2-Pivalamido-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide

ID: ALA4796667

PubChem CID: 3260381

Max Phase: Preclinical

Molecular Formula: C15H22N2O2S

Molecular Weight: 294.42

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)(C)C(=O)Nc1sc2c(c1C(N)=O)CCCCC2

Standard InChI:  InChI=1S/C15H22N2O2S/c1-15(2,3)14(19)17-13-11(12(16)18)9-7-5-4-6-8-10(9)20-13/h4-8H2,1-3H3,(H2,16,18)(H,17,19)

Standard InChI Key:  PIJDIDKYGUHLOR-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
   12.4427   -3.8188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6164   -3.8188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9314   -4.4835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9314   -3.1465    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.6769   -5.2697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8689   -5.4426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2306   -5.8832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1211   -4.5384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4535   -3.7847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0821   -3.0987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3396   -4.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7172   -4.2323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7173   -3.4017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3163   -2.9265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2033   -3.1032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3769   -3.1032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6164   -2.3875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9637   -2.3874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7935   -3.6865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3769   -3.9282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
  3 12  1  0
 13  4  1  0
  4  1  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 12 13  2  0
 13 14  1  0
 14 10  1  0
 11 12  1  0
  2 15  1  0
 15 16  1  0
 15 17  2  0
 16 18  1  0
 16 19  1  0
 16 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4796667

   2-(2,2-dimethylpropanoylamino)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 294.42

Molecular Weight (Monoisotopic): 294.1402

AlogP: 3.10

#Rotatable Bonds: 2

Polar Surface Area: 72.19

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.76

CX Basic pKa: ┄

CX LogP: 4.49

CX LogD: 4.49

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.82

Np Likeness Score: -1.89

References

1. Choi SH,Ryu S,Sim K,Song C,Shin I,Kim SS,Lee YS,Park JY,Sim T.  (2020)  Anti-glioma effects of 2-aminothiophene-3-carboxamide derivatives, ANO1 channel blockers.,  208  [PMID:32906067] [10.1016/j.ejmech.2020.112688]

2. Tradtrantip, Lukmanee L, Namkung, Wan W and Verkman, A S AS.  2010-01  Crofelemer, an antisecretory antidiarrheal proanthocyanidin oligomer extracted from Croton lechleri, targets two distinct intestinal chloride channels.  [PMID:19808995]

3. Kumar, Satish; Namkung, Wan; Verkman, A S and Sharma, Pawan K.  2012-07-15  Novel 5-substituted benzyloxy-2-arylbenzofuran-3-carboxylic acids as calcium activated chloride channel inhibitors.  [PMID:22739085]

4. Truong, Eric C EC and 11 more authors.  2017-06-08  Substituted 2-Acylaminocycloalkylthiophene-3-carboxylic Acid Arylamides as Inhibitors of the Calcium-Activated Chloride Channel Transmembrane Protein 16A (TMEM16A).  [PMID:28493701]

5. Seo, Yohan Y and 5 more authors.  2018-12-05  Synthesis and biological evaluation of novel Ani9 derivatives as potent and selective ANO1 inhibitors.  [PMID:30347323]

6. Choi, Seung-Hye and 8 more authors.  2020-12-15  Anti-glioma effects of 2-aminothiophene-3-carboxamide derivatives, ANO1 channel blockers.  [PMID:32906067]

Source

Source(1):

• Scientific Literature