6,7-dihydro-2-(4-[(propylamino)carbonyl]phenyl)-1,4-dithiepin-1,1,4,4-tetraoxide

ID: ALA3953131

PubChem CID: 90721869

Max Phase: Preclinical

Molecular Formula: C15H19NO5S2

Molecular Weight: 357.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCNC(=O)c1ccc(C2=CS(=O)(=O)CCCS2(=O)=O)cc1

Standard InChI:  InChI=1S/C15H19NO5S2/c1-2-8-16-15(17)13-6-4-12(5-7-13)14-11-22(18,19)9-3-10-23(14,20)21/h4-7,11H,2-3,8-10H2,1H3,(H,16,17)

Standard InChI Key:  COXZJCVTYQYWAT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    5.3266   -4.0151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6347   -6.2881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6388   -5.4631    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.9223   -5.8720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7421   -2.8637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0680   -3.6631    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.4903   -2.8640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8106   -4.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1320   -4.8157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9890   -4.8354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4668   -5.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6086   -3.6014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8926   -4.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1790   -3.5998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1813   -2.7735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8973   -2.3612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6109   -2.7752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4676   -2.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4693   -1.5346    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7524   -2.7707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7556   -1.1207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7572   -0.2957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0436    0.1182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0
  4  3  2  0
  6  5  2  0
  7  6  2  0
  1  6  1  0
  6  8  1  0
  1  9  2  0
  8 10  1  0
  9  3  1  0
 10 11  1  0
  3 11  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 12 17  2  0
 12  1  1  0
 15 18  1  0
 18 19  1  0
 18 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3953131

   N-propyl-4-(1,1,4,4-tetraoxo-6,7-dihydro-5H-1,4-dithiepin-2-yl)benzamide

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: 357.45

Molecular Weight (Monoisotopic): 357.0705

AlogP: 1.36

#Rotatable Bonds: 4

Polar Surface Area: 97.38

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: -0.43

CX LogD: -0.43

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.88

Np Likeness Score: -0.84

References

1.  (2002)  1,4-dithiin and 1,4-dithiepin-1,1,4,4, tetroxide derivatives useful as antagonists of the human galanin receptor, 

2. Scott, M K MK and 9 more authors.  2000-06  2,3-Dihydro-dithiin and -dithiepine-1,1,4,4-tetroxides: small molecule non-peptide antagonists of the human galanin hGAL-1 receptor.  [PMID:10896115]

3. Bulaj, Grzegorz G and 11 more authors.  2008-12-25  Design, synthesis, and characterization of high-affinity, systemically-active galanin analogues with potent anticonvulsant activities.  [PMID:19053761]

4. Zhang, Liuyin L and 5 more authors.  2009-03-12  Structural requirements for a lipoamino acid in modulating the anticonvulsant activities of systemically active galanin analogues.  [PMID:19199479]

5. Robertson, Charles R and 5 more authors.  2010-02-25  Engineering galanin analogues that discriminate between GalR1 and GalR2 receptor subtypes and exhibit anticonvulsant activity following systemic delivery.  [PMID:20121116]

6. Green, Brad R BR and 5 more authors.  2013-01-01  Cyclic analogs of galanin and neuropeptide Y by hydrocarbon stapling.  [PMID:23176753]

Source

Source(1):

• Patent Bioactivity Data