1-(4-methoxyphenyl)-3-(6-(trifluoromethoxy)benzo[d]thiazol-2-yl)urea

ID: ALA2235013

PubChem CID: 76318808

Max Phase: Preclinical

Molecular Formula: C16H12F3N3O3S

Molecular Weight: 383.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(NC(=O)Nc2nc3ccc(OC(F)(F)F)cc3s2)cc1

Standard InChI:  InChI=1S/C16H12F3N3O3S/c1-24-10-4-2-9(3-5-10)20-14(23)22-15-21-12-7-6-11(8-13(12)26-15)25-16(17,18)19/h2-8H,1H3,(H2,20,21,22,23)

Standard InChI Key:  YQGWCCKERDHBMH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   13.0984   -6.9007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0973   -7.7202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8053   -8.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8035   -6.4918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2930   -6.6394    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.5121   -6.8971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5147   -7.7220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3021   -7.9747    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7811   -7.3030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5982   -7.2986    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.0030   -6.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8202   -6.5812    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5907   -5.8811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2326   -7.2857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8238   -7.9964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2356   -8.7004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0535   -8.6964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4582   -7.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0444   -7.2776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3918   -6.4920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3918   -5.6748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4674   -9.4011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0641  -10.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0996   -5.2663    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.6841   -5.2662    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.3858   -4.8536    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  7  2  0
  6  4  2  0
  4  1  1  0
  6  7  1  0
  5  6  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
  1 20  1  0
 20 21  1  0
 17 22  1  0
 22 23  1  0
 21 24  1  0
 21 25  1  0
 21 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2235013

   1-(4-Methoxyphenyl)-3-[6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]urea

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: 383.35

Molecular Weight (Monoisotopic): 383.0551

AlogP: 4.85

#Rotatable Bonds: 4

Polar Surface Area: 72.48

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.29

CX Basic pKa: ┄

CX LogP: 5.22

CX LogD: 4.88

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.68

Np Likeness Score: -2.12

References

1. Caputo R, Calabro ML, Micale N, Schimmer AD, Ali M, Zappala M, Grasso S.  (2012)  Synthesis of benzothiazole derivatives and their biological evaluation as anticancer agents,  21  (9): [10.1007/s00044-011-9789-8]

2. Hroch L, Benek O, Guest P, Aitken L, Soukup O, Janockova J, Musil K, Dohnal V, Dolezal R, Kuca K, Smith TK, Gunn-Moore F, Musilek K..  (2016)  Design, synthesis and in vitro evaluation of benzothiazole-based ureas as potential ABAD/17β-HSD10 modulators for Alzheimer's disease treatment.,  26  (15): [PMID:27287370] [10.1016/j.bmcl.2016.05.087]

Source

Source(1):

• Scientific Literature