N-(3,5-Dichlorophenyl)-4-(2-fluorophenyl)-(2,4'-bithiazol)-2'-amine

ID: ALA5283668

Max Phase: Preclinical

Molecular Formula: C18H10Cl2FN3S2

Molecular Weight: 422.34

Names and Identifiers

Canonical SMILES:  Fc1ccccc1-c1csc(-c2csc(Nc3cc(Cl)cc(Cl)c3)n2)n1

Standard InChI:  InChI=1S/C18H10Cl2FN3S2/c19-10-5-11(20)7-12(6-10)22-18-24-16(9-26-18)17-23-15(8-25-17)13-3-1-2-4-14(13)21/h1-9H,(H,22,24)

Standard InChI Key:  XODLULCLYUBWDK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    2.3870    1.0674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7070    0.6002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0455    1.1214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3177    1.8795    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.1465    1.8520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2681    0.8463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1175    0.0353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7181   -0.0637    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0615    0.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4564    1.2306    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8582    0.8778    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4414    0.2946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2282   -0.5019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8103   -1.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6071   -0.8694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8212   -0.0770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2416    0.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1315    0.7122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8115    1.1791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5533    0.8242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6178    0.0017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9423   -0.4641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1963   -0.1134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4820   -0.5258    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6178    0.1363    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.5968   -1.8795    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
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  3  6  1  0
  7  6  2  0
  7  8  1  0
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  9 11  1  0
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 16 15  1  0
 17 16  2  0
 12 17  1  0
  1 18  1  0
 19 18  2  0
 20 19  1  0
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 22 21  1  0
 23 22  2  0
 18 23  1  0
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 16 25  1  0
 14 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5283668

   ---

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: 422.34

Molecular Weight (Monoisotopic): 420.9677

AlogP: 7.12

#Rotatable Bonds: 4

Polar Surface Area: 37.81

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.19

CX Basic pKa: 1.23

CX LogP: 7.21

CX LogD: 7.21

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.38

Np Likeness Score: -2.08

References

1. Mao J, Wang D, Xu P, Wang Y, Zhang H, Wang S, Xu F, Wang J, Zhang F..  (2022)  Structure-Based Drug Design and Synthesis of Novel N-Aryl-2,4-bithiazole-2-amine CYP1B1-Selective Inhibitors in Overcoming Taxol Resistance in A549 Cells.,  65  (24.0): [PMID:36512763] [10.1021/acs.jmedchem.2c01306]

Source

Source(1):

• Scientific Literature