(recemate)-11-(3-Bromo-4-fluoro-phenyl)-10,10-dioxo-2,3,4,5,6,7,8,9,10,11-decahydro-10lambda*6*-thia-5-aza-cyclohepta[b]naphthalen-1-one

ID: ALA3138601

PubChem CID: 9911084

Max Phase: Preclinical

Molecular Formula: C19H19BrFNO3S

Molecular Weight: 440.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1CCCC2=C1C(c1ccc(F)c(Br)c1)C1=C(CCCCS1(=O)=O)N2

Standard InChI:  InChI=1S/C19H19BrFNO3S/c20-12-10-11(7-8-13(12)21)17-18-14(5-3-6-16(18)23)22-15-4-1-2-9-26(24,25)19(15)17/h7-8,10,17,22H,1-6,9H2

Standard InChI Key:  VVARWESPYAHNMQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    2.7241    0.4261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3745    0.9524    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.9991    0.8156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2970    0.4004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7391   -0.4078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3075   -0.4211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0369   -0.8271    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9927    1.6372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5883    0.8027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2676    2.0351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0807    1.3760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5782    1.1580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2527    2.8648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9630    3.2884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6947    2.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5736    1.6242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6799    2.8822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1869    0.7761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6054   -0.8404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5359    3.2627    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.3957   -0.9189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9482    4.1098    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1262    0.3790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1114   -0.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5532    0.0274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2015   -0.7260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  3  1  0
  5  1  2  0
  6  7  1  0
  7  5  1  0
  8  3  1  0
  9  4  1  0
 10  8  2  0
 11  2  2  0
 12  2  2  0
 13 10  1  0
 14 17  1  0
 15  8  1  0
 16  9  2  0
 17 15  2  0
 18  2  1  0
 19  6  1  0
 20 13  1  0
 21  5  1  0
 22 14  1  0
 23  9  1  0
 24 19  1  0
 25 18  1  0
 26 21  1  0
 26 25  1  0
  4  6  2  0
 23 24  1  0
 13 14  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3138601

   11-(3-bromo-4-fluorophenyl)-1,1-dioxo-3,4,5,6,7,8,9,11-octahydro-2H-thiepino[3,2-b]quinolin-10-one

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: 440.33

Molecular Weight (Monoisotopic): 439.0253

AlogP: 4.09

#Rotatable Bonds: 1

Polar Surface Area: 63.24

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.28

CX LogD: 2.28

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.71

Np Likeness Score: -1.08

References

1. Carroll WA, Altenbach RJ, Bai H, Brioni JD, Brune ME, Buckner SA, Cassidy C, Chen Y, Coghlan MJ, Daza AV, Drizin I, Fey TA, Fitzgerald M, Gopalakrishnan M, Gregg RJ, Henry RF, Holladay MW, King LL, Kort ME, Kym PR, Milicic I, Tang R, Turner SC, Whiteaker KL, Yi L, Zhang H, Sullivan JP..  (2004)  Synthesis and structure-activity relationships of a novel series of 2,3,5,6,7,9-hexahydrothieno[3,2-b]quinolin-8(4H)-one 1,1-dioxide K(ATP) channel openers: discovery of (-)-(9S)-9-(3-bromo-4-fluorophenyl)-2,3,5,6,7,9- hexahydrothieno[3,2-b]quinolin-8(4H)-one 1,1-dioxide (A-278637), a potent K(ATP) opener that selectively inhibits spontaneous bladder contractions.,  47  (12): [PMID:15163196] [10.1021/jm030356w]

Source

Source(1):

• Scientific Literature