2-(3-(4-Chlorobenzoyl)thioureido)-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxamide

ID: ALA4791938

PubChem CID: 4504954

Max Phase: Preclinical

Molecular Formula: C16H14ClN3O2S2

Molecular Weight: 379.89

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  NC(=O)c1c(NC(=S)NC(=O)c2ccc(Cl)cc2)sc2c1CCC2

Standard InChI:  InChI=1S/C16H14ClN3O2S2/c17-9-6-4-8(5-7-9)14(22)19-16(23)20-15-12(13(18)21)10-2-1-3-11(10)24-15/h4-7H,1-3H2,(H2,18,21)(H2,19,20,22,23)

Standard InChI Key:  OZBIYLGREOSUQC-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   18.3097   -4.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4847   -4.1583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.7974   -4.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7974   -3.4871    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.5435   -5.6068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7367   -5.7793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0963   -6.2193    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.5864   -4.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3784   -4.8261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8637   -4.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3714   -3.4810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5879   -3.7483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0722   -3.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2472   -3.4438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.4847   -2.7294    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.8347   -4.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0098   -4.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2472   -4.8728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6022   -3.4444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7780   -3.4440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3647   -4.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7816   -4.8759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6045   -4.8728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5397   -4.1602    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
  3  8  1  0
 12  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
 10 11  1  0
 11 12  1  0
  8 12  2  0
  2 13  1  0
 13 14  1  0
 13 15  2  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 17  1  0
 21 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4791938

   Ano1-IN-2

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: 379.89

Molecular Weight (Monoisotopic): 379.0216

AlogP: 3.12

#Rotatable Bonds: 3

Polar Surface Area: 84.22

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.64

CX Basic pKa: ┄

CX LogP: 4.80

CX LogD: 4.80

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.72

Np Likeness Score: -2.52

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