7510-56-7

Usage

Uses

Used in Synthetic Organic Chemistry Research:
4-Phenyl-1H-pyrazole-3-carboxylic acid is utilized as a key intermediate in the synthesis of various organic compounds. Its unique structure allows for the development of novel chemical entities with potential applications in different fields.
Used in Pharmaceutical Development:
Due to its structural features, 4-Phenyl-1H-pyrazole-3-carboxylic acid can be used as a building block in the design and synthesis of new pharmaceutical agents. Its potential biological activities and interactions with biological targets may contribute to the discovery of new drugs.
Used in Material Science:
4-Phenyl-1H-pyrazole-3-carboxylic acid's structural properties may also find applications in material science, where it could be used to develop new materials with specific properties, such as conductivity, magnetism, or optical characteristics.

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

Upstream product

• 5932-28-5 4-phenyl-1H-pyrazole-3-carboxylic acid methyl ester 
• 6963-62-8 ethyl 4-phenyl-1H-pyrazole-3-carboxylate 
• 13788-84-6 3-Methyl-4-phenyl-1H-pyrazole 
• 60676-51-9 methyl (Z)-2-(acetylamino)-3-phenylpropenoate 
• 21462-02-2 methyl (Z)-2-benzoylamino-3-phenyl-2-propenoate 
• 96791-17-2 cis-4-phenyl-3-acetamido-3-carbomethoxy-Δ¹-pyrazoline 
• 96791-18-3 cis-4-phenyl-3-benzamido-3-carbomethoxy-Δ¹-pyrazoline 
• 4360-47-8 cinnamonitrile 
• 705-60-2 1-phenyl-2-nitroprop-1-ene 
• 408314-96-5 5-methyl-5-nitro-4-phenyl-4,5-dihydro-1H-pyrazole 
• 102-96-5 (2-nitroethenyl)benzene 
• 89864-91-5 3-cyano-4-phenyl-5-trimethylsilylpyrazole 
• 103-36-6 ethyl 3-phenyl-2-propenoate 
• 96256-53-0 4-phenyl-3-(trifluoromethyl)-1H-pyrazole 

Downstream Products

• 10199-69-6 1-methyl-4-phenyl-1H-pyrazole 
• 10199-68-5 4-phenyl-1H-pyrazole 

Relevant academic research and scientific papers

Preparations of 4-substituted 3-carboxypyrazoles

The scopes of three synthetic methods reported for the preparation of an array of 3-pyrazolecarboxylates featuring substituents on position 4 were investigated. The first one is based on the potassium permanganate oxidation of methylpyrazoles. The second starts with the condensation between DMF dimethylacetal and ethyl pyruvate and is followed by the addition of hydrazine hydrochloride. The last one makes use of the cycloaddition of diazomethane on acrylate esters followed by a bromine-based oxidative rearrangement into 4-substituted 3-pyrazole esters.

Pyrazole-3/5-carboxylic acids from 3/5-trifluoromethyl NH-pyrazoles

We report here the transformation of 3/5-trifluoromethylpyrazoles derivative into the corresponding NH-pyrazole-3/5-carboxylic acids. Moreover, from 4- or 5-iodinated-3/5-trifluoromethylpyrazoles building blocks and the use of Suzuki-Miyaura or Negishi reactions followed by the trifluoromethyl hydrolysis, we illustrate short and original accesses to many series of NH-pyrazole-3/5-carboxylic acids otherwise difficult to prepare.

COMBINATIONS OF PYRAZOLE KINASE INHIBITORS AND FURTHER ANTITUMOR AGENTS

The invention provides a combination of a compound having the formula (0) and two or more further anti-cancer agents: or salts or tautomers or N-oxides or solvates thereof; wherein X is a group R1-A-NR4- or a 5- or 6-membered carbocyclic or heterocyclic ring; A is a bond, SO2, C=O, NR9(C=O) or 0(C=O) wherein R9 is hydrogen or C1-4 hydrocarbyl optionally substituted by hydroxy or C1-4 alkoxy; Y is a bond or an alkylene chain of 1 , 2 or 3 carbon atoms in length; R1 is hydrogen; a carbocyclic or heterocyclic group having from 3 to 12 ring members; or a C1-8 hydrocarbyl group optionally substituted by one or more substituents selected from halogen (e.g. fluorine), hydroxy, C1-4 hydrocarbyloxy, amino, mono- or di-C1-4 hydrocarbylamino, and carbocyclic or heterocyclic groups having from 3 to 12 ring members, and wherein 1 or 2 of the carbon atoms of the hydrocarbyl group may optionally be replaced by an atom or group selected from O, S, NH, SO, SO2; R2 is hydrogen; halogen; C1-4 alkoxy (e.g. methoxy); or a C1-4 hydrocarbyl group optionally substituted by halogen (e.g. fluorine), hydroxyl or C1-4 alkoxy (e.g. methoxy); R3 is selected from hydrogen and carbocyclic and heterocyclic groups having from 3 to 12 ring members; and R4 is hydrogen or a C1-4 hydrocarbyl group optionally substituted by halogen (e.g. fluorine), hydroxyl or C1-4 alkoxy (e.g. methoxy).

PHARMACEUTICAL COMPOUNDS

The invention provides a combination of a cytotoxic compound or signalling inhibitor and a compound having the formula (0): or salts or tautomers or N-oxides or solvates thereof; wherein X is a group R1-A-NR4- or a 5- or 6-membered carbocyclic or heterocyclic ring; A is a bond, SO2, C=O, NRg(C=O) or 0(C=O) wherein Rg is hydrogen or C1-4 hydrocarbyl optionally substituted by hydroxy or C1-4alkoxy; Y is a bond or an alkylene chain of 1, 2 or 3 carbon atoms in length; R1 is hydrogen; a carbocyclic or heterocyclic group having from 3 to 12 ring members; or a C1-8hydrocarbyl group optionally substituted by one or more substituents selected from halogen (e.g. fluorine), hydroxy, C1-4 hydrocarbyloxy, amino, mono- or di-C1-4 hydrocarbylamino, and carbocyclic or heterocyclic groups having from 3 to 12 ring members, and wherein 1 or 2 of the carbon atoms of the hydrocarbyl group may optionally be replaced by an atom or group selected from O, S, NH, SO, SO2; R2 is hydrogen; halogen; C1-4 alkoxy (e.g. methoxy); or a C1-4 hydrocarbyl group optionally substituted by halogen (e.g. fluorine), hydroxyl or C1-4alkoxy (e.g. methoxy); R3 is selected from hydrogen and carbocyclic and heterocyclic groups having from 3 to 12 ring members; and R4 is hydrogen or a C1-4 hydrocarbyl group optionally substituted by halogen (e.g. fluorine), hydroxyl or C1-4 alkoxy (e.g. methoxy).

PHARMACEUTICAL COMPOUNDS

The invention provides a combination of an ancillary agent and a compound having the formula (0): or salts or tautomers or N-oxides or solvates thereof; wherein the ancillary agent is selected from: a monoclonal antibody, an alkylating agent, an anticancer agent, a further CDK inhibitor and a hormone, hormone agonist, hormone antagonist or hormone modulating agent; X is a group R1-A-NR4- or a 5- or 6-membered carbocyclic or heterocyclic ring; A is a bond, SO2, C=O, NR9(C=O) or 0(C=O) wherein R9 is hydrogen or C1-4hydrocarbyl optionally substituted by hydroxy or C1-4 alkoxy; Y is a bond or an alkylene chain of 1 , 2 or 3 carbon atoms in length; R1 is hydrogen; a carbocyclic or heterocyclic group having from 3 to 12 ring members; or a C1-8 hydrocarbyl group optionally substituted by one or more substituents selected from halogen (e.g. fluorine), hydroxy, C1-4 hydrocarbyloxy, amino, mono- or di-C1-4 hydrocarbylamino, and carbocyclic or heterocyclic groups having from 3 to 12 ring members, and wherein 1 or 2 of the carbon atoms of the hydrocarbyl group may optionally be replaced by an atom or group selected from O, S, NH, SO, SO2; R2 is hydrogen; halogen; C1-4alkoxy (e.g. methoxy); or a C1-4 hydrocarbyl group optionally substituted by halogen (e.g. fluorine), hydroxyl or C1-4 alkoxy (e.g. methoxy); R3 is selected from hydrogen and carbocyclic and heterocyclic groups having from 3 to 12 ring members; and R4 is hydrogen or a C1-4hydrocarbyl group optionally substituted by halogen (e.g. fluorine), hydroxyl or C1-4 alkoxy (e.g. methoxy).

NEW EFFICIENT SYNTHESIS OF 3(5)-CARBOMETHOXY-4-ARYLPYRAZOLES FROM 3-ARYL-2,3-DEHYDROAMINO ACID DERIVATIVES

3(5)-Carbomethoxy-4-arylpyrazoles can be easily obtained by aromatization with boron trifluoride etherate of 4-aryl-3-acetamido(or benzamido)-3-carbomethoxy-Δ1-pyrazolines synthesized by 1,3-dipolar cycloaddition of diazomethane with 3-aryl-2,3