N-[6-(4-Bromophenyl)-2-ethylimidazo[2,1-b][1,3,4]thiadiazol-5-ylmethylene]-N'-[4-(4-nitrophenyl)-3H-4-thiazol-2-yl]hydrazine

ID: ALA4583350

PubChem CID: 155566021

Max Phase: Preclinical

Molecular Formula: C22H16BrN7O2S2

Molecular Weight: 554.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCc1nn2c(/C=N/N=c3/[nH]c(-c4ccc([N+](=O)[O-])cc4)cs3)c(-c3ccc(Br)cc3)nc2s1

Standard InChI:  InChI=1S/C22H16BrN7O2S2/c1-2-19-28-29-18(20(26-22(29)34-19)14-3-7-15(23)8-4-14)11-24-27-21-25-17(12-33-21)13-5-9-16(10-6-13)30(31)32/h3-12H,2H2,1H3,(H,25,27)/b24-11+

Standard InChI Key:  IOQMHKOBSOMQDE-BHGWPJFGSA-N

Molfile:  

 
     RDKit          2D

 34 38  0  0  0  0  0  0  0  0999 V2000
   21.8379  -26.1572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.8195  -24.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3473  -25.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6127  -25.0601    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.6219  -25.8880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4124  -26.1380    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.8933  -25.4619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3975  -24.7969    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.5242  -25.5055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0989  -24.7921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2719  -24.8032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8692  -25.5269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2954  -26.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1210  -26.2264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5533  -24.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7410  -23.8722    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.4747  -23.0886    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.6668  -22.9281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3207  -22.1834    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5027  -22.2804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3422  -23.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0610  -23.4906    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   24.7170  -25.4528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1368  -26.1615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9452  -21.6783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1908  -20.8909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6323  -20.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8281  -20.4683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5853  -21.2599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1455  -21.8608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2657  -19.8648    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4625  -20.0479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5087  -19.0777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0456  -25.5394    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
  2 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 18  1  0
  7 23  1  0
 23 24  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 20 25  1  0
 31 32  2  0
 31 33  1  0
 28 31  1  0
 12 34  1  0
M  CHG  2  31   1  33  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4583350

   ---

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: 554.46

Molecular Weight (Monoisotopic): 552.9990

AlogP: 5.68

#Rotatable Bonds: 6

Polar Surface Area: 113.84

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 8.37

CX Basic pKa: 2.80

CX LogP: 5.82

CX LogD: 5.78

Aromatic Rings: 5

Heavy Atoms: 34

QED Weighted: 0.17

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