1698-53-9

Usage

Uses

Used in Pharmaceutical Industry:
1-Phenyl-4,5-dichloro-6-pyridazone is used as an anti-cancer agent for its ability to target and combat cancer cells. Its effectiveness in this application is attributed to its arylated pyridazin-3(2H)-one structure, which allows it to interact with specific biological targets and disrupt cancer cell growth.
Used in Agriculture Industry:
1-Phenyl-4,5-dichloro-6-pyridazone is used as a herbicide for its ability to control and eliminate unwanted plant growth. Its herbicidal activity is beneficial in maintaining the health and productivity of crops by reducing competition from weeds and other unwanted vegetation.

Synthesis Reference(s)

Journal of the American Chemical Society, 75, p. 1909, 1953 DOI: 10.1021/ja01104a038

InChI:InChI=1/C4H2Cl2N2O/c5-2-1-7-8-4(9)3(2)6/h1H,(H,8,9)

Upstream product

• 766-40-5 Mucochloric acid 
• 100-63-0 phenylhydrazine 
• 932-22-9 4,5-dichloro-2H-pyridazin-3-one 
• 71-43-2 benzene 
• 62-53-3 aniline 
• 1698-60-8 chloridazon 
• 87-56-9 mucochloric acid 
• 59-88-1 phenylhydrazine hydrochloride 
• 60420-82-8 2,3-dichloro-4-phenylhydrazono-cis-crotonic acid 

Downstream Products

• 5273-13-2 4-Chlor-2-phenyl-5-morpholino-3-oxo-2,3-dihydro-pyridazin 
• 153276-35-8 2-phenyl-4-chloro-5-(1-piperazinyl)-3(2H)-pyridazinone 
• 66597-67-9 4-Chloro-5-[(2-hydroxy-ethyl)-methyl-amino]-2-phenyl-2H-pyridazin-3-one 
• 2514-18-3 4-chloro-5-methoxy-2-phenyl-3(2H)-pyridazinone 
• 77541-60-7 5-chloro-4-ethoxy-2-phenyl-3(2H)-pyridazinone 
• 5509-73-9 4-chloro-5-ethoxy-2-phenyl-3(2H)-pyridazinone 
• 40849-58-9 5-chloro-4-ethylthio-2-phenyl-3(2H)-pyridazinone 
• 143703-07-5 (5-Chloro-6-oxo-1-phenyl-1,6-dihydro-pyridazin-4-ylamino)-acetic acid ethyl ester 
• 38387-54-1 5-chloro-4-phenoxy-2-phenyl-2H-pyridazin-3-one 
• 10005-39-7 2-phenyl-4,5-bis-phenylsulfanyl-2H-pyridazin-3-one 
• 92961-87-0 5-Chloro-4-cyclohexylamino-2-phenyl-2H-pyridazin-3-one 
• 98796-13-5 4-Chloro-5-cyclohexylamino-2-phenyl-2H-pyridazin-3-one 
• 82412-96-2 4-chloro-5-(2-hydroxyetylamino)-2-phenyl-3(2H)-pyridazinone 
• 86483-35-4 4-chloro-2-phenyl-5-phenylsulfanyl-2H-pyridazin-3-one 

Relevant academic research and scientific papers

Deaminative chlorination of aminoheterocycles

Selective modification of heteroatom-containing aromatic structures is in high demand as it permits rapid evaluation of molecular complexity in advanced intermediates. Inspired by the selectivity of deaminases in nature, herein we present a simple methodology that enables the NH2 groups in aminoheterocycles to be conceived as masked modification handles. With the aid of a simple pyrylium reagent and a cheap chloride source, C(sp2)?NH2 can be converted into C(sp2)?Cl bonds. The method is characterized by its wide functional group tolerance and substrate scope, allowing the modification of >20 different classes of heteroaromatic motifs (five- and six-membered heterocycles), bearing numerous sensitive motifs. The facile conversion of NH2 into Cl in a late-stage fashion enables practitioners to apply Sandmeyer- and Vilsmeier-type transforms without the burden of explosive and unsafe diazonium salts, stoichiometric transition metals or highly oxidizing and unselective chlorinating agents. [Figure not available: see fulltext.]

Design, synthesis, and bioactivities of novel pyridazinone derivatives containing 2-phenylthiazole or oxazole skeletons

A series of novel pyridazinone derivatives were designed and synthesized by replacing 4-(tert-butyl)phenyl moiety of pyridaben with 2-phenylthiazole or oxazole fragments via activity substructure connecting approach. The structures of all target compounds were characterized through NMR, MS, and elemental analysis. Bioassay results exhibit that most compounds showed potent bioactivities against Aphis fabae, Tetranychus urticae, Erysiphe graminis, and/or Puccinia polysora. Among the newly synthesized compounds, 2-(tert-butyl)-4-chloro-5-(((2-phenylthiazol-4-yl)methyl)thio)pyridazin-3(2H)-one (12b) displays remarkable insecticidal activity against A fabae. Its LC50 value (2.73 mg/L) is better than that of pyridaben (5.46 mg/L), although inferior to that of imidacloprid (0.51 mg/L). In addition to its extraordinary insecticidal activity, compound 12b also exerts 96.9% fungicidal activities against P polysora at 500 mg/L in vivo, significantly superior to that of pyridaben (50.0%), while slightly lower than that of tebuconazole (100%). This article discusses the synthesis, bioassay results, and structure-activity relationship of this series of novel pyridazinone derivatives.

COMPOSITIONS, METHODS, AND SYSTEMS FOR THE SYNTHESIS AND USE OF IMAGING AGENTS

The present invention provides compounds with imaging moieties for imaging a subject. The present invention also relates to systems, compositions, and methods for the synthesis and use of imaging agents, or precursors thereof. An imaging agent precursor may be converted to an imaging agent using the methods described herein. In some cases, a composition or plurality of imaging agents is enriched in 18 F. In some cases, an imaging agent may be used to image an area of interest in a subject, including, but not limited to, the heart, cardiovascular system, cardiac vessels, brain, and other organs.

Contrast agent and for the use of a synthetic composition, method and system (by machine translation)

The present invention provides compounds with imaging moieties for imaging a subject. The present invention also relates to systems, compositions, and methods for the synthesis and use of imaging agents, or precursors thereof. An imaging agent precursor may be converted to an imaging agent using the methods described herein. In some cases, a composition or plurality of imaging agents is enriched in 18 F. In some cases, an imaging agent may be used to image an area of interest in a subject, including, but not limited to, the heart, cardiovascular system, cardiac vessels, brain, and other organs.

Design, synthesis and SAR analysis of novel potent and selective small molecule antagonists of NPBWR1 (GPR7)

Novel small molecule antagonists of NPBWR1 (GPR7) are herein reported. A high-throughput screening (HTS) of the Molecular Libraries-Small Molecule Repository library identified 5-chloro-4-(4-methoxyphenoxy)-2-(p-tolyl) pyridazin-3(2H)-one as a NPBWR1 hit antagonist with micromolar activity. Design, synthesis and structure-activity relationships study of the HTS-derived hit led to the identification of 5-chloro-2-(3,5-dimethylphenyl)-4-(4-methoxyphenoxy) pyridazin-3(2H)-one lead molecule with submicromolar antagonist activity at the target receptor and high selectivity against a panel of therapeutically relevant off-target proteins. This lead molecule may provide a pharmacological tool to clarify the molecular basis of the in vivo physiological function and therapeutic utility of NPBWR1 in diverse disease areas including inflammatory pain and eating disorders.

The synthesis and structure-activity relationship of pyridazinones as glucan synthase inhibitors

A structure-activity relationship study of the lead 5-[4-(benzylsulfonyl) piperazin-1-yl]-4-morpholino-2-phenyl-pyridazin-3(2H)-one 1 has resulted in the identification of 2-(3,5-difluorophenyl)-4-(3-fluorocyclopentyloxy)-5-[4- (isopropylsulfonyl)piperazin-1-yl]-pyridazin-3(2H)-one 11c as a β-1,3-glucan synthase inhibitor. Compound 11c exhibited significant efficacy in an in vivo mouse model of Candida glabrata infection.

Synthesis and antiviral activities of α-aminophosphonate derivatives containing a pyridazine moiety

The title compounds (4) were obtained by the reaction of 2-phenyl-4-chloro-5-(4-amin ophenyl)pyridazin-3(2H)-one, aldehydes, and O,O′-dialkyl phosphite under reflux conditions using dry toluene as a solvent. The preliminary bioassays indicate that the synthesized compounds have moderate to good against tobacco mosaic virus (TMV) activity. It was found that compound 4b had a good inactivation effect in vivo against TMV, with an inhibition rate of 81.0%. Copyright Taylor & Francis Group, LLC.

Discovery and structure-activity relationship analysis of Staphylococcus aureus sortase A inhibitors

Methicillin resistant Staphylococcus aureus (MRSA) is a major health problem that has created a pressing need for new antibiotics. Compounds that inhibit the S. aureus SrtA sortase may function as potent anti-infective agents as this enzyme attaches virulence factors to the cell wall. Using high-throughput screening, we have identified several compounds that inhibit the enzymatic activity of the SrtA. A structure-activity relationship (SAR) analysis led to the identification of several pyridazinone and pyrazolethione analogs that inhibit SrtA with IC50 values in the sub-micromolar range. Many of these molecules also inhibit the sortase enzyme from Bacillus anthracis suggesting that they may be generalized sortase inhibitors.

Confirmation and prevention of halogen exchange: practical and highly efficient one-pot synthesis of dibromo- and dichloropyridazinones

Commercially available anilines were converted by a two step, one-pot process to the corresponding pyridazinones in good to excellent yields. During the process research, a significant halogen exchange was confirmed and prevented which allowed the process to be scaled to multikilogram quantities.

Efficient N-arylation of pyridazin-3(2H)-ones

A variety of substituted pyridazin-3(2H)-ones are directly N-arylated in good yield using lead tetraacetate/zinc chloride in benzene or in substituted benzenes including chloro- and bromobenzene. A variety of substituted pyridazin-3(2H)-ones are directly N-arylated in good yield using lead tetraacetate/zinc chloride in benzene or in substituted benzenes including chloro- and bromobenzene.