2-Benzyl-N'-(1-(4-chlorophenyl)ethylidene)-4-hydroxy-2H-1,2-benzothiazine-3-carbohydrazide 1,1-dioxide

ID: ALA4176805

PubChem CID: 145971242

Max Phase: Preclinical

Molecular Formula: C24H20ClN3O4S

Molecular Weight: 481.96

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C(=N\NC(=O)C1=C(O)c2ccccc2S(=O)(=O)N1Cc1ccccc1)c1ccc(Cl)cc1

Standard InChI:  InChI=1S/C24H20ClN3O4S/c1-16(18-11-13-19(25)14-12-18)26-27-24(30)22-23(29)20-9-5-6-10-21(20)33(31,32)28(22)15-17-7-3-2-4-8-17/h2-14,29H,15H2,1H3,(H,27,30)/b26-16+

Standard InChI Key:  XFGGITNRFLPLAB-WGOQTCKBSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
    5.6213  -12.9966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2168  -12.2909    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.8078  -12.9940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0940  -11.0692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0929  -11.8887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7991  -10.6603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5077  -11.0656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5111  -11.8862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9292  -11.8804    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9258  -11.0598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2128  -10.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2083   -9.8329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6323  -10.6490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3412  -11.0554    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6297   -9.8318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0477  -10.6446    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7566  -11.0510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6376  -12.2879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6389  -13.1051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9293  -13.5104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9303  -14.3268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6392  -14.7351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3486  -14.3210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3441  -13.5059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4631  -10.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1717  -11.0489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8777  -10.6388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8756   -9.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1616   -9.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4586   -9.8269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7592  -11.8682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5815   -9.4090    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  8 12  1  0
  9  2  1  0
  2 10  1  0
 10 11  1  0
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 10 19  1  0
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 18 26  1  0
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 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
 18 32  1  0
 29 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4176805

   ---

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: 481.96

Molecular Weight (Monoisotopic): 481.0863

AlogP: 4.31

#Rotatable Bonds: 5

Polar Surface Area: 99.07

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.35

CX Basic pKa: 0.81

CX LogP: 3.68

CX LogD: 1.70

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.42

Np Likeness Score: -1.30

References

1. Saddique FA, Zaib S, Jalil S, Aslam S, Ahmad M, Sultan S, Naz H, Iqbal M, Iqbal J..  (2018)  Synthesis, monoamine oxidase inhibition activity and molecular docking studies of novel 4-hydroxy-N'-[benzylidene or 1-phenylethylidene]-2-H/methyl/benzyl-1,2-benzothiazine-3-carbohydrazide 1,1-dioxides.,  143  [PMID:29126721] [10.1016/j.ejmech.2017.10.036]

Source

Source(1):

• Scientific Literature