636-99-7

Usage

Uses

Used in Pharmaceutical Industry:
4-Nitrophenylhydrazine hydrochloride is used as a pharmaceutical compound for its potential anticancer properties. It is being explored for its ability to target and inhibit the growth of cancer cells, making it a promising candidate for the development of novel anticancer drugs.
Used in Chemical Research:
In the field of chemical research, 4-Nitrophenylhydrazine hydrochloride serves as a valuable reagent and intermediate in the synthesis of various organic compounds. Its unique chemical properties allow it to be used in the development of new molecules with potential applications in various industries.
Used in Analytical Chemistry:
4-Nitrophenylhydrazine hydrochloride is employed as an analytical reagent in the detection and quantification of certain chemical substances. Its distinct color and reactivity make it a useful tool for researchers in analytical chemistry, enabling them to identify and measure specific compounds with precision.
Used in Material Science:
In the realm of material science, 4-Nitrophenylhydrazine hydrochloride is utilized in the development of new materials with unique properties. Its incorporation into various compounds can lead to the creation of materials with enhanced characteristics, such as improved stability, reactivity, or selectivity, which can be applied in a wide range of applications.

InChI:InChI=1/C6H7N3O2.ClH/c7-8-5-1-3-6(4-2-5)9(10)11;/h1-4,8H,7H2;1H

Upstream product

• 6299-51-0 3-(4-nitrophenyl)sydnone 
• 1352877-24-7 (3R,4S)-4-hydroxy-2-oxotetrahydrofuran-3-yl 2-(2-(4-nitrophenyl)hydrazinyl)-2-oxoacetate 
• 100-01-6 4-nitro-aniline 

Downstream Products

• 100128-06-1 tetrahydro-furan-2-carbaldehyde-(4-nitro-phenylhydrazone) 
• 88903-27-9 4-methyl-pent-3-en-2-one-(4-nitro-phenylhydrazone) 
• 7539-27-7 3-ethyl-4-methyl-1-(4-nitro-phenyl)-1H-pyrazole 
• 132685-44-0 phenyl-pyruvaldehyde bis-(4-nitro-phenylhydrazone) 
• 100394-77-2 1-(4-nitrophenyl)-4,5,6,7-tetrahydro-1H-indazole 
• 102408-71-9 4,5-Dihydroxy-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid trimethyl ester 
• 126749-28-8 5-[(4-Nitro-phenyl)-hydrazono]-4-oxo-4,5-dihydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid trimethyl ester 
• 129602-67-1 2,2,2-Trifluoro-1-[2-(4-nitro-phenyl)-3-trifluoromethyl-2H-benzo[g]indazol-5-yl]-ethanone 
• 87499-05-6 ethyl 1-p-nitrophenyl-5-hydroxy-1H-pyrazole-3-carboxylate 
• 73225-34-0 4-cyano-3,5-dimethyl-1-(p)nitrophenylpyrazole 

Relevant academic research and scientific papers

Design, Synthesis, and Antifungal Activity of 2,6-Dimethyl-4-aminopyrimidine Hydrazones as PDHc-E1 Inhibitors with a Novel Binding Mode

A series of novel 2,6-dimethyl-4-aminopyrimidine hydrazones 5 were rationally designed and synthesized as pyruvate dehydrogenase complex E1 (PDHc-E1) inhibitors. Compounds 5 strongly inhibited Escherichia coli (E. coli) PDHc-E1 (IC50 values 0.94-15.80 μM). As revealed by molecular docking, site-directed mutagenesis, enzymatic, and inhibition kinetic analyses, compounds 5 competitively inhibited PDHc-E1 and bound in a "straight"pattern at the E. coli PDHc-E1 active site, which is a new binding mode. In in vitro antifungal assays, most compounds 5 at 50 μg/mL showed more than 80% inhibition against the mycelial growth of six tested phytopathogenic fungi, including Botrytis cinerea, Monilia fructigena, Colletotrichum gloeosporioides, andBotryosphaeria dothidea. Notably, 5f and 5i were 1.8-380 fold more potent against M. fructigena than the commercial fungicides captan and chlorothalonil. In vivo, 5f and 5i controlled the growth of M. fructigena comparably to the commercial fungicide tebuconazole. Thus, 5f and 5i have potential commercial value for the control of peach brown rot caused by M. fructigena.

Synthesis, in vitro Antimicrobial, and Cytotoxic Activities of New 1,3,4-Oxadiazin-5(6H)-one Derivatives from Dehydroabietic Acid

A series of new 1,3,4-oxadiazin-5(6H)-one derivatives (6a–n) of dehydroabietic acid were designed and synthesized as potential antimicrobial and antitumor agents. Their structures were characterized by IR, 1H NMR, 13C NMR, MS, and elemental analyses. All the title compounds were evaluated for their antimicrobial activity against four bacterial and three fungal strains using the serial dilution method. Among them, compound 6e showed the highest antibacterial activity against Bacillus subtilis with a minimum inhibitory concentration (MIC) value of 1.9 μg/mL. In addition, the in vitro cytotoxic activities of the title compounds were also assayed against three human carcinoma cell lines (MCF-7, SMMC-7721, and HeLa) through the MTT colorimetric method. As a result, compounds 6b, 6g, 6k, and 6m exhibited significant inhibition against at least one cell line with IC50 values below 10 μM. Compound 6m was especially found to be the most potent derivative with IC50 values of 2.26 ± 0.23, 0.97 ± 0.11, and 1.89 ± 0.31 μM against MCF-7, SMMC-7721, and HeLa cells, respectively, comparable to positive control etoposide.

Synthesis and characterization of various alkyl, aryl and hetero aryl substituted hydrazines and study of their biological activity

Due to the presence of N-N linkage hydrazines are well-known for their diverse biological activity.N-N linkage has been used as a key structural motif in various bioactive agents. A series of aryl, alkyl and hetero aryl substituted hydrazine derivatives has been synthesized, for this diazotization of alkyl, aryl amines has been done, followed by reduction with stannous chloride or sodium sulfite. All synthesized compounds were characterized by elemental analysis, IR, 1H-NMR, Mass spectra and their biological activity has been studied.

Structure-activity relationships of pyrazole derivatives as potential therapeutics for immune thrombocytopenias

Idiopathic or immune thrombocytopenia (ITP) is a serious clinical disorder involving the destruction of platelets by macrophages. Small molecule therapeutics are highly sought after to ease the burden on current therapies derived from human sources. Earlier, we discovered that dimers of five-membered heterocycles exhibited potential to inhibit phagocytosis of human RBCs by macrophages. Here, we reveal a structure-activity relationship of the bis-pyrazole class of molecules with -C-C-, -C-N- and -C-O- linkers, and their evaluation as inhibitors of phagocytosis of antibody-opsonized human RBCs as potential therapeutics for ITP. We have uncovered three potential candidates, 37, 47 and 50, all carrying a different linker connecting the two pyrazole moieties. Among these compounds, hydroxypyrazole derivative 50 is the most potent compound with an IC50 of 14 ± 9 μM for inhibiting the phagocytosis of antibody-opsonized human RBCs by macrophages. None of the compounds exhibited significant potential to induce apoptosis in peripheral blood mononuclear cells (PBMCs). Current study has revealed specific functional features, such as up to 2-atom spacer arm and alkyl substitution at one of the N1 positions of the bivalent pyrazole core to be important for the inhibitory activity.

Design, synthesis, crystal structures, and insecticidal activities of eight-membered azabridge neonicotinoid analogues

Three series of novel azabridge neonicotinoid analogues were designed and synthesized, which were constructed by starting material A, glutaraldehyde, and primary amine hydrochlorides (aliphatic amines, phenylhydrazines, and anilines). Most of the eight-membered azabridge compounds presented higher insecticidal activities than oxabridged compound B against cowpea aphid (Aphis craccivora) and brown planthopper (Nilaparvata lugens). Compared with imidacloprid, some azabridged compounds exhibited excellent insecticidal activity against brown planthopper. The crystal structures and bioassay indicated that changing bridge atoms from O to N could lead to entirely different conformations, which might be the important influential factor of the bioactivities.

Piecing together the puzzle: Understanding a mild, metal free reduction method for the large scale synthesis of hydrazines

A key intermediate for the synthesis of hydrazines via a mild, metal free reduction of diazonium salts has been isolated and characterized by X-ray analysis. The presence of this intermediate is general, as demonstrated by the preparation of a number of analogues. A discussion of the mechanism and potential benefits of such a process are also described.

Synthesis and antimicrobial activities of novel 1H-dibenzo[a,c]carbazoles from dehydroabietic acid

A series of novel 1H-dibenzo[a,c]carbazole derivatives were synthesized in good yield through reaction of methyl 7-oxo-dehydroabietate with a variety of substituted phenylhydrazines. The structures of the newly synthesized compounds were confirmed by IR, 1H NMR, MS spectral studies and elemental analysis. All compounds were investigated for their activity against four bacteria (Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Pseudomonas fluorescens) and three fungi (Trichophyton rubrum, Candida albicans and Aspergillus niger). Among the compound tested, 6d, 6e, 6f and 6m exhibited pronounced antibacterial activities and 6e and 6m also showed moderate antifungal activities. Particularly, 6d exhibited stronger antibacterial activity against B. subtilis comparable to positive control.

Synthesis and structure of indoline spiropyrans of the coumarin series

New indoline spiropyrans of the coumarin series were synthesized by the condensation of indoline and hydroxyformylcoumarin derivatives. Spiropyrans, viz., derivatives of 8-formyl-7-hydroxy-4-methylcoumarin and 5-formyl-6-hydroxy-4-methylcoumarin, under irradiation are transformed into open forms, which are recyclized in the dark. The compounds formed by the condensation of the indoline derivatives with 3-formyl-4-hydroxycoumarin have an open structure of the merocyanine dyes and are transformed into spiro forms neither in the dark nor under irradiation with the visible light.

Syntheses of 4-(5-oxo-1,2,4-triazol-3-yl)-sydnones and 4(4-arylamino-5-oxo-1,2,4-triazol-3-yl)-sydnones from sydnone derivatives and their fragments

4-(5-oxo-1,2,4-triazol-3-yl)-sydnones 11 and 4-(4-arylamino-5-oxo-1,2,4-triazol-3-yl)-sydnones 13 have been obtained from a-chloroformylarylhydrazine hydrochloride 2. Moreover, the intermediates, including 3, 4, 9 and 10, in this study are synthetically informative and valuable. It is also noteworthy that three reactants, 1, 2 and sydnonecarbaldehydes, were prepared from sydnone derivatives and their fragments. The oxidative cyclizations of sydnonecarbaldehyde semicarbazones 9 and carbazpnes 10 with two different oxidizing agents (Cu(ClO4)2 and Fe(ClO4)3) have been extensively examined. The reaction time and the yields of cyclizations were affected by the substituents of semicarbazones 9 and carbazones 10.