(Z)-5-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methylene)-3-(2-(4-(pyridin-2-yl)piperazin-1-yl)acetyl)thiazolidine-2,4-dione

ID: ALA5283320

Max Phase: Preclinical

Molecular Formula: C23H22N4O5S

Molecular Weight: 466.52

Names and Identifiers

Canonical SMILES:  O=C(CN1CCN(c2ccccn2)CC1)N1C(=O)S/C(=C\c2ccc3c(c2)OCCO3)C1=O

Standard InChI:  InChI=1S/C23H22N4O5S/c28-21(15-25-7-9-26(10-8-25)20-3-1-2-6-24-20)27-22(29)19(33-23(27)30)14-16-4-5-17-18(13-16)32-12-11-31-17/h1-6,13-14H,7-12,15H2/b19-14-

Standard InChI Key:  IRPPWAUEOZWGMG-RGEXLXHISA-N

Molfile:  

 
     RDKit          2D

 33 37  0  0  0  0  0  0  0  0999 V2000
   -3.7239   -0.9449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4384   -0.5326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4384    0.2888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7289    0.6978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0172    0.2872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0172   -0.5301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3060    0.6978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5948    0.2872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8450    0.6211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2957    0.0111    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7060   -0.6997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5088   -0.5290    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2955   -1.4109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5254    0.0111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9360    0.7223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9360   -0.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7573   -0.7000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1678    0.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9890    0.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3997   -0.7000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9890   -1.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1678   -1.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2209   -0.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6333   -1.4141    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4540   -1.4141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8612   -0.7010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4504    0.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6317    0.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6324    1.4141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1498    0.6994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8612    0.2888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8612   -0.5326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1498   -0.9434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  2  0
  3  4  1  0
  5  4  2  0
  6  5  1  0
  1  6  2  0
  5  7  1  0
  7  8  2  0
  9  8  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12  8  1  0
 11 13  2  0
 10 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 18 17  1  0
 19 18  1  0
 20 19  1  0
 21 20  1  0
 22 21  1  0
 17 22  1  0
 23 20  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 23  2  0
  9 29  2  0
  3 30  1  0
 31 30  1  0
 31 32  1  0
 32 33  1  0
 33  2  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5283320

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 466.52

Molecular Weight (Monoisotopic): 466.1311

AlogP: 2.24

#Rotatable Bonds: 4

Polar Surface Area: 92.28

Molecular Species: NEUTRAL

HBA: 9

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.09

CX LogP: 2.36

CX LogD: 2.34

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.63

Np Likeness Score: -1.79

References

1. Bolchi C, Bavo F, Appiani R, Roda G, Pallavicini M..  (2020)  1,4-Benzodioxane, an evergreen, versatile scaffold in medicinal chemistry: A review of its recent applications in drug design.,  200  [PMID:32502862] [10.1016/j.ejmech.2020.112419]

Source

Source(1):

• Scientific Literature