866588-11-6

Basic information

• Product Name: 3-(4-FLUOROPHENYL)-1H-PYRAZOLE-5-CARBOXYLIC ACID ETHYL ESTER
• Synonyms: 3-(4-FLUOROPHENYL)-1H-PYRAZOLE-5-CARBOXYLIC ACID ETHYL ESTER;ethyl 5-(4-fluorophenyl)-1H-pyrazole-3-carboxylate
• CAS NO: 866588-11-6
• Molecular Formula: C₁₂H₁₁FN₂O₂
• Molecular Weight: 234.2263432
• Mol File: 866588-11-6.mol

Chemical Properties

• Boiling Point: 424.2°C at 760 mmHg
• Flash Point: 210.3°C
• Appearance: /
• Density: 1.266g/cm³
• Vapor Pressure: 2.11E-07mmHg at 25°C
• Refractive Index: 1.559
• CAS DataBase Reference: 3-(4-FLUOROPHENYL)-1H-PYRAZOLE-5-CARBOXYLIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-FLUOROPHENYL)-1H-PYRAZOLE-5-CARBOXYLIC ACID ETHYL ESTER(866588-11-6)
• EPA Substance Registry System: 3-(4-FLUOROPHENYL)-1H-PYRAZOLE-5-CARBOXYLIC ACID ETHYL ESTER(866588-11-6)

Safety Data

• Hazardous Substances Data: 866588-11-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-(4-Fluorophenyl)-1H-pyrazole-5-carboxylic acid ethyl ester is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its unique structure and functional groups make it a valuable building block in the development of new drugs.
Used in Organic Synthesis:
3-(4-Fluorophenyl)-1H-pyrazole-5-carboxylic acid ethyl ester is used as a reagent in organic synthesis, where its functional groups can be manipulated to form a variety of complex molecules. Its versatility in reactions makes it a useful tool in the synthesis of organic compounds.
Used in Research and Development:
3-(4-Fluorophenyl)-1H-pyrazole-5-carboxylic acid ethyl ester is used as a subject of research in the context of developing novel chemical entities. Its unique properties and potential applications make it an interesting candidate for further exploration and development in various fields.

InChI:InChI=1/C12H11FN2O2/c1-2-17-12(16)11-7-10(14-15-11)8-3-5-9(13)6-4-8/h3-7H,2H2,1H3,(H,14,15)

Upstream product

• 766-98-3 1-ethynyl-4-fluorobenzene 
• 98684-92-5 ethyl diazoacetate 
• 1224879-05-3 (Z)-ethyl 4-(4-fluorophenyl)-2-hydroxy-4-oxobut-2-enoate 
• 1450626-62-6 C₁₄H₁₄FNO₆ 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 31686-94-9 ethyl 4-(4-fluorophenyl)-2,4-dioxobutanoate 
• 623-73-4 diazoacetic acid ethyl ester 
• 405-99-2 para-fluorostyrene 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 64-17-5 ethanol 
• 890006-82-3 5-(4-fluoro-phenyl)-1H-pyrazole-3-carboxylic acid 
• 95-92-1 oxalic acid diethyl ester 

Downstream Products

• 1029088-09-2 ethyl 5-(4-fluorophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-3-carboxylate 
• 1137165-21-9 (3-(4-fluorophenyl)-1H-pyrazol-5-yl)methanol 
• 1107467-72-0 3-(4-fluoroyphenyl)-1H-pyrazole-5-carbaldehyde 

Relevant articles and documents

COMPOUNDS AS CASEIN KINASE INHIBITORS

Provided are novel casein kinase inhibitors, or pharmaceutically acceptable salts thereof. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also provided.

A new synthetic approach for pyrazolo[1,5-a]pyrazine-4(5H)-one derivatives and their antiproliferative effects on lung adenocarcinoma cell line

Abstract: Starting from the 3,5-dimethyl pyrazole ring and acetophenone derivatives, five different N-propargylated C-3 substituted pyrazoles were obtained. These derivatives were reacted with different amine derivatives using Cs2CO3 in methanol and 11 different pyrazolo [1,5-a] pyrazine-4(5H)-one derivatives were obtained, which are not found in the literature. The cytotoxic effects of these derivatives in the A549 cell line were investigated. The 160?μM concentration of two derivatives was found to increase cell death rate to 50%, and two derivatives increased cell death rate by up to 40%. The structure–activity relationship (SAR) study revealed an amide group with a long alkyl chain and benzene ring with a p-CF3 group could be important for efficiency. With theoretical ADMET studies of pyrazolopyrazine derivatives, pharmacokinetic phases were predicted to be suitable. Graphic abstract: [Figure not available: see fulltext.].

Design, synthesis, and biological evaluation of novel thiazolyl substituted bis-pyrazole oxime derivatives with potent antitumor activities by selectively inducing apoptosis and ros in cancer cells

Background: A large number of pyrazole derivatives have different biological activities such as anticancer, antimicrobial, anti-inflammatory, analgesic and antiepileptic activity. Among them, pyrazole oximes have attracted much attention due to their potential pharmacological activities, particularly anticancer activities. Objective: Our goal is to synthesize novel thiazolyl substituted bis-pyrazole oxime derivatives with potent antitumor activities by selectively inducing apoptosis and Reactive Oxygen Species (ROS) accumulation in cancer cells. Methods: Eighteen bis-pyrazole oximes were synthesized by conjugating thiazolyl substituted pyrazoles with pyrazoxime. The target compounds were characterized by1HNMR,13C NMR, and HRMS, and screened for their antiproliferative activity against four cancer cells in MTT assay. The most potent compound was examined for its inhibitory effect and ROS accumulation in both cancer cells HCT116 and normal intestinal epithelial cells CCD841. Finally, the most potent compound was further evaluated for its apoptotic induction by flow cytometry analysis and immunoblot analysis of apoptosis-related proteins and DNA damage proteins. Results: Most compounds displayed potent antiproliferative activity against four cancer cell lines in vitro, displaying potencies superior to 5-FU. In particular, the most potent compound 13l selectively inhibited proliferation of colorectal cancer HCT116 cells but not normal colon CCD841 cells. Furthermore, compound 13l also selectively promoted intracellular ROS accumulation in HCT116 which was involved in 13l inhibition of cancer cell proliferation and induction of cell apoptosis. Finally, compound 13l also dose-dependently induced cancer cell apoptosis by regulating apoptotic and DNA damage related proteins expressions. Conclusion: Our synthetic bis-pyrazole oxime derivatives possess potent antitumor activities by selectively inducing apoptosis and ROS accumulation in cancer cells, which may hold great promise as therapeutic agents for the treatment of human cancers.

The First Example of Azole-Fused Cyclic Anhydride Reacting in the Castagnoli-Cushman Way

Pyrazole-fused cyclic anhydrides have been employed for the first time as the Castagnoli-Cushman reaction partners to produce hitherto unknown 4-oxo-4,5,6,7-tetrahydropyrazolo[1,5- a ]pyrazine-7-carboxylates in remarkably convenient and speedy fashion. At

1. 3, 5 - tri-substituted pyrazole compound and its preparation method and application

The invention discloses 1,3,5-trisubstituted pyrazole compounds, and a preparation method and application thereof. The structure of the compounds is shown as a general formula (I), and in the general formula (I), R1 is hydrogen, halogens, methyl or triflu

Synthesis and biological evaluation of 3-(4-fluorophenyl)-1H-pyrazole derivatives as androgen receptor antagonists

A novel series of 3-(4-fluorophenyl)-1H-pyrazole derivatives were synthesized and evaluated for their antiproliferative activity against two prostate cancer cell lines (LNCaP and PC-3) and androgen receptor target gene prostate-specific antigen (PSA) inhibitory activity in LNCaP cells. Several compounds showed potent antiproliferative activity against LNCaP cells and showed a promising PSA downregulation rate. Among these, compound 10e selectively inhibited LNCaP cell growth with an IC50 value of 18 μmol/l and showed a PSA downregulation rate of 46%, which was better than the lead compound T3.

Substituted pyrazolo-piperazines as casein kinase 1 δ/ε inhibitors

The invention provides compounds of Formula (I): and pharmaceutically acceptable salts thereof. The compounds of Formula (I) inhibit protein kinase activity thereby making them useful as anticancer agents.

COMPOUNDS CAPABLE OF INHIBITING VOLTAGE GATED CALCIUM ION CHANNEL, AND PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME

Disclosed herein are an N-(pyrazolylmethyl)arylsulfonamide derivative useful as a calcium ion channel blocker, a pharmaceutically acceptable salt thereof, and the medicinal use thereof as a therapeutic agent using its calcium ion channel blocking effect.

Synthesis of (Z)-(arylamino)-pyrazolyl/isoxazolyl-2-propenones as tubulin targeting anticancer agents and apoptotic inducers

A new class of pyrazole and isoxazole conjugates were synthesized and evaluated for their cytotoxic activity against various human cancer cell lines. These compounds have shown significant cytotoxicity with lower IC50 values. FACS results revealed that A549 cells treated with these compounds arrested cells at the G2/M phase of the cell cycle apart from activating cyclin B1 protein levels. Particularly, compounds 9a and 9b demonstrated a remarkable inhibitory effect on tubulin polymerization and showed a pronounced inhibitory effect on tubulin polymerization with IC50 values of 1.28 μM and 0.28 μM respectively, whereas nocodazole, a positive control, has shown lower antitubulin activity with an IC50 value of 2.64 μM. Furthermore, these compounds induced apoptosis by loss of mitochondrial membrane potential, propidium iodide (PI) staining and the activation of caspase-3. Results of a fluorescence based competitive colchicine binding assay suggest that these conjugates bind successfully at the colchicine binding site of tubulin. These investigations reveal that such conjugates containing pyrazole with a trimethoxy phenyl ring and indole moieties have potential for the development of newer chemotherapeutic agents. This journal is