Category: piperidines

《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

《Discovery of the Potent, Selective, Orally Available CXCR7 Antagonist ACT-1004-1239》 was published in Journal of Medicinal Chemistry in 2020. These research results belong to Richard-Bildstein, Sylvia; Aissaoui, Hamed; Pothier, Julien; Schafer, Gabriel; Gnerre, Carmela; Lindenberg, Eleanor; Lehembre, Francois; Pouzol, Laetitia; Guerry, Philippe. COA of Formula: C10H20N2O2 The article mentions the following:

The chemokine receptor CXCR7, also known as ACKR3, is a seven-transmembrane G-protein-coupled receptor (GPCR) involved in various pathologies such as neurol. diseases, autoimmune diseases, and cancers. By binding and scavenging the chemokines CXCL11 and CXCL12, CXCR7 regulates their extracellular levels. From an original high-throughput screening campaign emerged an arylketoamide hit among others. The hit-to-lead optimization led to the discovery of a novel chemotype series of acylaminopiperidinecarboxamides. This series provided CXCR7 antagonists that block CXCL11- and CXCL12-induced ss-arrestin recruitment. Further structural modifications on the acylaminopiperidinecarboxamide framework yielded compounds with high CXCR7 antagonistic activities and balanced ADMET properties. The effort described herein culminated in the discovery of ACT-1004-1239 I. Biol. characterization of I demonstrated that it is a potent, insurmountable antagonist. Oral administration of I in mice up to 100 mg/kg led to a dose-dependent increase of plasma CXCL12 concentration In the part of experimental materials, we found many familiar compounds, such as 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. Examples of direct uses of amines and their salts are as corrosion inhibitors in boilers and in lubricating oils (morpholine), as antioxidants for rubber and roofing asphalt (diarylamines), as stabilizers for cellulose nitrate explosives (diphenylamine), as protectants against damage from gamma radiation (diarylamines), as developers in photography (aromatic diamines), as flotation agents in mining, as anticling and waterproofing agents for textiles, as fabric softeners, in paper coating, and for solubilizing herbicides.COA of Formula: C10H20N2O2

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

Shoji, Atsushi; Kuwahara, Masayasu; Ozaki, Hiroaki; Sawai, Hiroaki published an article on February 7 ,2007. The article was titled 《Modified DNA Aptamer That Binds the (R)-Isomer of a Thalidomide Derivative with High Enantioselectivity》, and you may find the article in Journal of the American Chemical Society.Recommanded Product: Benzyl (2,6-dioxopiperidin-3-yl)carbamate The information in the text is summarized as follows:

A thalidomide-binding aptamer was produced by systematic evolution of ligands by exponential enrichment from a library of non-natural DNA in which thymidine had been replaced with a modified deoxyuridine bearing a cationic functional group via a hydrophobic methylene linker at the C5 position. The addnl. functional group in the modified DNA aptamer could improve stability against nucleases and increase the binding affinity to thalidomide. The selected aptamer could recognize thalidomide enantioselectively, although a racemic thalidomide-attached gel was used for the selection. Surface plasmon resonance and fluorescence titration studies revealed that the selected modified DNA aptamer and a truncated version bound with an (R)-thalidomide derivative with high enantioselectivity, but not with the (S)-form. The modified group in the DNA aptamer is indispensable for the interaction with thalidomide, as the corresponding natural type DNA bearing the same base sequence showed no binding affinity with (R)- nor (S)-thalidomide. Computational sequence anal. suggested that the selected apatamer (108mer) could fold into a three-way junction structure; however, truncation of this aptamer (31mer) revealed that the thalidomide-binding site is a hairpin-bulge region that is a component of one of the arms of the three-way junction structure. The Kd value of the truncated 31mer aptamer for binding with the (R)-thalidomide derivative was 1.0 μM estimated from fluorescence titration study. The aptamer that can recognize a single enantiomer of thalidomide will be useful as a biochem. tool for the anal. and study of the biol. action of thalidomide enantiomers. The results came from multiple reactions, including the reaction of Benzyl (2,6-dioxopiperidin-3-yl)carbamate(cas: 24666-55-5Recommanded Product: Benzyl (2,6-dioxopiperidin-3-yl)carbamate)

Benzyl (2,6-dioxopiperidin-3-yl)carbamate(cas: 24666-55-5) belongs to anime. Acylation is one of the most important reactions of primary and secondary amines; a hydrogen atom is replaced by an acyl group (a group derived from an acid, such as RCOOH or RSO3H, by removal of ―OH, such as RC(=O)―, RS(O)2―, and so on). Reagents may be acid chlorides (RCOC1, RSO2C1), anhydrides ((RCO)2O), or even esters (RCOOR′); the products are amides of the corresponding acids.Recommanded Product: Benzyl (2,6-dioxopiperidin-3-yl)carbamate

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

Application In Synthesis of 3-(Piperidin-4-yl)benzoic acidOn October 15, 2010 ,《Design and synthesis of a new class of malonyl-CoA decarboxylase inhibitors with anti-obesity and anti-diabetic activities》 was published in Bioorganic & Medicinal Chemistry Letters. The article was written by Tang, Haifeng; Yan, Yan; Feng, Zhe; de Jesus, Reynalda K.; Yang, Lihu; Levorse, Dorothy A.; Owens, Karen A.; Akiyama, Taro E.; Bergeron, Raynald; Castriota, Gino A.; Doebber, Thomas W.; Ellsworth, Kenneth P.; Lassman, Michael E.; Li, Cai; Wu, Margaret S.; Zhang, Bei B.; Chapman, Kevin T.; Mills, Sander G.; Berger, Joel P.; Pasternak, Alexander. The article contains the following contents:

A new series of thiazole-substituted 1,1,1,3,3,3-hexafluoro-2-propanols, e.g. I, were prepared and evaluated as malonyl-CoA decarboxylase (MCD) inhibitors. Key analogs caused dose-dependent decreases in food intake and body weight in obese mice. Acute treatment with these compounds also led to a drop in elevated blood glucose in a murine model of type II diabetes. The results came from multiple reactions, including the reaction of 3-(Piperidin-4-yl)benzoic acid(cas: 766508-67-2Application In Synthesis of 3-(Piperidin-4-yl)benzoic acid)

3-(Piperidin-4-yl)benzoic acid(cas: 766508-67-2) belongs to piperidines. Piperidine derivatives are also used in solid-phase peptide synthesis (SPPS) and many degradation reactions. Application In Synthesis of 3-(Piperidin-4-yl)benzoic acid

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Application of 194726-40-4On May 10, 2018 ,《Strategic Approaches to Overcome Resistance against Gram-Negative Pathogens Using β-Lactamase Inhibitors and β-Lactam Enhancers: Activity of Three Novel Diazabicyclooctanes WCK 5153, Zidebactam (WCK 5107), and WCK 4234》 appeared in Journal of Medicinal Chemistry. The author of the article were Papp-Wallace, Krisztina M.; Nguyen, Nhu Q.; Jacobs, Michael R.; Bethel, Christopher R.; Barnes, Melissa D.; Kumar, Vijay; Bajaksouzian, Saralee; Rudin, Susan D.; Rather, Philip N.; Bhavsar, Satish; Ravikumar, Tadiparthi; Deshpande, Prasad K.; Patil, Vijay; Yeole, Ravindra; Bhagwat, Sachin S.; Patel, Mahesh V.; van den Akker, Focco; Bonomo, Robert A.. The article conveys some information:

Limited treatment options exist to combat infections caused by multidrug-resistant (MDR) Gram-neg. bacteria possessing broad-spectrum β-lactamases. The design of novel β-lactamase inhibitors is of paramount importance. Here, three novel diazabicyclooctanes (DBOs), WCK 5153, zidebactam (WCK 5107), and WCK 4234 (compounds 1-3, resp.), were synthesized and biochem. characterized against clin. important bacteria. Compound 3 inhibited class A, C, and D β-lactamases with unprecedented k2/K values against OXA carbapenemases. Compounds 1 and 2 acylated class A and C β-lactamses rapidly but not the tested OXAs. Compounds 1-3 formed highly stable acyl-complexes as demonstrated by mass spectrometry. Crystallog. revealed that 1-3 complexed with KPC-2 adopted a “”chair conformation”” with the sulfate occupying the carboxylate binding region. The cefepime-2 and meropenem-3 combinations were effective in murine peritonitis and neutropenic lung infection models caused by MDR Acinetobacter baumannii. Compounds 1-3 are novel β-lactamase inhibitors that demonstate potent cross-class inhibition, and clin. studies targeting MDR infections are warranted. In the part of experimental materials, we found many familiar compounds, such as (R)-1-tert-Butyl 3-ethyl piperidine-1,3-dicarboxylate(cas: 194726-40-4Application of 194726-40-4)

(R)-1-tert-Butyl 3-ethyl piperidine-1,3-dicarboxylate(cas: 194726-40-4) 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 of 194726-40-4

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