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

ID: ALA377035

PubChem CID: 16038016

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)c1ccccc1Cl

Standard InChI:  InChI=1S/C14H13ClN6O2S5/c15-9-3-1-2-4-10(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:  AVPKOUBDQYTMQB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    9.8193  -19.0534    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5919  -19.3503    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.1112  -18.7094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8647  -18.2322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6633  -18.0162    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7049  -17.1911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9323  -16.8943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4130  -17.5390    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9363  -18.7510    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.5918  -17.4937    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.1766  -16.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3537  -16.7803    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5918  -16.0669    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.8673  -16.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0821  -16.3689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0821  -17.1917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8673  -17.4466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1223  -18.2319    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5358  -18.8184    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.1223  -19.4011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9531  -18.2319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9531  -19.4011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1604  -19.1863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5781  -19.7682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7912  -20.5651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5919  -20.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1709  -20.1935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9666  -20.4024    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
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA377035

   2-(2-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: 8.67

CX Basic pKa: 1.61

CX LogP: 4.37

CX LogD: 4.35

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.52

Np Likeness Score: -1.83

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