2-Methyl-N'-(3,4,5-trimethoxybenzylidene)benzo[d]imidazo[2,1-b]thiazole-3-carbohydrazide

ID: ALA3763344

PubChem CID: 127042956

Max Phase: Preclinical

Molecular Formula: C21H20N4O4S

Molecular Weight: 424.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=N/NC(=O)c2c(C)nc3sc4ccccc4n23)cc(OC)c1OC

Standard InChI:  InChI=1S/C21H20N4O4S/c1-12-18(25-14-7-5-6-8-17(14)30-21(25)23-12)20(26)24-22-11-13-9-15(27-2)19(29-4)16(10-13)28-3/h5-11H,1-4H3,(H,24,26)/b22-11+

Standard InChI Key:  KGMYMLLNLRCWAY-SSDVNMTOSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   -0.4399   -1.9215    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7408   -1.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3010    0.3704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2039    0.3704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6669   -1.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2688   -1.0186    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7318    0.3704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5048    1.2733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1485   -1.3659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1672    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6810    1.1807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2225    1.5280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4974    2.7711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4550    3.3656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7929    3.5288    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7854    5.0296    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0809    5.7874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0734    7.2882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3672    8.0474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3566    9.5474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0523   10.2882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7586    9.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7691    8.0291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4521   10.2677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4179    9.6589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0387   11.7890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9944   12.3802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6526   10.3042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6952    9.7101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8756    0.7334    0.0000 C   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
  1  5  1  0
  6  7  1  0
  7  8  2  0
  2  6  2  0
  3  8  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  4 12  2  0
  5  9  2  0
 15 16  1  0
 13 14  2  0
 13 15  1  0
  8 13  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 18 23  2  0
 24 25  1  0
 22 24  1  0
 26 27  1  0
 21 26  1  0
 28 29  1  0
 20 28  1  0
 16 17  2  0
  7 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3763344

   ---

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: 424.48

Molecular Weight (Monoisotopic): 424.1205

AlogP: 3.65

#Rotatable Bonds: 6

Polar Surface Area: 86.45

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.67

CX Basic pKa: 2.49

CX LogP: 2.49

CX LogD: 2.49

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.38

Np Likeness Score: -1.53

References

1. Samala G, Devi PB, Saxena S, Meda N, Yogeeswari P, Sriram D..  (2016)  Design, synthesis and biological evaluation of imidazo[2,1-b]thiazole and benzo[d]imidazo[2,1-b]thiazole derivatives as Mycobacterium tuberculosis pantothenate synthetase inhibitors.,  24  (6): [PMID:26867485] [10.1016/j.bmc.2016.01.059]

Source

Source(1):

• Scientific Literature