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

ID: ALA3618282

PubChem CID: 101899357

Max Phase: Preclinical

Molecular Formula: C19H15ClN2OS

Molecular Weight: 354.86

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)C1=C(C)N=C2Sc3ccccc3N2C1c1ccc(Cl)cc1

Standard InChI:  InChI=1S/C19H15ClN2OS/c1-11-17(12(2)23)18(13-7-9-14(20)10-8-13)22-15-5-3-4-6-16(15)24-19(22)21-11/h3-10,18H,1-2H3

Standard InChI Key:  FKXGJEHXPKPHJG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
    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
    5.0406    2.7727    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
    6.0772    0.9715    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
    2.4660    7.2399    0.0000 Cl  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
 11 10  2  0
 23 14  2  0
 21  9  2  0
  8 19  1  0
  4  5  1  0
 18 15  2  0
 14  1  1  0
 16  8  2  0
  7 17  2  0
  4 20  2  0
 15 22  1  0
 14 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3618282

   1-[4-(4-chlorophenyl)-2-methyl-4H-pyrimido[2,1-b][1,3]benzothiazol-3-yl]ethanone

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: 354.86

Molecular Weight (Monoisotopic): 354.0594

AlogP: 5.23

#Rotatable Bonds: 2

Polar Surface Area: 32.67

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 1.44

CX LogP: 4.75

CX LogD: 4.75

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.74

Np Likeness Score: -1.31

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