537-47-3

Usage

Purification Methods

Crystallise it from water and dry it in a vacuum over KOH. [Beilstein 12 II 221, 12 III 822.]

InChI:InChI=1/C7H9N3O/c8-10-7(11)9-6-4-2-1-3-5-6/h1-5H,8H2,(H2,9,10,11)

Upstream product

• 603-54-3 N,N-diphenylurea 
• 17531-59-8 benzaldehyde N-phenylsemicarbazone 
• 2492-30-0 acetophenone semicarbazone 
• 62-53-3 aniline 
• 25445-76-5 N-ethoxycarbonyl-N'-(1-phenyl-ethylidene)-hydrazine 
• 110-20-3 acetone semicarbazone 
• 1010-53-3 3-phenyl-2,4-thiazolidinedione 
• 7803-57-8 hydrazine hydrate 
• 102-07-8 bis(diphenyl)urea 
• 103-71-9 phenyl isocyanate 
• 100-63-0 phenylhydrazine 
• 64-17-5 ethanol 
• 64-10-8 phenyl carbamate 
• 1006894-80-9 2-benz-(E)-ylidene-N-phenylhydrazinecarboxamide 

Downstream Products

• 147353-81-9 (E)-4-phenyl-1-(pyridine-2-ylmethylene)semicarbazide 
• 126713-58-4 pyridine-4-carbaldehyde-(4-phenyl semicarbazone) 
• 119034-13-8 FPSC 
• 106377-75-7 oxepan-4-one-(4-phenyl semicarbazone) 
• 106475-46-1 1-[3]furyl-propan-1-one-(4-phenyl semicarbazone) 
• 132649-74-2 1-[3]furyl-pentan-1-one-(4-phenyl semicarbazone) 
• 131003-42-4 N-phenyl-N'-phthalimido-urea 
• 131762-31-7 1-[3]furyl-heptan-1-one-(4-phenyl semicarbazone) 
• 133218-17-4 N-(5-Nitro-2-furfurylidene)-4-phenylsemicarbazide 
• 102029-10-7 [3]furyl-phenyl ketone-(4-phenyl semicarbazone) 
• 100725-18-6 2-hydroxy-1-(5-nitro-[2]furyl)-ethanone-(4-phenyl semicarbazone) 
• 24060-13-7 2-cyclohexylidene-N-phenylhydrazine-1-carboxamide 
• 61733-82-2 N⁴-phenyl acetic acid semicarbazide 
• 314285-37-5 3-(4-phenyl-semicarbazono)-butyric acid ethyl ester 

Relevant academic research and scientific papers

Design, synthesis and anticancer evaluation of novel spirobenzo[h]chromene and spirochromane derivatives with dual EGFR and B-RAF inhibitory activities

A novel series of spirobenzo[h]chromene and spirochromane derivatives was designed, synthesized and evaluated as potential anticancer agents against MCF-7 (human breast carcinoma), HT-29 (human colorectal adenocarcinoma) and A549 (human lung carcinoma) cell lines using MTT assay. Eight compounds 7, 8e, 13a-e and 16 showed a better anticancer activity than that of sorafenib, the multi-kinase inhibitor with IC50 values between 1.78 and 5.47 μM or erlotinib with IC50 values over 20 μM. Representative compounds 8e, 13c and 16 were selected for further mechanistic investigation via EGFR, B-RAF and tubulin polymerization assays. Compound 16 was the most potent EGFR inhibitor (IC50 = 1.2 μM), yet compounds 8e, 13c and 16 displayed moderate tubulin polymerization inhibition effects. Molecular docking studies of those compounds revealed their possible binding modes into the active sites of both EGFR and B-RAF kinases. The newly developed compounds represent a therapeutically promising approach for the treatment of different types of cancer.

Design and synthesis of novel pyrazole-phenyl semicarbazone derivatives as potential α-glucosidase inhibitor: Kinetics and molecular dynamics simulation study

A series of novel pyrazole-phenyl semicarbazone derivatives were designed, synthesized, and screened for in vitro α-glucosidase inhibitory activity. Given the importance of hydrogen bonding in promoting the α-glucosidase inhibitory activity, pharmacophore modification was established. The docking results rationalized the idea of the design. All newly synthesized compounds exhibited excellent in vitro yeast α-glucosidase inhibition (IC50 values in the range of 65.1–695.0 μM) even much more potent than standard drug acarbose (IC50 = 750.0 μM). Among them, compounds 8o displayed the most potent α-glucosidase inhibitory activity (IC50 = 65.1 ± 0.3 μM). Kinetic study of compound 8o revealed that it inhibited α-glucosidase in a competitive mode (Ki = 87.0 μM). Limited SAR suggested that electronic properties of substitutions have little effect on inhibitory potential of compounds. Cytotoxic studies demonstrated that the active compounds (8o, 8k, 8p, 8l, 8i, and 8a) compounds are also non-cytotoxic. The binding modes of the most potent compounds 8o, 8k, 8p, 8l and 8i was studied through in silico docking studies. Molecular dynamic simulations have been performed in order to explain the dynamic behavior and structural changes of the systems by the calculation of the root mean square deviation (RMSD) and root mean square fluctuation (RMSF).

Design, synthesis, and biological activity of novel semicarbazones as potent Ryanodine receptor1 inhibitors of Alzheimer's disease

Ryanodine receptors (RyRs) are important ligand-gated Ca2+ channels; their excessive activation leads to Ca2+ leakage in the sarcoplasmic reticulum that may cause neurological diseases. In this study, three series of novel potent RyR1 inhibitors based on dantrolene and bearing semicarbazone and imidazolyl moieties were designed and synthesized, and their biological activity was evaluated. Using a single-cell calcium imaging method, the calcium overload inhibitory activities of 26 target compounds were tested in the R614C cell line, using dantrolene as a positive control. The preliminary investigation showed that compound 12a suppressed Ca2+ release as evidenced by store overload-induced Ca2+release (SOICR) (31.5 ± 0.1%, 77.2 ± 0.1%, 93.7 ± 0.2%) at 0.1 μM, 3 μM and 10 μM, respectively. Docking simulation results showed that compound 12a could bind at the active site of the RyR1 protein. The Morris water-maze test showed that compound 12a significantly improved the cognitive behavior of AD-model mice. Further studies on the structural optimization of this series of derivatives are currently underway in our laboratory.

2-((disubstituted sulfonyl)methylene)-N-arylhydrazino-1-formamide derivative and preparation method and application thereof

The invention discloses a 2-((disubstituted sulfonyl)methylene)-N-arylhydrazino-1-formamide derivative and a preparation method and application thereof. In the structural general formula (I), R1 is asubstituent such as a hydrogen atom, 4-chlorphenyl, 4-fluorophenyl, 3-methylphenyl, 3, 5-xylyl, 2, 6-xylyl and the like, and R2 is substituent groups such as methyl, ethyl, propyl, isopropyl, benzyl and 4-methyl benzyl. The compound has excellent antibacterial activity in bacterial diseases such as bacterial blight of rice, bacterial streak of rice, bacterial wilt of tobacco, bacterial leaf spot of pepper, citrus canker and the like, and is simple in structure and relatively stable in compound property.

Design, Synthesis and Antifungal Activity of Benzofuran and Its Analogues

Benzofuran has antifungal activity as the inhibitor of N-myristoyltransferase. Twenty-nine novel benzofuran-semicarbazide hybrids were designed and synthesized by principle of drug combinationatory. On this basis, the benzofuran ring was simplified to a resorcinol structure, and sixteen novel 1,3-dialkoxybenzene-semicarbazide hybrids were designed and synthesized. All structures of the target compounds were characterized by HRMS and NMR. The in vitro antifungal activity of target compounds was evaluated using the microdilution broth method against eight strains of pathogenic fungi with fluconazole as positive control. According to the results of the target compounds, structure-activity relationship (SAR) is summarized. The inhibitory activity against the tested strains of simplified compounds (K01—K16) has different levels improvement compared with compounds Z01—Z29. K01—K16 showed significant antifungal activities against A. fumigatus, C. kruseii, and sensitive C. albicans 5314. Notably, compounds Z20, Z22, K10, K11 and K16 also displayed different activities against two fluconazole-resistance strains that were isolated from AIDS patients. The minimal inhibitory concentration (MIC) values against fluconazole-resistant strains were in the range of 2—8 μg/mL and 4—32μg/mL, respectively. Furthermore, molecular docking was performed to investigate the binding affinities and interaction modes between the target compound and N-myristoyltransferase.

Sulfonyl-containing thioformylhydrazine derivatives, preparation method and application thereof

The invention discloses sulfonyl-containing thioformylhydrazine derivatives, a preparation method and application thereof. A structural general formula (I) of the sulfonyl-containing thioformylhydrazine derivatives is as follows, wherein R1 is methyl, ethyl, benzyl, 4-methyl benzyl or 2,4-dichlorobenzyl; R2 is hydrogen atom, 4-chlorine, 4-fluoride, 3-methyl, 3,5-dimethyl or 2,6-dimethyl. The sulfonyl-containing thioformylhydrazine derivatives have excellent resistance to bacterial diseases such as rice bacterial leaf blight bacteria, rice bacterial streak bacteria, citrus canker bacteria and the like, and are simple in structure and relatively stable in compound properties. (Shown in the description).

N-substituent group-N-(substituted phenylaminocarbonyl)-1-substituted sulfonylthioformylhydrazide derivatives and application thereof

The invention discloses N-substituent group-N-(substituted phenylaminocarbonyl)-1-substituted sulfonylthioformylhydrazide derivatives as well as a preparation method and application thereof. The derivatives have a structural general formula (I) shown in the description, wherein n = 0, 1 or 2, and X = C, N, O or S; R1 is C1-4 alkyl or substituted benzyl; and R2 is a hydrogen atom, an o-position, anm-position, a p-position monosubstituted halogen atom, C1-4 alkyl, C1-2 alkoxy, or a polysubstituted halogen atom. The derivatives provided by the invention have excellent antibacterial activity against bacterial diseases such as xanthomonas oryzae, xanthomonas oryzicola and xanthomonas citri, the synthetic raw materials have low costs, and the synthetic method is simple and easy.

Design, synthesis and biological evaluation of novel semicarbazone-selenochroman-4-ones hybrids as potent antifungal agents

A series of novel 2,3-dihydro-4H-1-benzoselenin-4-one (thio)semicarbazone derivatives were designed and synthesized by using molecular hybridization approach. All the target compounds were characterized by HRMS and NMR and evaluated in vitro antifungal activity against five pathogenic strains. In comparison with precursor selenochroman-4-ones, the hybrid molecules in this study showed significant improvement in antifungal activities. Notably, compound B8 showed significant antifungal activity against other strains excluding Aspergillus fumigatus (0.25 μg/mL on Candida albicans, 2 μg/mL on Cryptococcus neoformans, 8 μg/mL on Candida zeylanoides and 2 μg/mL on fluconazole-sensitive strains of Candida albicans). Moreover, compounds B8, B9 and C2 also displayed most potent activities against four fluconazole-resistance strains. Especially the MIC values of the hybrid molecule B8 against fluconazole-resistant strains were in the range of 0.5–2 μg/mL. Therefore, the molecular hybridization approach in this study provided new ideas for the development of antifungal drug.

Design and synthesis of novel N-(4-(Pyridin-2-yloxy)benzylidene)-4-[4-(substituted)phenyl]semicarbazides as potential anticonvulsant agents

A new series of N-(4-(pyridin-2-yloxy)benzylidene)-4-[4-(substituted)phenyl]semicarbazides (PSSD1-8) were designed and synthesized keeping in view the structural requirement of pharmacophore and evaluated for their possible anticonvulsant activity. All the derivatives were synthesized by the given scheme and reaction process was monitored by thin layer chromatography. The structure of synthesized derivatives was confirmed by FT-IR, 1H NMR, mass spectroscopy and elemental analysis. The anticonvulsant activity was established after intraperitoneal administration in MES and scMET seizure models. The most active compound of the series was 1-(4-(pyridin-2-yloxy)-benzylidene)-4-p-tolylsemicarbazide (PSSD5). A molecular docking study was carried out in order to assess the interaction and binding modes with target receptor/enzyme. Titled compounds were found to strongly bind to human gamma-aminobutyric acid receptor (GABAAR-β3). A computational study was also carried to predict the pharmacokinetic properties of the synthesized compounds.

Highly Regioselective Carbamoylation of Electron-Deficient Nitrogen Heteroarenes with Hydrazinecarboxamides

The use of hydrazinecarboxamides as a new class of carbamoylating agents has been established through the dehydrazinative Minisci reaction of electron-deficient nitrogen heteroarenes. A wide range of electron-deficient nitrogen heteroarenes, including isoquinoline, quinoline, pyridine, phenanthridine, quinoxaline, and phthalazine, underwent copper/acid-catalyzed oxidative carbamoylation with hydrazinecarboxamide hydrochlorides to afford structurally diverse nitrogen-heteroaryl carboxamides as single regioisomers in moderate to excellent yields. The functional group tolerance was substantially demonstrated in the direct carbamoylation of quinine obviating multistep sequences involving protecting groups and prefunctionalization of the heterocycle.