Pyrazoloacridine

• CAT Number: I008926
• CAS Number: 99009-20-8
• Molecular Formula: C19H21N5O3
• Molecular Weight: 367.4
• Purity: ≥95%
• Solubility: Soluble in DMSO
• Storage: Store at -20°C
• IUPAC Name: 3-(4-methoxy-10-nitro-8,14,15-triazatetracyclo[7.6.1.02,7.013,16]hexadeca-1(15),2(7),3,5,9,11,13(16)-heptaen-14-yl)-N,N-dimethylpropan-1-amine
• InChI: InChI=1S/C19H21N5O3/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/h5-8,11,20H,4,9-10H2,1-3H3
• InChIKey: HZCWPKGYTCJSEB-UHFFFAOYSA-N
• SMILES: CN(C)CCCN1C2=C3C(=C(C=C2)[N+](=O)[O-])NC4=C(C3=N1)C=C(C=C4)OC

Pyrazoloacridine (Cat No.:I008926) is a compound with potent anticancer activity. It exerts its effects by inhibiting the activity of both topoisomerases 1 and 2, important enzymes involved in DNA replication and repair. In K562 myeloid leukemia cells, Pyrazoloacridine demonstrates an IC50 value of 1.25 μM after 24 hours of treatment, indicating its ability to effectively inhibit cell growth.

Reference

1:Combinatorial synthesis of pyrazoloquinoline and pyrazoloacridine derivatives with high regioselectivity. Chen DS, Zhou YJ, Li YL, Yao CS, Wang XS.Comb Chem High Throughput Screen. 2013 Jun 28;16(7):550-61. PMID: 23410044 2:Phase II trial of pyrazoloacridine (NSC#366140) in patients with metastatic breast cancer. Ramaswamy B, Mrozek E, Kuebler JP, Bekaii-Saab T, Kraut EH.Invest New Drugs. 2011 Apr;29(2):347-51. doi: 10.1007/s10637-009-9338-1. Epub 2009 Oct 21. PMID: 19844661 Free PMC Article3:Phase I/II trial of pyrazoloacridine and carboplatin in patients with recurrent glioma: a North Central Cancer Treatment Group trial. Galanis E, Buckner JC, Maurer MJ, Reid JM, Kuffel MJ, Ames MM, Scheithauer BW, Hammack JE, Pipoly G, Kuross SA.Invest New Drugs. 2005 Oct;23(5):495-503. PMID: 16133802 4:The metabolism of pyrazoloacridine (NSC 366140) by cytochromes p450 and flavin monooxygenase in human liver microsomes. Reid JM, Walker DL, Miller JK, Benson LM, Tomlinson AJ, Naylor S, Blajeski AL, LoRusso PM, Ames MM.Clin Cancer Res. 2004 Feb 15;10(4):1471-80. PMID: 14977851 Free Article5:Synergistic cytotoxicity of pyrazoloacridine with doxorubicin, etoposide, and topotecan in drug-resistant tumor cells. Hu Y, Krishan A, Nie W, Sridhar KS, Mayer LD, Bally M.Clin Cancer Res. 2004 Feb 1;10(3):1160-9. PMID: 14871996 Free Article6:Pyrazoloacridine is active in multidrug-resistant neuroblastoma cell lines with nonfunctional p53. Keshelava N, Tsao-Wei D, Reynolds CP.Clin Cancer Res. 2003 Aug 15;9(9):3492-502. PMID: 12960142 Free Article7:A phase I and pharmacologic study of pyrazoloacridine and cisplatin in patients with advanced cancer. Dees EC, Rowinsky EK, Noe DA, O/’Reilly S, Adjei AA, Elza-Brown K, Donehower RC.Invest New Drugs. 2003 Feb;21(1):75-84. PMID: 12795532 8:Phase II trial of pyrazoloacridine in advanced non-small cell carcinoma of the lung–a Kansas Cancer Institute and Thompson Cancer Survival Center Study. Bastasch M, Panella TJ, Kretzschmer SL, Graham D, Mayo M, Williamson S.Invest New Drugs. 2002 Aug;20(3):339-42. PMID: 12201497 9:A phase I and pharmacologic study of pyrazoloacridine (NSC 366140) and carboplatin in patients with advanced cancer. Adjei AA, Reid JM, Erlichman C, Sloan JA, Pitot HC, Alberts SR, Goldberg RM, Hanson LJ, Ruben S, Boemer SA, Atherton P, Ames MM, Kaufmann SH.Invest New Drugs. 2002 Aug;20(3):297-304. PMID: 12201492 10:A phase II trial of pyrazoloacridine (PZA) in squamous cell carcinoma of the cervix: a Gynecologic Oncology Group study. Plaxe SC, Blessing JA, Olt G, Husseinzadah N, Lentz SS, DeGeest K, Valea FA.Cancer Chemother Pharmacol. 2002 Aug;50(2):151-4. Epub 2002 Jul 5. PMID: 12172981