19353-92-5

Usage

Uses

Used in Photographic Industry:
4-Dimethylaminobenzhydrazide is used as a color developer for enhancing the color production in dye couplers and photographic materials. Its chemical properties allow for the creation of vibrant and stable colors in photographic films and papers, contributing to the quality and longevity of images.
Used in Hair Dye Industry:
In the hair dye industry, 4-Dimethylaminobenzhydrazide serves as a color developer, enabling the hair dye to penetrate the hair shaft and produce the desired color. Its use in hair dyes ensures a long-lasting and even color application, improving the overall effectiveness of hair coloring products.
Used as a Polymerization Inhibitor:
4-Dimethylaminobenzhydrazide is utilized as a polymerization inhibitor in industrial processes, particularly in the production of plastics and resins. It helps to prevent unwanted polymerization reactions that could affect the quality and consistency of the final product, ensuring a stable and uniform material.
Safety Considerations:
While 4-Dimethylaminobenzhydrazide has low acute toxicity, it is important to handle it with care due to its potential to cause skin and eye irritation. Proper safety measures, such as wearing protective gear and following safety guidelines, should be taken to minimize the risk of adverse effects.

InChI:InChI=1/C9H13N3O/c1-12(2)8-5-3-4-7(6-8)9(13)11-10/h3-6H,10H2,1-2H3,(H,11,13)

Upstream product

• 10287-53-3 ethyl p-dimethyaminolbenzoate 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 1644630-67-0 C₁₅H₁₃ClN₂O₄ 
• 302-01-2 hydrazine 
• 4755-50-4 4-(dimethylamino)benzoyl chloride 
• 613-94-5 benzoic acid hydrazide 
• 126929-66-6 1-<α-methylthio-(p-trimethylammonia)benzylidene>piperidinium bromide 
• 619-84-1 p-N,N-dimethylaminobenzoic acid 
• 380922-13-4 N-Boc-N'-[4-(N,N-dimethylamino)benzoyl]hydrazine 
• 118792-43-1 S-methyl 4-(dimethylamino)benzothioate 
• 21176-99-8 p-Dimethylamino-thiolbenzoesaeure-methylester-methoiodid 
• 1202-25-1 methyl 4-(N,N-dimethylamino)benzoate 

Downstream Products

• 101289-91-2 4-dimethylamino-benzoic acid-(4-amino-benzylidenehydrazide) 
• 90839-97-7 N,N-dimethyl-4-(1,3,4-oxadiazol-2-yl)aniline 
• 33706-99-9 N-{2-[5-(4-dimethylamino-phenyl)-[1,3,4]oxadiazol-2-yl]-ethyl}-phthalimide 
• 105000-74-6 3-(p-dimethylamino)phenyl-4-phenyl-5-(2-pyridyl)-1,2,4-triazole 
• 103653-53-8 2-[(4-Dimethylamino-benzoyl)-hydrazono]-5,5-dimethyl-4-oxo-hexanoic acid methyl ester 
• 742-62-1 2-<2-(4-Dimethylamino-benzoyl)-hydrazino>-5-nitroso-tropon 
• 6781-35-7 1-(4-biphenyl)-4-(4-dimethylaminophenyl)hydrazide 
• 263255-76-1 4-dimethylamino-benzoic acid N'-(3,4,5-trimethoxy-benzoyl)-hydrazide 
• 142068-34-6 (R)-1-phenyl-1-(2-p-dimethylaminobenzoylhydrazino)ethane 
• 142068-34-6 (S)-1-phenyl-1-(2-p-dimethylaminobenzoylhydrazino)ethane 
• 891616-64-1 N-4-(dimethylamino)benzamido-N'-1-naphthylthiourea 

Relevant academic research and scientific papers

A novel jointly colorimetric and fluorescent sensor for Cu2+ recognition and its complex for sensing S2? by a Cu2+ displacement approach in aqueous media

In this work, a simple and easily synthesized Schiff-based derivative colorimetric and fluorescent sensor (1), 4-dimethylamino-benzoic acid (2-imidazole formaldehyde)-hydrazide, was obtained for the detection of Cu2+ and S2?. The compound 1 exhibited dual spectral responses to Cu2+, that is, vivid color change and fluorescence enhancement in the presence of Cu2+. The detection limits were valued as 0.46 μM and 15 nM according to absorption and fluorescent response, respectively. Both of them are below the World Health Organization (WHO) guidelines for drinking water (31.5 μM). In addition, the ensemble (1-Cu2+) selectively and sensitively detected a low concentration of S2?. As the addition of S2? instantly removed Cu2+ from the ensemble (1-Cu2+) resulting in a color change from yellow to colorless and a “turn-off” fluorescent response. The detection limit for S2? was estimated as 0.12 μM (from fluorescent method) and 0.68 μM (from absorption method), respectively, each of which was also lower than the maximum allowable level of S2? (15 μM) in drinking water defined by the WHO. The binding process was confirmed via UV–vis absorption, fluorescence measurements, 1H NMR, mass spectroscopy and density functional theory calculation. What's more, successful practical application of test paper is used to inspect the S2? which means the convenient and rapid assay in real samples can be achieved.

Synthesis and spectral properties of non-symmetrical red and near IR emitter dibenzoBODIPYs

New symmetrical and non-symmetrical benzoBODIPYs have been synthesized from diketones. For the two series the 3 and 5 positions have been substituted by different aromatic rings and onto benzo sub-units different groups have been introduced. The methodology of diketones self-condensation provides symmetrical dyes. By cross-condensation reaction, these positions can be differentiated and specific functions connected to the desired positions. These molecules have been fully characterized and their optical properties analyzed by both experimental and theoretical means. They are red to NIR emitters with a range of emission from 679 to 780 nm in CH2Cl2. They show maxima of absorption between 651 nm and 732 nm, strong ε of around 100,000 M?1 cm?1 and quite good quantum yields from 16% to 75%. The thienyl moiety on α-positions of the nitrogens generates the highest red shifts. Meanwhile dimethylamino groups in the same positions bring, besides chemical properties, proton sensitive dyes. The bromine atom onto the dibenzo sub-units exhibits good reactivity through Sonogashira coupling reactions. This approach provides multifunctional red to NIR dyes with endless possibilities of combination of chemical properties.

A chromone hydrazide Schiff base fluorescence probe with high selectivity and sensitivity for the detection and discrimination of human serum albumin (HSA) and bovine serum albumin (BSA)

The discrimination and identification of human serum albumin (HSA) and bovine serum albumin (BSA) is very important, which is due to the vital roles of two SAs in biological and pharmaceutical research. Based on structural screening and docking calculation from a series of homologues, a coumarin Schiff base fluorescent probe 3-hydroxy-N′-((4-oxo-4H-chromen-3-yl)methylene)-2-naphthohydrazide (HCNH) has been designed and synthesized, which could effectively discriminate HSA and BSA. The probe HCNH exhibited superior sensitivity toward HSA and BSA with the detection limits of 10.62 nM and 16.03 nM in PBS solution, respectively. The binding mechanism of HCNH with SAs was studied by Job's plot analysis, SA destruction and displacement assay. Molecular docking and DFT methods were utilized to provide deep insight into the spatial conformation change of HCNH and binding sites in HSA/BSA. The conformation of HCNH was significantly influenced by the microenvironment provided by HSA and BSA, therefore its fluorescence emission was affected correspondingly. Non-toxic probe HCNH could be successfully used for fluorescence bio-imaging of HSA in cancer cells, which is significantly different from normal cells and favors the application in medical diagnosis.

Pleuromutilin derivative with 1, 3, 4-oxadiazole side chain and preparation and application thereof

The invention belongs to the field of medicinal chemistry, and particularly relates to a pleuromutilin derivative with a 1, 3, 4-oxadiazole side chain and preparation and application thereof The pleuromutilin derivative with the 1, 3, 4-oxadiazole side chain is a compound shown in a formula 2 or a pharmaceutically acceptable salt thereof, and a solvent compound, an enantiomer, a diastereoisomer and a tautomer of the compound shown in the formula 2 or the pharmaceutically acceptable salt thereof or a mixture of the solvent compound, the enantiomer, the diastereoisomer and the tautomer in any proportion, including a racemic mixture. The pleuromutilin derivative has good antibacterial activity, is especially suitable for being used as a novel antibacterial agent for systemic system infection of animals or human beings, and has good water solubility.

Design, synthesis, in vitro and in vivo evaluation against MRSA and molecular docking studies of novel pleuromutilin derivatives bearing 1, 3, 4-oxadiazole linker

A class of pleuromutilin derivatives containing 1, 3, 4-oxadiazole were designed and synthesized as potential antibacterial agents against Methicillin-resistant staphylococcus aureus (MRSA). The ultrasound-assisted reaction was proposed as a green chemistry method to synthesize 1, 3, 4-oxadiazole derivatives (intermediates 85–110). Among these pleuromutilin derivatives, compound 133 was found to be the strongest antibacterial derivative against MRSA (MIC = 0.125 μg/mL). Furthermore, the result of the time-kill curves displayed that compound 133 could inhibit the growth of MRSA in vitro quickly (- 4.36 log10 CFU/mL reduction). Then, compound 133 (- 1.82 log10 CFU/mL) displayed superior in vivo antibacterial efficacy than tiamulin (- 0.82 log10 CFU/mL) in reducing MRSA load in mice thigh model. Besides, compound 133 exhibited low cytotoxicity to RAW 264.7 cells. Molecular docking studies revealed that compound 133 was successfully localized in the binding pocket of 50S ribosomal subunit (ΔGb = -10.50 kcal/mol). The results indicated that these pleuromutilin derivatives containing 1, 3, 4-oxadiazole might be further developed into novel antibiotics against MRSA.

The development of coumarin Schiff base system applied as highly selective fluorescent/colorimetric probes for Cu2+ and tumor biomarker glutathione detection

Overexpression of tumor biomarker glutathione (GSH) has been documented in numerous types of cancers, therefor GSH-activated light-up chemosensors for tumor identification require great attention. A new colorimetric/fluorescent probe (7-(diethylamino)-2-oxo-2H-chromen-3-yl)methylene)-4-(dimethylamino) benzohydrazide (HL) was prepared, which could be applied in discriminating Cu2+ and further recognizing GSH based on its Cu complex. Firstly, the probe HL toward Cu2+ exhibited selective fluorescence quenching and obvious color change from yellow to orange-red under visible light. Further, when GSH was introduced to the Cu2+-2HL system, the fluorescence recovered rapidly due to the high affinity of GSH to Cu2+, meanwhile the color reverted back to former yellow. Based on fluorescence titration, the detection limits were calculated as 2.40 × 10?8 M and 1.29 × 10?7 M for Cu2+ and GSH, respectively. The combination mode of HL with Cu2+ was investigated in detail by Job plots, ESI-MS, FT-IR, and DFT studies. Probes HL and Cu2+-2HL showed relatively less toxicity and were employed for biological imaging in cells and zebrafish. Remarkably, the detection for endogenous GSH by this developed sensor platform implied great potential application prospect in cancer diagnosis.

5-Phenyl-1,3,4-oxadiazol-2(3 H)-ones Are Potent Inhibitors of Notum Carboxylesterase Activity Identified by the Optimization of a Crystallographic Fragment Screening Hit

Carboxylesterase Notum is a negative regulator of the Wnt signaling pathway. There is an emerging understanding of the role Notum plays in disease, supporting the need to discover new small-molecule inhibitors. A crystallographic X-ray fragment screen was performed, which identified fragment hit 1,2,3-Triazole 7 as an attractive starting point for a structure-based drug design hit-To-lead program. Optimization of 7 identified oxadiazol-2-one 23dd as a preferred example with properties consistent with drug-like chemical space. Screening 23dd in a cell-based TCF/LEF reporter gene assay restored the activation of Wnt signaling in the presence of Notum. Mouse pharmacokinetic studies with oral administration of 23dd demonstrated good plasma exposure and partial blood-brain barrier penetration. Significant progress was made in developing fragment hit 7 into lead 23dd (>600-fold increase in activity), making it suitable as a new chemical tool for exploring the role of Notum-mediated regulation of Wnt signaling.

A novel one-pot synthesis method of 3,4,5-triaryl-substituted 1,2,4-triazoles

[Figure not available: see fulltext.] A novel method for the preparation of 3,4,5-triaryl-substituted 1,2,4-triazoles by the reaction of hydrazides with secondary amides in polyphosphoric ester has been developed. The new method is characterized by mild conditions and ease of synthesis, including the stages of isolation and purification of the product. Additionally, product structures were confirmed by counter synthesis. It was shown that the proposed method is suitable for producing 1,2,4-triazoles with phenolic substituents without the stages of the protection and deprotection of the hydroxyl group. Using the new method, five 3,4,5-substituted 1,2,4-triazoles were obtained for the first time.

SAR Studies on Aromatic Acylhydrazone-Based Inhibitors of Fungal Sphingolipid Synthesis as Next-Generation Antifungal Agents

Recently, the fungal sphingolipid glucosylceramide (GlcCer) synthesis has emerged as a highly promising new target for drug discovery of next-generation antifungal agents, and we found two aromatic acylhydrazones as effective inhibitors of GlcCer synthesis based on HTP screening. In the present work, we have designed libraries of new aromatic acylhydrazones, evaluated their antifungal activities (MIC80 and time-kill profile) against C. neoformans, and performed an extensive SAR study, which led to the identification of five promising lead compounds, exhibiting excellent fungicidal activities with very large selectivity index. Moreover, two compounds demonstrated broad spectrum antifungal activity against six other clinically relevant fungal strains. These five lead compounds were examined for their synergism/cooperativity with five clinical drugs against seven fungal strains, and very encouraging results were obtained; e.g., the combination of all five lead compounds with voriconazole exhibited either synergistic or additive effect to all seven fungal strains.

Structural design, synthesis and substituent effect of hydrazone-N-acylhydrazones reveal potent immunomodulatory agents

4-(Nitrophenyl)hydrazone derivatives of N-acylhydrazone were synthesized and screened for suppress lymphocyte proliferation and nitrite inhibition in macrophages. Compared to an unsubstituted N-acylhydrazone, active compounds were identified within initial series when hydroxyl, chloride and nitro substituents were employed. Structure-activity relationship was further developed by varying the position of these substituents as well as attaching structurally-related substituents. Changing substituent position revealed a more promising compound series of anti-inflammatory agents. In contrast, an N-methyl group appended to the 4-(nitrophenyl)hydrazone moiety reduced activity. Anti-inflammatory activity of compounds is achieved by modulating IL-1β secretion and prostaglandin E2 synthesis in macrophages and by inhibiting calcineurin phosphatase activity in lymphocytes. Compound SintMed65 was advanced into an acute model of peritonitis in mice, where it inhibited the neutrophil infiltration after being orally administered. In summary, we demonstrated in great details the structural requirements and the underlying mechanism for anti-inflammatory activity of a new family of hydrazone-N-acylhydrazone, which may represent a valuable medicinal chemistry direction for the anti-inflammatory drug development in general.