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

ID: ALA473907

PubChem CID: 42598035

Max Phase: Preclinical

Molecular Formula: C16H11BrClN5O2S

Molecular Weight: 452.72

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N)c2c(n1)N(c1ccc(Br)cc1)c1ccc(Cl)cc1S2(=O)=O

Standard InChI:  InChI=1S/C16H11BrClN5O2S/c17-8-1-4-10(5-2-8)23-11-6-3-9(18)7-12(11)26(24,25)13-14(19)21-16(20)22-15(13)23/h1-7H,(H4,19,20,21,22)

Standard InChI Key:  YGAFTWHZBUDNJT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    1.1181   -9.8282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1181  -10.6532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4036  -11.0657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4036   -9.4157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3109   -9.8282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3109  -10.6532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0254  -11.0657    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0254   -9.4157    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6380   -8.6873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4127   -8.6873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0254  -11.8907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7398  -12.3032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7398  -13.1282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0254  -13.5407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3109  -13.1282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3109  -12.3032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7398   -9.8282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7398  -10.6532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4543  -11.0657    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1688  -10.6532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1688   -9.8282    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4543   -9.4157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4543   -8.5907    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8832  -11.0657    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0254  -14.3657    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.8325   -9.4157    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  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
  1 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA473907

   10-(4-Bromophenyl)-7-chloro-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: 452.72

Molecular Weight (Monoisotopic): 450.9505

AlogP: 3.67

#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: 3.94

CX LogD: 3.94

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.45

Np Likeness Score: -1.31

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