3-(4-isopropylpyridin-2-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)-1,2,4-thiadiazol-5-amine

ID: ALA5199506

PubChem CID: 155230580

Max Phase: Preclinical

Molecular Formula: C16H14F3N5S

Molecular Weight: 365.38

Names and Identifiers

Canonical SMILES:  CC(C)c1ccnc(-c2nsc(Nc3cc(C(F)(F)F)ccn3)n2)c1

Standard InChI:  InChI=1S/C16H14F3N5S/c1-9(2)10-3-5-20-12(7-10)14-23-15(25-24-14)22-13-8-11(4-6-21-13)16(17,18)19/h3-9H,1-2H3,(H,21,22,23,24)

Standard InChI Key:  SBLGTJLDOGKYAL-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   -1.8368   -2.8133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4462   -3.3448    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4924   -2.8859    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5051   -2.0579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6855   -1.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3539   -1.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8420   -0.5479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6616   -0.6383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9931   -1.3932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1485    0.0276    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8163    0.7812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0101    0.9539    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    1.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6790    2.1082    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2296    1.4947    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211    2.1805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4929    1.7682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2070    2.1805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2070    3.0051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4929    3.4173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211    3.0051    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9206    1.7666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4924    2.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9206    1.1069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  0
  2  4  1  0
  5  2  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
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 12 11  1  0
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 13 14  1  0
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 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
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 22 17  1  0
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 23 24  1  0
 25 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5199506

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 365.38

Molecular Weight (Monoisotopic): 365.0922

AlogP: 4.88

#Rotatable Bonds: 4

Polar Surface Area: 63.59

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.21

CX Basic pKa: 2.18

CX LogP: 5.18

CX LogD: 4.11

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.71

Np Likeness Score: -1.54

References

1. Hawryluk N, Robinson D, Shen Y, Kyne G, Bedore M, Menon S, Canan S, von Geldern T, Townson S, Gokool S, Ehrens A, Koschel M, Lhermitte-Vallarino N, Martin C, Hoerauf A, Hernandez G, Dalvie D, Specht S, Hübner MP, Scandale I..  (2022)  Discovery of Substituted Di(pyridin-2-yl)-1,2,4-thiadiazol-5-amines as Novel Macrofilaricidal Compounds for the Treatment of Human Filarial Infections.,  65  (16.0): [PMID:35972896] [10.1021/acs.jmedchem.2c00960]

Source

Source(1):

• Scientific Literature