2-(tert-Butoxy)-2-(5-methyl-2-phenyl-7-(m-tolyl)pyrazolo-[1,5-a]pyrimidin-6-yl)acetic Acid

ID: ALA4475105

PubChem CID: 70660283

Max Phase: Preclinical

Molecular Formula: C26H27N3O3

Molecular Weight: 429.52

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cccc(-c2c(C(OC(C)(C)C)C(=O)O)c(C)nc3cc(-c4ccccc4)nn23)c1

Standard InChI:  InChI=1S/C26H27N3O3/c1-16-10-9-13-19(14-16)23-22(24(25(30)31)32-26(3,4)5)17(2)27-21-15-20(28-29(21)23)18-11-7-6-8-12-18/h6-15,24H,1-5H3,(H,30,31)

Standard InChI Key:  VLWISWDZAAGZQS-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   35.8004   -5.8105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.5179   -5.3990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5151   -4.5679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7986   -4.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0846   -5.3994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0859   -4.5746    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.3015   -4.3197    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.8139   -4.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2996   -5.6517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9882   -4.9863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5791   -4.2686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7543   -4.2670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3377   -4.9824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7559   -5.7009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5793   -5.6989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2298   -5.8084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2248   -4.1504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9419   -4.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6558   -4.1450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.9450   -5.3880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.2218   -3.3249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.9356   -2.9115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9326   -2.0859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6527   -3.3194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6466   -2.4890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7935   -3.3361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5087   -2.9228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5011   -2.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7874   -1.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0714   -2.1082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0784   -2.9316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3564   -1.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  2  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
  8 10  1  0
  2 16  1  0
  3 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 17 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 22 25  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
  4 26  1  0
 30 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4475105

   2-[5-Methyl-7-(3-methylphenyl)-2-phenylpyrazolo[1,5-a]pyrimidin-6-yl]-2-[(2-methylpropan-2-yl)oxy]acetic acid

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: 429.52

Molecular Weight (Monoisotopic): 429.2052

AlogP: 5.62

#Rotatable Bonds: 5

Polar Surface Area: 76.72

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.93

CX Basic pKa: 1.37

CX LogP: 5.52

CX LogD: 2.32

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.45

Np Likeness Score: -1.07

References

1. Li G, Meanwell NA, Krystal MR, Langley DR, Naidu BN, Sivaprakasam P, Lewis H, Kish K, Khan JA, Ng A, Trainor GL, Cianci C, Dicker IB, Walker MA, Lin Z, Protack T, Discotto L, Jenkins S, Gerritz SW, Pendri A..  (2020)  Discovery and Optimization of Novel Pyrazolopyrimidines as Potent and Orally Bioavailable Allosteric HIV-1 Integrase Inhibitors.,  63  (5): [PMID:32081010] [10.1021/acs.jmedchem.9b01681]

Source

Source(1):

• Scientific Literature