38941-47-8

Usage

Uses

Used in Pharmaceutical Industry:
Cyclohexanecarboxylic acid hydrazide is used as a key intermediate in the synthesis of pharmaceuticals for its ability to react and form new compounds with potential therapeutic properties.
Used in Agrochemical Industry:
CYCLOHEXANECARBOXYLIC ACID HYDRAZIDE is utilized as a precursor in the production of herbicides, fungicides, and insecticides, contributing to the development of effective crop protection agents.
Used in Chemical Synthesis:
Cyclohexanecarboxylic acid hydrazide is used as a versatile building block in the synthesis of various organic compounds, showcasing its reactivity and structural adaptability in chemical processes.
Used in Corrosion Inhibition:
CYCLOHEXANECARBOXYLIC ACID HYDRAZIDE has been studied for its potential use in corrosion inhibition, indicating its application in protecting materials from degradation in various industrial settings.
Used in Dyes and Pigments Production:
Cyclohexanecarboxylic acid hydrazide serves as an intermediate in the production of dyes and pigments, highlighting its role in creating a diverse palette of colorants for different applications.

InChI:InChI=1/C7H14N2O/c8-9-7(10)6-4-2-1-3-5-6/h6H,1-5,8H2,(H,9,10)

Upstream product

• 3289-28-9 ethyl cyclohexanecarboxylate 
• 613-94-5 benzoic acid hydrazide 
• 4630-82-4 methyl cyclohexylcarboxylate 
• 98-89-5 Cyclohexanecarboxylic acid 
• 2719-27-9 cyclohexanylcarbonyl chloride 

Downstream Products

• 98427-18-0 5-cyclohexyl-1,3,4-oxadiazol-2-amine 
• 99976-69-9 cyclohexanecarboxylic acid (1-methylethylidene)hydrazide 
• 5814-04-0 1,2-bis-(cyclohexanecarbonyl)hydrazine 
• 1122-56-1 cyclohexylcarboxamide 
• 3173-53-3 Cyclohexyl isocyanate 
• 98173-37-6 N-(5-cyclohexyl-[1,3,4]oxadiazol-2-yl)-4-isopropyl-benzenesulfonamide 
• 93150-47-1 N-(5-cyclohexyl-[1,3,4]oxadiazol-2-yl)-4-ethyl-benzenesulfonamide 
• 93759-09-2 2,5-dichloro-N-(5-cyclohexyl-[1,3,4]oxadiazol-2-yl)-benzenesulfonamide 
• 93760-87-3 4-amino-N-(5-cyclohexyl-[1,3,4]oxadiazol-2-yl)-benzenesulfonamide 
• 93760-81-7 3-amino-N-(5-cyclohexyl-[1,3,4]oxadiazol-2-yl)-benzenesulfonamide 
• 92492-51-8 2-cyclohexyl-5-phenyl-1,3,4-oxadiazole 
• 14664-89-2 N-[2-(5-cyclohexyl-[1,3,4]oxadiazol-2-yl)-ethyl]-aniline 
• 14940-75-1 4-chloro-N-[2-(5-cyclohexyl-[1,3,4]oxadiazol-2-yl)-ethyl]-aniline 
• 93536-23-3 4-chloro-N-(5-cyclohexyl-[1,3,4]oxadiazol-2-yl)-benzenesulfonamide 

Relevant academic research and scientific papers

4-Alkyl-1,2,4-triazole-3-thione analogues as metallo-β-lactamase inhibitors

In Gram-negative bacteria, the major mechanism of resistance to β-lactam antibiotics is the production of one or several β-lactamases (BLs), including the highly worrying carbapenemases. Whereas inhibitors of these enzymes were recently marketed, they only target serine-carbapenemases (e.g. KPC-type), and no clinically useful inhibitor is available yet to neutralize the class of metallo-β-lactamases (MBLs). We are developing compounds based on the 1,2,4-triazole-3-thione scaffold, which binds to the di-zinc catalytic site of MBLs in an original fashion, and we previously reported its promising potential to yield broad-spectrum inhibitors. However, up to now only moderate antibiotic potentiation could be observed in microbiological assays and further exploration was needed to improve outer membrane penetration. Here, we synthesized and characterized a series of compounds possessing a diversely functionalized alkyl chain at the 4-position of the heterocycle. We found that the presence of a carboxylic group at the extremity of an alkyl chain yielded potent inhibitors of VIM-type enzymes with Ki values in the μM to sub-μM range, and that this alkyl chain had to be longer or equal to a propyl chain. This result confirmed the importance of a carboxylic function on the 4-substituent of 1,2,4-triazole-3-thione heterocycle. As observed in previous series, active compounds also preferentially contained phenyl, 2-hydroxy-5-methoxyphenyl, naphth-2-yl or m-biphenyl at position 5. However, none efficiently inhibited NDM-1 or IMP-1. Microbiological study on VIM-2-producing E. coli strains and on VIM-1/VIM-4-producing multidrug-resistant K. pneumoniae clinical isolates gave promising results, suggesting that the 1,2,4-triazole-3-thione scaffold worth continuing exploration to further improve penetration. Finally, docking experiments were performed to study the binding mode of alkanoic analogues in the active site of VIM-2.

Ultralow-Molecular-Weight Stimuli-Responsive and Multifunctional Supramolecular Gels Based on Monomers and Trimers of Hydrazides

The simpler, the better. A series of simple, neutral and ultralow-molecular-weight (MW: 140–200) hydrazide-derived supramolecular gelators have been designed and synthesized in two straightforward steps. For non-conjugated cyclohexane-derived hydrazides, their monomers can self-assemble to form gels through intermolecular hydrogen bonds and dipole-dipole interactions. Significantly, conjugated phthalhydrazide can self-aggregate into planar and circular trimers through intermolecular hydrogen bonds and then self-assemble to form gels through intermolecular π–π stacking interactions. It is interesting that these simple gelators exhibit unusual properties, such as self-healing, multi-response fluorescence, and visual and selective recognition of chiral (R)/(S)-1,1′-binaphthalene-2,2′-diamine and S2? through much different times of gel re-formation and blue-green color change, respectively. These results underline the importance of supramolecular gels and extend the scope of supramolecular gelators.

Synthesis, Dissociation Constants, and Antimicrobial Activity of Novel 2,3-Disubstituted-1,3-thiazolidin-4-one Derivatives

In this article, a new series of 2,3-disubstituted-1,3-thiazolidin-4-one derivatives have been designed, synthesized, and evaluated as antimicrobial agents. New compounds were prepared by the cyclization reaction of N-substituted carboxylic acid hydrazide derivatives with mercaptoacetic acid. The structures of the obtained compounds were confirmed by means of IR, 1H NMR, and 13C NMR spectra. The dissociation constants were determined using spectrophotometric method. All synthesized compounds were tested for their in vitro antibacterial and antifungal activities using the broth microdilution method.

Development of 3,5-Dinitrobenzylsulfanyl-1,3,4-oxadiazoles and Thiadiazoles as Selective Antitubercular Agents Active Against Replicating and Nonreplicating Mycobacterium tuberculosis

Herein, we report the discovery and structure-activity relationships of 5-substituted-2-[(3,5-dinitrobenzyl)sulfanyl]-1,3,4-oxadiazoles and 1,3,4-thiadiazoles as a new class of antituberculosis agents. The majority of these compounds exhibited outstanding in vitro activity against Mycobacterium tuberculosis CNCTC My 331/88 and six multidrug-resistant clinically isolated strains of M. tuberculosis, with minimum inhibitory concentration values as low as 0.03 μM (0.011-0.026 μg/mL). The investigated compounds had a highly selective antimycobacterial effect because they showed no activity against the other bacteria or fungi tested in this study. Furthermore, the investigated compounds exhibited low in vitro toxicities in four proliferating mammalian cell lines and in isolated primary human hepatocytes. Several in vitro genotoxicity assays indicated that the selected compounds have no mutagenic activity. The oxadiazole and thiadiazole derivatives with the most favorable activity/toxicity profiles also showed potency comparable to that of rifampicin against the nonreplicating streptomycin-starved M. tuberculosis 18b-Lux strain, and therefore, these derivatives, are of particular interest.

Acylhydrazone derivative used for treating heart failure

The invention belongs to the technical field of medicines, and relates to design and preparation method for acylhydrazone derivatives shown as a general formula I, and the acylhydrazone derivatives can be used for treating systolic heart failure comprising congestive heart failure.

Synthesis of 3-hydroxyindanones via potassium salt of amino acid catalyzed regioselective intramolecular aldolization of ortho-diacylbenzenes

First organocatalytic intramolecular aldolization of ortho-diacylbenzenes to construct highly functionalized 3-hydroxyindanones is described. In this transformation a high trans-selectivity is achieved by the use of metal salt of amino acid. This method allows an easy access to the strained spirocyclic 3-hydroxyindanones related to a number of natural product frameworks. Synthesis of a new class of indole skeleton substituted by 3-hydroxyindanones added an extra essence to this new protocol.

Designing and exploring active N′-[(5-nitrofuran-2-yl) methylene] substituted hydrazides against three Trypanosoma cruzi strains more prevalent in Chagas disease patients

Chagas disease affects around 8 million people worldwide and its treatment depends on only two nitroheterocyclic drugs, benznidazole (BZD) and nifurtimox (NFX). Both drugs have limited curative power in chronic phase of disease. Nifuroxazide (NF), a nitroheterocyclic drug, was used as lead to design a set of twenty one compounds in order to improve the anti-Trypanosoma cruzi activity. Lipinski's rules were considered in order to support drug-likeness designing. The set of N′-[(5-nitrofuran-2-yl) methylene] substituted hydrazides was assayed against three T. cruzi strains, which represent the discrete typing units more prevalent in human patients: Y (TcII), Silvio X10 cl1 (TcI), and Bug 2149 cl10 (TcV). All the derivatives, except one, showed enhanced trypanocidal activity against the three strains as compared to BZD. In the Y strain 62% of the compounds were more active than NFX. The most active compound was Ng€2-((5-nitrofuran-2-yl) methylene)biphenyl-4-carbohydrazide (C20), which showed IC50 values of 1.17 ± 0.12 μM; 3.17 ± 0.32 μM; and 1.81 ± 0.18 μ4M for Y, Silvio X10 cl1, and Bug 2149 cl10 strains, respectively. Cytotoxicity assays with human fibroblast cells have demonstrated high selectivity indices for several compounds. Exploratory data analysis indicated that primarily topological, steric/geometric, and electronic properties have contributed to the discrimination of the set of investigated compounds. The findings can be helpful to drive the designing, and subsequently, the synthesis of additional promising drugs against Chagas disease.

Novel orally active analgesic and anti-inflammatory cyclohexyl-N-acylhydrazone derivatives

The N-acylhydrazone (NAH) moiety is considered a privileged structure, being present in many compounds with diverse pharmacological activities. Among the activities attributed to NAH derivatives anti-inflammatory and analgesic ones are recurrent. As part of a research program aiming at the design of new analgesic and anti-inflammatory lead-candidates, a series of cyclohexyl-N-acylhydrazones 10-26 were structurally designed from molecular modification on the prototype LASSBio-294, representing a new class of cycloalkyl analogues. Compounds 10-26 and their conformationally restricted analogue 9 were synthetized and evaluated as analgesic and anti-inflammatory agents in classical pharmacologic protocols. The cyclohexyl-N-acylhydrazones 10-26 and the cyclohexenyl analogue 9 showed great anti-inflammatory and/or analgesic activities, but compound 13 stood out as a new prototype to treat acute and chronic painful states due to its important analgesic activity in a neuropathic pain model.

Structural feature evolution-from fluids to the solid phase-and crystal morphology study of LASSBio 1601: A cyclohexyl-N-acylhydrazone derivative

LASSBio-1601, a cyclohexyl-N-acylhydrazone derivative, was synthesized as part of a research program to develop a series of anti-inflammatory and analgesic compounds. A complete knowledge of the structure, including stereochemistry, is essential to lead o

ORGANOMETALLIC COMPLEX, LIGHT-EMITTING ELEMENT, DISPLAY DEVICE, ELECTRONIC DEVICE, AND LIGHTING DEVICE

Provided are organometallic complexes that can exhibit phosphorescence. One of the novel organometallic complexes is represented by General Formula (G1). In General Formula (G1), R1 represents any of an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms which may have a substituent, and an aralkyl group having 7 to 10 carbon atoms which may have a substituent. In addition, R2 represents any of an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms which may have a substituent, and an aryl group having 6 to 12 carbon atoms which may have a substituent. Further, Ar represents an arylene group having 6 to 13 carbon atoms which may have a substituent. Further, M represents a Group 9 element or a Group 10 element.