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

ID: ALA516345

PubChem CID: 42598729

Max Phase: Preclinical

Molecular Formula: C16H11Cl2N5O2S

Molecular Weight: 408.27

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  Nc1nc(N)c2c(n1)N(c1cccc(Cl)c1)c1ccc(Cl)cc1S2(=O)=O

Standard InChI:  InChI=1S/C16H11Cl2N5O2S/c17-8-2-1-3-10(6-8)23-11-5-4-9(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:  LJTRLMWYUAKVBP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    1.7104   -5.9116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7104   -6.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9960   -7.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9960   -5.4991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2815   -5.9116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2815   -6.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4330   -7.1491    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4330   -5.4991    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0457   -4.7706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8203   -4.7706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4330   -7.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1474   -8.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1474   -9.2116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4330   -9.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2815   -9.2116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2815   -8.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1474   -5.9116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1474   -6.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8619   -7.1491    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5764   -6.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5764   -5.9116    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8619   -5.4991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8619   -4.6741    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2909   -7.1491    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9960   -9.6241    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.4249   -5.4991    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
 15 25  1  0
 11 12  2  0
  1 26  1  0
M  END

Associated Targets(non-human)

Histidine-rich protein (528 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasmodium berghei (192651 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 408.27Molecular Weight (Monoisotopic): 407.0011AlogP: 3.56#Rotatable Bonds: 1
Polar Surface Area: 115.20Molecular Species: NEUTRALHBA: 7HBD: 2
#RO5 Violations: HBA (Lipinski): 7HBD (Lipinski): 4#RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: 2.25CX LogP: 3.77CX LogD: 3.77
Aromatic Rings: 3Heavy Atoms: 26QED Weighted: 0.49Np Likeness Score: -1.37

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