Month: October 2022

Product Details of 39546-32-2On June 1, 2020, Falsini, Matteo; Ceni, Costanza; Catarzi, Daniela; Varano, Flavia; Dal Ben, Diego; Marucci, Gabriella; Buccioni, Michela; Marti Navia, Aleix; Volpini, Rosaria; Colotta, Vittoria published an article in Bioorganic & Medicinal Chemistry Letters. The article was 《New 8-amino-1,2,4-triazolo[4,3-a]pyrazin -3-one derivatives. Evaluation of different moieties on the 6-aryl ring to obtain potent and selective human A2A adenosine receptor antagonists》. The article mentions the following:

In this work, further structural investigations on the 8-amino-2-phenyl-6-aryl-1,2,4-triazolo[4,3-a]pyrazin-3-one series were carried out to achieve potent and selective human A2A adenosine receptor (AR) antagonists. Different ether and amide moieties were attached at the para-position of the 6-Ph ring, thus leading to compounds 1-9 and 10-18, resp. Most of these moieties contained terminal basic rings (pyrrolidine, morpholine, piperidine and substituted piperazines) which were thought to confer good physicochem. and drug-like properties. Compounds 11-16, bearing the amide linker, possessed high affinity and selectivity for the hA2A AR (Ki = 3.6-11.8 nM). Also derivatives 1-9, featuring an ether linker, preferentially targeted the hA2A AR but with lower affinity, compared to those of the relative amide compounds Docking studies, carried out at the hA2A AR binding site, highlighted some crucial ligand-receptor interactions, particularly those provided by the appended substituent whose nature deeply affected hA2A AR affinity. The experimental part of the paper was very detailed, including the reaction process of Piperidine-4-carboxamide(cas: 39546-32-2Product Details of 39546-32-2)

Piperidine-4-carboxamide(cas: 39546-32-2) belongs to anime. The methylamines occur in small amounts in some plants. Many polyfunctional amines (i.e., those having other functional groups in the molecule) occur as alkaloids in plants—for example, mescaline, 2-(3,4,5-trimethoxyphenyl)ethylamine; the cyclic amines nicotine, atropine, morphine, and cocaine; and the quaternary salt choline, N-(2-hydroxyethyl)trimethylammonium chloride, which is present in nerve synapses and in plant and animal cells.Product Details of 39546-32-2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Kitamura, Seiya; Zheng, Qinheng; Woehl, Jordan L.; Solania, Angelo; Chen, Emily; Dillon, Nicholas; Hull, Mitchell V.; Kotaniguchi, Miyako; Cappiello, John R.; Kitamura, Shinichi; Nizet, Victor; Sharpless, K. Barry; Wolan, Dennis W. published an article in Journal of the American Chemical Society. The title of the article was 《Sulfur(VI) Fluoride Exchange (SuFEx)-Enabled High-Throughput Medicinal Chemistry》.Electric Literature of C6H12N2O The author mentioned the following in the article:

Optimization of small-mol. probes or drugs is a synthetically lengthy, challenging, and resource-intensive process. Lack of automation and reliance on skilled medicinal chemists is cumbersome in both academic and industrial settings. Here, we demonstrate a high-throughput hit-to-lead process based on the biocompatible sulfur(VI) fluoride exchange (SuFEx) click chem. A high-throughput screening hit benzyl (cyanomethyl)carbamate (Ki = 8μM) against a bacterial cysteine protease SpeB was modified with a SuFExable iminosulfur oxydifluoride [RN=S(O)F2] motif, rapidly diversified into 460 analogs in overnight reactions, and the products were directly screened to yield drug-like inhibitors with 480-fold higher potency (Ki = 18 nM). We showed that the improved mol. is active in a bacteria-host coculture. Since this SuFEx linkage reaction succeeds on picomole scale for direct screening, we anticipate our methodol. can accelerate the development of robust biol. probes and drug candidates. In the experiment, the researchers used many compounds, for example, Piperidine-4-carboxamide(cas: 39546-32-2Electric Literature of C6H12N2O)

Piperidine-4-carboxamide(cas: 39546-32-2) belongs to anime. Large quantities of aliphatic amines are made synthetically. The most widely used industrial method is the reaction of alcohols with ammonia at a high temperature, catalyzed by metals or metal oxide catalysts (e.g., nickel or copper). Mixtures of primary, secondary, and tertiary amines are thereby produced.Electric Literature of C6H12N2O

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Mitsakos, Voula; Dobson, Renwick C. J.; Pearce, F. Grant; Devenish, Sean R.; Evans, Genevieve L.; Burgess, Benjamin R.; Perugini, Matthew A.; Gerrard, Juliet A.; Hutton, Craig A. published an article on January 15 ,2008. The article was titled 《Inhibiting dihydrodipicolinate synthase across species: Towards specificity for pathogens?》, and you may find the article in Bioorganic & Medicinal Chemistry Letters.Name: Cis-piperidine-2,6-dicarboxylic acid The information in the text is summarized as follows:

Dihydrodipicolinate synthase (DHDPS) is a key enzyme in lysine biosynthesis and an important antibiotic target. The specificity of a range of heterocyclic product analogs against DHDPS from three pathogenic species, Bacillus anthracis, Mycobacterium tuberculosis and methicillin-resistant Staphylococcus aureus, and the evolutionarily related N-acetylneuraminate lyase, has been determined The results suggest that the development of species-specific inhibitors of DHDPS as potential antibacterials is achievable. In the experiment, the researchers used many compounds, for example, Cis-piperidine-2,6-dicarboxylic acid(cas: 59234-40-1Name: Cis-piperidine-2,6-dicarboxylic acid)

Cis-piperidine-2,6-dicarboxylic acid(cas: 59234-40-1) is a member of piperidine. Piperidine-containing compounds are also frequently employed in synthesis as ligands or auxiliaries. Accordingly, many efforts have been devoted to the development of novel methods for the synthesis of these compounds over the years.Name: Cis-piperidine-2,6-dicarboxylic acid

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

In 2019,Journal of Organometallic Chemistry included an article by Lahiji, Fatemeh Khadem; Ariafard, Alireza. Category: piperidines. The article was titled 《Revisiting the mechanism of acetylenic amine N-Oxide rearrangement catalyzed by Gold(I) complexes from a DFT perspective》. The information in the text is summarized as follows:

In this study, we used d. functional theory (DFT) to reinvestigate the mechanism proposed by Houk and Zhang et al. (J. Am. Chem. Soc. 2012, 134, 1078) for piperidinone formation through rearrangement of an acetylenic amine N-oxide catalyzed by phosphine gold(I) complexes. For this rearrangement, the C-C coupling was proposed to be the rate-determining step with activation energy as high as 35.8 kcal/mol. Such a barrier seems inconsistent with the fact that the actual reaction proceeds under very mild conditions (0 °C, 1 h, in CH2Cl2). In the original report, it was proposed that the C-C coupling takes place via a mechanism which we called “”front-side addition””. Interestingly, we found that the C-C coupling step becomes energetically more favorable if it occurs via another mechanism called “”back-side addition””. We explored the effect of different phosphine ligands on all conceivable steps of the catalytic reaction and found that while the other steps are not highly sensitive to the phosphine identity, the C-C coupling one shows a considerable degree of dependency; the more electron-donating the phosphine ligand, the lower the rate-limiting step barrier. The experimental process involved the reaction of 1-Methyl-4-piperidone(cas: 1445-73-4Category: piperidines)

1-Methyl-4-piperidone(cas: 1445-73-4) is a member of piperidine. Piperidine-containing compounds are also frequently employed in synthesis as ligands or auxiliaries. Accordingly, many efforts have been devoted to the development of novel methods for the synthesis of these compounds over the years.Category: piperidines

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

《Automated, Accelerated Nanoscale Synthesis of Iminopyrrolidines》 was written by Osipyan, Angelina; Shaabani, Shabnam; Warmerdam, Robert; Shishkina, Svitlana V.; Boltz, Harry; Doemling, Alexander. COA of Formula: C6H11NO And the article was included in Angewandte Chemie, International Edition in 2020. The article conveys some information:

Miniaturization and acceleration of synthetic chem. is an emerging area in pharmaceutical, agrochem., and materials research and development. Herein, we describe the synthesis of iminopyrrolidine-2-carboxylic acid derivatives using chiral glutamine, oxo components, and isocyanide building blocks in an unprecedented Ugi-3-component reaction. We used I-DOT, a pos.-pressure-based low-volume and non-contact dispensing technol. to prepare more than 1000 different derivatives in a fully automated fashion. In general, the reaction is stereoselective, proceeds in good yields, and tolerates a wide variety of functional groups. We exemplify a pipeline of fast and efficient nanomole-scale scouting to millimole-scale synthesis for the discovery of a useful novel reaction with great scope. In the part of experimental materials, we found many familiar compounds, such as 1-Methyl-4-piperidone(cas: 1445-73-4COA of Formula: C6H11NO)

1-Methyl-4-piperidone(cas: 1445-73-4) is a member of piperidine. Piperidine-containing compounds are also frequently employed in synthesis as ligands or auxiliaries. Accordingly, many efforts have been devoted to the development of novel methods for the synthesis of these compounds over the years.COA of Formula: C6H11NO

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

In 2022,Lehmann, Hansjoerg; Ruppen, Thomas; Knoepfel, Thomas published an article in Organic Process Research & Development. The title of the article was 《Scale-Up of Diazonium Salts and Azides in a Three-Step Continuous Flow Sequence》.Recommanded Product: tert-Butyl 4-aminopiperidine-1-carboxylate The author mentioned the following in the article:

Rapid synthesis and scale-up of active mols. to support the development process of new drug candidates is key in the pharmaceutical industry. Herein, the authors describe the development of a scalable continuous flow procedure for three key steps in the synthesis of 2H-indazoles, e.g., I, which were identified as highly potent and selective TLR7 and TLR8 antagonists. Transformation of hazardous diazonium salt and azide chemistries from the batch mode to continuous flow mode helped mitigate and limit the risks associated with the handling of large amounts of hazardous reagents and intermediates in the batch mode. In a two-step approach, the authors first screened and optimized the reaction parameter for a diazotization-azidation-cyclization three-step sequence using a com. research-scale plug flow reactor. In the next step, the robustness and scalability of this reaction sequence were demonstrated, which finally enabled the authors to rapidly prepare and deliver the required amount of material in high quality. In the experiment, the researchers used many compounds, for example, tert-Butyl 4-aminopiperidine-1-carboxylate(cas: 87120-72-7Recommanded Product: tert-Butyl 4-aminopiperidine-1-carboxylate)

tert-Butyl 4-aminopiperidine-1-carboxylate(cas: 87120-72-7) belongs to anime. To avoid the problem of multiple alkylation, methods have been devised for “blocking” substitution so that only one alkyl group is introduced. The Gabriel synthesis is one such method; it utilizes phthalimide, C6H4(CO)2NH, whose one acidic hydrogen atom has been removed upon the addition of a base such as KOH to form a salt.Recommanded Product: tert-Butyl 4-aminopiperidine-1-carboxylate

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem