Adamantane-containing drug delivery systems

Dragomanova, Stela; Andonova, Velichka

doi:10.3897/pharmacia.70.e111593

Cited by 5 publications

(2 citation statements)

References 84 publications

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“…239-241 • C (decomp.). 1 A mixture of calixarene 2 (0.414 g, 0.40 mmol) and anhydrous Cs 2 CO 3 (0.520 g, 1.60 mmol) in dry DMF (40 mL) was stirred at room temperature for 2 h. 1-Iodopropane (0.160 mL, 1.60 mmol) was added, and the mixture was stirred at room temperature for 48 h. The solvent was removed under reduced pressure with heating below 50 • C, and the residue was parted between dichloromethane and aqueous HCl (2 M). The organic layer was separated, washed with water, dried with MgSO 4 and concentrated to dryness.…”

Section: Methodsmentioning

confidence: 99%

“…The adamantane structure is well recognized as a molecular core for biomedical and pharmaceutical applications, which is due to its specific shape, size and lipophilicity, empowered by functionalization capabilities [1,2]. Since their introduction into calixarene chemistry three decades ago [3,4], adamantane-containing groups have been demonstrated to be useful building blocks capable of bringing receptor functionalities to the macrocycles or/and tuning their receptor properties.…”

Section: Introductionmentioning

confidence: 99%

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Adamantylated Calix[4]arenes Bearing CuAAC-Ready 2-Azidoethyl or Propargyl Functionalities

Gorbunov,

Malakhova,

Bezzubov

et al. 2024

Molbank

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1,3-Alternate calix[4]arenes were prepared, having bulky adamantyl groups in the p-positions of all four aromatic units of the macrocycles and pairs of propargyl or 2-azidoethyl groups alternating with n-propyl groups at the phenol oxygen atoms. The step-wise syntheses were carried out through a selective distal alkylation of the parent p-adamantylcalix[4]arene with propargyl bromide or 1,2-dibromoethane, resulting in calix[4]arenes bearing pairs of propargyl or 2-bromoethyl groups at their narrow rims. The bromine atoms were replaced by azide groups, and then both calix[4]arene diethers were exhaustively alkylated at the remaining OH-groups with 1-iodopropane under stereoselective conditions to fix the macrocycles in an 1,3-alternate shape. The structures of the prepared p-adamantylcalix[4]arenes were confirmed by NMR and HRMS data, and, for the 1,3-alternate dipropargyl ether, the X-ray diffraction data were also collected. Preliminary data on the reactivity of the prepared calixarenes under the CuAAC conditions suggested a strong steric hampering created by the adamantane units nearby the reacting alkyne or azide groups that affected the outcome of the two-fold cycloaddition involving the calixarene bis(azides) or bis(alkynes) as complementary partners.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Adamantylated Calix[4]arenes Bearing CuAAC-Ready 2-Azidoethyl or Propargyl Functionalities

Gorbunov,

Malakhova,

Bezzubov

et al. 2024

Molbank

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Controlled Drug Release Systems for Cerebrovascular Diseases

Martín‐Morales,

Caspani,

Desco

et al. 2024

Advanced Therapeutics

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This review offers a comprehensive exploration of optimized drug delivery systems tailored for controlled release and their crucial role in addressing cerebrovascular diseases. Through an in‐depth analysis, various controlled release methods, including nanoparticles, liposomes, hydrogels, and other emerging technologies are examined. Highlighting the importance of precise drug targeting, it is delved into the underlying mechanisms of these delivery systems and their potential to improve therapeutic outcomes while minimizing adverse effects. Additionally, the specific applications of these optimized drug delivery systems in treating cerebrovascular disorders such as ischemic stroke, cerebral aneurysms, and intracranial hemorrhage are discussed. By shedding light on the advancements in drug delivery techniques and their implications in cerebrovascular medicine, this review offers valuable insights into the future of therapeutic interventions in neurology.

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Synthesis of Alkylated Carbonyl‐Bearing Furans via Acid‐Catalyzed Friedel‐Crafts Reaction

Tkachenko,

Ivanova,

Khrapovitskaya

et al. 2024

Asian J Org Chem

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Carbonyl‐bearing furans, certain pyrroles, and thiophenes were alkylated using alcohols in an acidic medium. Some 5‐alkylated derivatives of 2‐furoic acid with various adamantyls‐, cycloalkyl‐, other 2°‐ and 3°‐alkyl substituents were synthesized using 2‐furoic acid as a biomass‐derived chemical platform. Side reaction resulted in the substitution of the carboxylic group, leading to the formation of 1,5‐dialkyl furans. In the alkylation of acyl and formyl furan, either mono‐ or di‐alkyl products were obtained, depending on the functional group present in the furan nucleus. Pyrroles (or thiophenes) with related functional groups exclusively (or near‐exclusively) yielded mono‐alkyl products. The resultant 5‐substituted carbonyl furans can be used as building blocks and synthetic equivalents for 1C and 4C synthons, as demonstrated by a series of reactions involving 5‐adamantan‐1‐yl‐2‐furoic acid.

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Adamantane-containing drug delivery systems

Cited by 5 publications

References 84 publications

Adamantylated Calix[4]arenes Bearing CuAAC-Ready 2-Azidoethyl or Propargyl Functionalities

Adamantylated Calix[4]arenes Bearing CuAAC-Ready 2-Azidoethyl or Propargyl Functionalities

Controlled Drug Release Systems for Cerebrovascular Diseases

Synthesis of Alkylated Carbonyl‐Bearing Furans via Acid‐Catalyzed Friedel‐Crafts Reaction

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