78703-53-4

Usage

Uses

Used in Pharmaceutical Industry:
1H-Pyrazole-4-carboxylic acid, 1,3-dimethyl-(9CI) is utilized as a key intermediate in the synthesis of various pharmaceuticals. Its incorporation into drug molecules is driven by its ability to enhance the pharmacological properties of the final products, such as potency, selectivity, and bioavailability.
Used in Medicinal Chemistry:
In the realm of medicinal chemistry, 1H-Pyrazole-4-carboxylic acid, 1,3-dimethyl-(9CI) serves as a valuable component in the design and development of new therapeutic agents. Its unique structure allows for the fine-tuning of drug candidates to target specific biological pathways or receptors, thereby increasing the effectiveness and selectivity of treatments.
Used in Drug Design:
1H-Pyrazole-4-carboxylicacid,1,3-dimethyl-(9CI) is also employed in drug design to create novel molecules with improved pharmacokinetic and pharmacodynamic profiles. Its presence in a drug molecule can influence factors such as solubility, stability, and the overall drug's interaction with its biological target.
Used in Agrochemicals:
1H-Pyrazole-4-carboxylic acid, 1,3-dimethyl-(9CI) may find applications in the agrochemical industry, potentially serving as a component in the development of new pesticides or herbicides. Its structural features could contribute to the creation of compounds with enhanced efficacy and selectivity in controlling pests or unwanted plant growth.
Used in Materials Science:
In the field of materials science, 1H-Pyrazole-4-carboxylicacid,1,3-dimethyl-(9CI) could be explored for its potential to contribute to the development of new materials with specific properties. Its chemical structure may allow for the engineering of materials with tailored characteristics for use in various applications, such as sensors, catalysts, or advanced materials for specific industries.

InChI:InChI=1/C6H8N2O2/c1-4-5(6(9)10)3-8(2)7-4/h3H,1-2H3,(H,9,10)

Upstream product

• 6214-65-9 5-acetyluracil 
• 60-34-4 methylhydrazine 
• 27006-82-2 5-chloro-1,3-dimethyl-4-pyrazolecarboxylic acid 
• 141-97-9 ethyl acetoacetate 
• 109-94-4 formic acid ethyl ester 
• 49836-24-0 (E)-2-(ethoxymethylene)-3-oxobutanoic acid ethyl ester 
• 134653-70-6 ethyl 2-[(dimethylamino)methylene]-3-oxobutanoate 
• 85290-78-4 ethyl 3-methylpyrazole-4-carboxylate 
• 3788-94-1 2-ethoxymethylene-3-oxobutanoic acid ethyl ester 
• 25016-12-0 1,3-dimethyl-1H-pyrazole-4-carbaldehyde 
• 85290-76-2 1-methyl-3-methyl-1H-pyrazole-4-carboxylic acid ethyl ester 
• 27006-76-4 5-chloro-4-formyl-1,3-dimethylpyrazole 
• 85290-70-6 5-chloro-N-<1,3-dimethyl-4-(phenylcarbamoyl)pyrazol-5-yl>-1,3-dimethyl-N-phenylpyrazole-4-carboxamide 
• 64429-35-2 1,3-dimethyl-5-oxo-N-phenyl-4,5-dihydro-1H-pyrazole-4-carboxamide 

Downstream Products

• 124845-21-2 1,3-dimethyl-1H-pyrazole-4-carboxamide 
• 113100-61-1 1,3-dimethyl-1H-pyrazole-4-carboxylic acid chloride 
• 103946-59-4 (1,3-dimethyl-1H-pyrazol-4-yl)methanol 
• 5775-82-6 4-bromo-1,3-dimethyl-1H-pyrazole 
• 78703-55-6 methyl 1,3-dimethyl-1H-pyrazole-4-carboxylate 

Relevant academic research and scientific papers

Synthesis method of 1, 3-dimethyl-1H-pyrazole-4-carboxylic acid

The invention relates to a synthesis method of 1, 3-dimethyl-1H-pyrazole-4-carboxylic acid, and the method comprises the following steps: 1, carrying out condensation reaction on N, N-dimethylamino ethyl acrylate, triethylamine and acetyl chloride to generate ethyl 2-dimethylamino-3-oxobutyrate and triethylamine hydrochloride; 2, carrying out a cyclization reaction on 2-dimethylamino ethyl-3-oxobutyrate and methylhydrazine to generate 1, 3-dimethyl-1H-pyrazole ethyl-4-formate and a dimethylamine aqueous solution; 3, carrying out a reaction on formic acid, ethyl acetoacetate and dimethylamine generated in the step 2 cyclization reaction to generate 2-dimethylamino ethyl-3-oxobutyrate and water, wherein the ethyl 2-dimethylamino-3-oxobutyrate generated in the step 3 is recycled as a reactantin the step 2; 4, hydrolyzing the ethyl 1, 3-dimethyl-1H-pyrazole-4-formate to obtain the 1, 3-dimethyl-1H-pyrazole-4-carboxylic acid. The 1, 3-dimethyl-1H-pyrazole-4-carboxylic acid has the advantages of few synthesis steps, safe reaction process and no three-waste pollution, and is suitable for industrial batch large-scale preparation.

Expedient discovery for novel antifungal leads targeting succinate dehydrogenase: Pyrazole-4-formylhydrazide derivatives bearing a diphenyl ether fragment

The pyrazole-4-carboxamide scaffold containing a flexible amide chain has emerged as the molecular skeleton of highly efficient agricultural fungicides targeting succinate dehydrogenase (SDH). Based on the above vital structural features of succinate dehydrogenase inhibitors (SDHI), three types of novel pyrazole-4-formylhydrazine derivatives bearing a diphenyl ether moiety were rationally conceived under the guidance of a virtual docking comparison between bioactive molecules and SDH. Consistent with the virtual verification results of a molecular docking comparison, the in vitro antifungal bioassays indicated that the skeleton structure of title compounds should be optimized as an N′-(4-phenoxyphenyl)-1H-pyrazole-4-carbohydrazide scaffold. Strikingly, N′-(4-phenoxyphenyl)-1H-pyrazole-4-carbohydrazide derivatives 11o against Rhizoctonia solani, 11m against Fusarium graminearum, and 11g against Botrytis cinerea exhibited excellent antifungal effects, with corresponding EC50 values of 0.14, 0.27, and 0.52 μg/mL, which were obviously better than carbendazim against R. solani (0.34 μg/mL) and F. graminearum (0.57 μg/mL) as well as penthiopyrad against B. cinerea (0.83 μg/mL). The relative studies on an in vivo bioassay against R. solani, bioactive evaluation against SDH, and molecular docking were further explored to ascertain the practical value of compound 11o as a potential fungicide targeting SDH. The present work provided a non-negligible complement for the structural optimization of antifungal leads targeting SDH.

Method for synthesizing 1,3-dimethyl-1H-pyrazole-4-carboxylic acid

The invention relates to a method for synthesizing 1,3-dimethyl-1H-pyrazole-4-carboxylic acid. The method comprises the step that 1,3-dimethyl-1H-pyrazole-4-carboxylic acid is prepared from the raw material: ethyl acetoacetate through condensation and ring closure, formylation, reductive dechlorination and oxidation. Compared with an existing method, the method has lower reaction cost, a higher yield and better economic performance; and the problems such as cost and environmental pollution caused by heavy metal oxidation are solved, and conditions are created for industrialization.

(1H-pyrazole-4-carboxamido) ethyl benzoate compound as well as preparation method and application thereof

The invention discloses an ethyl (1H-pyrazole-4-carboxamido) benzoate compound as well as a preparation method and application thereof. The structural formula of the (1H-pyrazole-4-carboxamido) ethylbenzoate compound is as shown in the formula (I), wherein the substituent groups R1 are phenyl or substituted phenyl, the number of substituent groups on a benzene ring of the substituted phenyl is one or more, and each substituent group is independently selected from H, halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C3 halogenated alkyl or nitro; and the substituent R2 is methyl, monofluoromethyl, difluoromethyl or trifluoromethyl. The invention discloses a novel compound with bactericidal activity, which is simple in preparation method and convenient to operate, and the obtained compound has betterinhibitory activity on pathogenic bacteria such as cucumber botrytis cinerea, fusarium oxysporum, cucumber corynespora leaf spot and the like under the concentration of 50 mg/mL.

Application of 1,3-dimethyl-1H-pyrazole-4-amide derivatives to herbicide preparation

The invention relates to an application of 1,3-dimethyl-1H-pyrazole-4-amide derivatives to herbicide preparation. Lettuce and Agrostis seeds are taken as test objects, and the following steps are carried out: sample treatment: the seeds are subjected to surface sterilization with 5%-10% Chlorox solution for 10 min before bioassay, and then the seeds are washed thoroughly by deionized water in a Millipore system and aired in an aseptic environment; sample treatment: 1 mM solutions are prepared from all samples by adopting acetone as a solvent; bioassay: bioassay is performed finally, and obtained compounds show better inhibition for lettuce and Agrostis. The compounds are new compounds with herbicidal activity, and the basis is provided for research and development of new pesticides.

Synthesis and Nematocidal Activity of N-Substituted 3-Methyl-1H-pyrazole-4-carboxamide Derivatives Against Meloidogyne incognita

A series of novel pyrazole carboxamides were designed and synthesized through multi-step reactions from ethyl acetoacetate and triethyl orthoformate, and their structures were characterized by Fourier transform infrared, 1H-NMR, 13C-NMR, mass spectrometry, and elemental analysis. The preliminary insecticidal activity showed that some of them possessed good insecticidal activities against Meloidogyne incognita.

1,3-dimethyl-1H-pyrazole-4-amide derivative as well as preparation method and application thereof

The invention relates to a 1,3-dimethyl-1H-pyrazole-4-amide derivative as well as a preparation method and application thereof. The derivative is prepared by the steps of carrying out reflux on ethylacetoacetate and triethyl orthoformate in acetic anhydride, adding into methylhydrazine so as to prepare 1,3-dimethyl-1H-pyrazole-4-ethyl formate, carrying out hydrolysis, adding hydrochloric acid soas to prepare 1,3-dimethyl-1H-pyrazole-4-carboxylic acid, reacting by virtue of 1,3-dimethyl-1H-pyrazole-4-carboxylic acid and sulfoxide chloride, adding dichloromethane for dilution, and adding arylalkylamine and triethylamine, so as to prepare the 1,3-dimethyl-1H-pyrazole-4-amide derivative. The preparation method is simple and convenient in operation; the obtained compound has optimal inhibitory activity to sclerotinia sclerotiorum at 50ppm, and the inhibition ratio reaches 87.5%; the obtained compound has relatively good inhibitory activity to macrophoma kawatsukai, and the inhibition ratio is equal to that of a contrast medicament; and the compound is a novel compound with bactericidal activity, and the foundation is provided for the research and development of novel pesticides.

Acyl thiourea compound containing 1,3-dimethyl-1H-pyrazole structure and preparation method and application thereof

The invention discloses an acyl thiourea compound containing a 1,3-dimethyl-1H-pyrazole structure and a preparation method and application thereof. The preparation method comprises the following steps: firstly using ethyl acetoacetate, triethyl orthoforma

Acyl urea compound containing 1,3-dimethyl-1H-pyrazole structure and preparation method and application thereof

The invention discloses an acyl urea compound containing a 1,3-dimethyl-1H-pyrazole structure and a preparation method and application thereof. The preparation method comprises the following steps: firstly using ethyl acetoacetate, triethyl orthoformate and methylhydrazine as raw materials to synthesize 1,3-dimethyl-1H-pyrazole-4-formic acid, performing the amidation to obtain 1,3-dimethyl-1H-pyrazole-4-formamide, and reacting with oxalyl chloride and substituted anilines to obtain a final product (I). The raw materials are simple and are easily obtained, the preparation method is simple, the aftertreatment is convenient, and the product yield is high. The compound has the antifungal activity, and has the good sterilizing effect in allusion to sclerotinia sclerotiorum, rhizoctonia solani, Cercospora arachidicola Hori, Macrophoma kawatsukai, and alternaria solani especially. The foundation is provided for new pesticide research and development.

Amide compound containing methylpyrazole and preparation method the application thereof

The invention discloses an amide compound containing methylpyrazole and a preparation method the application thereof. The compound, namely the N-substituted-(1,3-dimethyl-1H-pyrazol-4-yl) is a new compound having nematocidal activity and is especially used for preventing and controlling meloidogyn incognita and the like, and a foundation is provided for research and development of new pesticides.