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

ID: ALA472885

PubChem CID: 42598033

Max Phase: Preclinical

Molecular Formula: C17H14ClN5O3S

Molecular Weight: 403.85

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(N2c3ccc(Cl)cc3S(=O)(=O)c3c(N)nc(N)nc32)cc1

Standard InChI:  InChI=1S/C17H14ClN5O3S/c1-26-11-5-3-10(4-6-11)23-12-7-2-9(18)8-13(12)27(24,25)14-15(19)21-17(20)22-16(14)23/h2-8H,1H3,(H4,19,20,21,22)

Standard InChI Key:  BRMBJANHZBWVCJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   10.2695   -2.1524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2695   -2.9774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5550   -3.3899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5550   -1.7399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8406   -2.1524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8406   -2.9774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1261   -3.3899    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1261   -1.7399    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.5134   -1.0114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7388   -1.0114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1261   -4.2149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4116   -4.6274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4116   -5.4524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1261   -5.8649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8406   -5.4524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8406   -4.6274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4116   -2.1524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4116   -2.9774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6972   -3.3899    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9827   -2.9774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9827   -2.1524    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6972   -1.7399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6972   -0.9149    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2682   -3.3899    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1261   -6.6899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8406   -7.1024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9840   -1.7399    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
 14 25  1  0
 11 12  2  0
 25 26  1  0
  2  3  1  0
  1 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA472885

   7-Chloro-10-(4-methoxyphenyl)-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: 403.85

Molecular Weight (Monoisotopic): 403.0506

AlogP: 2.92

#Rotatable Bonds: 2

Polar Surface Area: 124.43

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.26

CX LogP: 3.01

CX LogD: 3.01

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.52

Np Likeness Score: -1.16

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