Tag: 100-200

《Site-selective α-C-H Functionalization of Trialkylamines via Reversible HAT-Catalysis》 was written by Shen, Yangyang; Funez-Ardoiz, Ignacio; Schoenebeck, Franziska; Rovis, Tomislav. Formula: C6H11NOThis research focused ontrialkylamine regioselective functionalization reversible HAT catalysis. The article conveys some information:

Despite the recent breakthrough of catalytic alkylation of dialkylamines, the selective α-C(sp3)-H bond functionalization of widely available trialkylamine scaffolds holds promise to streamline complex trialkylamine synthesis, accelerate drug discovery and execute late-stage pharmaceutical modification with complementary reactivity. However, the canonical methods always result in functionalization at the less-crowded site. Herein, authors describe a solution to switch the reaction site through fundamentally overcoming the steric control that dominates such processes. By rapidly establishing an equilibrium between α-amino C(sp3)-H bonds and a highly electrophilic thiol radical via reversible hydrogen atom transfer, authors leverage a slower radical-trapping step with electron-deficient olefins to selectively forge a C(sp3)-C(sp3) bond with the more-crowded α-amino radical, with the overall selectivity guided by Curtin-Hammett principle. This subtle reaction profile has unlocked a new strategic concept in direct C-H functionalization arena for forging C-C bonds from a diverse set of trialkylamines with high levels of site-selectivity and preparative utility. The broad consequences of this dynamic system, together with the ability to forge N-substituted quaternary carbon centers and implement late-stage functionalization techniques, holds potential to streamline complex trialkylamine synthesis and accelerate small-mol. drug discovery. In the experiment, the researchers used 1-Methyl-4-piperidone(cas: 1445-73-4Formula: C6H11NO)

1-Methyl-4-piperidone(cas: 1445-73-4) is a member of piperidine. Piperidine is a key saturated heterocyclic scaffold found in several of the top-selling small molecule pharmaceuticals and natural alkaloids, with a diverse range of biological activities. Hence, continuous efforts have been made to develop convenient methods to prepare piperidine derivatives.Formula: C6H11NO

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

《A Novel Synthesis of Pimavanserin: A Selective Serotonin 5-HT2A Receptor Inverse Agonist》 was written by Hu, Kun; Zhang, Meiju; Wu, Dongdong; Xie, Yuxuan; Ren, Jie. Safety of 1-Methyl-4-piperidone And the article was included in Organic Preparations and Procedures International in 2020. The article conveys some information:

The title compound I was prepared using a novel, low-cost, high-yielding, and eco-friendly procedure starting from (4-hydroxyphenyl)acetic acid. The total yield of I for the 10-step process is 33%. The experimental part of the paper was very detailed, including the reaction process of 1-Methyl-4-piperidone(cas: 1445-73-4Safety of 1-Methyl-4-piperidone)

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.Safety of 1-Methyl-4-piperidone

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

In 2016,Iwasaki, Takanori; Min, Xin; Fukuoka, Asuka; Kuniyasu, Hitoshi; Kambe, Nobuaki published 《Nickel-Catalyzed Dimerization and Alkylarylation of 1,3-Dienes with Alkyl Fluorides and Aryl Grignard Reagents》.Angewandte Chemie, International Edition published the findings.Recommanded Product: 622-26-4 The information in the text is summarized as follows:

In the presence of a nickel catalyst, 1,3-butadiene undergoes selective dimerization and alkylarylation with alkyl fluorides and aryl Grignard reagents to give 1,6-octadienes with alkyl and aryl groups at the 3- and 8-positions, resp., by the consecutive formation of three carbon-carbon bonds. The formation of an anionic nickel complex plays an important role in forming C-C bonds with alkyl fluorides.2-(Piperidin-4-yl)ethanol(cas: 622-26-4Recommanded Product: 622-26-4) was used in this study.

2-(Piperidin-4-yl)ethanol(cas: 622-26-4) can be used to synthese ursolic acid derivatives, spiroimidazolidinone NPC1L1 inhibitors, neurokinin-2 receptor antagonists, antagonists for inhibition of platelet aggregation.Recommanded Product: 622-26-4

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

In 2015,Iwasaki, Takanori; Shimizu, Ryohei; Imanishi, Reiko; Kuniyasu, Hitoshi; Kambe, Nobuaki published 《Copper-catalyzed regioselective hydroalkylation of 1,3-dienes with alkyl fluorides and Grignard reagents》.Angewandte Chemie, International Edition published the findings.Synthetic Route of C7H15NO The information in the text is summarized as follows:

Copper complexes generated in situ from CuCl2, alkyl Grignard reagents, and 1,3-dienes play important roles as catalytic active species for the 1,2-hydroalkylation of 1,3-dienes by alkyl fluorides through C-F bond cleavage. The alkyl group is introduced to an internal carbon atom of the 1,3-diene regioselectively, thus giving rise to the branched terminal alkene product.2-(Piperidin-4-yl)ethanol(cas: 622-26-4Synthetic Route of C7H15NO) was used in this study.

2-(Piperidin-4-yl)ethanol(cas: 622-26-4) can be used to synthese ursolic acid derivatives, spiroimidazolidinone NPC1L1 inhibitors, neurokinin-2 receptor antagonists, antagonists for inhibition of platelet aggregation.Synthetic Route of C7H15NO

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

In 2013,Iwasaki, Takanori; Takagawa, Hiroaki; Singh, Surya P.; Kuniyasu, Hitoshi; Kambe, Nobuaki published 《Co-Catalyzed Cross-Coupling of Alkyl Halides with Tertiary Alkyl Grignard Reagents Using a 1,3-Butadiene Additive》.Journal of the American Chemical Society published the findings.Computed Properties of C7H15NO The information in the text is summarized as follows:

In the presence of cobalt(II) chloride, lithium iodide, and either 1,3-butadiene or isoprene, alkyl Grignard reagents with β-hydrogen atoms such as tert-butylmagnesium chloride underwent coupling reactions with alkyl tosylates, fluorides, bromides, and iodides such as 1-bromooctane in THF at 50° to give alkanes such as 2,2-dimethyldecane in 55-91% isolated yields or in 58-95% GC yields; sterically congested quaternary carbon centers could be constructed by using tertiary alkyl Grignard reagents. Ester-, amide-, and tetrahydropyran-containing alkyl bromides were compatible with the reaction conditions. Coupling reactions of 6-bromo-1-hexene and cyclopropylmethyl bromide did not yield cyclized product and gave low yields (<4%) of ring-opened products, resp., while reaction in the presence of 9,10-dihydroanthracene gave product in low yield but with complete recovery of dihydroanthracene, implying that the coupling does not occur through radical intermediates. An ionic mechanism with inversion of stereochem. at the reacting site of the alkyl halide is proposed for the coupling reaction based on the stereoselectivity of reaction of a racemic dideuterated phenethyl bromide. The experimental part of the paper was very detailed, including the reaction process of 2-(Piperidin-4-yl)ethanol(cas: 622-26-4Computed Properties of C7H15NO)

2-(Piperidin-4-yl)ethanol(cas: 622-26-4) can be used to synthese ursolic acid derivatives, spiroimidazolidinone NPC1L1 inhibitors, neurokinin-2 receptor antagonists, antagonists for inhibition of platelet aggregation.Computed Properties of C7H15NO

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Application In Synthesis of TriacetonamineOn October 9, 2019 ,《Synthesis of a Hindered Amine-Grafted Lignin-Based Emulsifier and Its Application in a Green Emulsifiable Concentrate》 was published in Journal of Agricultural and Food Chemistry. The article was written by Zhou, Mingsong; Wang, Dongping; Peng, Ruifen; Yang, Dongjie; Qiu, Xueqing; Qian, Yong. The article contains the following contents:

The 4-amion-2,2,6,6-tetramethylpiperidine (Temp) was grafted into the Sodium Lignosulfonate (SL) to obtain the hindered amine modified lignosulfonate (SL-Temp). Then the polymer surfactant (SL-Temp-CTAB) was prepared by using cetyltrimethylammonium bromide (CTAB) and SL-Temperature The obtained SL-Temp-CTAB was used as emulsifier to prepare green Emulsifiable Concentrate (EC) of avermectin (AVM), which shows good emulsifying property and storage stability. The prepared AVM green EC can form AVM-loaded microspheres with nanometer particle size distribution after emulsification in water. After UV irradiation for 70 h, the AVM retention rate of the green EC prepared using SL-Temp-CTAB was 75.8%, which is much higher than that of com. EC (0.4%) and the green EC prepared using unmodified SL (31.4%). Moreover, the AVM green EC prepared using SL-Temp-CTAB has slow-release performance, and the release equilibrium time is 5.3 times of the com. EC. Therefore, the newly prepared AVM green EC using lignin-based functional emulsifier shows good anti-photolysis and slow-release performance compared with the traditional EC. In the experimental materials used by the author, we found Triacetonamine(cas: 826-36-8Application In Synthesis of Triacetonamine)

Triacetonamine(cas: 826-36-8) is a member of piperidine. Piperidine is ubiquitous structural motif widely occurred in diverse synthetically and naturally occurring bioactive molecules. Piperidines are an immensely important class of compounds medicinally: the piperidine ring is the most common heterocyclic subunit among FDA approved drugs.Application In Synthesis of Triacetonamine

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

《Synthesis, characterization and antimicrobial activity of piperidine derivatives》 was published in Journal of the Chemical Society of Pakistan in 2019. These research results belong to Zafar, Shaista; Akhtar, Shamim; Ali, Syed Imran; Mushtaq, Nausheen; Naeem, Sabahat; Ali, Mohsin. Computed Properties of C6H12N2O The article mentions the following:

Synthesis of various piperidine derivatives having important biol. and pharmacol. potentials has been discussed in the past. In present study we reported the synthesis of benzoyl and sulfonyl derivatives by taking Piperidine-4-carboxamide as principal mol. These compounds were characterized by various spectroscopic techniques such as NMR, FTIR and Mass spectrometry. Elemental composition was explored using CHN analyzer. Antimicrobial activity study of the synthesized compounds was performed using disk diffusion method. Dissociation constant (pKa) of the synthesized compounds were determined by potentiometric titration method. In addition The findings of the study predicted good absorption of these newly synthesized compounds Besides, compound III showed good antifungal activity which can be helpful in pharmacokinetics and pharmacodynamics approaches of antibiotics. In the experiment, the researchers used Piperidine-4-carboxamide(cas: 39546-32-2Computed Properties of C6H12N2O)

Piperidine-4-carboxamide(cas: 39546-32-2) belongs to anime. Amines have a free lone pair with which they can coordinate to metal centers. Amine–metal bonds are weaker because amines are incapable of backbonding, but they are still important for sensing applications.While stronger than hydrogen bonds, amine–metal bonds are still weaker than both covalent and ionic bonds.Computed Properties of C6H12N2O

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

《Piperidine-4-carboxamides target DNA gyrase in Mycobacterium abscessus》 was written by Negatu, Dereje Abate; Beuchel, Andreas; Madani, Abdeldjalil; Alvarez, Nadine; Chen, Chao; Aragaw, Wassihun Wedajo; Zimmerman, Matthew D.; Laleu, Benoit; Gengenbacher, Martin; Dartois, Veronique; Imming, Peter; Dicka, Thomas. COA of Formula: C6H12N2O And the article was included in Antimicrobial Agents and Chemotherapy on August 31 ,2021. The article conveys some information:

New, more-effective drugs for the treatment of lung disease caused by nontuberculous mycobacteria (NTM) are needed. Among NTM opportunistic pathogens, Mycobacterium abscessus is the most difficult to cure and intrinsically multidrug resistant. In a whole-cell screen of a compound collection active against Mycobacterium tuberculosis, we previously identified the piperidine-4-carboxamide (P4C) MMV688844 (844) as a hit against M. abscessus. Here, we identified a more potent analog of 844 and showed that both the parent and improved analog retain activity against strains representing all three subspecies of the M. abscessus complex. Furthermore, P4Cs showed bactericidal and antibiofilm activity. Spontaneous resistance against the P4Cs emerged at a frequency of 10-8/CFU and mapped to gyrA and gyrB encoding the subunits of DNA gyrase. Biochem. studies with recombinant M. abscessus DNA gyrase showed that P4Cs inhibit the wild-type enzyme but not the P4C-resistant mutant. P4C-resistant strains showed limited cross-resistance to the fluoroquinolone moxifloxacin, which is in clin. use for the treatment of macrolide-resistant M. abscessus disease, and no cross-resistance to the benzimidazole SPR719, a novel DNA gyrase inhibitor in clin. development for the treatment of mycobacterial diseases. Analyses of P4Cs in recA promoter-based DNA damage reporter strains showed induction of recA promoter activity in the wild type but not in the P4C-resistant mutant background. This indicates that P4Cs, similar to fluoroquinolones, cause DNA gyrase-mediated DNA damage. Together, our results show that P4Cs present a novel class of mycobacterial DNA gyrase inhibitors with attractive antimicrobial activities against the M. abscessus complex. After reading the article, we found that the author used Piperidine-4-carboxamide(cas: 39546-32-2COA of Formula: C6H12N2O)

Piperidine-4-carboxamide(cas: 39546-32-2) belongs to anime. Amines characteristically form salts with acids; a hydrogen ion, H+, adds to the nitrogen. With the strong mineral acids (e.g., H2SO4, HNO3, and HCl), the reaction is vigorous. Salt formation is instantly reversed by strong bases such as NaOH. Neutral electrophiles (compounds attracted to regions of negative charge) also react with amines; alkyl halides (R′X) and analogous alkylating agents are important examples of electrophilic reagents.COA of Formula: C6H12N2O

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Formula: C7H15NOIn 2020 ,《Discovery of 2-(4-(2-fluoroethoxy)piperidin-1-yl)-9-methyl-9H-pyrrolo[2,3-b:4,5-c’]dipyridine ([18F]PI-2014) as PET tracer for the detection of pathological aggregated tau in Alzheimer’s disease and other tauopathies》 appeared in European Journal of Medicinal Chemistry. The author of the article were Gabellieri, Emanuele; Capotosti, Francesca; Molette, Jerome; Sreenivasachary, Nampally; Mueller, Andre; Berndt, Mathias; Schieferstein, Hanno; Juergens, Tanja; Varisco, Yvan; Oden, Felix; Schmitt-Willich, Heribert; Hickman, David; Dinkelborg, Ludger; Stephens, Andrew; Pfeifer, Andrea; Kroth, Heiko. The article conveys some information:

The compound screening was initiated with a direct staining assay to identify compounds binding to Tau aggregates and not Abeta plaques using human brain sections derived from late stage Alzheimer’s disease donors. The binding of Tau aggregate selective compounds was then quant. assessed with human brain derived paired helical filaments utilizing the label-free Back Scattering Interferometry assay. In vivo biodistribution experiments of selected fluorine-18 labeled compounds were performed in mice to assess brain uptake, brain washout, and defluorination. Compound 11 emerged as the most promising candidate, displaying high in vitro binding affinity and selectivity to neurofibrillary tangles. Fluorine-18 labeled compound 11 showed high brain uptake and rapid washout from the mouse brain with no observed bone uptake. Furthermore, compound 11 was able to detect Tau aggregates in tauopathy brain sections from corticobasal degeneration, progressive supranuclear palsy, and Pick’s disease donors. Thus, 2-(4-(2-fluoroethoxy)piperidin-1-yl)-9-methyl-9H-pyrrolo[2,3-b:4,5-c’]dipyridine (PI-2014, compound 11) was selected for characterization in a first-in-human study. In addition to this study using 2-(Piperidin-4-yl)ethanol, there are many other studies that have used 2-(Piperidin-4-yl)ethanol(cas: 622-26-4Formula: C7H15NO) was used in this study.

2-(Piperidin-4-yl)ethanol(cas: 622-26-4) have been used as an intermediate in the synthetic preparation of cellular-active allosteric inhibitors of FAKFormula: C7H15NO

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Pasqualetto, Gaia; Pileggi, Elisa; Schepelmann, Martin; Varricchio, Carmine; Rozanowska, Malgorzata; Brancale, Andrea; Bassetto, Marcella published their research in European Journal of Medicinal Chemistry on December 15 ,2021. The article was titled 《Ligand-based rational design, synthesis and evaluation of novel potential chemical chaperones for opsin》.Name: Piperidine-4-carboxamide The article contains the following contents:

Inherited blinding diseases retinitis pigmentosa (RP) and a subset of Leber’s congenital amaurosis (LCA) are caused by the misfolding and mistrafficking of rhodopsin mols., which aggregate and accumulate in the endoplasmic reticulum (ER), leading to photoreceptor cell death. One potential therapeutic strategy to prevent the loss of photoreceptors in these conditions is to identify opsin-binding compounds that act as chem. chaperones for opsin, aiding its proper folding and trafficking to the outer cell membrane. Aiming to identify novel compounds with such effect, a rational ligand-based approach was applied to the structure of the visual pigment chromophore, 11-cis-retinal, and its locked analog 11-cis-6mr-retinal. Following mol. docking studies on the main chromophore binding site of rhodopsin, 49 novel compounds, e.g., I, were synthesized according to optimized one-to seven-step synthetic routes. These agents were evaluated for their ability to compete for the chromophore binding site of opsin, and their capacity to increase the trafficking of the P23H opsin mutant from the ER to the cell membrane. Different new mols. displayed an effect in at least one assay, acting either as chem. chaperones or as stabilizers of the 9-cis-retinal-rhodopsin complex. These compounds could provide the basis to develop novel therapeutics for RP and LCA. In the experiment, the researchers used many compounds, for example, Piperidine-4-carboxamide(cas: 39546-32-2Name: Piperidine-4-carboxamide)

Piperidine-4-carboxamide(cas: 39546-32-2) belongs to anime. Halogenation, in which one or more hydrogen atoms of an amine is replaced by a halogen atom, occurs with chlorine, bromine, and iodine, as well as with some other reagents, notably hypochlorous acid (HClO). With primary amines the reaction proceeds in two stages, producing N-chloro- and N,N-dichloro-amines, RNHCl and RNCl2, respectively. With tertiary amines, an alkyl group may be displaced by a halogen.Name: Piperidine-4-carboxamide

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem