2,4-Diamino-7-chloro-10H-(3',4'-dichlorophenyl)-pyrimido-[5,4-b]benzothiazine 5,5-dioxide

ID: ALA514160

PubChem CID: 42598730

Max Phase: Preclinical

Molecular Formula: C16H10Cl3N5O2S

Molecular Weight: 442.71

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N)c2c(n1)N(c1ccc(Cl)c(Cl)c1)c1ccc(Cl)cc1S2(=O)=O

Standard InChI:  InChI=1S/C16H10Cl3N5O2S/c17-7-1-4-11-12(5-7)27(25,26)13-14(20)22-16(21)23-15(13)24(11)8-2-3-9(18)10(19)6-8/h1-6H,(H4,20,21,22,23)

Standard InChI Key:  IVEZIVLSKCQYPJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   10.2497   -5.9848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2497   -6.8098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5352   -7.2223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5352   -5.5723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8207   -5.9848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8207   -6.8098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1063   -7.2223    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1063   -5.5723    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.4936   -4.8439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7190   -4.8439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1063   -8.0473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3918   -8.4598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3918   -9.2848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1063   -9.6973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8207   -9.2848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8207   -8.4598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3918   -5.9848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3918   -6.8098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6773   -7.2223    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9629   -6.8098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9629   -5.9848    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6773   -5.5723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6773   -4.7473    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2484   -7.2223    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5352   -9.6973    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.1063  -10.5223    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.9642   -5.5723    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
  3  6  2  0
 13 14  2  0
  1  2  2  0
 14 15  1  0
  5  8  1  0
 15 16  2  0
 16 11  1  0
  7 11  1  0
 17 18  2  0
  6  7  1  0
  7 18  1  0
 17  8  1  0
  5  4  2  0
  8  9  2  0
  4  1  1  0
 17 22  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
  8 10  2  0
 22 23  1  0
  5  6  1  0
 20 24  1  0
 15 25  1  0
 11 12  2  0
 14 26  1  0
  2  3  1  0
  1 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA514160

   7-Chloro-10-(3,4-dichlorophenyl)-5,5-dioxopyrimido[5,4-b][1,4]benzothiazine-2,4-diamine

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: 442.71

Molecular Weight (Monoisotopic): 440.9621

AlogP: 4.22

#Rotatable Bonds: 1

Polar Surface Area: 115.20

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.25

CX LogP: 4.37

CX LogD: 4.37

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.45

Np Likeness Score: -1.45

References

1. Barazarte A, Lobo G, Gamboa N, Rodrigues JR, Capparelli MV, Alvarez-Larena A, López SE, Charris JE..  (2009)  Synthesis and antimalarial activity of pyrazolo and pyrimido benzothiazine dioxide derivatives.,  44  (3): [PMID:18835067] [10.1016/j.ejmech.2008.08.005]

Source

Source(1):

• Scientific Literature