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

ID: ALA411235

PubChem CID: 24822927

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(-c2cccc(OC)c2)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)9-10-32-23)14-7-6-8-15(11-14)29-3/h6-11,18,24H,1-5H3

Standard InChI Key:  FSIQXUICPOXCJV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   -2.4936  -18.3003    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2386  -17.5157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9060  -17.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6298  -13.5933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6298  -14.4229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9154  -14.8354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1964  -14.4229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1964  -13.5933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9154  -13.1764    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4815  -13.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3452  -13.1826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4825  -14.8364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4836  -15.6613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7675  -14.4249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0537  -14.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3442  -14.8354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0586  -14.4229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3442  -15.6603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7731  -14.8354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3185  -18.3003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5779  -17.5140    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4059  -17.5176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6582  -18.3063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9862  -18.7899    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4549  -17.2605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8420  -17.8142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0580  -17.5599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1142  -16.7522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5038  -16.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2854  -16.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5548  -18.1123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3829  -18.9191    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
 27 31  1  0
 14 15  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA411235

   Dimethyl 4-[6-(3-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: 3.23

CX LogP: 2.41

CX LogD: 2.41

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.59

Np Likeness Score: -1.16

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. Locatelli A, Cosconati S, Micucci M, Leoni A, Marinelli L, Bedini A, Ioan P, Spampinato SM, Novellino E, Chiarini A, Budriesi R..  (2013)  Ligand based approach to L-type calcium channel by imidazo[2,1-b]thiazole-1,4-dihydropyridines: from heart activity to brain affinity.,  56  (10): [PMID:23586669] [10.1021/jm301839q]

4. 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