5-Ethyl-2-{[2-(4-nitrophenyl)-1H-indol-3-yl-methylene]hydrazono}thiazolidin-4-one

ID: ALA4566659

PubChem CID: 155560979

Max Phase: Preclinical

Molecular Formula: C20H17N5O3S

Molecular Weight: 407.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCC1S/C(=N\N=C\c2c(-c3ccc([N+](=O)[O-])cc3)[nH]c3ccccc23)NC1=O

Standard InChI:  InChI=1S/C20H17N5O3S/c1-2-17-19(26)23-20(29-17)24-21-11-15-14-5-3-4-6-16(14)22-18(15)12-7-9-13(10-8-12)25(27)28/h3-11,17,22H,2H2,1H3,(H,23,24,26)/b21-11+

Standard InChI Key:  KLEUBAPJNMSHHT-SRZZPIQSSA-N

Molfile:  

 
     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   33.1913  -19.7806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0172  -19.7806    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   34.2743  -18.9955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6043  -18.5082    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.9385  -18.9955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0602  -18.7414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.6732  -19.2948    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.4590  -19.0408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0720  -19.5942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2894  -20.1376    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.8773  -19.4219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7359  -20.7506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9832  -20.4129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3164  -20.8956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4011  -21.7159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1583  -22.0513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8219  -21.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2127  -18.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0354  -18.5831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3712  -17.8293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8855  -17.1603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0602  -17.2498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7281  -18.0037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1529  -18.7407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.7049  -20.4480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8837  -20.3607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2226  -16.4017    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.7361  -15.7342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.0439  -16.3142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  3  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 13  1  0
 12 10  1  0
 10 11  1  0
 11  9  2  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 11 18  1  0
  5 24  2  0
  1 25  1  0
 25 26  1  0
 27 28  2  0
 27 29  1  0
 21 27  1  0
M  CHG  2  27   1  29  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4566659

   ---

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: 407.46

Molecular Weight (Monoisotopic): 407.1052

AlogP: 4.07

#Rotatable Bonds: 5

Polar Surface Area: 112.75

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.83

CX Basic pKa: ┄

CX LogP: 4.17

CX LogD: 4.04

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.38

Np Likeness Score: -1.11

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]

2. Schadich E,Kryshchyshyn-Dylevych A,Holota S,Polishchuk P,Džubak P,Gurska S,Hajduch M,Lesyk R.  (2020)  Assessing different thiazolidine and thiazole based compounds as antileishmanial scaffolds.,  30  (23.0): [PMID:33091607] [10.1016/j.bmcl.2020.127616]

Source

Source(1):

• Scientific Literature