1,1-Dioxo-6-phenyl-2,3-dihydro-1H-1lambda*6*-imidazo[2,1-b]thiazole-5-carboxylic acid(2,6-dichloro-phenyl)-amide

ID: ALA2289504

PubChem CID: 15163454

Max Phase: Preclinical

Molecular Formula: C18H13Cl2N3O3S

Molecular Weight: 422.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1c(Cl)cccc1Cl)c1c(-c2ccccc2)nc2n1CCS2(=O)=O

Standard InChI:  InChI=1S/C18H13Cl2N3O3S/c19-12-7-4-8-13(20)15(12)21-17(24)16-14(11-5-2-1-3-6-11)22-18-23(16)9-10-27(18,25)26/h1-8H,9-10H2,(H,21,24)

Standard InChI Key:  ZDRYTJBYXIYVOZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   18.1060  -17.1296    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.4657  -17.6499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2365  -17.9442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1705  -15.7963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6541  -16.4396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9419  -16.0889    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9004  -16.9171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6753  -17.2124    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1956  -16.5668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7423  -15.8724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0196  -16.6080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0361  -15.1015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8507  -14.9705    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.5153  -14.4616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1446  -14.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9585  -14.0724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2524  -13.3023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7314  -12.6614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9130  -12.7957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6228  -13.5658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8089  -13.7007    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   22.4776  -14.7138    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   21.3920  -17.3429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2152  -17.3844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6638  -16.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2831  -15.9540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4610  -15.9161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  1  3  2  0
  1  7  1  0
  6  4  1  0
  4  5  1  0
  5  1  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  6  1  0
  9 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 20 21  1  0
 16 22  1  0
 11 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 11  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2289504

   N-(2,6-dichlorophenyl)-1,1-dioxo-6-phenyl-2,3-dihydroimidazo[2,1-b][1,3]thiazole-5-carboxamide

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: 422.29

Molecular Weight (Monoisotopic): 421.0055

AlogP: 3.90

#Rotatable Bonds: 3

Polar Surface Area: 81.06

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.40

CX Basic pKa: ┄

CX LogP: 3.84

CX LogD: 3.84

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.69

Np Likeness Score: -1.24

References

1. Andreani A, Rambaldi M, Locatelli A..  (1995)  Synthesis and fungicide activity of 2,3-dihydroimidazo [2,1-b]thiazole-5-carboxamides.,  70  (4): [PMID:8765698] [10.1016/0031-6865(95)00038-0]

Source

Source(1):

• Scientific Literature