2-Bromo-6-{2-(5,6-dihydro-[1,4,2]dioxazin-3-yl)-2-[4-(4-nitro-phenyl)-thiazol-2-ylamino]-ethylsulfanylmethyl}-5-hydroxy-3-methoxy-benzoic acid methyl ester

ID: ALA157769

PubChem CID: 9895647

Max Phase: Preclinical

Molecular Formula: C24H23BrN4O8S2

Molecular Weight: 639.51

Molecule Type: Small molecule

Names and Identifiers

Synonyms: BAY-507952 | CHEMBL157769|BAY-507952|BAY 50-7952|BDBM50473497

Canonical SMILES:  COC(=O)c1c(Br)c(OC)cc(O)c1CSC[C@H](Nc1nc(-c2ccc([N+](=O)[O-])cc2)cs1)C1=NOCCO1

Standard InChI:  InChI=1S/C24H23BrN4O8S2/c1-34-19-9-18(30)15(20(21(19)25)23(31)35-2)10-38-11-17(22-28-37-8-7-36-22)27-24-26-16(12-39-24)13-3-5-14(6-4-13)29(32)33/h3-6,9,12,17,30H,7-8,10-11H2,1-2H3,(H,26,27)/t17-/m0/s1

Standard InChI Key:  MRGBDARDZKENAD-KRWDZBQOSA-N

Molfile:  

     RDKit          2D

 39 42  0  0  0  0  0  0  0  0999 V2000
   -2.7286   -7.8830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7299   -8.7106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0169   -9.1235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2976   -8.7101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3007   -7.8790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0189   -7.4703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4449   -9.1221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1587   -8.7085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0183   -9.9485    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.0227   -6.6453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5884   -7.4630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5924   -6.6381    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1200   -6.2221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8364   -6.6310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5828   -9.1219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5820   -9.9469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1328  -10.3587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1313   -8.7088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8406   -7.4559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5570   -7.8642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5489   -6.2149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8041   -8.6478    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6290   -8.6551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8909   -7.8728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2278   -7.3821    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.0311   -9.3737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6085  -10.0834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0117  -10.8022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8376  -10.8124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2584  -10.0979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8526   -9.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2455  -11.5357    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0704  -11.5444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8256  -12.2458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2630   -6.6297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9732   -6.2172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9733   -5.3919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2570   -4.9808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5405   -5.3950    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
 19 20  1  0
  6 10  1  0
 14 21  1  1
 20 22  2  0
  2  3  1  0
  5 11  1  0
  5  6  2  0
 11 12  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 20  1  0
  6  1  1  0
 12 13  1  0
 26 27  2  0
  1  2  2  0
 27 28  1  0
 13 14  1  0
 28 29  2  0
  2  7  1  0
 29 30  1  0
  4 15  1  0
 30 31  2  0
 31 26  1  0
 23 26  1  0
  3  4  2  0
 15 16  1  0
  7  8  1  0
 32 33  2  0
 32 34  1  0
 29 32  1  0
 21 35  1  0
 16 17  1  0
 15 18  2  0
  3  9  1  0
 14 19  1  0
 21 39  2  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
M  CHG  2  32   1  34  -1
M  END

Alternative Forms

1. Parent:

   

   ALA157769

   methyl 2-bromo-6-[[(2R)-2-(5,6-dihydro-1,4,2-dioxazin-3-yl)-2-[[4-(4-nitrophenyl)-1,3-thiazol-2-yl]amino]ethyl]sulfanylmethyl]-5-hydroxy-3-methoxybenzoate

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: 639.51

Molecular Weight (Monoisotopic): 638.0141

AlogP: 5.06

#Rotatable Bonds: 11

Polar Surface Area: 154.64

Molecular Species: NEUTRAL

HBA: 13

HBD: 2

#RO5 Violations: 3

HBA (Lipinski): 12

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 8.42

CX Basic pKa: 2.87

CX LogP: 5.50

CX LogD: 5.47

Aromatic Rings: 3

Heavy Atoms: 39

QED Weighted: 0.16

Np Likeness Score: -0.84

References

1. Rudolph J, Theis H, Hanke R, Endermann R, Johannsen L, Geschke F..  (2001)  seco-Cyclothialidines: new concise synthesis, inhibitory activity toward bacterial and human DNA topoisomerases, and antibacterial properties.,  44  (4): [PMID:11170652] [10.1021/jm0010623]

2. Brvar M, Perdih A, Oblak M, Masic LP, Solmajer T..  (2010)  In silico discovery of 2-amino-4-(2,4-dihydroxyphenyl)thiazoles as novel inhibitors of DNA gyrase B.,  20  (3): [PMID:20045642] [10.1016/j.bmcl.2009.12.060]

Source

Source(1):

• Scientific Literature