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Pyrazoloacridine

ID: ALA5202951

PubChem CID: 168292724

Max Phase: Preclinical

Molecular Formula: C19H23N5O3

Molecular Weight: 369.43

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  COc1ccc2c(c1)C1=NN(CCCN(C)C)C3=CC=C([N+](=O)[O-])C(N2)C31

Standard InChI:  InChI=1S/C19H23N5O3/c1-22(2)9-4-10-23-15-7-8-16(24(25)26)19-17(15)18(21-23)13-11-12(27-3)5-6-14(13)20-19/h5-8,11,17,19-20H,4,9-10H2,1-3H3

Standard InChI Key:  BDIMLIUORNILTF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   -2.3834   -0.4539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6688   -0.0416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9570   -0.4536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9570   -1.2787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6670   -1.6905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3834   -1.2824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2423   -0.0410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4722   -0.4536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4722   -1.2788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2423   -1.6914    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8999   -0.4552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9017   -1.2762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1900   -1.6929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1849   -0.0427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0707    0.7660    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9245    0.7867    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0981   -0.0413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8127   -0.4539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1900   -2.5181    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4754   -2.9307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9046   -2.9307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3371    1.5014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1623    1.5014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5749    2.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4001    2.2160    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8127    2.9307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8127    1.5014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  3  7  1  0
  8  7  1  0
  9  8  1  0
 10  9  1  0
  4 10  1  0
 12 11  1  0
 13 12  2  0
  9 13  1  0
 11 14  2  0
  8 14  1  0
  7 15  2  0
 15 16  1  0
 16 14  1  0
  1 17  1  0
 17 18  1  0
 19 13  1  0
 19 20  1  0
 19 21  2  0
 16 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
M  CHG  2  19   1  20  -1
M  END

Alternative Forms

  1. Parent:

    ALA5202951

    ---

Associated Targets(Human)

TOP1 Tclin DNA topoisomerase I (7553 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TOP2A Tclin DNA topoisomerase II alpha (6317 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Mycobacterium tuberculosis (203094 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

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

Calculated Properties

Molecular Weight: 369.43Molecular Weight (Monoisotopic): 369.1801AlogP: 2.13#Rotatable Bonds: 6
Polar Surface Area: 83.24Molecular Species: BASEHBA: 7HBD: 1
#RO5 Violations: HBA (Lipinski): 8HBD (Lipinski): 1#RO5 Violations (Lipinski):
CX Acidic pKa: 10.39CX Basic pKa: 9.35CX LogP: 0.04CX LogD: -1.69
Aromatic Rings: 1Heavy Atoms: 27QED Weighted: 0.61Np Likeness Score: -0.62

References

1. Yang X, Wang ZP, Xiang S, Wang D, Zhao Y, Luo D, Qiu Y, Huang C, Guo J, Dai Y, Zhang SL, He Y..  (2022)  Optimization of the Natural Product Calothrixin A to Discover Novel Dual Topoisomerase I and II Inhibitors with Improved Anticancer Activity.,  65  (11.0): [PMID:35612499] [10.1021/acs.jmedchem.2c00615]
2. Nehra B, Rulhania S, Jaswal S, Kumar B, Singh G, Monga V..  (2020)  Recent advancements in the development of bioactive pyrazoline derivatives.,  205  [PMID:32795767] [10.1016/j.ejmech.2020.112666]
3. Uehling, D E DE and 9 more authors.  1995-03-31  Synthesis, topoisomerase I inhibitory activity, and in vivo evaluation of 11-azacamptothecin analogs.  [PMID:7707314]
4. Luzzio, M J MJ and 9 more authors.  1995-02-03  Synthesis and antitumor activity of novel water soluble derivatives of camptothecin as specific inhibitors of topoisomerase I.  [PMID:7853331]
5. Wall, M E ME and 8 more authors.  1993-09-03  Plant antitumor agents. 30. Synthesis and structure activity of novel camptothecin analogs.  [PMID:8410981]
6. Lackey, K K and 10 more authors.  1996-02-02  Water soluble inhibitors of topoisomerase I: quaternary salt derivatives of camptothecin.  [PMID:8576914]
7. Saulnier, Mark G MG and 23 more authors.  2005-04-07  Discovery of a fluoroindolo[2,3-a]carbazole clinical candidate with broad spectrum antitumor activity in preclinical tumor models superior to the marketed oncology drug, CPT-11.  [PMID:15801816]
8. Sunami, Satoshi S and 5 more authors.  2009-05-28  Synthesis and biological activities of topoisomerase I inhibitors, 6-arylmethylamino analogues of edotecarin.  [PMID:19397324]

Source