2-(3-Benzoylthioureido)-6-(tert-butyl)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide

ID: ALA4784760

PubChem CID: 4487947

Max Phase: Preclinical

Molecular Formula: C21H25N3O2S2

Molecular Weight: 415.58

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)(C)C1CCc2c(sc(NC(=S)NC(=O)c3ccccc3)c2C(N)=O)C1

Standard InChI:  InChI=1S/C21H25N3O2S2/c1-21(2,3)13-9-10-14-15(11-13)28-19(16(14)17(22)25)24-20(27)23-18(26)12-7-5-4-6-8-12/h4-8,13H,9-11H2,1-3H3,(H2,22,25)(H2,23,24,26,27)

Standard InChI Key:  FSFFJPSVZZOESD-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   22.9475  -25.7963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1225  -25.7963    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.4353  -26.4599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4353  -25.1251    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.1814  -27.2448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3745  -27.4173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7341  -27.8573    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.2212  -26.2044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9321  -26.6133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6461  -26.2022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6448  -25.3776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9294  -24.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3591  -24.9647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0738  -25.3768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3586  -24.1396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0713  -24.5463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2129  -25.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7100  -25.0818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8850  -25.0818    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1225  -24.3673    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   20.4725  -25.7963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6475  -25.7963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8850  -26.5107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2401  -25.0824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4158  -25.0820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0024  -25.7971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4194  -26.5139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2423  -26.5107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
  3  8  1  0
 17  4  1  0
  4  1  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
 17 12  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
  8 17  2  0
  2 18  1  0
 18 19  1  0
 18 20  2  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
 22 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4784760

   6-Tert-butyl-2-{[(phenylcarbonyl)carbamothioyl]amino}-4,5,6,7-tetrahydro-1-benzothiophene-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: 415.58

Molecular Weight (Monoisotopic): 415.1388

AlogP: 4.12

#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: 5.96

CX LogD: 5.96

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.66

Np Likeness Score: -1.84

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