17846-15-0

Usage

Uses

Used in Pharmaceutical Industry:
ADAMANTANE-1-CARBOHYDRAZIDE is used as a building block for the synthesis of various pharmaceuticals and organic compounds. Its unique molecular structure and properties contribute to the development of diverse functional materials and pharmaceuticals.
Used in Materials Science:
ADAMANTANE-1-CARBOHYDRAZIDE is used as a starting material for the preparation of diverse functional materials. Its high thermal stability makes it suitable for applications in materials science.
Used as a Corrosion Inhibitor:
ADAMANTANE-1-CARBOHYDRAZIDE is used as a corrosion inhibitor, providing protection against corrosion in various industrial applications.
Used in Medicine:
ADAMANTANE-1-CARBOHYDRAZIDE has potential applications in the field of medicine, although specific uses are not detailed in the provided materials. Its unique properties may contribute to the development of new medical treatments or therapies.

InChI:InChI=1/C11H18N2O/c12-13-10(14)11-4-7-1-8(5-11)3-9(2-7)6-11/h7-9H,1-6,12H2,(H,13,14)

Upstream product

• 2094-73-7 ethyl 1-adamantanecarboxylate 
• 896109-93-6 ethyl 2-(1-adamantylcarbonyl)-3-oxobutanoate 
• 711-01-3 methyl adamantane-1-carboxylate 
• 326488-61-3 1-(adamantane-1-carbonyl)imidazolide 
• 828-51-3 1-Adamantanecarboxylic acid 

Downstream Products

• 81375-02-2 C₁₇H₂₂N₂O₃S 
• 35196-43-1 C₁₈H₂₉N₃OS 
• 206051-44-7 3-Adamantan-1-yl-5-m-tolyl-1H-[1,2,4]triazole 
• 206051-43-6 3-Adamantan-1-yl-5-p-tolyl-1H-[1,2,4]triazole 
• 94527-38-5 benzoic acid N'-(adamantane-1-carbonyl)hydrazide 
• 866461-46-3 adamantane-1-carboxylic acid N'-phenylacetyl-hydrazide 
• 581788-99-0 3-(1-adamantyl)-5-(3,4,5-trimethoxyphenyl)-4-methyl-4H-1,2,4-triazole 
• 1334814-46-8 (Z)-N'-(2-oxo-1-phenylindolin-3-ylidene)adamantane-1-carbohydrazide 
• 1469862-36-9 C₂₀H₂₆N₄S 
• 1469862-45-0 C₂₆H₂₆ClF₃N₄S 
• 1469862-46-1 C₂₆H₂₆ClF₃N₄S 
• 1469862-47-2 C₂₆H₂₆ClF₃N₄S 
• 1469862-48-3 C₂₅H₂₅ClF₂N₄S 
• 1469862-49-4 C₂₅H₂₅Cl₃N₄S 

Relevant academic research and scientific papers

Synthesis and structure insights of two novel broad-spectrum antibacterial candidates based on (E)-N0-[(Heteroaryl)methylene]adamantane-1carbohydrazides

Two new N0-heteroarylidene-1-carbohydrazide derivatives, namely; E-N0-[(pyridine-3yl)methylidene]adamantane-1-carbohydrazide (1) and E-N0-[(5-nitrothiophen-2-yl)methylidene] adamantane-1-carbohydrazide (2), were produced v

Novel antitumor adamantane-azole gold(I) complexes as potential inhibitors of thioredoxin reductase

Gold complexes that could act as antitumor agents have attracted great attention. Heterocyclic compounds and their metal complexes display a broad spectrum of pharmacological properties. The present study reports the preparation and characterization of fo

In-silico identification of the binding mode of synthesized adamantyl derivatives inside cholinesterase enzymes

Aim: To investigate the binding mode of synthesized adamantly derivatives inside of cholinesterase enzymes using molecular docking simulations. Methods: A series of hybrid compounds containing adamantane and hydrazide moieties was designed and synthesized

Synthesis, in vitro cytotoxic and apoptotic effects, and molecular docking study of novel adamantane derivatives

[4-(Adamantane-1-carboxamido)-3-oxo-1-thia-4-azaspiro[4.4]nonan-2-yl]acetic acid (4a) and [4-(adamantane-1-carboxamido)-8-nonsubstituted/substituted-3-oxo-1-thia-4-azas-piro[4.5]decane-2-yl]acetic acid (4b–g) derivatives were synthesized; their structures were verified by elemental analysis, infrared spectroscopy, 1H nuclear magnetic resonance (NMR), 13C NMR, and mass?spectroscopy data; and their in vitro cytotoxicity activities were investigated against human hepatocellular carcinoma, human prostate adenocarcinoma, and human lung carcinoma cell lines (HepG2, PC-3, and A549, respectively), and a mouse fibroblast cell line (NIH/3T3). All compounds, except?compound 4e, were found as cytotoxic, especially on A549 cells as compared with the other cells (selectivity index = 2.01–11.6). As a further step, the effects of compounds 4a–c on apoptosis induction were tested and the expression of selected apoptosis genes was analyzed. Among the selected compounds, compound 4a induced apoptosis remarkably. Moreover, computational calculations of the binding of compounds 4a–c to the BIR3 domain of the human inhibitor of apoptosis protein revealed ligand–protein interactions at the atomistic level and emphasized the importance of a hydrophobic moiety on the ligands for better binding.

Novel adamantane-pyrazole and hydrazone hybridized: Design, synthesis, cytotoxic evaluation, SAR study and molecular docking simulation as carbonic anhydrase inhibitors

A series of pyrazole derivatives 4, 5, 6, 12, 13, 14 as well as hydrazone derivatives 7, 10, 11 were synthesized starting from adamantane-1-carbohydrazide as the bioactive core. All newly designed adamantane derivates were established by full characterized using different spectroscopic methods. The novel derivatives were investigated for their antitumor activity against three cell line MCF-7, HepG-2 and A549. They displayed good IC50 values ranged between 1.55 to 42.17 μM in comparison to Doxorubicin (IC50 =3.58–8.19 μM). Surprisingly, adamantine derivatives revealed more sensitivity and selectivity to lung cancer cells (A549) with eight compounds (4, 5, 9a, 9b, 9c, 12, 13a and 14c) having IC50 less than or equal ten micromoles. The most promising three adamantane derivatives 9a, 12 and 13a with IC50 values less than 5 μM were selected to study enzymatic assay for isoenzyme hCAIX and hCAXII. Also, pyrazole core 13a and 12 showed higher KI values than hydrazone derivatives 9a with submicromolar between (0.085–0.527 μM), in comparison to Acetazolamide (0.041–0.068 μM). Compound 13a is the most promising derivatives with anti-proliferative (A549) (IC50=1.55 ± 0.08 μM) which showed CAIX/XII inhibitory activity (KI = 0.085 and 0.14 μM), respectively. Finally, molecular docking simulation was performed to determine the binding modes and possible interaction of the adamantane derivatives within the active site of 3IAI and 1JD0 for CAIX / XII respectively with low binding affinity.

Synthesis and bioactivity of hydrazide-hydrazones with the 1-adamantyl-carbonyl moiety

Reaction of 1-adamantyl carbohydrazide (1) with various substituted benzaldehydes and acetophenones yielded the corresponding hydrazide-hydrazones with a 1-adamantane carbonyl moiety. The new synthesized compounds were tested for activities against some Gram-negative and Gram-positive bacteria, and the fungus Candida albicans. Compounds 4a, 4b, 5a, and 5c displayed potential antibacterial activity against tested Gram-positive bacteria and C. albicans, while compounds 4e and 5e possessed cytotoxicity against tested human cancer cell lines.

Facile synthesis and antimycobacterial activity of isoniazid, pyrazinamide and ciprofloxacin derivatives

Several rationally designed isoniazid (INH), pyrazinamide (PZA) and ciprofloxacin (CPF) derivatives were conveniently synthesized and evaluated in vitro against H37Rv Mycobacterium tuberculosis (M. tb) strain. CPF derivative 16 displayed a modest activity

Schiff Bases of Isatin and Adamantane-1-Carbohydrazide: Synthesis, Characterization and Anticonvulsant Activity

Epilepsy is the most common neurological condition and cause of substantial morbidity and mortality. In the present study, the molecular hybridization tool was adopted to obtain six Schiff bases of isatin and adamantane-1-carbohydrazide (18-23). Then, their anticonvulsant activity was evaluated using pentylenetetrazole- (PTZ-) induced seizure model using phenobarbitone as a positive control. Our findings showed that compounds 18-23 provided significant protection against PTZ-induced seizure, and maximum activities were associated with compound 23. Moreover, all investigated compounds increased the latency of induced convulsion and reduced the duration of epilepsy with compound 23 being the best. Interestingly, most of the synthesized molecules showed reduction in neurological symptoms and severity of the seizure. Molecular docking studies suggest GABA-A receptor as a potential target, and in silico ADME screening revealed that the pharmaceutical properties of compound 23 are within the specified limit. Thus, compound 23 was identified as a promising candidate that warrants further drug discovery processes.

FLOW CHEMISTRY SYNTHESIS OF ISOCYANATES

The disclosure provides, inter alia, safe and environmentally-friendly methods, such as flow chemistry, to synthesize isocyanates, such as methylene diphenyl diisocyanate, toluene diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, and tetramethylxylene diisocyanate.

Synthesis and Evaluation of Nifurtimox–Adamantane Adducts with Trypanocidal Activity

The synthesis and pharmacological evaluation of C1-substituted adamantane hydrazones, their C2-substituted isomers, and C1-substituted adamantane furanoic carboxamides is described. These new adamantane derivatives exhibited an interesting pharmacological profile in terms of trypanocidal activity and selectivity. The most active adduct with the best selectivity in this study was found to be the phenylacetoxy hydrazone 1 b (2-[4-(tricyclo[3.3.1.13,7]dec-1-yl)phenyl]-N′-[(5-nitrofuran-2-yl)methylene]acetohydrazide; EC50=11±0.9 nm, SITb=770).