WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 408172
CAS#: 880487-62-7
Description: Phthalazinone pyrazole is a potent inhibitor of Aurora A kinase (IC50 = 31 nM). Phthalazinone pyrazole displays good pharmacological profiles with significantly improved oral bioavailability compared to the well studied Aurora inhibitor VX-680.
MedKoo Cat#: 408172
Name: Phthalazinone pyrazole
CAS#: 880487-62-7
Chemical Formula: C18H15N5O
Exact Mass: 317.1277
Molecular Weight: 317.352
Elemental Analysis: C, 68.13; H, 4.76; N, 22.07; O, 5.04
Related CAS #: 880487-62-7
Synonym: Phthalazinone pyrazole
IUPAC/Chemical Name: 4-((5-methyl-1H-pyrazol-3-yl)amino)-2-phenylphthalazin-1(2H)-one
InChi Key: DSDIWWSXOOXFSI-UHFFFAOYSA-N
InChi Code: InChI=1S/C18H15N5O/c1-12-11-16(21-20-12)19-17-14-9-5-6-10-15(14)18(24)23(22-17)13-7-3-2-4-8-13/h2-11H,1H3,(H2,19,20,21,22)
SMILES Code: O=C1C2=C(C=CC=C2)C(NC3=NNC(C)=C3)=NN1C4=CC=CC=C4
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: To be determined
Shelf Life: >2 years if stored properly
Drug Formulation: To be determined
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 317.352 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
1: Wan T, Wen Z, Laudadio G, Capaldo L, Lammers R, Rincón JA, García-Losada P, Mateos C, Frederick MO, Broersma R, Noël T. Accelerated and Scalable C(sp3)-H Amination via Decatungstate Photocatalysis Using a Flow Photoreactor Equipped with High-Intensity LEDs. ACS Cent Sci. 2022 Jan 26;8(1):51-56. doi: 10.1021/acscentsci.1c01109. Epub 2021 Dec 16. PMID: 35106372; PMCID: PMC8796300.
2: Malik MS, Asghar BH, Syed R, Alsantali RI, Morad M, Altass HM, Moussa Z, Althagafi II, Jassas RS, Ahmed SA. Novel Pyran-Linked Phthalazinone-Pyrazole Hybrids: Synthesis, Cytotoxicity Evaluation, Molecular Modeling, and Descriptor Studies. Front Chem. 2021 May 24;9:666573. doi: 10.3389/fchem.2021.666573. PMID: 34109154; PMCID: PMC8181751.
3: Wang W, Feng X, Liu HX, Chen SW, Hui L. Synthesis and biological evaluation of 2,4-disubstituted phthalazinones as Aurora kinase inhibitors. Bioorg Med Chem. 2018 Jul 23;26(12):3217-3226. doi: 10.1016/j.bmc.2018.04.048. Epub 2018 Apr 23. PMID: 29705376.
4: Choi YJ, Kim H, Kim JW, Song CW, Kim DS, Yoon S, Park HJ. Phthalazinone Pyrazole Enhances the Hepatic Functions of Human Embryonic Stem Cell-Derived Hepatocyte-Like Cells via Suppression of the Epithelial-Mesenchymal Transition. Stem Cell Rev Rep. 2018 Jun;14(3):438-450. doi: 10.1007/s12015-017-9795-4. PMID: 29238913.
5: Vincent-Rocan JF, Ivanovich RA, Clavette C, Leckett K, Bejjani J, Beauchemin AM. Cascade reactions of nitrogen-substituted isocyanates: a new tool in heterocyclic chemistry. Chem Sci. 2016 Jan 1;7(1):315-328. doi: 10.1039/c5sc03197d. Epub 2015 Sep 23. PMID: 29861985; PMCID: PMC5952554.
6: Nguyen HN, Cee VJ, Deak HL, Du B, Faber KP, Gunaydin H, Hodous BL, Hollis SL, Krolikowski PH, Olivieri PR, Patel VF, Romero K, Schenkel LB, Geuns-Meyer SD. Synthesis of 4-substituted chlorophthalazines, dihydrobenzoazepinediones, 2-pyrazolylbenzoic acid, and 2-pyrazolylbenzohydrazide via 3-substituted 3-hydroxyisoindolin-1-ones. J Org Chem. 2012 Apr 20;77(8):3887-906. doi: 10.1021/jo3000628. Epub 2012 Apr 5. PMID: 22458369.
7: Prime ME, Courtney SM, Brookfield FA, Marston RW, Walker V, Warne J, Boyd AE, Kairies NA, von der Saal W, Limberg A, Georges G, Engh RA, Goller B, Rueger P, Rueth M. Phthalazinone pyrazoles as potent, selective, and orally bioavailable inhibitors of Aurora-A kinase. J Med Chem. 2011 Jan 13;54(1):312-9. doi: 10.1021/jm101346r. Epub 2010 Dec 3. PMID: 21128645.
8: Pakulska W, Malinowski Z, Szczesniak AK, Czarnecka E, Epsztajn J. Synthesis and pharmacological evaluation of N-(dimethylamino)ethyl derivatives of benzo- and pyridopyridazinones. Arch Pharm (Weinheim). 2009 Jan;342(1):41-7. doi: 10.1002/ardp.200800016. PMID: 19051195.
9: Abdelrazek FM, Michael FA, Mohamed AE. Synthesis and molluscicidal activity of some 1,3,4-triaryl-5-chloropyrazole, pyrano[2,3-c]pyrazole, pyrazolylphthalazine and pyrano[2,3-d]thiazole derivatives. Arch Pharm (Weinheim). 2006 Jun;339(6):305-12. doi: 10.1002/ardp.200500259. PMID: 16649159.
10: Facchini V, Timbrell JA. Determination of hydralazine metabolites: 4-hydrazino-phthalazin-1-one and n-acetylhydrazinophthalazin-1-one by gas chromatography and s-triazolo[3,4-alpha]phthalazine and phthalazinone by high- performance liquid chromatography. J Chromatogr. 1980 Aug 8;183(2):167-73. doi: 10.1016/s0378-4347(00)81690-4. PMID: 7400275.
