Ethyl 2-methyl-4-(4-nitrophenyl)-4H-pyrimido[2,1-b][1,3]benzothiazole-3-carboxylate

ID: ALA3618298

PubChem CID: 122190934

Max Phase: Preclinical

Molecular Formula: C20H17N3O3S

Molecular Weight: 379.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(=O)C1=C(C)N=C2Sc3ccccc3N2C1c1ccc([N+](=O)[O-])cc1

Standard InChI:  InChI=1S/C20H17N3O3S/c1-3-16(24)18-12(2)21-20-22(15-6-4-5-7-17(15)27-20)19(18)13-8-10-14(11-9-13)23(25)26/h4-11,19H,3H2,1-2H3

Standard InChI Key:  ZNVRZQSWGYGQHI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    3.7663    5.2907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4915   -1.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4732    1.5389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0387    1.5727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3375    0.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7006   -0.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7006    0.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2274   -0.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2274   -0.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1691    3.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4684    3.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2274    0.8244    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7672    3.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4668    6.0399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7372   -0.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4732   -1.3190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4915    1.5389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7372    0.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.3190    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.0406    2.7727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2274    0.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7737   -1.2093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1682    5.2891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3779    1.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4689    7.5408    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5086    8.1399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4304    8.1419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 12  3  1  0
  6  7  1  0
  9  2  1  0
 13 11  1  0
 17 21  1  0
 10 23  1  0
  1 13  2  0
 21 12  1  0
  3 11  1  0
 12  8  1  0
 18  3  1  0
 15 16  1  0
 18  4  1  0
  2  6  2  0
 19  9  1  0
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 23 14  2  0
 21  9  2  0
  8 19  1  0
  4  5  1  0
 18 15  2  0
 14  1  1  0
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  7 17  2  0
  4 20  2  0
 15 22  1  0
  5 24  1  0
 25 26  2  0
 25 27  1  0
 14 25  1  0
M  CHG  2  25   1  27  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3618298

   ---

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: 379.44

Molecular Weight (Monoisotopic): 379.0991

AlogP: 4.87

#Rotatable Bonds: 4

Polar Surface Area: 75.81

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.43

CX LogP: 4.79

CX LogD: 4.79

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.56

Np Likeness Score: -1.33

References

1. Chikhale R, Thorat S, Pant A, Jadhav A, Thatipamula KC, Bansode R, Bhargavi G, Karodia N, Rajasekharan MV, Paradkar A, Khedekar P..  (2015)  Design, synthesis and pharmacological evaluation of pyrimidobenzothiazole-3-carboxylate derivatives as selective L-type calcium channel blockers.,  23  (20): [PMID:26385444] [10.1016/j.bmc.2015.09.009]

Source

Source(1):

• Scientific Literature