10407-20-2

Upstream product

• 100-52-7 benzaldehyde 
• 3471-32-7 4-Methoxyphenylhydrazine 
• 19501-58-7 4-methoxyphenylhydrazine hydrochloride 
• 588-64-7 benzaldehyde phenylhydrazone 
• 2725-46-4 1-benzyl-2-benzylidene-1-phenylhydrazine 
• 100-39-0 benzyl bromide 
• 104-94-9 4-methoxy-aniline 

Downstream Products

• 1200448-90-3 1-(4-methoxyphenyl)-3,6-diphenyl-4-tosyl-1,4,5,6-tetrahydro-1,2,4-triazine 
• 28772-59-0 1-benzyl-2-benzylidene-1-(4-methoxyphenyl)hydrazine 
• 100-52-7 benzaldehyde 
• 142108-79-0 2-(4-methoxyphenyl)-4,5-diphenyl-2H-1,2,3-triazole 
• 123-11-5 4-methoxy-benzaldehyde 
• 60981-60-4 1-(chlorophenylmethylene)-2-(4-methoxyphenyl)hydrazine 
• 1223079-60-4 4-ethyl(carbethoxy)amino-2-(4-methoxyphenyl)-5-phenyl-2H-1,2,4-triazol-3(4H)-one 
• 313650-76-9 C₂₂H₂₃N₃O 
• 313650-75-8 C₂₁H₂₁N₃O 
• 88246-22-4 (4-Methoxy-phenyl)-[phenyl-(4,5,6,7-tetrahydro-benzo[1,3]dithiol-2-ylidene)-methyl]-diazene 

Relevant academic research and scientific papers

Broad-Spectrum Antifungal Agents: Fluorinated Aryl- and Heteroaryl-Substituted Hydrazones

Fluorinated aryl- and heteroaryl-substituted monohydrazones displayed excellent broad-spectrum activity against various fungal strains, including a panel of clinically relevant Candida auris strains relative to a control antifungal agent, voriconazole (VRC). These monohydrazones displayed less hemolysis of murine red blood cells than that of VRC at the same concentrations, possessed fungicidal activity in a time-kill study, and exhibited no mammalian cell cytotoxicity. In addition, these monohydrazones prevented the formation of biofilms that otherwise block antibiotic effectiveness and did not trigger the development of resistance when exposed to C. auris AR Bank # 0390 over 15 passages.

Identification of novel 1,3-diaryl-1,2,4-triazole-capped histone deacetylase 6 inhibitors with potential anti-gastric cancer activity

Histone deacetylase 6 (HDAC6) has emerged as a critical regulator of many cellular pathways in tumors due to its unique structure basis and abundant substrate types. Over the past few decades, the role played by HDAC6 inhibitors as anticancer agents has sparked great interest of biochemists worldwide. However, they were less reported for gastric cancer therapy. In this paper, with the help of bioisosteric replacement, in-house library screening, and lead optimization strategies, we designed, synthesized and verified a series of 1,3-diaryl-1,2,4-triazole-capped HDAC6 inhibitors with promising anti-gastric cancer activities. Amongst, compound 9r displayed the best inhibitory activity towards HDAC6 (IC50 = 30.6 nM), with 128-fold selectivity over HDAC1. Further BLI and CETSA assay proved the high affinity of 9r to HDAC6. In addition, 9r could dose-dependently upregulate the levels of acetylated α-tubulin, without significant effect on acetylated histone H3 in MGC803 cells. Besides, 9r exhibited potent antiproliferative effect on MGC803 cells, and promoted apoptosis and suppressed the metastasis without obvious toxicity, suggesting 9r would serve as a potential lead compound for the development of novel therapeutic agents of gastric cancer.

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

Discovery of pyrazole derivatives as cellular active inhibitors of histone lysine specific demethylase 5B (KDM5B/JARID1B)

KDM5B (also known as PLU-1 and JARID1B) is 2-oxoglutarate and Fe2+ dependent oxygenase that acts as a histone H3K4 demethylase, which is a key participant in inhibiting the expression of tumor suppressors as a drug target. Here, we present the discovery of pyrazole derivatives compound 5 by structure-based virtual screening and biochemical screening with IC50 of 9.320 μM against KDM5B, and its subsequent optimization to give 1-(4-methoxyphenyl)-N-(2-methyl-2-morpholinopropyl)-3-phenyl-1H-pyrazole-4-carboxamide (27 ab), a potent KDM5B inhibitor with IC50 of 0.0244 μM. In MKN45 cells, compound 27 ab can bind and stabilize KDM5B and induce the accumulation of H3K4me2/3, bona fide substrates of KDM5B, while keep the amount of H3K4me1, H3K9me2/3 and H3K27me2 without change. Further biological study also indicated that compound 27 ab is a potent cellular active KDM5B inhibitor that can inhibit MKN45 cell proliferation, wound healing and migration. In sum, our finding gives a novel structure for the discovery of KDM5B inhibitor and targeting KDM5B may be a new therapeutic strategy for gastric cancer treatment.

Radical Addition of Hydrazones by α-Bromo Ketones to Prepare 1,3,5-Trisubstituted Pyrazoles via Visible Light Catalysis

A novel efficient tandem reaction of hydrazones and α-bromo ketones is reported for the preparation of 1,3,5-trisubstituted pyrazoles by visible light catalysis. In this system, the monosubstituted hydrazones show wonderful reaction activity with alkyl radicals, generated from α-bromo ketones. A radical addition followed by intramolecular cyclization affords the important pyrazole skeleton in good to excellent yields. This efficient strategy under mild conditions with wide group tolerance provides a potential approach to the 1,3,5-trisubstituted pyrazoles.

A one-pot synthesis of bisarylhydrazones by Cu(I)-catalyzed aerobic oxidation

An efficient Cu(I)-catalyzed one-pot synthesis of N-substituted (or NH) bisarylhydrazones is reported. A further cyclization reaction could occur towards the synthesis of benzimidazoles or triazoles with elevated temperature. A plausible alkylation-oxidation-alkylation mechanism is proposed based on experimental results and literature.

NOVEL CATALYSTS

The present invention provides novel compounds and ligands that are useful in transition metal catalyzed cross-coupling reactions. For example, the compounds and ligands of the present invention are useful in palladium or gold catalyzed cross-coupling reactions.

Copper-mediated synthesis of substituted 2-aryl-N-benzylbenzimidazoles and 2-arylbenzoxazoles via C-H functionalization/C-N/C-O bond formation

An efficient method for the transformation of N-benzyl bisarylhydrazones and bisaryloxime ethers to functionalized 2-aryl-N-benzylbenzimidazoles and 2-arylbenzoxazoles is described. The protocol involves a copper(II)-mediated cascade C-H functionalization/C-N/C-O bond formation under neutral conditions. Substrates having either electron-donating or -withdrawing substituents undergo the cyclization to afford the target heterocycles at moderate temperature.

Palladium-catalyzed cross-coupling of aryl chlorides and tosylates with hydrazine

Hydrazine is not a problem anymore: The title transformation is the first reaction to yield aryl hydrazines through the cross-coupling of aryl chlorides and tosylates with hydrazine. An appropriately designed palladium catalyst allows this reaction to proceed rapidly under mild conditions, and with excellent chemoselectivity (see scheme; Ad=adamantyl, Ts=4-toluenesulfonyl).

An improved synthesis of 1,2,4-triazoles using Ag2CO3

An improved synthesis of 1,3,5-trisubstituted 1,2,4-triazoles via Ag2CO3 mediated cyclization of triazenes has been developed. This approach is flexible and compatible with a wide range of functional groups. The reaction was complete within 3 h and the products were isolated in moderate to high yields. The influence of the β-substituents of the amines on the triazole formation was also studied. (C) 2000 Elsevier Science Ltd.