Day: October 21, 2022

Bey, Philippe; Vevert, Jean Paul published their research in Journal of Organic Chemistry on August 1 ,1980. The article was titled 《Stereospecific alkylation of the Schiff base ester of alanine with 2-substituted-(E)- and -(Z)-vinyl bromides. An efficient synthesis of 2-methyl-(E)-3,4-didehydroglutamic acid, a potent substrate-induced irreversible inhibitor of L-glutamate-1-decarboxylase》.HPLC of Formula: 24666-55-5 The article contains the following contents:

Vinylation of PhCH:NCHMeCO2Me (I) by (E)- or (Z)-RCH:CHBr (R = CO2Me, CONH2, CN) in THF containing LiN(CHMe2)2 proceeded stereospecifically to give RCH:CHCMe(N:CHPh)CO2Me with retention of configuration of the double bond. Thus, I was vinylated with (E)-MeO2CCH:CHBr to give (E)-MeO2CCH:CHCMe(N:CHPh)CO2Me, which was hydrolyzed by aqueous HCl for 24 h at 60° to give the title dehydroglutamic acid. In the experimental materials used by the author, we found Benzyl (2,6-dioxopiperidin-3-yl)carbamate(cas: 24666-55-5HPLC of Formula: 24666-55-5)

Benzyl (2,6-dioxopiperidin-3-yl)carbamate(cas: 24666-55-5) belongs to anime. Nitrous acid converts secondary amines (aliphatic or aromatic) to N-nitroso compounds (nitrosamines): R2NH + HNO2 → R2N―NO. Some nitrosamines are potent cancer-inducing substances, and their possible formation is a serious consideration when nitrites, which are salts of nitrous acid, are present in foods or pharmaceutical preparations. Tertiary amines give rise to nitrosamines more slowly; an alkyl group is eliminated as an aldehyde or ketone, along with nitrous oxide, N2O.HPLC of Formula: 24666-55-5

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Huang, Xixian; Zhu, Nengwu; Wei, Xiaorong; Ding, Yang; Ke, Yixin; Wu, Pingxiao; Liu, Zehua published their research in Journal of Hazardous Materials on December 5 ,2020. The article was titled 《Mechanism Insight into Efficient Peroxydisulfate activation by Novel Nano Zero-valent Iron Anchored yCo3O4 (nZVI/yCo3O4) Composites》.SDS of cas: 826-36-8 The article contains the following contents:

Novel nano zero-valent iron anchored bio-matrix supported Co3O4 (nZVI/yCo3O4) composites were fabricated for tetracycline (TC) efficient degradation by activating peroxydisulfate (PS). The systematical characterizations verified that the nZVI/yCo3O4 composites with magnetism have higher surface area than yCo3O4 and pure Co3O4, contributing to more accessible active sites. Various catalytic parameters (nZVI mass ratio, leached ions, initial pH, catalyst dosage, PS concentration and coexisting anions) were thoroughly investigated. In nZVI/yCo3O4/PS system, 97.6%, 93.4% and 77.3% TC were degraded within 15 min at pH 3.0, 6.0 and 9.0, resp. Based on four successive degradation runs, the excellent mineralization rate and reusability of nZVI/yCo3O4 composites were mainly benefited from the suppressed metals leaching. The PS activated mechanisms were proposed as non-radicals (1O2) dominated pattern at acidic conditions and radicals (SO•-4) predominant pattern at alk. environment, which may be highly related to the electron donating capacity of nZVI at different pH and the M(n+1)+/Mn+ redox cycling between Fe or Co metal. The plausible degradation routes of TC were presented based on the detected intermediates. Overall, the synthesized heterogeneous nZVI/yCo3O4 composites can efficiently active PS at a wide pH range, and further broaden the application of Co-based catalysts in PS activation. After reading the article, we found that the author used Triacetonamine(cas: 826-36-8SDS of cas: 826-36-8)

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.SDS of cas: 826-36-8

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Liu, Gang; Campbell, Brian T.; Holladay, Mark W.; Ford Pulido, Julia M.; Hua, Helen; Gitnick, Dana; Gardner, Michael F.; James, Joyce; Breider, Mike A.; Brigham, Daniel; Belli, Barbara; Armstrong, Robert C.; Treiber, Daniel K. published their research in ACS Medicinal Chemistry Letters on December 13 ,2012. The article was titled 《Discovery of AC710, a Globally Selective Inhibitor of Platelet-Derived Growth Factor Receptor-Family Kinases》.Quality Control of 1-Cyclopropylpiperidin-4-ol The article contains the following contents:

A series of potent, selective platelet-derived growth factor receptor-family kinase inhibitors was optimized starting from a globally selective lead mol. 4 through structural modifications aimed at improving the physiochem. and pharmacokinetic properties, as exemplified by 18b. Further clearance reduction via per-methylation of the α-carbons of a solubilizing piperidine nitrogen resulted in advanced leads 22a and 22b. Results from a mouse tumor xenograft, a collagen-induced arthritis model, and a 7 day rat in vivo tolerability study culminated in the selection of compound 22b (AC710) as a preclin. development candidate. In the experiment, the researchers used 1-Cyclopropylpiperidin-4-ol(cas: 851847-62-6Quality Control of 1-Cyclopropylpiperidin-4-ol)

1-Cyclopropylpiperidin-4-ol(cas: 851847-62-6) belongs to piperidines. Piperidine derivatives are also used in solid-phase peptide synthesis (SPPS) and many degradation reactions. Quality Control of 1-Cyclopropylpiperidin-4-ol

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Madsen, Ulf; Brehm, Lotte; Schaumburg, Kjeld; Joergensen, Flemming S.; Krogsgaard-Larsen, Povl published an article on January 31 ,1990. The article was titled 《Relationship between structure, conformational flexibility, and biological activity of agonists and antagonists at the N-methyl-D-aspartic acid subtype of excitatory amino acid receptors》, and you may find the article in Journal of Medicinal Chemistry.Application In Synthesis of Cis-piperidine-2,6-dicarboxylic acid The information in the text is summarized as follows:

The relationship between conformational flexibility and agonist or antagonist actions at the N-methyl-D-aspartic acid (NMDA) subtype of central L-glutamic acid (GLU) receptors of a series of racemic piperidinedicarboxylic acids (PDAs) was studied. The conformational analyses were based on 1H NMR spectroscopy and supported by computer simulations and mol. mechanics calculations While the trans-forms of 2,3-PDA and 2,4-PDA and cis-2,5-PDA show NMDA receptor agonist activities, cis-2,3-PDA and cis-2,4-PDA are NMDA antagonists. The compounds trans-2,5-PDA and cis-2,6-PDA did not interact with NMDA receptors. Each of the 3 cyclic acidic amino acids showing NMDA agonist activities existed as an equilibrium mixture of 2 conformers in aqueous solution In contrast, the NMDA antagonists cis-2,3-PDA and cis-2,4-PDA as well as the inactive compounds trans-2,5-PDA and cis-2,6-PDA exist predominantly in a single conformation. These results seem to indicate that a certain degree of conformational flexibility of analogs of GLU is prerequisite for activation of, but not for binding to, the NMDA receptor. The results came from multiple reactions, including the reaction of Cis-piperidine-2,6-dicarboxylic acid(cas: 59234-40-1Application In Synthesis of 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.Application In Synthesis of Cis-piperidine-2,6-dicarboxylic acid

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Swain, C. J.; Baker, R.; Kneen, C.; Moseley, J.; Saunders, J.; Seward, E. M.; Stevenson, G.; Beer, M.; Stanton, J.; Watling, K. published an article on January 31 ,1991. The article was titled 《Novel 5-HT3 antagonists. Indole oxadiazoles》, and you may find the article in Journal of Medicinal Chemistry.Safety of Methyl 1-methylpiperidine-3-carboxylate The information in the text is summarized as follows:

The synthesis and biochem. evaluation of a series of oxadiazole and indolyloxadiazole 5-HT3 (hydroxytryptamine) antagonists are described. The key pharmacophoric elements have been defined as a basic nitrogen, a linking group capable of H-bonding interactions, and an aromatic moiety. The steric limitations of the aromatic binding site have been determined by substitution about the indole ring. Variation of the heterocyclic linking group has shown that while 2 H-bonding interactions are possible, only 1 is essential for high affinity. The environment of the basic nitrogen has been investigated and shown to be optimal when constrained within an azabicyclic system. These results have been incorporated into a proposed binding model for the 5-HT3 antagonist binding site, in which the optimum distance between the aromatic binding site and the basic amine is 8.4-8.9 Å and the steric limitations are defined by van der Waals difference mapping. The experimental process involved the reaction of Methyl 1-methylpiperidine-3-carboxylate(cas: 1690-72-8Safety of Methyl 1-methylpiperidine-3-carboxylate)

Methyl 1-methylpiperidine-3-carboxylate(cas: 1690-72-8) 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 Methyl 1-methylpiperidine-3-carboxylate

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

《Discovery, Optimization, and Characterization of ML417: A Novel and Highly Selective D3 Dopamine Receptor Agonist》 was published in Journal of Medicinal Chemistry in 2020. These research results belong to Moritz, Amy E.; Free, R. Benjamin; Weiner, Warren S.; Akano, Emmanuel O.; Gandhi, Disha; Abramyan, Ara; Keck, Thomas M.; Ferrer, Marc; Hu, Xin; Southall, Noel; Steiner, Joseph; Aube, Jeffrey; Shi, Lei; Frankowski, Kevin J.; Sibley, David R.. Electric Literature of C7H15NO The article mentions the following:

To identify novel D3 dopamine receptor (D3R) agonists, we conducted a high-throughput screen using a β-arrestin recruitment assay. Counterscreening of the hit compounds provided an assessment of their selectivity, efficacy, and potency. The most promising scaffold was optimized through medicinal chem. resulting in enhanced potency and selectivity. The optimized compound, ML417 (20)(I), potently promotes D3R-mediated β-arrestin translocation, G protein activation, and ERK1/2 phosphorylation (pERK) while lacking activity at other dopamine receptors. Screening of ML417 against multiple G protein-coupled receptors revealed exceptional global selectivity. Mol. modeling suggests that ML417 interacts with the D3R in a unique manner, possibly explaining its remarkable selectivity. ML417 was also found to protect against neurodegeneration of dopaminergic neurons derived from iPSCs. Together with promising pharmacokinetics and toxicol. profiles, these results suggest that ML417 is a novel and uniquely selective D3R agonist that may serve as both a research tool and a therapeutic lead for the treatment of neuropsychiatric disorders. In the experiment, the researchers used many compounds, for example, 2-(Piperidin-4-yl)ethanol(cas: 622-26-4Electric Literature 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.Electric Literature of C7H15NO

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Miyazaki, Ray; Jin, Xiongjie; Yoshii, Daichi; Yatabe, Takafumi; Yabe, Tomohiro; Mizuno, Noritaka; Yamaguchi, Kazuya; Hasegawa, Jun-ya published an article in 2021. The article was titled 《Mechanistic study of C-H bond activation by O2 on negatively charged Au clusters: α,β-dehydrogenation of 1-methyl-4-piperidone by supported Au catalysts》, and you may find the article in Catalysis Science & Technology.Application In Synthesis of 1-Methyl-4-piperidone The information in the text is summarized as follows:

Au nanoparticles supported on the manganese oxide octahedral mol. sieve OMS-2 can efficiently catalyze α,β-dehydrogenation of β-N-substituted saturated ketones using O2 as the terminal oxidant. However, despite the utility of this reaction, the active sites and the reaction mechanism remain unclear. Here, the reaction mechanism for the Au/OMS-2-catalyzed aerobic α,β-dehydrogenation of 1-methyl-4-piperidone was investigated mainly by using d. functional theory (DFT) calculations From control experiments under various reaction conditions, we found that O2 plays an important role in the α,β-dehydrogenation over Au nanoparticles. Thus, we attempted to clarify the mechanism for the α,β-dehydrogenation of 1-methyl-4-piperidone on Au nanoparticle catalysts by DFT calculations using Au cluster models. The reaction was found to cleave the C-Hα and C-Hβ bonds in that order. An O2 mol. adsorbed on the neg. charged Au cluster caused by charge transfer from OMS-2 was found to be sufficiently activated to abstract the Hα atom in the 1-methyl-4-piperidone substrate. This indirect Hα abstraction by the activated O2 was energetically more favorable than direct Hα abstraction by the Au cluster. The subsequent Hβ abstraction was found to be promoted by adsorbed oxygen species (i.e., HOO, OH, and O) formed after the Hα abstraction. The reaction mechanism proposed in this study provides general insight into the aerobic C-H bond activation by supported Au catalysts. In addition to this study using 1-Methyl-4-piperidone, there are many other studies that have used 1-Methyl-4-piperidone(cas: 1445-73-4Application In Synthesis of 1-Methyl-4-piperidone) was used in this study.

1-Methyl-4-piperidone(cas: 1445-73-4) 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 1-Methyl-4-piperidone

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

In 2022,Li, Haobin; Cai, Maohua; Cao, Fei; Yu, Dehua; Yang, Jing; Yu, Wenkai; Chu, Chu; Guan, Xiaoqing; Qin, Jiang-Jiang; Dong, Jinyun published an article in Bioorganic & Medicinal Chemistry. The title of the article was 《S3I-201 derivative incorporating naphthoquinone unit as effective STAT3 inhibitors: Design, synthesis and anti-gastric cancer evaluation》.COA of Formula: C10H20N2O2 The author mentioned the following in the article:

Signal transducer and activator of transcription 3 (STAT3) is a key regulator of many human cancers and has been widely recognized as a promising target for cancer therapy. A variety of small-mol. inhibitors have been developed for targeting STAT3, and some of them are now undergoing clin. trials. S3I-201, a known STAT3 inhibitor, may block STAT3 function in cancer cells by binding to the STAT3 SH2 domain to disrupt STAT3 protein complex formation. Using S3I-201 as a starting point for drug development, we synthesized a series of new STAT3 inhibitors 9a-x in this study by introducing naphthoquinone unit, a privileged fragment in STAT3 inhibitors. Most of the compounds exhibited strong anti-proliferation activity of gastric cancer cells (MGC803, MKN28, MNK1, and AGS). The representative compound 9n (SIL-14) could effectively inhibit the colony formation and migration of gastric cancer cells MGC803, arrest the cell cycle and induce MGC803 cell apoptosis at low micromolar concentrations in vitro. In addition, SIL-14 can also inhibit the phosphorylation of STAT3 protein and significantly decrease the expression of total STAT3, suggesting that it may exert anticancer effects by blocking the STAT3 signaling pathway. These results support that SIL-14 may be a promising STAT3 inhibitor for the further development of potential anti-gastric cancer candidates. In the experimental materials used by the author, we found tert-Butyl 4-aminopiperidine-1-carboxylate(cas: 87120-72-7COA of Formula: C10H20N2O2)

tert-Butyl 4-aminopiperidine-1-carboxylate(cas: 87120-72-7) belongs to anime. The reaction of alkyl halides, R―X, where X is a halogen, or analogous reagents with ammonia (or amines) is useful with certain compounds. Not all alkyl halides are effective reagents; the reaction is sluggish with secondary alkyl groups and fails with tertiary ones. Its usefulness is largely confined to primary alkyl halides (those having two hydrogen atoms on the reacting site).COA of Formula: C10H20N2O2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

In 2022,Tao, Maoling; Wang, An-Jun; Guo, Peng; Li, Weipiao; Zhao, Liang; Tong, Jie; Wang, Haoyang; Yu, Yanbo; He, Chun-Yang published an article in Advanced Synthesis & Catalysis. The title of the article was 《Visible-Light-Induced Regioselective Deaminative Alkylation of Coumarins via Photoredox Catalysis》.Synthetic Route of C10H20N2O2 The author mentioned the following in the article:

A site-selective photocatalytic deaminative alkylation of coumarins utilizing pyridinium-activated aliphatic primary amines as alkylation reagents were reported. The protocol was highlighted by its mild reaction conditions, operational simplicity and broad functional group compatibility. Moreover, this strategy enabled late-stage modification of some pharmaceuticals and natural products, thus providing an appealing approach to valuable mols. in medicinal chem. After reading the article, we found that the author used tert-Butyl 4-aminopiperidine-1-carboxylate(cas: 87120-72-7Synthetic Route of C10H20N2O2)

tert-Butyl 4-aminopiperidine-1-carboxylate(cas: 87120-72-7) belongs to anime. Milder oxidation, using reagents such as NaOCl, can remove four hydrogen atoms from primary amines of the type RCH2NH2 to form nitriles (R―C≡N), and oxidation with reagents such as MnO2 can remove two hydrogen atoms from secondary amines (R2CH―NHR′) to form imines (R2C=NR′). Tertiary amines can be oxidized to enamines (R2C=CHNR2) by a variety of reagents.Synthetic Route of C10H20N2O2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

In 2022,Ma, Xueji; Wang, Qingyun; Wu, Jinge; Zhang, Liyuan; Sun, Aili; Wang, Zhanyong published an article in Organic & Biomolecular Chemistry. The title of the article was 《NHC-alcohol adduct-mediated photocatalytic deoxygenation for the synthesis of 6-phenanthridine derivatives》.Category: piperidines The author mentioned the following in the article:

NHC-alc. adduct-mediated deoxygenation of alcs. ROH (R = t-Bu, cyclopentyl, N-bocpiperidin-4-yl, etc.) under photocatalytic conditions is described. This process provides various alkyl radicals, which can react with 2-isocyanobiaryls I (R1 = H, Me, F; R2 = H, Cl; R3 = H, MeO, CF3; R4 = H, F, Me, MeO; R5 = H, MeO, CF3; R6 = H, Me, F) to afford 6-substituted phenanthridine derivatives II in moderate to good yields. This method offered the first example of directly using alcs. as radical sources for 6-phenanthridine synthesis. The experimental process involved the reaction of tert-Butyl 4-hydroxypiperidine-1-carboxylate(cas: 109384-19-2Category: piperidines)

tert-Butyl 4-hydroxypiperidine-1-carboxylate(cas:109384-19-2) is a 4-hydroxypyridine with a boc protecting group used in the preparation of neurologically active agents and other pharmaceutical compounds.Category: piperidines

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem