3471-32-7

Usage

Uses

(4-Methoxyphenyl)hydrazine is a useful reagent for the preparation of pyrazolopyridazine derivatives as anticancer agents.

InChI:InChI=1/C7H10N2O/c1-10-7-4-2-6(9-8)3-5-7/h2-5,9H,8H2,1H3

Upstream product

• 17333-79-8 p-methoxybenzenediazonium 
• 4346-59-2 para-methoxyphenyldiazonium chloride 
• 104-94-9 4-methoxy-aniline 
• 459-64-3 4-methoxybenzenediazonium tetrafluoroborate 
• 19501-58-7 4-methoxyphenylhydrazine hydrochloride 
• 623-12-1 4-chloromethoxybenzene 
• 696-62-8 para-iodoanisole 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 23197-23-1 4-hydroxyphenylhydrazine 
• 74-88-4 methyl iodide 
• 95854-01-6 7-nicotinoylheptanoic acid 
• 219753-93-2 di-tert-butyl 1-(4-methoxyphenyl)hydrazine-1,2-dicarboxylate 

Downstream Products

• 62833-10-7 ethyl 2-(4-methoxyphenyl)hydrazinecarboxylate 
• 66875-54-5 4-methyl-benzaldehyde-(4-methoxy-phenylhydrazone) 
• 35496-18-5 1-(4'-methoxyphenyl)-3-methyl-5-pyrazolone 
• 66390-61-2 isobutyric acid N'-(4-methoxyphenyl)hydrazide 
• 5705-10-2 N-benzyl-N-(4-methoxy-phenyl)-hydrazine; hydrochloride 
• 103185-59-7 1-(4-methoxybenzylidene)-2-(4-methoxyphenyl)hydrazine 
• 17473-78-8 N’-(4-methoxyphenyl)acetohydrazide 
• 17473-74-4 N¹-benzoyl-N²-(4-methoxyphenyl)hydrazine 
• 6107-53-5 1-(4-methoxyphenyl)pyrazolidin-3-one 
• 3449-49-8 6-methoxy-2,3,4,9-tetrahydro-1H-carbazol-1-one 
• 31241-19-7 5-Methoxy-2,3,3-trimethyl-3H-indole 
• 35292-54-7 N-methyl-N-(p-methoxyphenyl)hydrazine 
• 857810-42-5 5-methoxy-2-methyl-3-(2-phenoxy-ethyl)-indole 
• 113115-03-0 phenyl-glyoxal-bis-(4-methoxy-phenylhydrazone) 

Relevant academic research and scientific papers

Synthesis, structure and supramolecular properties of 1,7′-bis[4-(3-methyl-2,3-dihydro-pyrazol-1-yl)phenol]-1,4,7-trioxaheptane

A new pyrazole derivative, 1,7′-bis[4-(3-methyl-2,3-dihydro-pyrazol-1-yl)phenol]-1,4,7-trioxaheptane with m.f. C24H24N4O5 has been synthesized and the crystal structure was determined by single crystal X-ray diffraction. Interestingly, the title compound are linked by intermolecular O2-H22?N2 hydrogen bonds into a 36 atoms' macro-ring which is further held together into one dimensional beaded chain via C-H?O hydrogen bonding between another phenol oxygen atom and one methylene carbon atom.

Syntheses, structure, DNA-binding and DFT studies of a Cu(II) complex based on a pyrazolone derivative

A Cu(II) complex based on a pyrazolone derivative, 2-hydroxy-N′-((1-(4-methoxyphenyl)-3methyl-5-oxo-4,5-dihydro-1H-pyrazol-4-yl)(phenyl)methylene)benzohydrazide (H2L), has been prepared. IR spectra, UV-vis spectra, elemental analysis and single-crystal X-ray diffraction indicate that the Cu(II) complex was mononuclear with the chemical composition of [Cu(HL)Cl]·CH3OH. The Cu(II) compound presented herein exhibits interesting supramolecular characteristics and a novel 3D supramolecular architecture resulted due to the appropriate synergy of multiple intermolecular hydrogen bonds. The interaction of the Cu(II) complex with calf-thymus DNA was investigated by electronic absorption titration as well as EB-DNA competition experiment, and the results indicate that the Cu(II) compound which has a strong affinity for binding DNA is combined with DNA in an embedded manner. Furthermore, Time-Dependent Density Functional Theory calculations (TD-DFT) have been performed on optimized geometries for a better understanding of the electronic transitions in the UV-vis spectra of H2L and Cu(II) complex.

Cross-Coupling between Hydrazine and Aryl Halides with Hydroxide Base at Low Loadings of Palladium by Rate-Determining Deprotonation of Bound Hydrazine

Reported here is the Pd-catalyzed C–N coupling of hydrazine with (hetero)aryl chlorides and bromides to form aryl hydrazines with catalyst loadings as low as 100 ppm of Pd and KOH as base. Mechanistic studies revealed two catalyst resting states: an arylpalladium(II) hydroxide and arylpalladium(II) chloride. These compounds are present in two interconnected catalytic cycles and react with hydrazine and base or hydrazine alone to give the product. The selectivity of the hydroxide complex with hydrazine to form aryl over diaryl hydrazine was lower than that of the chloride complex, as well as the catalytic reaction. In contrast, the selectivity of the chloride complex closely matched that of the catalytic reaction, indicating that the aryl hydrazine is derived from this complex. Kinetic studies showed that the coupling process occurs by rate-limiting deprotonation of a hydrazine-bound arylpalladium(II) chloride complex to give an arylpalladium(II) hydrazido complex.

Visible-light-mediated phosphonylation reaction: formation of phosphonates from alkyl/arylhydrazines and trialkylphosphites using zinc phthalocyanine

In this work, we developed a ligand- and base-free visible-light-mediated protocol for the photoredox syntheses of arylphosphonates and, for the first time, alkyl phosphonates. Zinc phthalocyanine-photocatalyzed Csp2-P and Csp3-P bond formations were efficiently achieved by reacting aryl/alkylhydrazines with trialkylphosphites in the presence of air serving as an abundant oxidant. The reaction conditions tolerated a wide variety of functional groups.

One-Pot Synthesis of Indoles and Pyrazoles via Pd-Catalyzed Couplings/Cyclizations Enabled by Aqueous Micellar Catalysis

An effective one-pot synthesis of either indoles or pyrazoles can be achieved via Pd-catalyzed aminations followed by subsequent cyclizations facilitated by aqueous micellar catalysis. This new technology includes efficient couplings with low loadings of palladium, a more stable source of the required hydrazine moiety, greater atom economy for the initial coupling, and reduced reaction temperatures, all leading to environmentally responsible processes.

Lewis Acid Catalyzed Annulation of Cyclopropane Carbaldehydes and Aryl Hydrazines: Construction of Tetrahydropyridazines and Application Toward a One-Pot Synthesis of Hexahydropyrrolo[1,2- b]pyridazines

In this report, a facile synthesis of tetrahydropyridazines via a Lewis acid catalyzed annulation reaction of cyclopropane carbaldehydes and aryl hydrazines has been demonstrated. Moreover, the generated tetrahydropyridazine further participated in a cycloaddition reaction with donor-acceptor cyclopropanes to furnish hexahydropyrrolo[1,2-b]pyridazines. We also performed these two steps in one pot in a consecutive manner. In addition, a monodecarboxylation reaction of hexahydropyrrolo[1,2-b]pyridazine was achieved with a good yield.

Preparation method of selective estrogen receptor modulator bazedoxifene and key intermediate thereof

The invention discloses a preparation method of a selective estrogen receptor modulator bazedoxifene and a key intermediate thereof. The chemical name of the selective estrogen receptor modulator bazedoxifene is 1-[4-(2-azacyclo cycloheptane-1-ethoxyl-benzyl)]-2-(4-hydroxyl-phenyl)-3-methyl-1H-indole-5-phenol. The chemical formula of the selective estrogen receptor modulator is C30H34N2O3. The preparation process is concise in process, the raw materials are easily available, the preparation method is economical and environment-friendly, the product yield and the product purity are high, industrialization is favorably achieved, and the production cost is lowered. The preparation method is suitable for batched production. The searched novel intermediate and the preparation method thereof areof great significance in economic technology of bazedoxifene.

(phenoxy)alkoxy-1H-indole derivatives or pharmaceutically acceptable salts thereof, preparation method therof and pharmaceutical composition for use in preventing or treating PPARα, PPARγ and PPARδ related diseases containing the same as an active ingredient

The present invention relates to (phenoxy)alkoxy-1H-indole derivatives or pharmaceutically allowable salts thereof, to a manufacturing method thereof, and to a pharmaceutical composition for preventing or treating PPARandalpha;, PPARandgamma; and PPARanddelta;-related diseases comprising the derivatives or salt thereof as an active ingredient. The (phenoxy)alkoxy-1H-indole derivatives have excellent abilities of activating PPARandalpha;, PPARandgamma; and PPARanddelta;, thereby being used for preventing or treating PPARandalpha;, PPARandgamma; and PPARanddelta;-related diseases of metabolic diseases, cardiovascular system diseases, cancer, inflammation, etc. as a PPAR agonist.COPYRIGHT KIPO 2017

Synthesis of benzofuro[3,2-b] indoline amines via deamination-interrupted Fischer indolization and their unexpected reactivity towards nucleophiles

We report the access to the benzofuro[3,2-b]indoline framework of phalarine from benzofuran-2-ones via the Fischer indolization reaction which was interrupted at the deamination step. Unexpectedly, allyl nucleophiles did not add to the aminal position of these benzofuro[3,2-b]indoline amines but to the adjacent ring junction center in the presence of trifluoroborane to deliver 3,3-disubstituted indolines containing a difluoroboron-containing six-membered ring with fluorescence properties.

Synthesis and biological evaluation of 4-(2-fluorophenoxy)-3,3′-bipyridine derivatives as potential c-met inhibitors

Six series of novel 4-(2-fluorophenoxy)-3,3′-bipyridine derivatives conjugated with aza-aryl formamide/amine scaffords were designed and synthesized through a structure-based molecular hybridization approach. The target compounds were evaluated for c-Met kinase inhibitory activities and cytotoxicity against four cancer cell lines (HT-29, A549, MKN-45 and MDA-MB-231) in vitro. Most compounds exhibited moderate to excellent potency, and the most promising candidate 26c (c-Met kinase IC50 = 8.2 nM) showed a 4.7-fold increase in cytotoxicity against c-Met-addicted MKN-45 cell line in vitro (IC50 = 3 nM), superior to that of Foretinib (IC50 = 23 nM). The preliminary structure-activity relationship indicated that a 1H-benzo [e] [1,3,4]thiadiazine-3-carboxamide-4,4-dioxide moiety as linker contributed to the antitumor potency.