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N-(1,2,3,4-tetrahydro-1,3,4-trioxoisoquinolin-7-yl)-4-nitrobenzamide

ID: ALA204245

PubChem CID: 11652994

Max Phase: Preclinical

Molecular Formula: C16H9N3O6

Molecular Weight: 339.26

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  O=C1NC(=O)c2cc(NC(=O)c3ccc([N+](=O)[O-])cc3)ccc2C1=O

Standard InChI:  InChI=1S/C16H9N3O6/c20-13-11-6-3-9(7-12(11)15(22)18-16(13)23)17-14(21)8-1-4-10(5-2-8)19(24)25/h1-7H,(H,17,21)(H,18,22,23)

Standard InChI Key:  NGYGGBLAVBSGBJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    2.2907   -9.6711    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5698   -9.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8554   -9.6713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5633   -8.4337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1430   -9.2567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5747   -9.6694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5734  -10.4985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1418  -10.9110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8559  -10.4988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0092   -8.4254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0081   -9.2481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7266   -9.6605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7248   -8.0129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4397   -8.4260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4385   -9.2501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1507   -9.6609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8686   -9.2480    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8657   -8.4238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1489   -8.0126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1489   -7.1881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5889   -8.0134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1525  -10.4853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2896  -10.9161    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2887  -11.7409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0043  -10.5044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  2  0
  8  9  1  0
  9  3  2  0
  3  5  1  0
  2  3  1  0
  5  6  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 14 15  1  0
 19 20  2  0
 18 21  2  0
 11 12  1  0
 16 22  2  0
 12 15  2  0
 10 11  2  0
 14 13  2  0
 13 10  1  0
 14 19  1  0
 15 16  1  0
  1 11  1  0
  1  2  1  0
  6  7  1  0
  2  4  2  0
 23 24  2  0
 23 25  1  0
  7 23  1  0
M  CHG  2  23   1  25  -1
M  END

Associated Targets(Human)

CASP3 Tchem Caspase-3 (3632 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CAPNS1 Tbio Calpain 1 (176 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PRSS1 Tclin Trypsin (2137 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
F2 Tclin Thrombin (11687 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CASP2 Tchem Caspase-2 (173 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CASP6 Tchem Caspase-6 (1213 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CASP7 Tchem Caspase-7 (3146 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CASP8 Tchem Caspase-8 (1006 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Papain (844 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Biocomponents

Calculated Properties

Molecular Weight: 339.26Molecular Weight (Monoisotopic): 339.0491AlogP: 1.30#Rotatable Bonds: 3
Polar Surface Area: 135.48Molecular Species: ACIDHBA: 6HBD: 2
#RO5 Violations: HBA (Lipinski): 9HBD (Lipinski): 2#RO5 Violations (Lipinski):
CX Acidic pKa: 5.56CX Basic pKa: CX LogP: 1.58CX LogD: -0.01
Aromatic Rings: 2Heavy Atoms: 25QED Weighted: 0.37Np Likeness Score: -1.12

References

1. Chen YH, Zhang YH, Zhang HJ, Liu DZ, Gu M, Li JY, Wu F, Zhu XZ, Li J, Nan FJ..  (2006)  Design, synthesis, and biological evaluation of isoquinoline-1,3,4-trione derivatives as potent caspase-3 inhibitors.,  49  (5): [PMID:16509578] [10.1021/jm050896o]
2. Isabel, Elise E and 14 more authors.  2003-07-07  Nicotinyl aspartyl ketones as inhibitors of caspase-3.  [PMID:12798321]
3. Becker, Joseph W JW and 17 more authors.  2004-05-06  Reducing the peptidyl features of caspase-3 inhibitors: a structural analysis.  [PMID:15115390]
4. Mellon, Christophe C and 16 more authors.  2005-09-01  Lipophilic versus hydrogen-bonding effect in P3 on potency and selectivity of valine aspartyl ketones as caspase 3 inhibitors.  [PMID:16023344]
5. Chu, Wenhua W and 8 more authors.  2005-12-01  N-benzylisatin sulfonamide analogues as potent caspase-3 inhibitors: synthesis, in vitro activity, and molecular modeling studies.  [PMID:16302804]
6. Chen, Yi-Hua YH and 9 more authors.  2006-03-09  Design, synthesis, and biological evaluation of isoquinoline-1,3,4-trione derivatives as potent caspase-3 inhibitors.  [PMID:16509578]
7. Putt, Karson S KS and 12 more authors.  2006-10  Small-molecule activation of procaspase-3 to caspase-3 as a personalized anticancer strategy.  [PMID:16936720]
8. Isabel, Elise E and 17 more authors.  2007-03-15  Solid-phase analogue synthesis of caspase-3 inhibitors via palladium-catalyzed amination of 3-bromopyrazinones.  [PMID:17251019]
9. Chu, Wenhua W, Rothfuss, Justin J, Chu, Yunxiang Y, Zhou, Dong D and Mach, Robert H RH.  2009-04-23  Synthesis and in vitro evaluation of sulfonamide isatin Michael acceptors as small molecule inhibitors of caspase-6.  [PMID:19326941]
10. Lakshmi, P Jhansi PJ and 8 more authors.  2009-08-15  Design, synthesis, and discovery of novel non-peptide inhibitor of Caspase-3 using ligand based and structure based virtual screening approach.  [PMID:19631549]
11. Havran, Lisa M LM and 16 more authors.  2009-11-15  3,4-Dihydropyrimido(1,2-a)indol-10(2H)-ones as potent non-peptidic inhibitors of caspase-3.  [PMID:19836248]
12. Chu, Wenhua; Rothfuss, Justin; Zhou, Dong and Mach, Robert H.  2011-04-15  Synthesis and evaluation of isatin analogs as caspase-3 inhibitors: introduction of a hydrophilic group increases potency in a whole cell assay.  [PMID:21441025]
13. Maillard, Michel C MC and 17 more authors.  2011-10-01  Exploiting differences in caspase-2 and -3 S₂ subsites for selectivity: structure-based design, solid-phase synthesis and in vitro activity of novel substrate-based caspase-2 inhibitors.  [PMID:21903398]
14. Prime, Michael E ME and 29 more authors.  2012-02-09  Discovery and structure-activity relationship of potent and selective covalent inhibitors of transglutaminase 2 for Huntington's disease.  [PMID:22224594]

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