3-[(1S)-1-(4-Bromophenyl)-ethyl]amino-6-chloro-4H-thieno[3,2-e]-1,2,4-thiadiazine1,1-dioxide

ID: ALA209313

PubChem CID: 135489349

Max Phase: Preclinical

Molecular Formula: C13H11BrClN3O2S2

Molecular Weight: 420.74

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](NC1=NS(=O)(=O)c2sc(Cl)cc2N1)c1ccc(Br)cc1

Standard InChI:  InChI=1S/C13H11BrClN3O2S2/c1-7(8-2-4-9(14)5-3-8)16-13-17-10-6-11(15)21-12(10)22(19,20)18-13/h2-7H,1H3,(H2,16,17,18)/t7-/m0/s1

Standard InChI Key:  ZLDWZKGIJDMEKL-ZETCQYMHSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  1  0  0  0  0  0999 V2000
    9.7460  -25.6575    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.4585  -25.2513    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4585  -24.4263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7460  -24.0076    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2488  -25.5036    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.0334  -25.2513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0334  -24.4263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2479  -24.1698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7677  -24.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3269  -26.2421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1578  -26.2421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1748  -24.0137    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9427  -24.8417    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.8886  -24.4304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6048  -24.0179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3153  -24.4382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0269  -24.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0297  -23.2005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3151  -22.7882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6023  -23.1982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8862  -25.2554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7413  -22.7912    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  6  7  2  0
  1 11  2  0
  3 12  1  0
  7  4  1  0
  9 13  1  0
  6  1  1  0
 12 14  1  0
  1  2  1  0
 14 15  1  0
  2  3  2  0
 15 16  2  0
  5  6  1  0
 16 17  1  0
  7  8  1  0
 17 18  2  0
  8  9  2  0
 18 19  1  0
  9  5  1  0
 19 20  2  0
 20 15  1  0
  3  4  1  0
 14 21  1  6
  1 10  2  0
 18 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA209313

   ---

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: 420.74

Molecular Weight (Monoisotopic): 418.9165

AlogP: 3.99

#Rotatable Bonds: 2

Polar Surface Area: 70.56

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.02

CX Basic pKa: 1.09

CX LogP: 4.02

CX LogD: 4.02

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.77

Np Likeness Score: -1.30

References

1. Nielsen FE, Ebdrup S, Jensen AF, Ynddal L, Bodvarsdottir TB, Stidsen C, Worsaae A, Boonen HC, Arkhammar PO, Fremming T, Wahl P, Kornø HT, Hansen JB..  (2006)  New 3-alkylamino-4H-thieno-1,2,4-thiadiazine 1,1-dioxide derivatives activate ATP-sensitive potassium channels of pancreatic beta cells.,  49  (14): [PMID:16821773] [10.1021/jm060042j]

Source

Source(1):

• Scientific Literature