Refernces
10.1016/j.ejmech.2011.08.021
The study presents the design, synthesis, and evaluation of a novel series of indole and azaindole (pyrrolopyridine) cannabinoid (CB) receptor agonists. These compounds were developed to target cannabinoid 1 (CB1) and cannabinoid 2 (CB2) receptors, which are G protein-coupled receptors involved in various physiological processes and have therapeutic potential in conditions such as osteoporosis, multiple sclerosis, Alzheimer's disease, and cancer, among others. The researchers introduced a biphenyl moiety as a novel lipophilic indole 3-acyl substituent and replaced the 3-carbonyl tether with a carboxamide linker to improve physicochemical properties. They also designed azaindole (pyrrolopyridine) nuclei as indole bioisosteres to enhance lipophilicity and aqueous solubility. The purpose of these chemical modifications was to identify high-affinity CB1/CB2 dual cannabinoid receptor ligands with improved physicochemical properties, which could lead to more effective therapeutic agents. The study involved the synthesis and testing of various compounds, including indole-3-carboxamide derivatives and azaindoles, to evaluate their binding affinity, functional activity, and selectivity for CB1 and CB2 receptors.
10.1002/ejic.201500489
This research aimed to develop a colorimetric sensor for the detection of spermine, a biogenic amine, using the CuII complex of an imine-based organic nanoaggregate in aqueous medium. The study synthesized a Schiff-base receptor from dipicolinic acid hydrazide and characterized it using various spectroscopic techniques. The receptor was then processed into organic nanoaggregates (O1) and tested for metal ion recognition, showing selectivity for Cu2+. The CuII complex (O1·Cu2+) was used as a sensor for detecting biogenic amines, demonstrating selective sensing of spermine with a detection limit of 7.62 nM. The sensor exhibited a color change upon addition of spermine, which could be observed with the naked eye, and was stable within the physiological pH range. The chemicals used in the process included dipicolinic acid hydrazide, salicylaldehyde, and various metal nitrate salts for testing metal ion selectivity. The study concluded that the developed organic nanoaggregates could selectively chemosense spermine in aqueous medium, with the detection limit and UV/Vis spectral profile confirming the effectiveness of the O1·Cu2+ complex for this purpose.
10.1021/jo702062n
The research describes a novel and efficient method for the synthesis of indazoles, a subunit commonly found in pharmaceuticals with significant biological and pharmacological activities. The study aimed to overcome the limitations of previous methods, such as harsh reaction conditions and multi-step processes, by utilizing the [3+2] cycloaddition of diazo compounds with arynes in the presence of CsF or TBAF at room temperature. The chemicals involved in this process include a variety of diazo compounds, o-(trimethylsilyl)aryl triflates as aryne precursors, and CsF or TBAF as fluoride reagents. The conclusions of the research highlight the successful development of a simple, efficient, and general method for synthesizing a wide range of substituted indazoles with good to excellent yields under mild reaction conditions. The method also allows for the selective formation of N-unsubstituted or N-arylated indazoles, depending on the stoichiometry and reaction conditions, and includes the observation of acyl migration in dicarbonyl-containing diazo compounds to afford 1-acyl or 1-alkoxycarbonyl indazoles selectively. This new route to indazoles is expected to be useful in constructing molecules with potential biological properties and pharmaceutical applications.
10.1002/jps.2600700835
The research focuses on the synthesis and biological evaluation of new polyamine derivatives for potential cancer chemotherapeutic applications. The purpose of the study was to investigate the effects of various homologs, analogs, and acylated derivatives of spermine and spermidine, as well as several heterocyclic and aromatic compounds containing a novoldiamine side chain, on the growth of neoplastic cells. The researchers hypothesized that these compounds could be useful in oncology due to the role of polyamines in cellular protein synthesis and the structure and activity of tRNA. The study concluded that several of these compounds showed activity against B-16 melanoma and human epidermoid carcinoma of the nasopharynx. Key chemicals used in the synthesis process included N,N-Bis(2-cyanoethyl)amine, 1-methylpiperazin, 1,4'-bipiperidine, novoldiamine, and various acylating agents such as palmitoyl chloride. The biological testing involved the use of alloxanized mice for hypoglycemic activity and various cell cultures for antineoplastic activity.
10.1021/ja00476a050
The study investigates the catalytic irreversible inhibition of mammalian ornithine decarboxylase (ODC) by substrate and product analogues. The chemicals involved include the diamine putrescine and the polyamines spermidine and spermine, which are implicated in growth regulation. The researchers synthesized and tested various inhibitors, such as 5-hexyne-1,4-diamine (2) and trans-hex-2-en-5-yne-1,4-diamine (3), to determine their effects on ODC. They found that these compounds irreversibly inactivated ODC by forming covalent bonds with the enzyme's active site. The study also explores the mechanisms of inhibition, proposing that the inhibitors are activated by the enzyme itself, leading to the formation of reactive intermediates that bind to the enzyme. This research provides valuable insights into the design of specific, irreversible inhibitors for ODC and other decarboxylases, which could have significant implications for understanding the biological roles of polyamines and for potential therapeutic applications.
10.1002/anie.201306511
The research focuses on the development of a traceless directing group strategy for C-H borylation reactions of nitrogen heterocycles and anilines. The main content revolves around the use of the (pinacolato)boron (Bpin) group as a traceless directing group, which can be readily installed and removed without additional steps, offering an alternative to traditional methods that require installation and removal of directing groups. The experiments involved the borylation of various substrates, including pyrroles, indoles, azaindoles, pyrazoles, and anilines, using the Bpin group. Reactants such as HBpin and iridium catalysts were used, along with tertiary amines to facilitate N-borylation. The analyses included monitoring the reactions by 1H and 11B NMR spectroscopy, and evaluating the yields and selectivity of the borylated products. The study demonstrated that the Bpin-directed approach is operationally simpler and generally higher yielding than the Boc-directed counterparts, and it expands the scope of C-H borylation by enabling functionalization at different positions on the substrates.
10.1021/acs.jnatprod.9b00415
This research aimed to develop a safe and effective method for neutralizing the malodorous organosulfur compounds found in skunk spray using a naturally occurring electrophilic compound, pericosine A. The study demonstrated that pericosine A, derived from fungi, readily reacts with skunk-spray secretions to transform them into odorless products. Mechanistic and computational studies suggested that pericosine A and its synthetic analogues react with thiols and thioacetates under aqueous conditions to generate stable thioethers via SN2′-type mechanisms. The researchers found pericosine A to be non-irritating to skin and eyes and highly effective at deodorizing skunk anal gland secretions when formulated with cosmetic ingredients. Key chemicals used in the process included pericosine A, 2-phenylethanethiol, 4-bromo-α-toluene thioacetate, and spermine as a catalyst, with propylene glycol serving as a cosolvent. The study concluded that pericosine A and its analogues offer a promising, non-toxic approach to counteract noxious sulfur-containing chemicals, with potential applications in odor neutralization and the development of new materials to combat a range of malodorous substances.
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