1-(4-bromophenyl)-N-(4-methoxyphenyl)-5-(4-methyl-2-pivalamidothiazol-5-yl)-1H-pyrazole-3-carboxamide

ID: ALA1098166

PubChem CID: 46221405

Max Phase: Preclinical

Molecular Formula: C26H26BrN5O3S

Molecular Weight: 568.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(NC(=O)c2cc(-c3sc(NC(=O)C(C)(C)C)nc3C)n(-c3ccc(Br)cc3)n2)cc1

Standard InChI:  InChI=1S/C26H26BrN5O3S/c1-15-22(36-25(28-15)30-24(34)26(2,3)4)21-14-20(31-32(21)18-10-6-16(27)7-11-18)23(33)29-17-8-12-19(35-5)13-9-17/h6-14H,1-5H3,(H,29,33)(H,28,30,34)

Standard InChI Key:  TVFKIHOEEAGATR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    9.3482   -0.7305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3981    0.0931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6274    0.3945    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1072   -0.2447    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   10.8256    0.1575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0561    1.3615    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   11.4028    3.0723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7111    2.6265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8347    3.1381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5675    2.7592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2826   -0.2606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8598    0.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.6364   -0.2930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0672   -1.0016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8899   -0.9824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8116   -0.3102    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    8.2484   -1.7055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4500   -1.9134    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.4009   -2.7369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1690   -3.0381    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6927   -2.4006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5162   -2.4497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7058   -3.1813    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7431   -4.0054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0480   -4.4498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4755   -4.3852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3156   -4.0700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0852   -5.2739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3382   -4.8733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  2  0
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  3  6  1  0
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 26 27  2  0
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  1 24  1  0
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 28 29  1  0
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 26 30  1  0
  6  7  2  0
 30 31  1  0
 12 15  1  0
 31 32  1  0
  2  3  1  0
 31 33  2  0
 15 16  1  0
 32 34  1  0
  6  8  1  0
 32 35  1  0
  5 17  1  0
 32 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1098166

   1-(4-bromophenyl)-5-[2-(2,2-dimethylpropanoylamino)-4-methyl-1,3-thiazol-5-yl]-N-(4-methoxyphenyl)pyrazole-3-carboxamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 568.50

Molecular Weight (Monoisotopic): 567.0940

AlogP: 6.31

#Rotatable Bonds: 6

Polar Surface Area: 98.14

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 7.90

CX Basic pKa: ┄

CX LogP: 6.22

CX LogD: 6.11

Aromatic Rings: 4

Heavy Atoms: 36

QED Weighted: 0.28

Np Likeness Score: -1.77

References

1. Ye L, Knapp JM, Sangwung P, Fettinger JC, Verkman AS, Kurth MJ..  (2010)  Pyrazolylthiazole as DeltaF508-cystic fibrosis transmembrane conductance regulator correctors with improved hydrophilicity compared to bithiazoles.,  53  (9): [PMID:20373765] [10.1021/jm100235h]

2. Liessi N, Cichero E, Pesce E, Arkel M, Salis A, Tomati V, Paccagnella M, Damonte G, Tasso B, Galietta LJV, Pedemonte N, Fossa P, Millo E..  (2018)  Synthesis and biological evaluation of novel thiazole- VX-809 hybrid derivatives as F508del correctors by QSAR-based filtering tools.,  144  [PMID:29272749] [10.1016/j.ejmech.2017.12.030]

Source

Source(1):

• Scientific Literature