4-(5-(Furan-3-yl)-4-methyl-2-propionylthiophen-3-yl)benzenesulfonamide

ID: ALA4475756

PubChem CID: 60168995

Max Phase: Preclinical

Molecular Formula: C18H17NO4S2

Molecular Weight: 375.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCC(=O)c1sc(-c2ccoc2)c(C)c1-c1ccc(S(N)(=O)=O)cc1

Standard InChI:  InChI=1S/C18H17NO4S2/c1-3-15(20)18-16(11(2)17(24-18)13-8-9-23-10-13)12-4-6-14(7-5-12)25(19,21)22/h4-10H,3H2,1-2H3,(H2,19,21,22)

Standard InChI Key:  OQAQFUUCFJQMEV-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    3.1862   -3.2440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5989   -3.9539    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.0074   -3.2415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9585   -5.7410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7757   -5.7410    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.0300   -4.9643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3671   -4.4822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7083   -4.9643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3658   -3.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8076   -4.7128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4773   -6.4015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6647   -6.3150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8087   -7.1485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1835   -6.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9310   -4.7121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7640   -3.9141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9876   -3.6618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3796   -4.2092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5533   -5.0120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3296   -5.2605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9956   -4.5059    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4676   -5.1944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1294   -4.7150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8780   -3.9374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0608   -3.9364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  4  2  0
  7  9  1  0
  6 10  1  0
  4 11  1  0
 11 12  1  0
 11 13  2  0
 12 14  1  0
  8 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 18  2  1  0
  2 21  1  0
 10 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 10  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4475756

   4-[5-(Furan-3-yl)-4-methyl-2-propanoylthiophen-3-yl]benzenesulfonamide

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: 375.47

Molecular Weight (Monoisotopic): 375.0599

AlogP: 4.22

#Rotatable Bonds: 5

Polar Surface Area: 90.37

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.13

CX Basic pKa: ┄

CX LogP: 3.70

CX LogD: 3.69

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.68

Np Likeness Score: -0.69

References

1. Sinha N, Karche NP, Verma MK, Walunj SS, Nigade PB, Jana G, Kurhade SP, Hajare AK, Tilekar AR, Jadhav GR, Thube BR, Shaikh JS, Balgude S, Singh LB, Mahimane V, Adurkar SK, Hatnapure G, Raje F, Bhosale Y, Bhanage D, Sachchidanand S, Dixit R, Gupta R, Bokare AM, Dandekar M, Bharne A, Chatterjee M, Desai S, Koul S, Modi D, Mehta M, Patil V, Singh M, Gundu J, Goel RN, Shah C, Sharma S, Bakhle D, Kamboj RK, Palle VP..  (2020)  Discovery of Novel, Potent, Brain-Permeable, and Orally Efficacious Positive Allosteric Modulator of α7 Nicotinic Acetylcholine Receptor [4-(5-(4-Chlorophenyl)-4-methyl-2-propionylthiophen-3-yl)benzenesulfonamide]: Structure-Activity Relationship and Preclinical Characterization.,  63  (3): [PMID:31755711] [10.1021/acs.jmedchem.9b01569]

Source

Source(1):

• Scientific Literature