60798-12-1

Upstream product

• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 539-44-6 N-4-methylphenylhydrazine 
• 637-60-5 p-tolylhydrazine hydrochloride 

Downstream Products

• 87277-63-2 4-Isopropylidene-5-phenyl-2-p-tolyl-2,4-dihydro-pyrazol-3-one 
• 108255-30-7 C₃₇H₃₂N₄O₂ 
• 87277-58-5 4,6,6-Trimethyl-3-phenyl-1-p-tolyl-1,6-dihydro-pyrano[2,3-c]pyrazole 
• 1078132-16-7 C₂₃H₁₇ClN₂O₂ 
• 1242100-61-3 1,4,5,6-tetrahydro-6-methyl-1-(4-methylphenyl)-3,6-diphenyl-pyrano[2,3-c]pyrazole 
• 1311144-35-0 C₃₃H₂₆N₄O₂ 

Relevant academic research and scientific papers

Targeting fungal virulence factor by small molecules: Structure-based discovery of novel secreted aspartic protease 2 (SAP2) inhibitors

Secreted aspartic protease 2 (SAP2), a kind of virulence factor, is an emerging new antifungal target. Using docking-based virtual screening and structure-based inhibitor design, a series of novel SAP2 inhibitors were successfully identified. Among them, indolone derivative 24a showed potent SAP2 inhibitory activity (IC50 = 0.92 μM). It blocked fungi biofilm and hypha formation by down-regulating the expression of genes SAP2, ECE1, ALS3 and EFG1. As a virulence factor inhibitor, compound 24a was inactive in vitro and showed potent in vivo efficacy in a murine model of invasive candidiasis. It represents a promising lead compound for the discovery of novel antifungal agents.

Regioselective N-Addition/Substitution Reaction of α-Alkylidene Pyrazolinones with Propargyl Sulfonium Salts to Construct Allylthio-Containing Pyrazolones

The regioselective N-addition/substitution reaction between α-alkylidene pyrazolinones and propargyl sulfonium salts has been developed to construct functionalized allylthio-containing pyrazolones with moderate to excellent yields. α-Alkylidene pyrazolinones act as N-nucleophilic agents which are distinguished from reported C-nucleophilic reactions. Excellent regioselectivity, readily available starting materials, the broad range of substrates, gram-scale synthesis, and simple operation illustrate the synthetic advantages of this new reaction pathway.

Asymmetric synthesis of atropisomeric pyrazole: Via an enantioselective reaction of azonaphthalene with pyrazolone

The first catalytic asymmetric reaction of azonaphthalene with pyrazolone has been established. A wide range of axially chiral pyrazole derivatives have been achieved in good yields (68-99%) with excellent enantioselectivities (83-98% ee) by utilizing chiral phosphoric acid as a catalyst. This strategy provides an efficient and facile approach for the construction of axially chiral pyrazole derivatives. Theoretical calculations were carried out to elucidate the origins of enantioselectivity.

Combined inorganic base promoted N-addition/[2,3]-sigmatropic rearrangement to construct homoallyl sulfur-containing pyrazolones

The first sequentially combined inorganic base promoted N-addition/[2,3]-sigmatropic rearrangement reaction of α-alkylidene pyrazolinones and propargyl sulfonium salts has been reported to construct homoallyl sulfur-containing pyrazolones with moderate to excellent yields. α-Alkylidene pyrazolinones function as N-nucleophilic agents distinguished from the reported C-addition reactions. Propargyl sulfonium salts were first involved in the [2,3]-sigmatropic rearrangement protocol differentiated from the well-established annulation reactions. The excellent regioselectivity, the broad scope of substrates, gram-scale synthesis and convenient transformation embody the synthetic superiority of this cascade process.

Asymmetric [3 + 3] Annulation of Copper-Allenylidenes with Pyrazolones: Synthesis of Chiral 1,4-Dihydropyrano[2,3- c]pyrazoles

The copper-catalyzed asymmetric [3 + 3] annulation of ethynyl benzoxazinanones with pyrazolones has been achieved, providing simple access to 1,4-dihydropyrano[2,3-c]pyrazole derivatives in moderate to excellent yields with excellent enantioselectivities (up to 99% ee). Compared with previous annulation reactions of copper-allenylidenes from ethynyl benzoxazinanones, the current reaction fused the three carbon atoms of the propargyl moiety into a heterocyclic framework.

One-pot multistep mechanochemical synthesis of fluorinated pyrazolones

Solventless mechanochemical synthesis represents a technique with improved sustainability metrics compared to solvent-based processes. Herein, we describe a methodical process to run one solventless reaction directly into another through multistep mechanochemistry, effectively amplifying the solvent savings. The approach has to consider the solid form of the materials and compatibility of any auxiliary used. This has culminated in the development of a two-step, one-jar protocol for heterocycle formation and subsequent fluorination that has been successfully applied across a range of substrates, resulting in 12 difluorinated pyrazolones in moderate to excellent yields.

Synthesis, crystal structure and evaluation of cancer inhibitory activity of 4-[indol-3-yl-methylene]-1H-pyrazol-5(4H)-one derivatives

A series of 4-(1H-indol-3-yl-methylene)-1H-pyrazol-5(4H)-one derivatives have been synthesised. The Z structure of 4-[(1-methyl-1H-indol-3-yl)methylene]- 3-phenyl-1-p-tolyl-1H-pyrazol-5-one was determined by X-ray crystallography. The antitumour activity was evaluated against five cancer cells by MTT assay. [(1H-Indol-3-yl)methylene]-1-(2,4-dinitrophenyl)- 3-methyl-1H-pyrazole-5-one and 4-{4-[(1-benzyl-1H-indol-3-yl)methylene]-3-methyl-5-oxo-4,5-dihydro-1Hpyrazol- 1-yl}-benzoic acid have similar anticancer activity with 5-UF on the test cancer cells (exception of A375). Almost all the target compounds displayed antitumour activity against A549 and PC-9, and those with benzyl at 1- position of indole had higher activity against PC-9 (IC50 value lower than 30 μM). Those with benzyl at the indole and carboxyl at the phenyl part of of pyrazole were more active against PC-9 and A549 cells, providing a good indication for subsequent optimisation as lung cancer inhibitory agents.

Synthesis, biological evaluation and SAR study of novel pyrazole analogues as inhibitors of Mycobacterium tuberculosis

As a continuation of our previous work that turned toward the identification of antimycobacterial compounds with innovative structures, two series of pyrazole derivatives were synthesized by parallel solution-phase synthesis and were assayed as inhibitors of Mycobacterium tuberculosis (MTB), which is the causative agent of tuberculosis. One of these compounds showed high activity against MTB (MIC = 4 μg/mL). The newly synthesized pyrazoles were also computationally investigated to analyze their fit properties to the pharmacophoric model for antitubercular compounds previously built by us and to refine structure-activity relationship analysis.