ethyl 7-methyl-3-(3-(4-sulfamoylbenzyl)thioureido)pyrazolo[1,5-a]pyrimidine-6-carboxylate

ID: ALA4846275

PubChem CID: 156587366

Max Phase: Preclinical

Molecular Formula: C18H20N6O4S2

Molecular Weight: 448.53

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1cnc2c(NC(=S)NCc3ccc(S(N)(=O)=O)cc3)cnn2c1C

Standard InChI:  InChI=1S/C18H20N6O4S2/c1-3-28-17(25)14-9-20-16-15(10-22-24(16)11(14)2)23-18(29)21-8-12-4-6-13(7-5-12)30(19,26)27/h4-7,9-10H,3,8H2,1-2H3,(H2,19,26,27)(H2,21,23,29)

Standard InChI Key:  INPDIBARMWLENP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   31.2844   -9.3110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.8663   -9.8930    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   32.0793   -9.0980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.5604  -17.1197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2657  -17.5242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9710  -17.1197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9710  -16.3026    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.5581  -16.2987    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.2657  -15.8898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0956  -15.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2827  -15.0054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9507  -15.7520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.8539  -17.5303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2657  -18.3414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5580  -18.7500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.9734  -18.7500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.9734  -19.5672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6811  -19.9758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6422  -14.4831    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.3894  -13.7060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9360  -13.0985    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.5900  -13.5363    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   29.6833  -12.3214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2299  -11.7139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0285  -11.8883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5749  -11.2817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3222  -10.5036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5182  -10.3356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9753  -10.9436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6677  -10.0640    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  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 27  2  1  0
  2 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4846275

   ---

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: 448.53

Molecular Weight (Monoisotopic): 448.0987

AlogP: 1.35

#Rotatable Bonds: 6

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: 10.22

CX Basic pKa: 0.61

CX LogP: 1.56

CX LogD: 1.56

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.38

Np Likeness Score: -2.11

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