N'-(1-Naphthoyl)-2-methylimidazo[1,2-a]pyridine-3-carbohydrazide

ID: ALA3309662

PubChem CID: 27699376

Max Phase: Preclinical

Molecular Formula: C20H16N4O2

Molecular Weight: 344.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nc2ccccn2c1C(=O)NNC(=O)c1cccc2ccccc12

Standard InChI:  InChI=1S/C20H16N4O2/c1-13-18(24-12-5-4-11-17(24)21-13)20(26)23-22-19(25)16-10-6-8-14-7-2-3-9-15(14)16/h2-12H,1H3,(H,22,25)(H,23,26)

Standard InChI Key:  UFGNAQNKTJBWOW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    0.9563   -3.8025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1594   -4.0160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0541   -4.8129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5292   -5.3962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3261   -5.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5396   -4.3858    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3308   -3.0674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1457   -3.1964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2747   -4.0113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0098   -4.3858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0530   -5.2097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7243   -3.9733    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4387   -4.3858    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7290   -2.6131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1532   -3.1483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4387   -2.7358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4387   -1.9108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1532   -1.4983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8677   -1.9108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5821   -1.4983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2966   -1.9108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2966   -2.7358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5821   -3.1483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8677   -2.7358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1532   -3.9733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8677   -4.3858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  1  6  1  0
  7  8  1  0
  8  9  2  0
  6  9  1  0
  1  7  2  0
 12 13  1  0
 10 11  2  0
 10 12  1  0
  9 10  1  0
  8 14  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 15 24  2  0
 19 24  1  0
 15 25  1  0
 25 26  2  0
 13 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3309662

   2-methyl-N'-(naphthalene-1-carbonyl)imidazo[1,2-a]pyridine-3-carbohydrazide

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: 344.37

Molecular Weight (Monoisotopic): 344.1273

AlogP: 2.87

#Rotatable Bonds: 2

Polar Surface Area: 75.50

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.11

CX Basic pKa: 4.38

CX LogP: 1.92

CX LogD: 1.91

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.55

Np Likeness Score: -1.89

References

1. Samala G, Nallangi R, Devi PB, Saxena S, Yadav R, Sridevi JP, Yogeeswari P, Sriram D..  (2014)  Identification and development of 2-methylimidazo[1,2-a]pyridine-3-carboxamides as Mycobacterium tuberculosis pantothenate synthetase inhibitors.,  22  (15): [PMID:24953948] [10.1016/j.bmc.2014.05.038]

Source

Source(1):

• Scientific Literature