ethyl 7-methyl-3-(3-(3-sulfamoylphenyl)thioureido)pyrazolo[1,5-a]pyrimidine-6-carboxylate

ID: ALA4851544

PubChem CID: 164611692

Max Phase: Preclinical

Molecular Formula: C17H18N6O4S2

Molecular Weight: 434.50

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1cnc2c(NC(=S)Nc3cccc(S(N)(=O)=O)c3)cnn2c1C

Standard InChI:  InChI=1S/C17H18N6O4S2/c1-3-27-16(24)13-8-19-15-14(9-20-23(15)10(13)2)22-17(28)21-11-5-4-6-12(7-11)29(18,25)26/h4-9H,3H2,1-2H3,(H2,18,25,26)(H2,21,22,28)

Standard InChI Key:  ONRGSRZYJKDFNW-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   32.6340   -3.7269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.8168   -3.7269    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   32.2254   -4.4346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.2892   -4.9073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9945   -5.3117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6998   -4.9073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6998   -4.0901    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.2870   -4.0862    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.9945   -3.6774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8244   -2.8781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0116   -2.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6795   -3.5396    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.5827   -5.3179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9945   -6.1289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2868   -6.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.7022   -6.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.7022   -7.3547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4099   -7.7633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3710   -2.2706    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.1704   -2.4403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7170   -1.8328    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.4231   -3.2174    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   30.5164   -2.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7670   -2.7806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5655   -2.9505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1131   -2.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8565   -1.5623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0585   -1.3962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2710   -4.3349    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  8  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  9  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  8  1  0
  4 13  1  0
  5 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 10 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 25  2  1  0
  2 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4851544

   ---

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: 434.50

Molecular Weight (Monoisotopic): 434.0831

AlogP: 1.67

#Rotatable Bonds: 5

Polar Surface Area: 140.71

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.09

CX Basic pKa: 0.61

CX LogP: 1.85

CX LogD: 1.85

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.40

Np Likeness Score: -2.37

References

1. Gumus A, Bozdag M, Angeli A, Peat TS, Carta F, Supuran CT, Selleri S..  (2021)  Privileged scaffolds in medicinal chemistry: Studies on pyrazolo[1,5-a]pyrimidines on sulfonamide containing Carbonic Anhydrase inhibitors.,  49  [PMID:34371130] [10.1016/j.bmcl.2021.128309]

Source

Source(1):

• Scientific Literature