N1-(2-Ethyl-6-(4-bromophenyl)imidazo[2,1-b]-1,3,4-thiadiazole-5-ylmethylidene)-N2-(4-hydroxyphenyl)thiosemicarbazone

ID: ALA4534866

PubChem CID: 155549205

Max Phase: Preclinical

Molecular Formula: C20H17BrN6OS2

Molecular Weight: 501.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCc1nn2c(/C=N/NC(=S)Nc3ccc(O)cc3)c(-c3ccc(Br)cc3)nc2s1

Standard InChI:  InChI=1S/C20H17BrN6OS2/c1-2-17-26-27-16(11-22-25-19(29)23-14-7-9-15(28)10-8-14)18(24-20(27)30-17)12-3-5-13(21)6-4-12/h3-11,28H,2H2,1H3,(H2,23,25,29)/b22-11+

Standard InChI Key:  NHJRLSVLJTVGOE-SSDVNMTOSA-N

Molfile:  

 
     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   17.4938  -30.7363    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.4755  -29.4024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0046  -30.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2662  -29.6467    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2754  -30.4720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0634  -30.7171    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.5428  -30.0474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0485  -29.3844    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1841  -30.0907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7602  -29.3796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9358  -29.3907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5344  -30.1122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9592  -30.8198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7822  -30.8052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3680  -30.0382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7865  -30.7446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2100  -28.6213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7502  -27.9987    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.4848  -27.2176    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0291  -26.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7596  -25.8139    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8390  -26.7578    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.3039  -25.1955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1119  -25.3558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6561  -24.7340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3866  -23.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5721  -23.7950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0358  -24.4180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9302  -23.3286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7092  -30.1247    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  5  2  0
  4  2  1  0
  2  3  2  0
  3  1  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  4  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  3  9  1  0
  7 15  1  0
 15 16  1  0
  2 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 26 29  1  0
 12 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4534866

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 501.44

Molecular Weight (Monoisotopic): 500.0089

AlogP: 4.81

#Rotatable Bonds: 5

Polar Surface Area: 86.84

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.54

CX Basic pKa: 2.06

CX LogP: 5.96

CX LogD: 5.95

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.16

Np Likeness Score: -2.07

References

1. Kryshchyshyn A, Kaminskyy D, Karpenko O, Gzella A, Grellier P, Lesyk R..  (2019)  Thiazolidinone/thiazole based hybrids - New class of antitrypanosomal agents.,  174  [PMID:31051403] [10.1016/j.ejmech.2019.04.052]

Source

Source(1):

• Scientific Literature