19026-80-3

Usage

Uses

Used in Pharmaceutical Industry:
ADAMANTAN-1-YL-ACETIC ACID HYDRAZIDE is used as a key intermediate in the synthesis of antiviral and antitumor agents for its potential therapeutic applications.
Used in Medicinal Chemistry Research:
ADAMANTAN-1-YL-ACETIC ACID HYDRAZIDE is employed as a valuable tool in the study of medicinal chemistry, aiding in the understanding of enzyme inhibition and biological processes relevant to disease treatment.
Used in Drug Design:
ADAMANTAN-1-YL-ACETIC ACID HYDRAZIDE is utilized in drug design to develop novel pharmaceuticals with improved efficacy and selectivity, leveraging its unique structural properties and biochemical interactions.

InChI:InChI=1/C12H20N2O/c13-14-11(15)7-12-4-8-1-9(5-12)3-10(2-8)6-12/h8-10H,1-7,13H2,(H,14,15)

Upstream product

• 4942-47-6 (adamant-1-yl)-acetic acid 
• 15782-66-8 ethyl 4-(adamant-1-yl)-phenyl acetate 

Downstream Products

• 1226513-80-9 (adamantan-1-yl)acetic acid (5-tert-butyl-2-hydroxybenzylidene)hydrazide 
• 1226514-01-7 (adamantan-1-yl)acetic acid (2-hydroxy-3,5-dinitrobenzylidene)hydrazide 
• 1226513-72-9 (adamantan-1-yl)acetic acid (4-chloro-2-hydroxybenzylidene)hydrazide 

Relevant academic research and scientific papers

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).

New hydrazones of 5-nitro-2-furaldehyde with adamantanealkanohydrazides: Synthesis and: In vitro trypanocidal activity

Nifurtimox, a hydrazone of 5-nitro-2-furaldehyde is used therapeutically against Trypanosoma brucei and Trypanosoma cruzi infections. Exploiting our previous observation that adamantane derivatives display trypanocidal activity, we designed and synthesised a range of hydrazones of 5-nitro-2-furaldehyde with adamantane alkanohydrazides. The most promising compounds had >20 times greater activity (IC50 ～ 100 nM) than nifurtimox, with selectivity indices of 20-80. SAR studies revealed that activity is associated with increased lipophilicity and influenced by conformational flexibility. Derivatives lacking a nitro group were practically inactive against both parasites. The approaches described demonstrate the feasibility of enhancing the potency of chemical entities with known trypanocidal activity.