dimethyl 4-(6-(2-methoxyphenyl)imidazo[2,1-b]thiazol-5-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

ID: ALA260309

PubChem CID: 24823574

Max Phase: Preclinical

Molecular Formula: C23H23N3O5S

Molecular Weight: 453.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1c(-c2ccccc2OC)nc2sccn12

Standard InChI:  InChI=1S/C23H23N3O5S/c1-12-16(21(27)30-4)18(17(13(2)24-12)22(28)31-5)20-19(25-23-26(20)10-11-32-23)14-8-6-7-9-15(14)29-3/h6-11,18,24H,1-5H3

Standard InChI Key:  LKADTWJGOPRQFA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   14.1295   -9.7988    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3844   -9.0142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7170   -8.5293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9932   -5.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9932   -5.9214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7076   -6.3339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4267   -5.9214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4267   -5.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7076   -4.6748    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1415   -4.6801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   15.1406   -6.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1395   -7.1598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8555   -5.9234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5694   -6.3368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2788   -6.3339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5644   -5.9214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2788   -7.1588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8499   -6.3339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3045   -9.7988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0451   -9.0125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2171   -9.0162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9648   -9.8049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6368  -10.2885    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.1682   -8.7591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7811   -9.3129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5651   -9.0585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7373   -8.2508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1193   -7.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3377   -7.9551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6087  -10.1196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2212  -10.6722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  9  1  0
  5 16  1  0
  5  6  1  0
 16 17  1  0
  6  7  1  0
 16 18  2  0
  7  8  2  0
 17 19  1  0
  6  3  1  0
 20 21  1  0
  8  9  1  0
 20  1  2  0
  8 10  1  0
  4 11  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 20  1  0
  1  2  1  0
  7 12  1  0
 25 26  2  0
  2  3  2  0
 26 27  1  0
 12 13  2  0
 27 28  2  0
  3 21  1  0
 28 29  1  0
 12 14  1  0
 29 30  2  0
 30 25  1  0
  2 25  1  0
  4  5  2  0
 26 31  1  0
 14 15  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA260309

   Dimethyl 4-[6-(2-methoxyphenyl)imidazo[2,1-b][1,3]thiazol-5-yl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

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: 453.52

Molecular Weight (Monoisotopic): 453.1358

AlogP: 3.65

#Rotatable Bonds: 5

Polar Surface Area: 91.16

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.15

CX LogP: 2.41

CX LogD: 2.41

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.59

Np Likeness Score: -1.01

References

1. Budriesi R, Ioan P, Locatelli A, Cosconati S, Leoni A, Ugenti MP, Andreani A, Di Toro R, Bedini A, Spampinato S, Marinelli L, Novellino E, Chiarini A..  (2008)  Imidazo[2,1-b]thiazole system: a scaffold endowing dihydropyridines with selective cardiodepressant activity.,  51  (6): [PMID:18303827] [10.1021/jm070681+]

2. Budriesi R, Ioan P, Leoni A, Pedemonte N, Locatelli A, Micucci M, Chiarini A, Galietta LJ..  (2011)  Cystic fibrosis: a new target for 4-Imidazo[2,1-b]thiazole-1,4-dihydropyridines.,  54  (11): [PMID:21568323] [10.1021/jm200199r]

3. Leoni A, Frosini M, Locatelli A, Micucci M, Carotenuto C, Durante M, Cosconati S, Budriesi R..  (2019)  4-Imidazo[2,1-b]thiazole-1,4-DHPs and neuroprotection: preliminary study in hits searching.,  169  [PMID:30861492] [10.1016/j.ejmech.2019.02.075]

Source

Source(1):

• Scientific Literature