Pyrazoloacridine
Basic information
- CAS
99009-20-8- Standard SMILES
COc1ccc2c(c1)-c1nn(CCCN(C)C)c3ccc([N+](=O)[O-])c(c13)N2- InChIKey
HZCWPKGYTCJSEB-UHFFFAOYSA-N- Molecular formula
- C19H21N5O3
- Average molar mass
- 367.4 g/mol
- Monoisotopic mass
- 367.16443955
Overview
Pyrazoloacridine has been used in trials studying the treatment of Lung Cancer, Liver Cancer, Breast Cancer, Melanoma (Skin), and Metastatic Cancer, among others.
Names & identifiers
- Preferred name
- Pyrazoloacridine
- IUPAC
- 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
- English name
- NSC 366140
- Molecular formula
- C19H21N5O3
- Molecular weight
- 367.4
Names & synonyms
Pyrazoloacridine99009-20-8PD-115934PD 115934NSC-366140L24XJN68OWNSC-627168DTXSID301316714RefChem:177465DTXCID901440628(3-(4-methoxy-10-nitro-8,14,15-triazatetracyclo(7.6.1.0^(2,7).0^(13,16))hexadeca-1(15),2,4,6,9(16),10,12-heptaen-14-yl)propyl)dimethylamineN,N-Dimethyl-9-methoxy-5-nitropyrazolo(3,4,5-kl)acridine-2(6H)-propanamine
Show more names
PD 115NSC 366140Pd 115,934Brn 4211902Pyrazoloacridine, 10 mM in DMSOPyrazolo(3,4,5-kl)acridine-2(6H)-propanamine, N,N-dimethyl-9-methoxy-5-nitro-
3-(9-Methoxy-5-nitropyrazolo[3,4,5-kl]acridin-2(6H)-yl)-N,N-dimethylpropan-1-amineNSC627168Pyrazolo-acridine (free base)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-amineNSC 366140; NSC 627168; PD 115934; PZApyrazolo(3,4,5-kL)acridine-2(6H)-propanamine, 9-methoxy-N,N-dimethyl-5-nitro-Pyrazolo[3,4,5-kl]acridine-2(6H)-propanamine, 9-methoxy-N,N-dimethyl-5-nitro-UNII-L24XJN68OW
Properties
Computed structural properties
- XLogP
- 3
- Topological polar surface area
- 88.1 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 5
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 542
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Solubility
Water > 10.12 (mg/mL)
Buffer, pH 4 > 9.99 (mg/mL)
Buffer, pH 9 < 0.67 (mg/mL)
Ethanol > 0.66 (mg/mL)
Dimethylacetamide 5.05 - 10.10 (mg/mL)
DMSO > 10.18 (mg/mL)
Stability/Shelf LifeBulk: Test samples stored for 3 months at 25 °C and 50 °C under light and dark conditions showed no degradation (HPLC).
Solution: Aqueous solutions 2 mg/mL) showed no degradation after 48 hr at 25 °C.
Physicochemical properties
- Boiling point
- 584.3 · 584.3±50.0 °C(Predicted)
- Density
- 1.38 · 1.38±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- pka
- 9.35 · 9.35±0.28(Predicted)
- form
- Solid
- color
- Light brown to orange
- EWG's Food Scores
- 1 · 1
Chemistry & industry
Pharmacology
Metabolism/MetabolitesPyrazoloacridine has known human metabolites that include N-DEMETHYL Pyrazoloacridine.
MeSH Pharmacological Classification
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Agents that are capable of inserting themselves between the successive bases in DNA, thus kinking, uncoiling or otherwise deforming it and therefore preventing its proper functioning. They are used in the study of DNA.
Applications
UsesPyrazoloacridine (NSC 366140), an intercalating agent with anti-cancer activity, inhibits the activity of topoisomerases 1 and 2. Pyrazoloacridine (NSC 366140) exhibits an IC50 of 1.25 μM in K562 myeloid leukemia cells for 24 h treatment[1][2].
Upstream & downstream products
Upstream raw materials
Suppliers
Loading…
Open inquiries
Loading…
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…