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

ID: ALA441337

PubChem CID: 24823885

Max Phase: Preclinical

Molecular Formula: C24H23ClN4O8S

Molecular Weight: 562.99

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1c(-c2c(OC)ccc(OC)c2[N+](=O)[O-])nc2sc(Cl)cn12

Standard InChI:  InChI=1S/C24H23ClN4O8S/c1-10-15(22(30)36-5)18(16(11(2)26-10)23(31)37-6)21-19(27-24-28(21)9-14(25)38-24)17-12(34-3)7-8-13(35-4)20(17)29(32)33/h7-9,18,26H,1-6H3

Standard InChI Key:  FVMDXEBQLUAISH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 38 41  0  0  0  0  0  0  0  0999 V2000
    4.9639  -18.6034    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6271  -18.1129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3663  -17.3280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6424  -13.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6424  -14.7203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3569  -15.1327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0758  -14.7203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0758  -13.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3569  -13.4737    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9271  -13.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7897  -15.1337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9281  -15.1327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2923  -18.1244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8616  -16.8558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1982  -17.3512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4645  -18.1352    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.4133  -18.3603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5906  -19.1670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3765  -19.4153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9857  -18.8577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8038  -18.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0181  -17.8043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5058  -13.8973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4100  -17.4894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1977  -17.7347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8337  -16.9968    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0464  -16.7508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4405  -16.4379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9818  -19.7236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1954  -19.4747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4103  -17.1067    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  6  3  1  0
 19 20  1  0
  7  8  2  0
  8  9  1  0
 19  1  2  0
  8 10  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 19  1  0
  4 11  1  0
  1  2  1  0
 24 25  2  0
  7 12  1  0
 25 26  1  0
  2  3  2  0
 26 27  2  0
 12 13  2  0
 27 28  1  0
  3 20  1  0
 28 29  2  0
 29 24  1  0
  2 24  1  0
 12 14  1  0
 14 30  1  0
  4  5  2  0
 28 31  1  0
  5 15  1  0
 31 32  1  0
  4  9  1  0
 15 16  1  0
  5  6  1  0
 33 34  2  0
 33 35  1  0
 29 33  1  0
 15 17  2  0
 25 36  1  0
  6  7  1  0
 36 37  1  0
 16 18  1  0
 22 38  1  0
M  CHG  2  33   1  35  -1
M  END

Alternative Forms

1. Parent:

   

   ALA441337

   Dimethyl 4-[2-chloro-6-(3,6-dimethoxy-2-nitrophenyl)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: 562.99

Molecular Weight (Monoisotopic): 562.0925

AlogP: 4.22

#Rotatable Bonds: 7

Polar Surface Area: 143.53

Molecular Species: NEUTRAL

HBA: 12

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 2.88

CX LogP: 2.97

CX LogD: 2.97

Aromatic Rings: 3

Heavy Atoms: 38

QED Weighted: 0.25

Np Likeness Score: -0.69

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. 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