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

ID: ALA4764417

PubChem CID: 2250029

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)c2ccccc2Cl)sc2c1CCC2

Standard InChI:  InChI=1S/C16H14ClN3O2S2/c17-10-6-2-1-4-8(10)14(22)19-16(23)20-15-12(13(18)21)9-5-3-7-11(9)24-15/h1-2,4,6H,3,5,7H2,(H2,18,21)(H2,19,20,22,23)

Standard InChI Key:  CWWDUCFRJAUOSH-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   26.4842  -27.1287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6592  -27.1287    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.9721  -27.7924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9721  -26.4576    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   26.7181  -28.5773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9112  -28.7498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.2708  -29.1897    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.7609  -27.5438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5530  -27.7966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0382  -27.1214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5459  -26.4514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7625  -26.7188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2468  -26.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4219  -26.4143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.6593  -25.6998    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   24.0094  -27.1287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1844  -27.1287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4219  -27.8432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7769  -26.4149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9526  -26.4146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5393  -27.1295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9562  -27.8464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7791  -27.8432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1957  -28.5553    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
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4764417

   2-[(2-chlorobenzoyl)carbamothioylamino]-5,6-dihydro-4H-cyclopenta[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: 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: -2.61

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