16269-16-2

Usage

Uses

Used in Pharmaceutical Industry:
3-(1-Adamantyl)propanoic acid is used as a precursor in the synthesis of pharmaceuticals for its unique molecular structure and potential therapeutic applications. It plays a crucial role in the development of drugs targeting neurological disorders, such as Parkinson's disease, due to its ability to modulate specific neurotransmitter systems and provide symptomatic relief.
Used in Agrochemical Industry:
In the agrochemical industry, 3-(1-Adamantyl)propanoic acid serves as a key intermediate in the production of various agrochemicals. Its unique adamantanyl group contributes to the development of novel compounds with enhanced biological activity and selectivity, making it a valuable building block for the creation of effective and environmentally friendly pesticides and other agrochemical products.
Used in Polymer-Based Materials:
3-(1-Adamantyl)propanoic acid is utilized in the production of polymer-based materials due to its versatile chemical properties and potential to improve material performance. Its adamantanyl group can be incorporated into polymer structures, resulting in materials with enhanced mechanical strength, thermal stability, and other desirable properties. This makes it a promising component in the development of advanced polymers for various applications, such as coatings, adhesives, and composite materials.
Used in Organic Chemistry Research:
3-(1-Adamantyl)propanoic acid is considered a promising and versatile building block in organic chemistry. Its unique molecular structure allows for various chemical modifications and functionalizations, enabling the synthesis of a wide range of novel compounds with potential applications in different fields. Researchers can leverage its properties to explore new chemical reactions, develop innovative synthetic routes, and create new molecules with unique biological activities or material properties.

InChI:InChI=1/C13H20O2/c14-12(15)1-2-13-6-9-3-10(7-13)5-11(4-9)8-13/h9-11H,1-8H2,(H,14,15)

Upstream product

• 29542-59-4 methyl 3-(adamantan-1-yl)propanoate 
• 828-51-3 1-Adamantanecarboxylic acid 
• 768-95-6 1-adamanthanol 
• 711-01-3 methyl adamantane-1-carboxylate 
• 113249-58-4 trans-3-(1-adamantyl)acrylic acid 
• 136258-27-0 trans-3-(1-adamantyl)acrylic acid 
• 1660-05-5 1-(adamantan-1-yl)propan-1-one 
• 19835-39-3 1-(1-adamantyl)propan-2-one 
• 26831-48-1 2-(adamantan-1-yl)ethyl-4-methylbenzenesulfonate 
• 6240-11-5 2-(adamant-1-yl)ethanol 
• 52582-89-5 3-((3r,5r,7r)-adamantan-1-yl)propanenitrile 
• 768-90-1 1-Adamantyl bromide 
• 4942-47-6 (adamant-1-yl)-acetic acid 
• 2094-74-8 1-Adamantanecarbaldehyde 

Downstream Products

• 536739-80-7 3-Adamantan-1-yl-propionic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyl ester 
• 455333-76-3 5-adamantan-1-yl-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)pentanoic acid ethyl ester 
• 869584-28-1 5-(2-adamantan-1-yl-ethyl)-2-phenyl-1H-imidazole-4-carboxylic acid 
• 269071-77-4 5-(2-adamantan-1-yl-ethyl)-2-phenyl-1H-imidazole-4-carboxylic acid ethyl ester 
• 269071-86-5 5-(2-adamantan-1-ylethyl)-2-o-tolyl-1H-imidazole-4-carboxylic acid 
• 269071-81-0 5-(2-adamantan-1-ylethyl)-2-o-tolyl-1H-imidazole-4-carboxylic acid ethyl ester 
• 269072-21-1 5-(2-adamantan-1-yl-ethyl)-2-cyclohexyl-1H-imidazole-4-carboxylic acid 
• 869997-25-1 5-(2-adamantan-1-yl-ethyl)-2-(2,6-dimethyl-phenyl)-1H-imidazole-4-carboxylic acid 
• 869997-24-0 5-(2-adamantan-1-yl-ethyl)-2-(2,4-dimethyl-phenyl)-1H-imidazole-4-carboxylic acid 
• 869997-11-5 5-(2-adamantan-1-yl-ethyl)-2-cyclohexyl-1H-imidazole-4-carboxylic acid ethyl ester 
• 869997-36-4 5-(2-adamantan-1-yl-ethyl)-2-(1-methyl-cyclohexyl)-1H-imidazole-4-carboxylic acid 
• 869997-02-4 5-(2-adamantan-1-yl-ethyl)-2-(2,4-dimethyl-phenyl)-1H-imidazole-4-carboxylic acid ethyl ester 
• 869997-03-5 5-(2-adamantan-1-yl-ethyl)-2-(2,6-dimethyl-phenyl)-1H-imidazole-4-carboxylic acid ethyl ester 
• 869997-26-2 5-(2-adamantan-1-yl-ethyl)-2-(2,4,6-trimethyl-phenyl)-1H-imidazole-4-carboxylic acid 

Relevant academic research and scientific papers

Binding study on 1-adamantylalkyl(benz)imidazolium salts to cyclodextrins and cucurbit[n]urils

Multitopic guests are used as key components of molecular triggers, switchers, sensors, or reactors in recent supramolecular chemistry studies. The increasing complexity of these compounds correlates with the need for versatile, synthetically available binding motifs (building blocks) with tuneable supramolecular properties. The utilisation of a favoured 1-adamantylmethyl moiety in ammonium, imidazolium and pyridinium salts is sometimes restricted by synthetic difficulties most likely related to the adamantane cage bulkiness. Therefore, we prepared a series of new adamantylated (benz)imidazolium salts with longer flexible linkers between the adamantane cage and cationic moiety. We tested the supramolecular properties of these binding motifs towards the natural cyclodextrins α-CD, β-CD and γ-CD and cucurbit[n]urils (n= 7, 8) using NMR, mass spectrometry and titration calorimetry. All tested guests formed 1:1 complexes with the abovementioned hosts, retaining binding strengths, selectivity, and complex geometries in comparison to the parent methylene-linked homologues. We did not confirm our original concern that longer linkers would negatively affect the binding strength towards CBns due to the reduction in the ion-dipole interaction contribution. Therefore, we believe that adamantylalkyl imidazolium binding motifs can be used for multitopic supramolecular guest construction.

Peculiar Features of the Willgerodt–Kindler Reaction of 1-Adamantylpropan-2-one and Its Derivatives

The Willgerodt–Kindler reaction of 1-(1-adamantyl)propan-2-one and its derivatives was studied by gas chromatography–mass spectrometry. The reaction time was found to be 3–4 times longer than in the case of alkyl aryl ketones due to considerable steric hindrances in the molecules of adamantyl ketones. The use of diglyme as solvent and sodium butyl xanthate as catalyst significantly shortened the reaction time and improved the yield to 92%.

Synthesis and Structure-Activity Relationships of Ring-Opened Bengamide Analogues against Methicillin-Resistant Staphylococcus aureus?

Methicillin-resistant Staphylococcus aureus (MRSA) has become a major threat on public health because of the increase of clinically isolated strains that exhibit resistance to many antibiotics. Therefore, development of new antibiotics for the treatment of MRSA infection is a sustained challenge. We have previously identified a ring-opened bengamide analogue L472-2 that displays moderate activity against the growth of S. aureus. In our previous work, we started from L472-2 and identified a class of analogues containing alkynyl groups which have the potential to activate SaClpP activity but moderate antibacterial activity. Herein, we focused on the antibacterial activity of L472-2, and a novel series of ring-opened bengamide analogues were synthesized and their activities were evaluated against MRSA. By conducting a compact analysis of the structure-activity relationships (SAR) of these analogues, we found that an adamantane ethanol ester bengamide 2j showed excellent antibacterial activity towards six S. aureus strains, including MRSA, while it does not activate ClpP. Therefore, these bengamide analogues represent a new class of candidates that suppress MRSA viability.

Controlling Plasma Stability of Hydroxamic Acids: A MedChem Toolbox

Hydroxamic acids are outstanding zinc chelating groups that can be used to design potent and selective metalloenzyme inhibitors in various therapeutic areas. Some hydroxamic acids display a high plasma clearance resulting in poor in vivo activity, though they may be very potent compounds in vitro. We designed a 57-member library of hydroxamic acids to explore the structure-plasma stability relationships in these series and to identify which enzyme(s) and which pharmacophores are critical for plasma stability. Arylesterases and carboxylesterases were identified as the main metabolic enzymes for hydroxamic acids. Finally, we suggest structural features to be introduced or removed to improve stability. This work thus provides the first medicinal chemistry toolbox (experimental procedures and structural guidance) to assess and control the plasma stability of hydroxamic acids and realize their full potential as in vivo pharmacological probes and therapeutic agents. This study is particularly relevant to preclinical development as it allows obtaining compounds equally stable in human and rodent models.

HISTONE DEACETYLASE INHIBITORS FOR THE TREATMENT OF FUNGAL INFECTIONS

Described are bridged compounds of the formula (I), their analogs, tautomeric forms, stereoisomers, geometrical isomers, polymorphs, hydrates, solvates, pharmaceutically acceptable salts, pharmaceutical compositions, metabolites and prodrugs thereof. The invention relates to compositions and methods to treat fungal infection. These compounds are selective HDAC inhibitors that act as inherent antifungal compounds or enhance the activity of other antifungal compounds such as azoles.

DERIVATIVES OF 4-(2-AMINO-1-HYDROXYETHYL)PHENOL AS AGONISTS OF THE BETA2 ADRENERGIC RECEPTOR

The present invention provides a compound of formula (I): wherein: ? R1 is a group selected from -CH2OH,-NH(CO)H and ? R2 is a hydrogen atom; or ? R1together with R2 form the group -NH-C(O)-CH=CH-, wherein the nitrogen atom is bound to the carbon atom in the phenyl ring holding R1and the carbon atom is bound to the carbon atom in the phenyl ring holding R2 ? R3a and R3bare independently selected from the group consisting of hydrogen atoms and C1-4alkyl groups, ? n represents an integer from 1 to 3; ? Ad represents 1-adamantyl or 2-adamantyl group, or a pharmaceutically-acceptable salt or solvate or stereoisomer thereof.

Design, synthesis, and biological evaluation of platensimycin analogues with varying degrees of molecular complexity

The molecular design, chemical synthesis, and biological evaluation of two distinct series of platensimycin analogues with varying degrees of complexity are described. The first series of compounds probes the biological importance of the benzoic acid subunit of the molecule, while the second series explores the tetracyclic cage domain. The biological data obtained reveal that, while the substituted benzoic acid domain of platensimycin is a highly conserved structural motif within the active compounds with strict functional group requirements, the cage domain of the molecule can tolerate considerable structural modifications without losing biological action. These findings refine our present understanding of theplatensimycin pharmacophore and establish certain structure-activity re lationships from which the next generation of designed analogues of thisnew antibiotic may emerge.

RCM-based synthesis of a variety of β-C-glycosides and their in vitro anti-solid tumor activity

(Chemical Equation Presented) The synthesis of a number of biologically relevant C-glycosides has been carried out through the use of an esterification-ring-closing metathesis (RCM) strategy. The required acid precursors were readily prepared via a number of standard chemical transformations followed by dehydrative coupling of these acids with several olefin alcohols 1 to yield the precursor esters 3 in excellent yield. Methylenation of the esters 3 was followed by RCM and in situ hydroboration-oxidation of the formed glycals to furnish the protected β-C-glycosides 6 in good overall yield. Several examples were converted to the corresponding C-glycoglycerolipids 17 and subsequently screened against solid-tumor cell lines for in vitro differential cytotoxicity.