(S(-))-9-(3-Bromo-4-fluoro-phenyl)-1,1-dioxo-1,2,3,4,5,6,7,9-octahydro-1lambda*6*-thieno[3,2-b]quinolin-8-one

ID: ALA3138607

Cas Number: 227609-66-7

PubChem CID: 9887869

Max Phase: Preclinical

Molecular Formula: C17H15BrFNO3S

Molecular Weight: 412.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1CCCC2=C1[C@H](c1ccc(F)c(Br)c1)C1=C(CCS1(=O)=O)N2

Standard InChI:  InChI=1S/C17H15BrFNO3S/c18-10-8-9(4-5-11(10)19)15-16-12(2-1-3-14(16)21)20-13-6-7-24(22,23)17(13)15/h4-5,8,15,20H,1-3,6-7H2/t15-/m0/s1

Standard InChI Key:  LHVKVMMIMWOYFR-HNNXBMFYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  1  0  0  0  0  0999 V2000
    2.6546    0.4642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4281    0.7499    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.6928   -0.3584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9171    0.8338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2338    0.3981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2595   -0.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0019   -0.8110    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8872    1.6567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5037    0.7888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4901   -0.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9453    0.1037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1494    2.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2157    1.0031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8193    1.3087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1108    2.8654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8103    3.3101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5785    2.1010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4779    1.6120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5402    2.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5677   -0.8569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3813    3.2437    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.7721    4.1327    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1959    0.3441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1618   -0.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1873    1.2203    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  1  1  0
  5  4  1  0
  6  5  2  0
  7  3  1  0
  8  4  1  0
  9  5  1  0
 10  3  1  0
 11  2  1  0
 12  8  2  0
 13  2  2  0
 14  2  2  0
 15 12  1  0
 16 19  1  0
 17  8  1  0
 18  9  2  0
 19 17  2  0
 20  6  1  0
 21 15  1  0
 22 16  1  0
 23  9  1  0
 24 23  1  0
  4 25  1  1
  7  6  1  0
 11 10  1  0
 15 16  2  0
 24 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3138607

   Thieno(3,2-b)quinolin-8(4H)-one, 9-(3-bromo-4-fluorophenyl)-2,3,5,6,7,9-hexahydro-, 1,1-dioxide, (9S)-

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: 412.28

Molecular Weight (Monoisotopic): 410.9940

AlogP: 3.31

#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: 1.32

CX LogD: 1.32

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.77

Np Likeness Score: -1.13

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]

2. Carroll WA, Agrios KA, Altenbach RJ, Buckner SA, Chen Y, Coghlan MJ, Daza AV, Drizin I, Gopalakrishnan M, Henry RF, Kort ME, Kym PR, Milicic I, Smith JC, Tang R, Turner SC, Whiteaker KL, Zhang H, Sullivan JP..  (2004)  Synthesis and structure-activity relationships of a novel series of tricyclic dihydropyridine-based KATP openers that potently inhibit bladder contractions in vitro.,  47  (12): [PMID:15163197] [10.1021/jm030357o]

3. Altenbach RJ, Brune ME, Buckner SA, Coghlan MJ, Daza AV, Fabiyi A, Gopalakrishnan M, Henry RF, Khilevich A, Kort ME, Milicic I, Scott VE, Smith JC, Whiteaker KL, Carroll WA..  (2006)  Effects of substitution on 9-(3-bromo-4-fluorophenyl)-5,9-dihydro-3H,4H-2,6-dioxa-4- azacyclopenta[b]naphthalene-1,8-dione, a dihydropyridine ATP-sensitive potassium channel opener.,  49  (23): [PMID:17154517] [10.1021/jm060549u]

Source

Source(1):

• Scientific Literature