16917-42-3

Upstream product

• 5877-51-0 N-(4-bromobenzylidene)aniline 
• 1122-91-4 4-bromo-benzaldehyde 
• 100-63-0 phenylhydrazine 
• 59-88-1 phenylhydrazine hydrochloride 
• 62-53-3 aniline 
• 2826-24-6 4-bromobenzylidenemalononitrile 
• 108-98-5 thiophenol 

Downstream Products

• 1122-91-4 4-bromo-benzaldehyde 
• 25939-12-2 4-bromo-N-phenylbenzohydrazonoyl chloride 
• 1223079-66-0 4-ethyl(carbethoxy)amino-5-(4-bromophenyl)-2-phenyl-2H-1,2,4-triazol-3(4H)-one 
• 955355-42-7 1-benzyl-2-(4-bromophenyl)-1H-benzo[d]imidazole 
• 380313-95-1 2-(4-bromobenzylidene)-1-benzyl-1-phenylhydrazine 
• 43120-28-1 methyl 1H-indazole-3-carboxylate 
• 1239843-02-7 5-(1H-indazol-3-yl)-3-phenyl-1,2,4-oxadiazole 
• 1338663-47-0 3-(3-methylphenyl)-5-(3-indazolyl)-1,2,4-oxadiazole 
• 1338667-43-8 3-(3-fluorophenyl)-5-(3-indazolyl)-1,2,4-oxadiazole 
• 1630015-70-1 4-bromobenzylideneaminoisatine 
• 4498-67-3 1H-Indazole-3-carboxylic acid 
• 1043884-02-1 ethyl 3-(4-bromophenyl)-5-methyl-1-phenyl-1H-pyrazole-4-carboxylate 

Relevant academic research and scientific papers

Blatter-Radical-Grafted Mesoporous Silica as Prospective Nanoplatform for Spin Manipulation at Ambient Conditions

Quantum computing and quantum information processing (QC/QIP) crucially depend on the availability of suitable quantum bits (qubits) and methods of their manipulation. Most qubit candidates known to date are not applicable at ambient conditions. Herein, we propose radical-grafted mesoporous silica as a versatile and prospective nanoplatform for spin-based QC/QIP. Extremely stable Blatter-type organic radicals are used, whose electron spin decoherence time is profoundly long even at room temperature (up to Tm≈2.3 μs), thus allowing efficient spin manipulation by microwave pulses. The mesoporous structure of such composites is nuclear-spin free and provides additional opportunities of embedding guest molecules into the channels. Robustness and tunability of these materials promotes them as highly promising nanoplatforms for future QC/QIP developments.

Synthesis of 1,1′-([1,1′-Biphenyl]-4,4′-diyl)bis(3-aryl-5-phenylformazans) and 1,1′-([1,1′-Biphenyl]-4,4′-diyl)bis(3-aryl-5-phenyl-5,6-dihydro-1,2,4,5-tetrazin-1-ium) Perchlorates

Abstract: New bis-formazans and bis(5,6-dihydro-1,2,4,5-tetrazin-1-ium) perchlorates were synthesized with high yields under mild conditions. 1,1′-([1,1′-Biphenyl]-4,4′-diyl)bis(3-aryl-5-phenylformazans) were obtained by diazo coupling of para-substituted benzaldehyde phenylhydrazones with [1,1′-biphenyl]-4,4′-bis(diazonium chloride). Treatment of the obtained bis-formazans with formaldehyde in the presence of perchloric acid in dioxane afforded 1,1′-([1,1′-biphenyl]-4,4′-diyl)bis(3-aryl-5-phenyl-5,6-dihydro-1,2,4,5-tetrazin-1-ium) diper-chlorates. The structure of the synthesized compounds was confirmed by elemental analyses and UV, IR, and 1H and 13C NMR spectra.

Synthesis of and characterization of some Heterocyclic Compounds derived from Thiophenol

This research work involved preparation of heterogeneous pent lateral cyclic compounds (thiazolidine -4- one, benzothiazole, triazole, 4-oxothiazolidin) using thiophenol as raw materials: Thiophenol was reacted with mono chloroacetic acid in the presence of potassium hydroxide to prepare (sh1) followed by ortho amino aniline results the (sh2). The reaction of thiophenol with ethylchloroacetate afforded (sh3) and the reaction of (sh3) with thiosemicarbazide and 4% NaOH leads to ring closure giving 1,2,4- triazole (sh5). A treatment of thiophenol with hydrazine hydrate to obtain the intermediate (sh6) with aromatic aldehyde synthesized azomethines (sh7- sh9) then treated with mercaptoacetic acid to obtained (sh10-sh12). A treatment of thiophenol with chloroacetyl chloride produced (sh13) compound then treated with hydrazine hydrate to obtain (sh14) compound followed by bromobenzaldehyde synthesized azomethine (sh15) compound then treated with mercaptoacetic acid to obtained (sh16) compound. Characterization results for the prepared compounds using IR spectroscopy, NMR and melting points confirmed their chemical structures.

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

Attempts to access a series of pyrazoles lead to new hydrazones with antifungal potential against candida species including azole‐resistant strains

The treatment of benzylidenemalononitriles with phenylhydrazines in refluxing ethanol did not provide pyrazole derivatives, but instead furnished hydrazones. The structure of hydra-zones was secured by X‐ray analysis. The chemical proof was also obtained by direct reaction of 3,4,5‐trimethoxybenzaldehyde with 2,4‐dichlorophenylhydrazine. Newly synthesized hydrazones were tested against eight Candida spp. strains in a dose response assay to determine the minimum inhibitory concentration (MIC99). Five compounds were identified as promising antifungal agents against Candida spp. (C. albicans SC5314, C. glabrata, C. tropicalis, C. parapsilosis and C. glabrata (R azoles)), with MIC99 values ranging from 16 to 32 μg/mL and selective antifungal activity over cy-totoxicity.

Triarylverdazyl radicals as promising redox-active components of rechargeable organic batteries

A novel design of electroactive components of rechargeable organic batteries based on stable verdazyl radicals bearing various substituents is proposed. 3-Positioned aromatic substituents at the verdazyl moiety affect the reduction potentials and almost do not affect the oxidation potential, while 1-positioned aromatic substituents affect contrariwise the oxidation potential of this radical without any influence on the reduction potential. The acquired electrochemical data allowed us to reveal the structure—potential relationship for the cathodic and anodic processes, which provided the design of triarylverdazyl radicals possessing record-breaking parameters of the “electrochemical gap”.

From Phenylhydrazone to 1H-1,2,4-Triazoles via Nitrification, Reduction and Cyclization

Herein we report an annulation of phenylhydrazone via a tandem nitrification, reduction, cyclization protocol employing cobalt nitrate and 1,2-dichloroethane to produce substituted 1H-1,2,4-triazoles. Notably, 1,2-dichloroethane serves both the solvent and a hydrogen source for transfer hydrogenation. This methodology works under mild conditions, providing a direct approach for the synthesis of 1H-1,2,4-triazoles. (Figure presented.).

Synthesis of hybrid polycycles containing fused hydroxy benzofuran and 1H-indazoles via a domino cyclization reaction

A stoichiometry controlled domino cyclization reaction of hydrazone and p-benzoquinone to an angularly fused 3H-benzofuro[3,2-e]indazole core with an embedded oxygenated dibenzofuran framework under mild reaction conditions is disclosed. The reaction involves palladium catalyzed 5-hydroxy-1H-indazole formation followed by TFA mediated [3+2] annulation between the in situ formed 5-hydroxy-1H-indazole and p-benzoquinone. The developed method is attractive because of the concomitant formation of two heterocyclic rings with consecutive multiple bond forming events that include two C-C, one C-N and one C-O bonds. Spectroscopic and theoretical studies of the blue emissive benzofuroindazole derivatives have also been described.

Stereospecific copper(II)-catalyzed tandem ring opening/oxidative alkylation of donor-acceptor cyclopropanes with hydrazones: Synthesis of tetrahydropyridazines

Aerobic copper(II)-catalyzed tandem ring opening and oxidative C-H alkylation of donor-acceptor cyclopropanes with bisaryl hydrazones is accomplished to produce tetrahydropyridazines, in which copper(II) plays dual role as a Lewis acid as well as redox catalyst. The reaction is stereospecific, and optically active cyclopropanes can be reacted with high optical purities (89-98% enantiomeric excess). The substrate scope, functional group tolerance, dual role of the copper(II) catalyst, and the use of air as an oxidant are the important practical features. A product bearing a 3-bromoaryl group can be subjected to Pd-catalyzed Suzuki coupling with boronic acid in high yield.