36590-52-0

Usage

InChI:InChI=1/C13H10Cl2N2/c14-11-8-6-10(7-9-11)13(15)17-16-12-4-2-1-3-5-12/h1-9,16H/b17-13-

Upstream product

• 2829-26-7 N-(4-chlorobenzylidene)-N'-phenylhydrazine 
• 873-76-7 para-Chlorobenzyl alcohol 
• 100-63-0 phenylhydrazine 
• 122-01-0 4-chloro-benzoyl chloride 
• 74-11-3 para-chlorobenzoic acid 
• 15089-07-3 2-(4-Chlorbenzoyl)-1-phenylhydrazid 
• 104-88-1 4-chlorobenzaldehyde 

Downstream Products

• 117600-57-4 3-(4-Chlorphenyl)-1,8a-dihydro-1-phenyl<1,2,4>triazolo<4,3-a>pyridin 
• 128671-04-5 3-(4-Chloro-phenyl)-1-phenyl-1H-pyrazolo[3,4-b]pyrazine 
• 128671-03-4 2-[(4-Chloro-phenyl)-(phenyl-hydrazono)-methyl]-2H-[1,2,4]triazol-3-ylamine 
• 128901-00-8 3-(4-Chloro-phenyl)-1,4,7-triphenyl-8-thia-1,2,6-triaza-spiro[4.4]nona-2,6-dien-9-one 
• 132703-81-2 N-[1-(4-Chloro-phenyl)-1-[1,2,4]triazol-4-yl-meth-(E)-ylidene]-N'-phenyl-hydrazine 
• 128670-98-4 3-(4-Chloro-phenyl)-7-[(4-chloro-phenyl)-(phenyl-hydrazono)-methyl]-1-phenyl-1H-pyrazolo[5,1-c][1,2,4]triazol-6-one 
• 128670-96-2 3-(4-Chloro-phenyl)-6-methyl-1-phenyl-1H-pyrazolo[5,1-c][1,2,4]triazole 
• 128670-93-9 3-(4-Chloro-phenyl)-1,6-diphenyl-1H-pyrazolo[5,1-c][1,2,4]triazole 
• 17359-64-7 3-(4-Chlorphenyl)-5-methyl-1-phenyl-2-pyrazolin-5-carbonsaeure-methylester 
• 117600-66-5 3-(4-Chloro-phenyl)-1-phenyl-1H-[1,2,4]triazolo[4,3-a]pyridin-4-ylium; perchlorate 
• 1036487-58-7 2-p-chlorobenzoylbenzotriazole phenylhydrazone 
• 1036487-56-5 1-p-chlorobenzoylbenzotriazole phenylhydrazone 
• 1112193-93-7 2-(2-(3-(4-chlorophenyl)-1-phenyl-1H-pyrazol-5-yl)propan-2-yl)-N-methylaniline 
• 1107664-61-8 (E)-2-(1,3-dimethyl-1H-[1,2]pyrazol-4-ylcarbonylimino)-5-(p-chlorophenyl)-3-phenyl-2,3-dihydro-[1,3,4]thiadiazole 

Relevant academic research and scientific papers

Regioselective Decarboxylative Cycloaddition Route to Fully Substituted 3-CF3-Pyrazoles from Nitrilimines and Isoxazolidinediones

1,4-Diaryl-5-carboxamido substituted 3-trifluoromethylpyrazoles are obtained with exclusive regioselectivity under transition-metal-free conditions. This decarboxylative [3+2] cycloaddition protocol was enabled by employing trifluoromethyl nitrilimines as 1,3-dipoles, and isoxazolidinediones as CO2-masked alkynyl dipolarophiles. The applicability of this method is further manifested by its compatibility with difluoromethyl, alkyl, aryl, and heteroaryl nitrilimines, as well as the preparation of 4-carboxylic amido analogue of drug Celebrex. (Figure presented.).

Sequential [3+2] annulation reaction of prop-2-ynylsulfonium salts and hydrazonyl chlorides: Synthesis of pyrazoles containing functional motifs

A novel sequential [3+2] annulation reaction has been developed using prop-2-ynylsulfonium salts and hydrazonyl chlorides, affording a series of pyrazoles with functional motifs that can be post modified in the preparation of various drugs or drug candidates. Further transformation and gram-scale operations could also be achieved efficiently. This journal is

Copper-Catalyzed Tandem Dehydrocyanation and [3+2] Cyclo-addition Reactions of Phenacylmalononitriles: Regioselective Synthesis of Functionalized 4-Benzoyl-5-cyanopyrazoles under Mild Conditions

A novel copper-catalyzed [3+2] cycloaddition reaction with concomitant in situ generation of benzoylacrylonitriles and nitrile imines from phenacylmalononitriles and hydrazonoyl chlorides, respectively, is reported. The reaction was performed using copper(I) chloride as catalyst and N-methylimidazole as a clean complexing agent/weak base to afford the functionalized 4-benzoyl-5-cyanopyrazoles in moderate to good yields and excellent regioselectivity under ambient conditions. This method provides rapid access to a wide range of highly functionalized 4-benzoyl-5-cyanopyrazoles.

A formal [3+2] cycloaddition reaction of: N -methylimidazole as a masked hydrogen cyanide: Access to 1,3-disubstitued-1 H -1,2,4-triazoles

N-Methylimidazole (NMI) can act as a masked HCN in the synthesis of 1,3-disubstitued-1H-1,2,4-triazoles via a formal cycloaddition reaction of hydrazonoyl chloride with NMI. The product was proved to be formed via an initial nucleophilic substitution of hydrazonoyl chloride with NMI following cyclization and two sequential C-N bond cleavages. This journal is

Facile One-Pot Transformation of Primary Alcohols into 3-Aryl- and 3-Alkyl-isoxazoles and -pyrazoles

Various primary alcohols were smoothly transformed into 3-aryl- and 3-alkylisoxazoles in good yields in one pot by successive treatment with PhI(OAc) 2 in the presence of TEMPO, NH 2 OH, and then NCS, followed by reaction with alkynes in the presence of Et 3 N. Similarly, various primary alcohols were smoothly transformed into 3-aryl- and 3-alkylpyrazoles in good yields in one pot by successive treatment with PhI(OAc) 2 in the presence of TEMPO, PhNHNH 2, and then NCS and decyl methyl sulfide, followed by reaction with alkynes in the presence of Et 3 N. Thus, both 3-aryl- and 3-alkylisoxazoles, and 3-aryl- and 3-alkylpyrazoles could be prepared from readily available primary alcohols in one pot under transition-metal-free conditions.

Synthesis, reactions, and antimicrobial activity of some novel pyrazolo[3,4-d]pyrimidine, pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine, and pyrazolo[4,3-e][1,2,4]triazolo[3,4-c]pyrimidine derivatives

Treatment of N-phenyl-substituted benzenecarbo-hydrazonoyl chlorides 1a-d with malononitrile in sodium ethoxide solution gave 5-amino-4-cyanopyrazole derivatives 2-5. Compounds 2-5 were converted to formidate derivatives 6-9 upon treatment with TEOF in ac

Intramolecular Diels-Alder and [3+2] Cycloaddition Reactions in the One-Pot Synthesis of Epoxypyrrolo[3,4-g]indazoles

A one-pot approach for the synthesis of epoxypyrrolo[3,4- g ]indazoles is presented. The first step was initiated by a three-component reaction of an isocyanide, a dialkyl acetylenedicarboxylate, and 2-furancarboxylic acid, and led to 1,3-dioxoepoxyisoindole, followed by the addition of hydrazonoyl chloride through a [3+2]-cycloaddition reaction in the second step. The key step in the formation of final compound involves a bicyclization strategy through intramolecular Diels-Alder (IMDA) reaction.

[3+2]-cycloaddition of in situ generated nitrile imines and acetylene for assembling of 1,3-disubstituted pyrazoles with quantitative deuterium labeling

A novel synthetic methodology for the preparation of 1,3-disubstituted pyrazoles from in situ generated nitrile imines and acetylene is reported. The reactions are performed in a simple two-chamber reactor. One part of the reactor is loaded with hydrazonoyl chloride precursors of active nitrile imine species and a base. The other part is used to generate acetylene from CaC2 and water. Partitioning of the reactants improves the yields of desired pyrazoles up to 99% and simplifies their isolation to a simple procedure of solvent evaporation. The approach requires no complex equipment and utilizes inexpensive, safe, and easy to handle calcium carbide as a starting material. A model deuterium incorporation is carried out according to the developed methodology, producing a series of novel 4,5-dideuteropyrazoles with excellent deuterium enrichment. Theoretical calculations on reaction mechanism and characterization of possible intermediate structures were performed.

COMPOUNDS AND COMPOSITIONS FOR THE TREATMENT OF CANCER

The present disclosure provides compounds, pharmaceutical compositions, and methods for the treatment of cancer and fibrosis. The disclosed pharmaceutical compositions may include one or more pyrazolyl-containing compounds, or a derivative thereof.

Spirotriazoline oxindoles: A novel chemical scaffold with in vitro anticancer properties

The design and synthesis of a library of twenty-six spirotriazoline oxindoles and their in vitro evaluation as potential anticancer agents is reported. The antiproliferative activity of the synthesized compounds was assessed against four different cancer cell lines (HCT-116 p53 (+/+), HCT-116 p53 (?/?), MCF-7, and MDA-MB-231). Four spirotriazoline oxindoles showed selectivity against the four cancer cell lines tested over the non-cancer derived HEK 293T cell line. To characterize the molecular mechanisms involved in compound antitumoral activity, two spirotriazoline oxindoles were selected for further studies. Both compounds were able to induce apoptosis and cell cycle arrest at G0/G1 phase and upregulated p53 steady-state levels, while decreasing its main inhibitor MDM2, in HCT-116 cells. Importantly, cytotoxic effects induced by spirotriazoline oxindoles occurred in cancer cells without eliciting cell death in non-malignant CCD-18Co human colon fibroblasts. In addition, four spirotriazoline oxindoles showed selectivity against the triple-negative breast cancer cell line MDA-MB-231 with IC50 values of 3.5–6.7 μM. These results highlight the anticancer potential of spirotriazoline oxindoles, especially when dealing with aggressive and challenging triple-negative breast cancer.