(Z)-2-(5-((9-(4-bromobenzyl)-9H-carbazol-3-yl)methylene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid

ID: ALA4211412

PubChem CID: 145966188

Max Phase: Preclinical

Molecular Formula: C25H17BrN2O3S2

Molecular Weight: 537.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CN1C(=O)/C(=C/c2ccc3c(c2)c2ccccc2n3Cc2ccc(Br)cc2)SC1=S

Standard InChI:  InChI=1S/C25H17BrN2O3S2/c26-17-8-5-15(6-9-17)13-27-20-4-2-1-3-18(20)19-11-16(7-10-21(19)27)12-22-24(31)28(14-23(29)30)25(32)33-22/h1-12H,13-14H2,(H,29,30)/b22-12-

Standard InChI Key:  SESSOUVXNDDDDX-UUYOSTAYSA-N

Molfile:  

     RDKit          2D

 33 37  0  0  0  0  0  0  0  0999 V2000
    1.9260  -21.4409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9249  -22.2605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6329  -22.6694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6311  -21.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3397  -21.4373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3445  -22.2559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1246  -22.5044    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1168  -21.1799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5975  -21.8377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4056  -21.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7340  -21.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2483  -20.3461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4419  -20.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3837  -23.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1845  -23.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4395  -24.2158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2394  -24.3791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7819  -23.7668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5189  -22.9886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7196  -22.8290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5747  -19.5970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3867  -19.5051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9367  -20.1066    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.6806  -19.7683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5887  -18.9562    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7881  -18.7928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4488  -18.0494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3916  -20.1713    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.1916  -18.4046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9708  -18.6508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5737  -18.0992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1471  -19.4488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5829  -23.9288    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  9  1  0
  8  5  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  7 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 12 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 22  1  0
 26 27  2  0
 24 28  2  0
 25 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
 18 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4211412

   ---

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: 537.46

Molecular Weight (Monoisotopic): 535.9864

AlogP: 5.89

#Rotatable Bonds: 5

Polar Surface Area: 62.54

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.90

CX Basic pKa: ┄

CX LogP: 6.28

CX LogD: 3.06

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.25

Np Likeness Score: -1.31

References

1. Jiang H, Zhang WJ, Li PH, Wang J, Dong CZ, Zhang K, Chen HX, Du ZY..  (2018)  Synthesis and biological evaluation of novel carbazole-rhodanine conjugates as topoisomerase II inhibitors.,  28  (8): [PMID:29545100] [10.1016/j.bmcl.2018.03.017]

Source

Source(1):

• Scientific Literature