878-61-5

Usage

Uses

Used in Pharmaceutical Industry:
1-BROMO-3-ETHYLADAMANTANE is used as a synthetic intermediate for the development of various pharmaceutical compounds. Its adamantane core provides a stable scaffold that can be modified to create new drug candidates with potential therapeutic applications.
Used in Organic Synthesis:
1-BROMO-3-ETHYLADAMANTANE is used as a key building block in the synthesis of 1-adamantyloxyalkanols. These compounds have potential applications in various fields, including the development of new pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Chemical Research:
1-BROMO-3-ETHYLADAMANTANE is utilized as a research compound in the study of adamantane-based chemistry. Its unique structure allows chemists to explore new reactions and mechanisms, leading to the discovery of novel synthetic routes and applications.

InChI:InChI=1/C12H19Br/c1-2-11-4-9-3-10(5-11)7-12(13,6-9)8-11/h9-10H,2-8H2,1H3

Upstream product

• 770-69-4 1-ethyladamantane 
• 768-90-1 1-Adamantyl bromide 
• 773-37-5 1-(2-bromo-ethyl)-adamantane 
• 26831-48-1 2-(adamantan-1-yl)ethyl-4-methylbenzenesulfonate 
• 6240-11-5 2-(adamant-1-yl)ethanol 

Downstream Products

• 101974-67-8 1-ethyl-3-phenyladamantane 
• 1266678-99-2 2-(3-ethyladamant-1-yloxy)ethanol 
• 1266679-00-8 3-(3-ethyladamant-1-yloxy)propan-1-ol 
• 15598-87-5 3-ethyladamantane-1-ol 
• 41100-45-2 1-amino-3-ethyl-adamantane 
• 137910-36-2 (3,5-Dimethyl-1-adamantyl)bis(p-tolylcarbamoyl)phosphine 
• 137910-35-1 (3-Ethyl-1-adamantyl)bis(phenylcarbamoyl)phosphine 

Relevant academic research and scientific papers

ADAMANTANE DERIVATIVES FOR THE TREATMENT OF FILOVIRUS INFECTION

Compounds of structural Formula I were developed for the treatment of infections by filoviruses including Ebolavirus and Marburgvirus, wherein, R1, R2, R3, X and Y are defined in the specification.

Preparation process of amantadine nitrate derivative

The invention discloses a preparation process of an amantadine nitrate derivative, and the amantadine nitrate derivative is prepared from substituted or unsubstituted adamantane as a raw material by the following steps: (1) synthesizing of adamantanol; (2) carboxylation of the adamantanol; (3) amidation of adamantane acid; (4) reduction; (5) hydrolysis of acylamino adamantanol and boc protection of amino; (6) crystallization of Boc-protected amantadine alcohol; (7) nitric acid esterification of Boc-protected amantadine alcohol; (8) refining of a nitric acid esterification product; (9) amino deprotection and salt formation; and (10) refinement of amantadine nitrate. The amantadine amine nitrate derivative is as shown in the specification, wherein R1 and R2 are same or different, and are respectively hydrogen, a linear or branched alkyl group, a substituted or unsubstituted aryl group and a hetero aryl group. The preparation process is efficient, economic, green, safe and reliable and issuitable for industrial production.

Synthesis and biological evaluation of memantine nitrates as a potential treatment for neurodegenerative diseases

A series of memantine nitrate derivatives, as dual functional compounds with neuroprotective and vasodilatory activity for neurodegenerative diseases, was designed and synthesized. These compounds combined the memantine skeleton and a nitrate moiety, and thus inhibited the N-methyl-d-aspartic acid receptor and released NO in the central nervous system. The biological evaluation results revealed that the new memantine nitrates were effective in protecting neurons against glutamate-induced injury in vitro. Moreover, memantine nitrates dilated aortic rings against phenylephrine-induced contraction. The structure-activity relationships of neuroprotection and vasodilation were both analyzed. In further studies, compound MN-05 significantly protected cortical neurons by inhibiting Ca2+ influx, reducing free radical production and maintaining the mitochondrial membrane potential. Further research on MN-05 is warranted.

Cationic ring-opening polymerization of novel 1,3-dehydroadamantanes with various alkyl substituents: Synthesis of thermally stable poly(1,3-adamantane)s

Cationic ring-opening polymerizations of 5-alkyl- or 5,7-dialkyl-1,3- dehydroadamantanes, such as 5-hexyl- (4), 5-octyl- (5), 5-butyl-7-isobutyl- (6), 5-ethyl-7-hexyl- (7), and 5-butyl-7-hexyl-1,3-dehydroadamantane (8), were carried out with super Bronsted acids, such as trifluoromethanesulfonic acid or trifluoromethanesulfonimide in CH2Cl2 or n-heptane. The ring-opening polymerizations of inverted carbon-carbon bonds in 4-8 proceeded to afford corresponding poly(1,3-adamantane)s in good to quantitative yields. Poly(4-8)s possessing alkyl substituents were soluble in 1,2-dichlorobenzene, although a nonsubstituted poly(1,3-adamantane) was not soluble in any organic solvent. In particular, poly(8) exhibited the highest molecular weight at around 7500 g mol-1 and showed excellent solubility in common organic solvents, such as THF, CHCl3, benzene, and hexane. The resulting poly(4-8)s containing adamantane-1,3-diyl linkages showed good thermal stability, and 10% weight loss temperatures (T10) were observed over 400 °C.

Adamantane derivatives in the prevention and treatment of cerebral ischemia

A method for the prevention and treatment of cerebral ischemia using an adamantane derivative of the formula STR1 wherein R1 and R2 are identical or different, representing hydrogen or a straight or branched alkyl group of 1 to 6 C atoms or, in conjunction with N, a heterocyclic group with 5 or 6 ring C atoms; wherein R3 and R4 are identical or different, being selected from hydrogen, a straight or branched alkyl group of 1 to 6 C atoms, a cycloalkyl group with 5 or 6 C atoms, and phenyl; wherein R5 is hydrogen or a straight or branched C1 -C6 alkyl group, or a pharmaceutically-acceptable salt thereof, is disclosed.

Structure-Anti-Parkinson Activity Relationships in the Aminoadamantanes. Influence of Bridgehead Substitution

A limited series of bridgehead alkyl-, dialkyl- and trialkyl-substituted amantadines was synthesized and tested for potential anti-Parkinson activity as dopamine (DA) agonists.The compounds were evaluated using a battery of three murine bioassays, including stimulation of locomotor activity, induction of circling in animals with unilateral striatal lesions, and reversal of reserpine/α-methyltyrosine induced akinesia.Apparent mechanistic differences were seen between the methyl-substituted series and the ethyl-substituted series.While activities in both series increase with increasing liphophilicity, the methyl series (1b-d), as well as amantadine itself (1a) exhibits only indirect DA agonist activity, as evidenced by ipsilateral rotation in the circling model and no significant difference from control in reversal of akinesia.The ethyl series (1e,f) exhibits weak but reprodicible direct DA agonist activity, as shown by contralateral rotation in the circling assay for 1e and reversal of akinesia by 1e and 1f.The 3-n-propyl derivative (1g) was devoid of any DA agonist activity.