17846-15-0

Basic information

• Product Name: ADAMANTANE-1-CARBOHYDRAZIDE
• Synonyms: IFLAB-BB F0020-1578;AKOS BC-0549;ADAMANTANE-1-CARBOHYDRAZIDE;tricyclo[3.3.1.1~3,7~]decane-1-carboxylic acid, hydrazide;1-Adamantylcarboxylic acid hydrazide;NSC 354302;Adamantane-1-carboxylic acid hydrazide
• CAS NO: 17846-15-0
• Molecular Formula: C₁₁H₁₈N₂O
• Molecular Weight: 194.27
• Product Categories: Adamantane derivatives
• Mol File: 17846-15-0.mol
• Article Data: 17

Chemical Properties

• Melting Point: 151 °C
• Boiling Point: 370.8°Cat760mmHg
• Flash Point: 178°C
• Appearance: /
• Density: 1.203±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 1.08E-05mmHg at 25°C
• Refractive Index: 1.581
• PKA: 13.71±0.20(Predicted)
• CAS DataBase Reference: ADAMANTANE-1-CARBOHYDRAZIDE(CAS DataBase Reference)
• NIST Chemistry Reference: ADAMANTANE-1-CARBOHYDRAZIDE(17846-15-0)
• EPA Substance Registry System: ADAMANTANE-1-CARBOHYDRAZIDE(17846-15-0)

Safety Data

• Hazard Codes: Xi:Irritant
• Statements: 36/37/38
• Safety Statements: 26-37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 17846-15-0(Hazardous Substances Data)

Usage

General Description

ADAMANTANE-1-CARBOHYDRAZIDE is a chemical compound with the molecular formula C12H20N2O, commonly used as a building block in the synthesis of pharmaceuticals and organic compounds. It is a hydrazine derivative and belongs to the class of adamantane derivatives. This chemical is known for its high thermal stability and is used as a starting material for the preparation of diverse functional materials and pharmaceuticals. It is also used as a corrosion inhibitor and has potential applications in the field of medicine and materials science. Its unique molecular structure and properties make it a versatile compound with a wide range of potential uses in various industries.

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 
• 828-51-3 1-Adamantanecarboxylic acid 
• 326488-61-3 1-(adamantane-1-carbonyl)imidazolide 

Downstream Products

• 139158-45-5 1-(1-adamantylcarbonyl)-4-benzylthiosemicarbazide 
• 81375-02-2 C₁₇H₂₂N₂O₃S 
• 94527-38-5 benzoic acid N'-(adamantane-1-carbonyl)hydrazide 
• 26526-57-8 [(5-adamantan-1-yl)-2-amino-2-yl]-1,3,4-thiadiazole 
• 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 
• 1469862-50-7 C₂₇H₃₁ClN₄OS 
• 1293994-81-6 3-(1-adamantyl)-1-{[4-(2-methoxyphenyl)piperazin-1-yl]methyl}-4-methyl-1H-1,2,4-triazole-5(4H)-thione 
• 1450766-65-0 C₂₅H₃₂F₃N₅S 

Relevant articles and documents

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

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

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.

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

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.