2-(3-Bromo-4,5-dimethoxyphenyl)-5,6,7,8-tetrahydrobenzothieno[2,3-d]pyrimidin-4(3H)-one

ID: ALA4799426

PubChem CID: 53268365

Max Phase: Preclinical

Molecular Formula: C18H17BrN2O3S

Molecular Weight: 421.32

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc(-c2nc3sc4c(c3c(=O)[nH]2)CCCC4)cc(Br)c1OC

Standard InChI:  InChI=1S/C18H17BrN2O3S/c1-23-12-8-9(7-11(19)15(12)24-2)16-20-17(22)14-10-5-3-4-6-13(10)25-18(14)21-16/h7-8H,3-6H2,1-2H3,(H,20,21,22)

Standard InChI Key:  NQGJMKNUTZFWGK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   21.4822   -2.5878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4822   -3.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1916   -3.8177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1916   -2.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9010   -2.5878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9055   -3.4056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6848   -3.6569    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.6776   -2.3322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1546   -2.9904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9593   -2.9049    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.2932   -2.1620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8121   -1.5038    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.0012   -1.5883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1077   -2.0776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5879   -2.7402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4040   -2.6549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7410   -1.9035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2516   -1.2407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4373   -1.3293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5188   -0.9246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.5577   -1.8167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.0391   -2.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8832   -3.3168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.5496   -4.0628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5798   -0.4923    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  1  0
  3  6  1  0
  5  4  1  0
  5  6  2  0
  6  7  1  0
  7  9  1  0
  8  5  1  0
  8  9  2  0
  8 13  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 11 14  1  0
 13 20  2  0
 17 21  1  0
 21 22  1  0
 16 23  1  0
 23 24  1  0
 18 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4799426

   2-(3-bromo-4,5-dimethoxyphenyl)-5,6,7,8-tetrahydro-3H-[1]benzothiolo[2,3-d]pyrimidin-4-one

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 421.32

Molecular Weight (Monoisotopic): 420.0143

AlogP: 4.31

#Rotatable Bonds: 3

Polar Surface Area: 64.21

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.03

CX Basic pKa: 0.71

CX LogP: 4.61

CX LogD: 4.53

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.68

Np Likeness Score: -1.27

References

1. Gold M,Köhler L,Lanzloth C,Andronache I,Anant S,Dandawate P,Biersack B,Schobert R.  (2020)  Synthesis and bioevaluation of new vascular-targeting and anti-angiogenic thieno[2,3-d]pyrimidin-4(3H)-ones.,  189  [PMID:31958738] [10.1016/j.ejmech.2020.112060]

Source

Source(1):

• Scientific Literature