1672-58-8

Usage

Uses

Used in Pharmaceutical Industry:
N-(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)formamide is used as an intermediate compound for the synthesis of various pharmaceutical products due to its structural properties and origin as a metabolite of Dipyrone, a nonsteroidal anti-inflammatory drug. Its role in the pharmaceutical industry is to serve as a building block for the development of new medications with potential anti-inflammatory and analgesic properties.
Used in Research and Development:
In the field of research and development, N-(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)formamide is utilized as a key compound for studying the structure-activity relationships of pyrazolone derivatives. This helps scientists understand the molecular mechanisms underlying their biological activities and potentially leads to the discovery of new drugs with improved efficacy and safety profiles.
Used in Quality Control and Analytical Chemistry:
N-(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)formamide can be employed as a reference material in quality control and analytical chemistry for the validation of analytical methods and the determination of the purity and stability of related compounds. Its light tan solid form makes it suitable for various analytical techniques, such as high-performance liquid chromatography (HPLC) and mass spectrometry (MS).

InChI:InChI=1/C12H13N3O2/c1-9-11(13-8-16)12(17)15(14(9)2)10-6-4-3-5-7-10/h3-8H,1-2H3,(H,13,16)

Upstream product

• 64-18-6 formic acid 
• 83-07-8 4-amino-2,3-dimethyl-1-phenylpyrazolin-5-one 
• 77287-34-4 formamide 
• 42513-41-7 (Z)-1-chlorotetradec-9-ene 
• 127-08-2 potassium acetate 
• 16538-47-9 (Z)-1-iodohex-1-ene 
• 13175-40-1 1-(2-tetrahydropyranyloxy)-7-octene 
• 75-36-5 acetyl chloride 
• 592-41-6 1-hexene 
• 50816-18-7 9-decen-1-yl acetate 
• 15848-22-3 5-bromo-1-pentanyl acetate 
• 59499-29-5 (Z)-4-nonenyl bromide 
• 29541-97-7 9-acetoxynonal 
• 21406-61-1 pentyltriphenylphosphonium bromide 

Downstream Products

• 43200-52-8 4-{[(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-formyl-amino]-methyl}-4-methyl-morpholin-4-ium; iodide 

Relevant academic research and scientific papers

Antinociceptive activity of metamizol metabolites in a rat model of arthritic pain

Preclinical Research The aim of the present study was to evaluate the antinociceptive activity of the main metamizol (MET) metabolites, 4-methylaminoantipyrine (MAA), 4-aminoantipyrine (AA), 4-formylaminoantipyrine (FAA), and 4-acetylaminoantipyrine (AAA) using the "pain-induced functional impairment in rat" model (PIFIR model). The antinociceptive efficacies of MAA and AA were 288.3% h and 281.1% h, respectively, close to the efficacy of MET (333.80% h). The effective dose to attain 50% of the maximum response (ED50) values for MET, MAA and AA were 126.1, 124.9, and 110.7 mg/kg, respectively. FAA and AAA were essentially inactive in this experimental model. Part of the antinociceptive effect showed by MET in this study might be attributed to the effect of the metabolites MAA and AA on cyclooxygenases COX-1 and COX-2 activity.

SYNTHESIS OF PHEROMONE DERIVATIVES VIA Z-SELECTIVE OLEFIN METATHESIS

Disclosed herein are methods for synthesizing fatty olefin metathesis products of high Z-isomeric purity from olefin feedstocks of low Z-isomeric purity. The methods include contacting a contacting an olefin metathesis reaction partner, such as acylated alkenol or an alkenal acetal, with an internal olefin in the presence of a Z-selective metathesis catalyst to form the fatty olefin metathesis product. In various embodiments, the fatty olefin metathesis products are insect pheromones. Pheromone compositions and methods of using them are also described.

Cytochrome P450 1A2 is the most important enzyme for hepatic metabolism of the metamizole metabolite 4-methylaminoantipyrine

Aims: Metamizole (dipyrone) is a prodrug not detectable in serum or urine after oral ingestion. The primary metabolite, 4-methylaminoantipyrine (4-MAA), can be N-demethylated to 4-aminoantipyrine (4-AA) or oxidized to 4-formylaminoantipyrine (4-FAA) by cytochrome P450 (CYP)-dependent reactions. We aimed to identify the CYPs involved in 4-MAA metabolism and to quantify the effect of CYP inhibition on 4-MAA metabolism. Methods: We investigated the metabolism of 4-MAA in vitro using CYP expressing supersomes and the pharmacokinetics of metamizole in the presence of CYP inhibitors in male subjects. Results: The experiments in supersomes revealed CYP1A2 as the major CYP for 4-MAA N-demethylation and 4-FAA formation with CYP2C19 and CYP2D6 contributing to N-demethylation. In the clinical study, we investigated the influence of ciprofloxacin (CYP1A2 inhibitor), fluconazole (CYP2C19 inhibitor) and the combination ciprofloxacin/fluconazole on the pharmacokinetics of metamizole in n =?12 male subjects in a randomized, placebo-controlled, double-blind study. The geometric mean ratios for the area under the concentration–time curve of 4-MAA after/before treatment were 1.17 (90% CI 1.09–1.25) for fluconazole, 1.51 (90% CI 1.42–1.60) for ciprofloxacin and 1.92 (90% CI 1.81–2.03) for ciprofloxacin/fluconazole. Fluconazole increased the half-life of 4-MAA from 3.22 hours by 0.47 hours (95% CI 0.13–0.81, P .05), ciprofloxacin by 0.69 hours (95% CI 0.44–0.94, P .001) and fluconazole/ciprofloxacin by 2.85 hours (95% CI 2.48–3.22, P .001). Conclusion: CYP1A2 is the major CYP for the conversion of 4-MAA to 4-AA and 4-FAA. The increase in 4-MAA exposure by the inhibition of CYP1A2 and by the combination CYP1A2/CYP2C19 may be relevant for dose-dependent adverse reactions of 4-MAA.

Continuous Flow Z-Stereoselective Olefin Metathesis: Development and Applications in the Synthesis of Pheromones and Macrocyclic Odorant Molecules**

The first continuous flow Z-selective olefin metathesis process is reported. Key to realizing this process was the adequate choice of stereoselective catalysts combined with the design of an appropriate continuous reactor setup. The designed continuous process permits various self-, cross- and macro-ring-closing-metathesis reactions, delivering products in high selectivity and short residence times. This technique is exemplified by direct application to the preparation of a range of pheromones and macrocyclic odorant molecules and culminates in a telescoped Z-selective cross-metathesis/ Dieckmann cyclisation sequence to access (Z)-Civetone, incorporating a serial array of continually stirred tank reactors.

Method for synthesizing grassland spodoptera litura sex pheromone active ingredients

The invention belongs to the technical field of green pesticide synthesis, and discloses a novel method for synthesizing grassland spodoptera litura sex pheromone active ingredients (Z)-9-dodecene-1-alcohol acetate, (Z)-9-tetradecene-1-alcohol acetate and (Z)-11-hexadecene-1-alcohol acetate. The method comprises the steps: using bromo-alcohol as a starting raw material; and firstly generating hydroxyl phosphonium salt with triphenylphosphine, then respectively carrying out Wittig coupling reaction with propionaldehyde and valeraldehyde to generate Z-type enol, and finally carrying out acetylation reaction with acetic anhydride to prepare (Z)-9-dodecene-1-alcohol acetate, (Z)-9-tetradecene-1-alcohol acetate and (Z)-11-hexadecene-1-alcohol acetate. According to the method, hydroxyl phosphonium salt is used for Wittig reaction, two steps of hydroxyl protection and deprotection are omitted, the synthetic route is simplified, and the method has the advantages of being environmentally friendly and the like.

PRODUCTION OF FATTY OLEFIN DERIVATIVES VIA OLEFIN METATHESIS

In one aspect, the invention provides a method for synthesizing a fatty olefin derivative. The method includes: a) contacting an olefin according to Formula I with a metathesis reaction partner according to Formula IIb in the presence of a metathesis catalyst under conditions sufficient to form a metathesis product according to Formula IIIb: and b) converting the metathesis product to the fatty olefin derivative. Each R1 is independently selected from H, C1-18 alkyl, and C2-18 alkenyl; R2b is C1-8 alkyl; subscript y is an integer ranging from 0 to 17; and subscript z is an integer ranging from 0 to 17. In certain embodiments, the metathesis catalyst is a tungsten catalyst or a molybdenum catalyst. In various embodiments, the fatty olefin derivative is a pheromone. Pheromone compositions and methods of using them are also described.

Transamidation of carboxamides catalyzed by Fe(III) and water

The highly efficient transamidation of several primary, secondary, and tertiary amides with aliphatic and aromatic amines (primary and secondary) is described. The reaction is performed in the presence of a 5 mol % concentration of different hydrated salts of Fe(III), and the results show that the presence of water is crucial. The methodology was also applied to urea and phthalimide to demonstrate its versatility and wide substrate scope. An example of its use is an intramolecular application in the synthesis of 2,3-dihydro-5H-benzo[b]-1,4- thiazepin-4-one, which is the bicyclic core of diltiazem and structurally related drugs (Budriesi, R.; Cosimelli, B.; Ioan, P.; Carosati, E.; Ugenti, M. P.; Spisani, R. Curr. Med. Chem. 2007, 14, 279-287). A plausible mechanism that explains the role of water is proposed on the basis of experimental observations and previous mechanistic suggestions for transamidation reactions catalyzed by transition metals such as copper and aluminum. This methodology represents a significant improvement over other existing methods; it can be performed in air and with wet or technical grade solvents.

Synthesis, crystal structure, vibration spectral, and DFT studies of 4-Aminoantipyrine and its derivatives

Three compounds derived from 4-Aminoantipyrine (AA) were synthesized and their structures confirmed by melting point, elemental analysis, FT-IR, and 1H-NMR. The molecular structures of the four compounds were characterized by single-crystal X-ray diffraction and calculated by using the density functional theory (DFT) method with 6-31G (d) basis set. The calculated molecular geometries and the vibration frequencies of the AA derivatives in the ground state have been compared with the experimental data. The results show that the optimized geometries can reproduce well the crystal structural parameters, and the theoretical vibration frequencies show good agreement with the experimental data, although the experimental data are different from the theoretical ones due to the intermolecular forces. Besides, the molecular electrostatic potential (MEP) and the frontier molecular orbital (FMO) analysis of the compounds were investigated by theoretical calculations.

A direct, straightforward conversion of methoxymethyl ethers into acetates

The direct transformation of MOM-protected alcohols into the corresponding acetates by acetic anhydride/ferric chloride in CH2Cl2, in a one-step process and good to excellent yields, is reported. The reaction has been applied to a variety of substrates and occurs with retention of configuration.

A versatile approach to the synthesis of 9(Z)-unsaturated acyclic insect pheromones from undec-10-enoic acid

A general approach to the synthesis of 9(Z)-unsaturated acyclic insect pheromones from undec-10-enoic acid was developed. The method comprises the conversion of the acid into undec-10-enyl acetate, shortening of its carbon chain to afford dec-9-enyl acetate (via 11-acetoxyundecanoic acid), and a two-step transformation of the latter into the key intermediate, dec-9-yn-1-ol, by sequential bromination - dehydrobromination. The elimination of two HBr molecules from the dibromide is effectively performed using Bu1OK in the presence of dibenzo-18-crown-6 as the catalyst.