N-(5,6-Dihydroxybenzo[d]thiazol-2-yl)-2,2-bis-(4-chlorophenyl)acetamide

ID: ALA4877937

PubChem CID: 164628555

Max Phase: Preclinical

Molecular Formula: C21H14Cl2N2O3S

Molecular Weight: 445.33

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(Nc1nc2cc(O)c(O)cc2s1)C(c1ccc(Cl)cc1)c1ccc(Cl)cc1

Standard InChI:  InChI=1S/C21H14Cl2N2O3S/c22-13-5-1-11(2-6-13)19(12-3-7-14(23)8-4-12)20(28)25-21-24-15-9-16(26)17(27)10-18(15)29-21/h1-10,19,26-27H,(H,24,25,28)

Standard InChI Key:  VHZRMIJXJMVSNK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   23.2003   -3.8103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1992   -4.6369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9138   -5.0514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9121   -3.4001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6232   -3.8067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6234   -4.6324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4089   -4.8901    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.8958   -4.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4085   -3.5527    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   22.4859   -3.4005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4845   -5.0504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.7200   -4.2208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.1297   -3.5064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9539   -3.5061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7195   -2.7923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.3684   -4.2203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3679   -2.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1972   -2.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6110   -2.0819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1965   -1.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3681   -1.3722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9579   -2.0839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9519   -4.9298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3657   -5.6435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1907   -5.6437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6003   -4.9242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1883   -4.2134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5966   -6.3492    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   29.6084   -0.6512    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  1  0
  1 10  1  0
  2 11  1  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 14 16  1  0
 14 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 16 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 16  1  0
 25 28  1  0
 20 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4877937

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 445.33

Molecular Weight (Monoisotopic): 444.0102

AlogP: 5.78

#Rotatable Bonds: 4

Polar Surface Area: 82.45

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.68

CX Basic pKa: 0.17

CX LogP: 6.15

CX LogD: 5.96

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.35

Np Likeness Score: -1.24

References

1. Maus H, Barthels F, Hammerschmidt SJ, Kopp K, Millies B, Gellert A, Ruggieri A, Schirmeister T..  (2021)  SAR of novel benzothiazoles targeting an allosteric pocket of DENV and ZIKV NS2B/NS3 proteases.,  47  [PMID:34509861] [10.1016/j.bmc.2021.116392]

Source

Source(1):

• Scientific Literature