4-(2-Chlorophenyl)-N-(4-morpholinophenyl)-(2,4'-bithiazol)-2'-amine

ID: ALA5273468

Max Phase: Preclinical

Molecular Formula: C22H19ClN4OS2

Molecular Weight: 455.01

Names and Identifiers

Canonical SMILES:  Clc1ccccc1-c1csc(-c2csc(Nc3ccc(N4CCOCC4)cc3)n2)n1

Standard InChI:  InChI=1S/C22H19ClN4OS2/c23-18-4-2-1-3-17(18)19-13-29-21(25-19)20-14-30-22(26-20)24-15-5-7-16(8-6-15)27-9-11-28-12-10-27/h1-8,13-14H,9-12H2,(H,24,26)

Standard InChI Key:  GUGCCAUPCRJXRT-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    2.8631    1.5438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1832    1.0766    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5217    1.5978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7939    2.3559    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.6227    2.3284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7443    1.3227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5937    0.5118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2420    0.4126    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5853    1.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0197    1.7071    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3821    1.3542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9653    0.7710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7520   -0.0255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3341   -0.6065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1309   -0.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3450    0.3994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7654    0.9855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6077    1.1886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2877    1.6555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0294    1.3006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0940    0.4782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4185    0.0122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6725    0.3629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7141   -0.9761    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5007   -1.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0839   -2.3559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8805   -2.1424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0940   -1.3459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5108   -0.7627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9582   -0.0493    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
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 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
 15 24  1  0
 25 24  1  0
 26 25  1  0
 27 26  1  0
 28 27  1  0
 29 28  1  0
 24 29  1  0
 23 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5273468

   ---

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: 455.01

Molecular Weight (Monoisotopic): 454.0689

AlogP: 6.17

#Rotatable Bonds: 5

Polar Surface Area: 50.28

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 2.44

CX LogP: 6.35

CX LogD: 6.35

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.39

Np Likeness Score: -2.09

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