2-[4-Nitrophenyl(piperazinyl)methyl]-4,6-dimethylisothiazolo[5,4-b]pyridin-3(2H)-one

ID: ALA2419969

PubChem CID: 24848659

Max Phase: Preclinical

Molecular Formula: C19H21N5O3S

Molecular Weight: 399.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(C)c2c(=O)n(CN3CCN(c4ccc([N+](=O)[O-])cc4)CC3)sc2n1

Standard InChI:  InChI=1S/C19H21N5O3S/c1-13-11-14(2)20-18-17(13)19(25)23(28-18)12-21-7-9-22(10-8-21)15-3-5-16(6-4-15)24(26)27/h3-6,11H,7-10,12H2,1-2H3

Standard InChI Key:  MNFQUFGMUWCABK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    9.7466   -9.3927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9995  -11.2353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8576  -11.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5716  -11.2353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0965  -10.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3320  -10.1067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2856  -11.6499    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0402   -9.3695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2856   -9.1747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2714  -10.8248    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5070   -8.6787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7840  -10.1540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2856   -9.9997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0965   -9.3927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3320   -8.6787    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7840  -11.4915    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.9995  -10.4102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5070  -10.1067    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5716  -10.4102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7418   -7.9669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5623   -7.9702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9720   -7.2592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5604   -6.5473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7347   -6.5511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3287   -7.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9709   -5.8327    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5584   -5.1225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7922   -5.8306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  7  1  0
 19  4  2  0
 12  8  2  0
  2 17  1  0
 17 13  2  0
  5 18  1  0
 16 10  1  0
 18  6  1  0
 10  5  1  0
 13  9  1  0
 18 14  1  0
  2  7  2  0
  2 16  1  0
  4  3  1  0
 13 19  1  0
  1 15  1  0
 15 11  1  0
 11 14  1  0
 10 12  1  0
  6  1  1  0
 17 12  1  0
 15 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 26 27  2  0
 26 28  1  0
 23 26  1  0
M  CHG  2  26   1  28  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2419969

   4,6-Dimethyl-2-[4-(4-nitrophenyl)piperazin-1-ylmethyl]isothiazolo[5,4-b]pyridin-3(2H)-one

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: 399.48

Molecular Weight (Monoisotopic): 399.1365

AlogP: 2.76

#Rotatable Bonds: 4

Polar Surface Area: 84.51

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.74

CX LogP: 3.41

CX LogD: 3.41

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.50

Np Likeness Score: -1.67

References

1. Malinka W, Swiątek P, Sliwińska M, Szponar B, Gamian A, Karczmarzyk Z, Fruziński A..  (2013)  Synthesis of novel isothiazolopyridines and their in vitro evaluation against Mycobacterium and Propionibacterium acnes.,  21  (17): [PMID:23850103] [10.1016/j.bmc.2013.06.027]

Source

Source(1):

• Scientific Literature