35580-76-8

Usage

Uses

Used in Pharmaceutical Industry:
N-(2-CHLOROPHENYL)-1-HYDRAZINECARBOXAMIDE is used as a building block for the synthesis of various pharmaceuticals due to its chemical properties and reactivity, contributing to the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, N-(2-CHLOROPHENYL)-1-HYDRAZINECARBOXAMIDE serves as a key intermediate in the production of agrochemicals, playing a crucial role in the synthesis of compounds that can be used in pest control and crop protection.
Used as an Anti-inflammatory and Analgesic Agent:
N-(2-CHLOROPHENYL)-1-HYDRAZINECARBOXAMIDE is used in biological research and development as an anti-inflammatory and analgesic agent, given its potential to exhibit these therapeutic effects, which are under investigation for possible clinical applications.
Used in Organic Dyes and Pigments Production:
N-(2-CHLOROPHENYL)-1-HYDRAZINECARBOXAMIDE is also utilized as an intermediate in the production of organic dyes and pigments, where its chemical structure contributes to the color and properties of the final products, finding applications in various industries such as textiles, paints, and plastics.

Upstream product

• 95-51-2 o-chloroaniline 
• 917-61-3 sodium isocyanate 
• 3320-83-0 o-chlorophenyl isocyanate 
• 114-38-5 (2-chlorophenyl)urea 

Downstream Products

• 1357066-55-7 4-[(5-[2-chlorophenylamino]-1,3,4-oxadiazol-2-yl)methylamino]-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one 
• 527684-69-1 2',3',5'-tri-O-acetyl-2-[3-(2-chlorophenyl)aminocarbonyltriazene-1-yl]adenosine 
• 33714-28-2 C₁₅H₁₄ClN₃O₂ 
• 33714-29-3 benzo[1,3]dioxole-5-carbaldehyde 4-(2-chloro-phenyl)-semicarbazone 
• 89938-45-4 2-N-(2-chlorophenyl)-1,3,4-oxadiazole-2,5-diamine 
• 1312809-72-5 4-(2-chlorophenyl)-4,5-dihydro-1H-1,2,4-triazol-5-one 

Relevant academic research and scientific papers

GPR139 RECEPTOR MODULATORS

Compounds are provided that modulate the GPR139 receptor, compositions containing the same, and to methods of their preparation and use for treatment of a malcondition wherein modulation of the GPR139 receptor is medically indicated or beneficial. Such compounds have the structure of Formula (I): or a pharmaceutically acceptable isomer, racemate, hydrate, solvate, isotope, or salt thereof, wherein R1, R4, R5, R9, R10, Q6, Q7, and Q12 are as defined herein.

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.

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.

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.

Synthesis and anticonvulsant evaluation of 2-(substituted benzylidene/ethylidene)-N-(substituted phenyl)hydrazinecarboxamide analogues

In the present investigation, we described herein the molecular properties prediction by Molinspiration (2008) and synthesized a series of 17 2-(substituted benzylidene/ethylidene)-N-(substituted phenyl) hydrazinecarboxamide analogues. All the title compounds (4a-q) followed the Lipinski "Rule of Five." The synthesized compounds were characterised by elemental analyses and spectral data followed by anticonvulsant activity according to the Antiepileptic Drug Development Programme Protocol. 2-(4-Hydroxybenzylidene)-N-(2-chlorophenyl)hydrazinecarboxamide (4j) was found to be the most active compound of the series showing protection at 4.0 h at a dose of 100 mg/kg against maximal electroshock seizure test and 50 % (2/4, 0.25, 1-2 h) and 100 % (4/4, 0.5 h) protection in 6 Hz psychomotor seizure test without showing any neurotoxicity. N-(2-chlorophenyl)hydrazine carboxamide (3b) showed 100 % (4/4, 0.25-2 h) and 66.6 % (2/3, 4 h) protection in 6 Hz psychomotor seizure test.

Synthesis and anticonvulsant and neurotoxicity evaluation of N 4-phthalimido phenyl (thio) semicarbazides

The phenyl (thio) semicarbazide derivatives of phthalimido pharmacophore were synthesized and evaluated for their anticonvulsant and neurotoxic properties. Initial anticonvulsant screening was performed using intraperitoneal (i.p.), maximal electroshock-induced seizure (MES), subcutaneous pentylenetetrazole (scPTZ) and subcutaneous strychnine (sc STY)-induced seizure threshold tests in mice. Compound 2c afforded protection in all the three screens. Compounds except 1d, 2a and 2d showed no neurotoxicity up to 300mg/kg. Compounds 1a, 1b, 2c, 2d, 2g and 2i were found to show oral MES activity. The compounds exhibited CNS depression and behavioral despair side effects, lesser than the conventional antiepileptic drugs.

N6-cyclopentyl-2-(3-phenylaminocarbonyltriazene-1-yl)adenosine (TCPA), a very selective agonist with high affinity for the human adenosine A1 receptor

Four subtypes of adenosine receptors are currently known, that is, A1, A2A, A2B, and A3 receptors. Interestingly, quite substantial species differences exist especially between human and rat A3 receptors. As a result, ligands such as CCPA, which are very selective for the rat A1 receptor versus the human A3 receptor, are substantially less selective when the human A1 and A3 receptors are compared. New 2-substituted and 2,N6-disubstituted adenosines were synthesized, and their affinities for the human adenosine A1, A2A, A2B, and A3 receptors were determined. Although large substituents on the C2-position are generally thought to yield adenosine A2A receptor selective ligands, the reported series of 2-triazeno-substituted adenosines had a very high affinity for the A1 receptor. For example, 2-(3-phenylaminocarbonyltriazene-1-yl)adenosine had an affinity of 6.1 ± 1.3 nM for the human adenosine A1 receptor. Introduction of a diphenethyl substituent at the N6-position of this compound resulted in a high-affinity agonist, 3.1 ± 0.9 nM, for the human adenosine A1 receptor with 316- and 45-fold selectivity versus the human A2A and human A3 receptors, respectively. The most selective, high-affinity human adenosine A1 receptor agonist was the disubstituted compound N6-cyclopentyl-2-(3-phenylaminocarbonyltriazene-1-yl)adenosine (TCPA). TCPA had an affinity of 2.8 ± 0.8 nM for the human adenosine A1 receptor and was 75-fold and 214-fold selective versus the human A2A and human A3 receptors, respectively. In addition, TCPA was a full agonist and inhibited the forskolin-induced cAMP production of CHO cells stably transfected with the human adenosine A1 receptor with an IC50 of 1.5 ± 0.5 nM.

Design of semicarbazones and their bio-isosteric analogues as potential anticonvulsants

A series of semicarbazones and hydrazones were prepared and evaluated for anticonvulsant activity. Some compounds provided significant protection against maximal electroshock (MES) and subcutaneous strychnine induced seizures (ScSty). Compound 2a emerged as the most active compound at a dose of 30 mg/kg in ScSty test. The compounds 1a, 1g and 2a-e showed significant potentiation of sedative and hypnotic activity of pentobarbitone sodium. Thus compound 2a could serve as a prototype for future developments.