4-(4-bromophenyl)-2-(2-((9-methyl-9H-carbazol-3yl)methylene)hydrazinyl)thiazole

ID: ALA4557760

PubChem CID: 155554834

Max Phase: Preclinical

Molecular Formula: C23H17BrN4S

Molecular Weight: 461.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cn1c2ccccc2c2cc(/C=N/Nc3nc(-c4ccc(Br)cc4)cs3)ccc21

Standard InChI:  InChI=1S/C23H17BrN4S/c1-28-21-5-3-2-4-18(21)19-12-15(6-11-22(19)28)13-25-27-23-26-20(14-29-23)16-7-9-17(24)10-8-16/h2-14H,1H3,(H,26,27)/b25-13+

Standard InChI Key:  ZPNWAFQXUMHUES-DHRITJCHSA-N

Molfile:  

 
     RDKit          2D

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   10.4405   -6.3187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4393   -7.1383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1474   -7.5473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1456   -5.9099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8542   -6.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8545   -7.1338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6331   -7.3865    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6327   -6.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1123   -6.7222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9219   -6.6361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2529   -5.8905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7682   -5.2301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9604   -5.3195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0968   -4.4819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9090   -4.3923    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2376   -3.6441    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8871   -8.1633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0498   -3.5545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5948   -4.1587    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.3396   -3.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2500   -3.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4498   -2.8445    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.8575   -2.4627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6367   -2.7128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2408   -2.1636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0670   -1.3642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2836   -1.1169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6829   -1.6678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6706   -0.8134    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
 12 14  1  0
 14 15  2  0
 15 16  1  0
  7 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 18  2  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
 21 23  1  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4557760

   ---

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: 461.39

Molecular Weight (Monoisotopic): 460.0357

AlogP: 6.66

#Rotatable Bonds: 4

Polar Surface Area: 42.21

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.75

CX Basic pKa: 5.36

CX LogP: 7.29

CX LogD: 7.25

Aromatic Rings: 5

Heavy Atoms: 29

QED Weighted: 0.24

Np Likeness Score: -1.56

References

1. Shaikh MS, Kanhed AM, Chandrasekaran B, Palkar MB, Agrawal N, Lherbet C, Hampannavar GA, Karpoormath R..  (2019)  Discovery of novel N-methyl carbazole tethered rhodanine derivatives as direct inhibitors of Mycobacterium tuberculosis InhA.,  29  (16): [PMID:31227345] [10.1016/j.bmcl.2019.06.015]

Source

Source(1):

• Scientific Literature