula: C14H13ClN6O2S5

Molecular Weight: 493.09

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=S(=O)(NC1=NCCN1C(=S)SN1CCn2c1nsc2=S)c1cccc(Cl)c1

Standard InChI:  InChI=1S/C14H13ClN6O2S5/c15-9-2-1-3-10(8-9)28(22,23)18-11-16-4-5-19(11)14(25)27-21-7-6-20-12(21)17-26-13(20)24/h1-3,8H,4-7H2,(H,16,18)

Standard InChI Key:  ZGHYJHPWNLCBRG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    1.6458  -24.0871    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4184  -24.3841    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.9377  -23.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6912  -23.2660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4899  -23.0500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5314  -22.2249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7588  -21.9280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2395  -22.5728    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7628  -23.7847    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.4183  -22.5273    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0031  -21.8140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8198  -21.8140    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4183  -21.1006    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3062  -21.1476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0914  -21.4026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0914  -22.2254    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3062  -22.4804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0511  -23.2656    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6377  -23.8521    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0511  -24.4349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2204  -23.2656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2204  -24.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0131  -24.2201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5954  -24.8019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3823  -25.5988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5816  -25.8106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0026  -25.2272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3658  -26.6047    0.0000 Cl  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
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA212324

   2-(3-Chloro-benzenesulfonylimino)-imidazolidine-1-carbodithi oic 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: 493.09

Molecular Weight (Monoisotopic): 491.9392

AlogP: 2.73

#Rotatable Bonds: 3

Polar Surface Area: 82.83

Molecular Species: NEUTRAL

HBA: 10

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.06

CX Basic pKa: 1.61

CX LogP: 4.37

CX LogD: 4.36

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.52

Np Likeness Score: -1.88

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