19064-73-4

Basic information

• Product Name: 4-Bromophthalazin-1(2H)-one
• Synonyms: 4-Bromophthalazin-1(2H)-one;4-bromo-2H-phthalazin-1-one
• CAS NO: 19064-73-4
• Molecular Formula: C₈H₅BrN₂O
• Molecular Weight: 225.04
• Mol File: 19064-73-4.mol
• Article Data: 11

Chemical Properties

• Melting Point: 273 °C
• Appearance: /
• Density: 1.82±0.1 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)
• PKA: 10.58±0.40(Predicted)
• CAS DataBase Reference: 4-Bromophthalazin-1(2H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromophthalazin-1(2H)-one(19064-73-4)
• EPA Substance Registry System: 4-Bromophthalazin-1(2H)-one(19064-73-4)

Safety Data

• Hazardous Substances Data: 19064-73-4(Hazardous Substances Data)

Usage

Description

4-Bromophthalazin-1(2H)-one is an organic compound with the molecular formula C8H6BrNO. It is a derivative of phthalazinone, which is a heterocyclic compound consisting of a phthalazine ring fused to an isoindole ring. 4-Bromophthalazin-1(2H)-one is characterized by the presence of a bromine atom at the 4-position, which imparts unique chemical and biological properties to the molecule.

Uses

Used in Pharmaceutical Industry:
4-Bromophthalazin-1(2H)-one is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and reactivity make it a valuable building block for the development of new drugs with potential therapeutic applications.
Used in the Synthesis of Aurora-A Kinase Inhibitors:
4-Bromophthalazin-1(2H)-one is used as a starting material for the synthesis of Phthalazinone Pyrazoles, which have been identified as potent, selective, and orally bioavailable inhibitors of Aurora-A Kinase. Aurora-A Kinase is a serine/threonine protein kinase that plays a crucial role in cell division, and its inhibition has been shown to have potential anti-cancer properties.
Used in the Development of Novel Proteasome Inhibitors:
4-Bromophthalazin-1(2H)-one is also utilized in the development of novel proteasome inhibitors based on the phthalazinone scaffold. Proteasome inhibitors are a class of drugs that block the activity of the proteasome, a cellular enzyme responsible for the degradation of proteins. These inhibitors have shown promise in the treatment of various cancers by disrupting the cell's ability to degrade proteins involved in cell cycle regulation and apoptosis.

Upstream product

• 1445-69-8 2,3-dihydrophthalazine-1,4-dione 
• 7789-69-7 phosphorus pentabromide 
• 3660-90-0 1,4-dibromophthalazine 
• 85-44-9 phthalic anhydride 
• 119-39-1 phthalazone 
• 119-67-5 o-carboxybenzaldehyde 

Downstream Products

• 880489-31-6 2-(4-toluylsulfonate)-4-(5-methyl-1H-pyrazol-3-ylamino)-2H-phthalazin-1-one 
• 880489-35-0 2-(methyl-3-pyridine)-4-(5-methyl-1H-pyrazol-3-ylamino)-2H-phthalazin-1-one 
• 1259300-52-1 4-(1H-indazol-3-ylamino)-2-phenyl-2H-phthalazin-1-one 

Relevant articles and documents

Regioselective Synthesis of Substituted 4-Alkylamino and 4-Arylaminophthalazin-1(2 H)-ones

(Chemical Equation Presented). An efficient regioselective synthesis of substituted 4-alkylamino and 4-arylaminophthalazin-1(1H)-ones 5 is described. This new method features the formation of substituted phthalazin-1(1H)-ones 3 by the reaction of 2-formylbenzoic acids 1 or 3-hydroxyisobenzofuran-1(3H)-ones 2 with hydrazine to generate phthalazin-1(2H)-ones 3. Subsequent regioselective bromination of phthalazin-1(2H)-ones 3 with benzyltrimethylammonium tribromide (BTMA-Br3) followed by mixed copper-copper oxide-catalyzed amination of 4-bromophthalazin-1(2H)-ones 4 with primary amines generates aminophthalazin-1(2H)-ones in good overall yields.

The synthesis and anti‐tumour properties of novel 4-substituted phthalazinones as Aurora B kinase inhibitors

A series of novel 4-substituted phthalazinones as Aurora B kinase inhibitors was synthesized and evaluated the anti-proliferative activities against A549, HCT116, MCF-7 and HepG2 cells. 1-(4-(2-((4-Oxo-3,4-dihydrophthalazin-1-yl)amino)ethyl) phenyl)-3-(3-(trifluoromethyl)phenyl)urea (17b) exhibited the most potent anti-proliferative activity against HCT116 cells with IC50 value of 4.35 ± 1.21 μM, as well as the moderate Aurora B inhibitory activity with the IC50 value of 142 nM. Furthermore, 17b inhibited the phosphorylation of Aurora B on Thr232, leading to cell cycle arrest in the G2/M phase by down-regulating the expression of CyclinB1 and Cdc2 proteins, and apoptosis by up-regulating the expression of BAD and Bax proteins in HCT116 cells. In addition, a docking study revealed that 17b could form key hydrogen bonds with Ala173, Glu171 and Glu177 in Aurora B. All the results reveal that 17b is worthy of further development as an Aurora B kinase inhibitor.

Synthesis of 4-alkylsulfanylphthalazin-1(2H)-ones via palladium catalyzed sulfanylation of substituted 4-bromophthalazin-1(2H)-ones

The synthesis of a series of new alkylsulfanyl phthalazinone and phthalazine derivatives is described. The target compounds were efficiently synthesized in a four step sequence, consisting of (1) cyclization of 2-formylbenzoic acid with hydrazine hydrate to form phthalazinone, (2) the direct bromination of phthalazinone core with KBr3, (3) alkylation of the obtained 4-bromolactam (Mitsunobu procedure) to make N- and also O-alkyl derivatives and finally (4) palladium-catalyzed coupling reactions of 2-alkyl-4-bromophthalazinone and 1-alkyloxy-4-bromophthalazine derivatives with aliphatic mercaptanes. Furthermore, the synthesis of 2-methyl-8-(propan-2-yl)sulfanyl-pyrido[3,4-d]pyridazin-1(2H)-one from 2-methyl-pyrido[3,4-d]pyridazin-1(2H)-one via bromination reaction with KBr3and subsequent sulfanylation by isopropyl mercaptan under catalyzed coupling reaction conditions is also described.