1698-54-0

Usage

Uses

Used in Pharmaceutical Industry:
3-Hydroxy-1-phenyl-6-pyridazone is used as a key intermediate in the synthesis of pharmaceuticals for its potential anti-inflammatory and antitumor properties. Its ability to modulate inflammatory and tumorigenic pathways makes it a valuable compound in the development of novel therapeutic agents for various diseases.
Used in Agrochemical Industry:
3-Hydroxy-1-phenyl-6-pyridazone is used as a building block in the synthesis of agrochemicals, such as pesticides and herbicides, due to its potential bioactivity against pests and weeds. Its incorporation into these products can enhance their effectiveness and selectivity, leading to improved crop protection.
Used in Gout and Hyperuricemia Treatment:
3-Hydroxy-1-phenyl-6-pyridazone is used as a xanthine oxidase inhibitor for the treatment of gout and hyperuricemia. Its ability to inhibit the enzyme responsible for uric acid production can help reduce the severity and frequency of gout attacks and manage hyperuricemia effectively.
Used in Colorimetric Detection:
3-Hydroxy-1-phenyl-6-pyridazone is used as a colorimetric reagent in analytical chemistry for the detection and quantification of various analytes. Its color-changing properties upon interaction with specific substances make it a valuable tool for sensitive and selective assays.
Used in Analytical Chemistry:
3-Hydroxy-1-phenyl-6-pyridazone is used as a versatile compound in analytical chemistry for the development of novel methods and techniques. Its unique chemical properties and reactivity enable the design of innovative analytical protocols for the detection, separation, and quantification of various compounds in complex samples.

InChI:InChI=1/C10H8N2O2/c13-9-6-7-10(14)12(11-9)8-4-2-1-3-5-8/h1-7H,(H,11,13)

Upstream product

• 108-31-6 maleic anhydride 
• 100-63-0 phenylhydrazine 
• 59-88-1 phenylhydrazine hydrochloride 
• 64-19-7 acetic acid 
• 110-16-7 maleic acid 

Downstream Products

• 26608-21-9 2,2'-diphenyl-2H,2'H-6,6'-disulfanediyl-bis-pyridazine-3-thione 
• 342786-03-2 1-(4-bromo-butyl)-2-phenyl-1,2-dihydro-pyridazine-3,6-dione 
• 402913-71-7 1-(3-chloro-propyl)-2-phenyl-1,2-dihydro-pyridazine-3,6-dione 
• 13817-74-8 2-methyl-1-phenyl-1,2-dihydro-3,6-pyridazinedione 
• 14634-50-5 6-methoxy-2-phenyl-2H-pyridazin-3-one 

Relevant academic research and scientific papers

On the spectroscopic analyses of 3-Hydroxy-1-Phenyl-Pyridazin-6(2H)one (HPHP): A comparative experimental and computational study

We have systematically calculated various physical characteristics such as optimized molecular structural parameters, vibrational frequencies, HOMO-LUMO energy gap, total dipole moment and thermochemical parameters: nuclear repulsion energy, ionization energy, electron affinity, global hardness, electronic chemical potential, global electrophilicity index and finally softness (ζ) using DFT/B3LYP utilizing 6-311G(d,p) basis set for 3-Hydroxy-1-Phenyl-Pyridazin-6(2H)one (HPHP). Also, HPHP nonlinear optical (NLO) properties have been checked by DFT/B3LYP utilizing 6-311G(d,p) basis set. In addition, we have investigated the influence of exposure to UV radiation on HPHP physical properties at the same level of theory. Our results show that HPHP possesses a dipole moment (2.68?Debye) and HOMO-LUMO energy gap of 3.99?eV that emphasize its high applicability for manufacturing photovoltaic devices such as solar cells. After exposure to UV radiation, the HPHP dipole moment has been lowered from 2.68 to 2.3?Debye due to UV radiation. Moreover, a double spin in HPHP has been observed, as electrons are aligned according to their spin state. Electrons (spin ↑) and (spin ↓) are aligned in alpha and beta levels with energy gaps 3.82 and 3.17?eV, respectively. This anomalous behavior may be justified by considering that HPHP undergoes anomalous Zeeman-like effect. The presence of this phenomenon in HPHP introduces it as a modern organic semiconductor which has high applicability to be used in modern spintronics.

Synthesis and biological evaluation of new 6-hydroxypyridazinone benzisoxazoles: Potential multi-receptor-targeting atypical antipsychotics

In recent years, multi-targeting directed ligands have attracted great interest as possible new atypical antipsychotics. Combinations of dopamine and serotonin receptor ligands within single molecules might afford new therapeutic opportunities. Herein, we describe the synthesis of a novel series of 6-hydroxypyridazinone benzisoxazoles and their binding behaviors to different receptors in terms of atypical antipsychotic behaviors. The most potent compound (46) exhibited excellent affinities for certain receptors (D2, Ki?=?0.5?±?0.07?nM; 5-HT1A, Ki?=?5.9?±?0.8?nM; 5-HT2A, Ki?=?0.3?±?0.01?nM; 5-HT6, Ki?=?0.5?±?0.04?nM) and combined with low affinities for the H1, 5-HT2C, and adrenergic α1receptors. In contrast to risperidone, compound 46 exhibited a high cataleptic threshold; this may be useful in the development of a novel class of drugs treating schizophrenia.

Ru(II)-Catalyzed C-H Hydroxyalkylation and Mitsunobu Cyclization of N-Aryl Phthalazinones

Ruthenium(II)-catalyzed C(sp2)-H functionalization of N-Aryl phthalazinones with a range of aldehydes and activated ketone is described. Initial formation of hydroxyalkylated phthalazinones and subsequent Mitsunobu cyclization provided facile access to biologically relevant indazolophthalazinones. The utility of this method is highlighted by synthetic transformations into a series of potentially bioactive scaffolds.

Phthalazinone-Assisted C-H Amidation Using Dioxazolones under Rh(III) Catalysis

The preparation of phthalazinone derivatives is pivotal for their utilization as pharmaceutical agents and other entities. Herein, we report the phthalazinone-assisted carbon-nitrogen bond forming reaction using dioxazolones as robust amidation sources under Rh(III) catalysis. The broad functional group tolerance and complete site-selectivity are observed. Notably, a series of transformations of synthesized compounds into biologically relevant N-heterocycles demonstrates the applicability of the developed methodology.

Synthesis of phenylpyridazinone derivative and application thereof

The invention relates to the field of medicine, and concretely the invention relates to a phenylpyridazine derivative and an application thereof. Concretely, the invention relates to a phenylpyridazinone derivative, a pharmaceutical composition containing the phenylpyridazinone derivative, and applications of the composition and the phenylpyridazinone derivative to preparation of medicines for preventing or treating nervous and mental diseases. The phenylpyridazinone derivative has a structure as shown in a formula (I). Experiments show that the compound can be used for preventing or treatingnervous and mental diseases.

Pyridazinone derivative and application thereof

The invention relates to the field of medicines, particularly relates to a pyridazinone derivative and application thereof, and more particularly relates to a pharmaceutical composition of the pyridazinone derivative and application of the pyridazinone derivative in preparing drugs for preventing or treating aches of any part of the body. The pyridazinone derivative has a structure as shown in a formula (I). It is found through experiments that the compound can be used for preventing or treating the aches of any part of the body. Please see the formula I in the description.

Synthesis and Biological Evaluation of Novel σ1 Receptor Ligands for Treating Neuropathic Pain: 6-Hydroxypyridazinones

By use of the 6-hydroxypyridazinone framework, a new series of potent σ1 receptor ligands associated with pharmacological antineuropathic pain activity was synthesized and is described in this article. In vitro receptor binding studies revealed high σ1 receptor affinity (Ki σ1 = 1.4 nM) and excellent selectivity over not only σ2 receptor (1366-fold) but also other CNS targets (adrenergic, μ-opioid, sertonerigic receptors, etc.) for 2-(3,4-dichlorophenyl)-6-(3-(piperidin-1-yl)propoxy)pyridazin-3(2H)-one (compound 54). Compound 54 exhibited dose-dependent antiallodynic properties in mouse formalin model and rats chronic constriction injury (CCI) model of neuropathic pain. In addition, functional activity of compound 54 was evaluated using phenytoin and indicated that the compound was a σ1 receptor antagonist. Moreover, no motor impairments were found in rotarod tests at antiallodynic doses and no sedative side effect was evident in locomotor activity tests. Last but not least, good safety and favorable pharmacokinetic properties were also noted. These profiles suggest that compound 54 may be a member of a novel class of candidate drugs for treatment of neuropathic pain.

Expedient synthesis of new cinnoline diones by Ru-catalyzed regioselective unexpected deoxygenation-oxidative annulation of propargyl alcohols with phthalazinones and pyridazinones

Ruthenium-catalyzed simple, cascade and one-pot synthesis of cinnoline-fused diones has been carried out by the C-H activation of phthalazinones/pyridazinones accomplished by the unusual deoxygenation of propargyl alcohols. The bond selectivity is accredited to the traceless directing nature of the hydroxyl group of propargyl alcohol. A sequential C-H activation, insertion and deoxy-oxidative annulation has been proposed based on the preliminary mechanistic study.

Concise routes to pyrazolo[1,5-a]pyridin-3-yl pyridazin-3-ones

Cycloaddition of pyridine N-imine with 6-alkyl-4-oxohex-5-ynoates followed by condensation with hydrazine provides concise access to pharmacologically active 6-(pyrazolo[1,5-a]pyridin-3-yl)pyridazinones. For the first time alkynyl heterocycles are also shown to be effective dipolarophiles for pyridine N-imine, and analogous compounds can be accessed directly in modest yields through the reaction of 6-(alkyn-1-yl)pyridazin-3-one derivatives. The Royal Society of Chemistry 2008.