3-[4-(2-Adamantyl)-1,3-thiazol-2-yl]-2-(2,5-dimethoxyphenyl)-1,3-thiazolidin-4-one

ID: ALA3735075

PubChem CID: 127035260

Max Phase: Preclinical

Molecular Formula: C24H28N2O3S2

Molecular Weight: 456.63

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(OC)c(C2SCC(=O)N2c2nc(C34CC5CC(CC(C5)C3)C4)cs2)c1

Standard InChI:  InChI=1S/C24H28N2O3S2/c1-28-17-3-4-19(29-2)18(8-17)22-26(21(27)13-30-22)23-25-20(12-31-23)24-9-14-5-15(10-24)7-16(6-14)11-24/h3-4,8,12,14-16,22H,5-7,9-11,13H2,1-2H3

Standard InChI Key:  LMMLDMOJNDEABH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 36  0  0  0  0  0  0  0  0999 V2000
   -4.0702    1.0031    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8535    1.8804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6682    0.9900    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1118   -0.4305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6118   -0.4251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4027   -1.3986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8388    3.3811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5991    4.2162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7038    5.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0520    6.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2955    5.5312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1908    4.0349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3710    2.7193    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2078    1.3354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9296    0.3574    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1909    1.1452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8659    2.5965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5602    0.5726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7345    1.5436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7345    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8300    2.8133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5893   -0.5726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5602    2.2656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1246    2.2656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1246    0.5726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2034   -0.5726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0291    0.0249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2496    3.5595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7451    4.2307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6459    6.1863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6397    5.5138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  1  5  1  0
  4  6  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  7 12  2  0
  2  7  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 13 17  1  0
 16 18  1  0
  3 14  1  0
 19 20  1  0
 19 21  1  0
 20 22  1  0
 21 23  1  0
 22 18  1  0
 23 18  1  0
 24 25  1  0
 21 24  1  0
 20 26  1  0
 18 27  1  0
 27 25  1  0
 25 26  1  0
 28 29  1  0
  8 28  1  0
 11 30  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3735075

   ---

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: 456.63

Molecular Weight (Monoisotopic): 456.1541

AlogP: 5.41

#Rotatable Bonds: 5

Polar Surface Area: 51.66

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.94

CX LogD: 4.94

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.60

Np Likeness Score: -0.72

References

1. Pitta E, Tsolaki E, Geronikaki A, Petrovic J, Glamoclija J, Sokovic M, Crespan E, Maga G, Bhunia SS, Saxena AK.  (2015)  4-Thiazolidinone derivatives as potent antimicrobial agents: microwave-assisted synthesis, biological evaluation and docking studies,  6  (2): [10.1039/C4MD00399C]

Source

Source(1):

• Scientific Literature