Category: piperidines

Cobalt-Catalyzed Aerobic Oxidative Cleavage of Alkyl Aldehydes: Synthesis of Ketones, Esters, Amides, and 浼?Ketoamides was written by Li, Tingting;Hammond, Gerald B.;Xu, Bo. And the article was included in Chemistry – A European Journal in 2021.Safety of 1-Tosylpiperidin-4-one This article mentions the following:

A widely applicable approach was developed to synthesize ketones, esters, amides via the oxidative C-C bond cleavage of readily available alkyl aldehydes. Green and abundant mol. oxygen (O₂) was used as the oxidant, and base metals (cobalt and copper) were used as the catalysts. This strategy can be extended to the one-pot synthesis of ketones from primary alcs. and 浼?ketoamides from aldehydes. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Safety of 1-Tosylpiperidin-4-one).

1-Tosylpiperidin-4-one (cas: 33439-27-9) belongs to piperidine derivatives. Piperidine has a role as a reagent, a protic solvent, a base, a catalyst, a plant metabolite, a human metabolite and a non-polar solvent. Fluorinated piperidines are also the subject of continued interest in medicinal chemistry, for example in the synthesis of selective dipeptidyl peptidase II (DPP II) inhibitors. Piperidine derivatives are also used in solid-phase peptide synthesis (SPPS) and many degradation reactions.Safety of 1-Tosylpiperidin-4-one

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthesis, pharmacological evaluation and QSAR modeling of mono-substituted 4-phenylpiperidines and 4-phenylpiperazines was written by Pettersson, Fredrik;Svensson, Peder;Waters, Susanna;Waters, Nicholas;Sonesson, Clas. And the article was included in European Journal of Medicinal Chemistry in 2013.Recommanded Product: 4-(2-Methoxyphenyl)piperidine This article mentions the following:

A series of mono-substituted 4-phenylpiperidines and -piperazines have been synthesized and their effects on the dopaminergic system tested in vivo. The structure activity relationship (SAR) revealed that the position and physicochem. character of the aromatic substituent proved to be critical for the levels of 3,4-dihydroxyphenylacetic acid (DOPAC) in the brain of freely moving rats. In order to investigate how the structural properties of these compounds affect the response, a set of tabulated and calculated physicochem. descriptors were modeled against the in vivo effects using partial least square (PLS) regression. Furthermore, the binding affinities to the dopamine D₂ (DA D₂) receptor and monoamine oxidase A (MAO A) enzyme were determined for a chosen subset and QSAR models using the same descriptors as in the in vivo model were produced to investigate the mechanisms leading to the observed DOPAC response. These models, in combination with a strong correlation between the levels of striatal DOPAC and the affinities to DA D₂ and MAO A, provide a comprehensive understanding of the biol. response for compounds in this class. In the experiment, the researchers used many compounds, for example, 4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8Recommanded Product: 4-(2-Methoxyphenyl)piperidine).

4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8) belongs to piperidine derivatives. The piperidine structural motif is present in numerous natural alkaloids. These include piperine, which gives black pepper its spicy taste. Several piperidine alkaloids isolated from natural herbs, were found to exhibit antiproliferation and antimetastatic effects on various types of cancers both in vitro and in vivo for example Piperine, Evodiamine, Matrine, Berberine and Tetrandine.Recommanded Product: 4-(2-Methoxyphenyl)piperidine

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Structure-activity relationship in the oxazolidinone-quinolone hybrid series: influence of the central spacer on the antibacterial activity and the mode of action was written by Hubschwerlen, Christian;Specklin, Jean-Luc;Baeschlin, Daniel K.;Borer, Yves;Haefeli, Sascha;Sigwalt, Christine;Schroeder, Susanne;Locher, Hans H.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2003.Synthetic Route of C13H17NO3 This article mentions the following:

Oxazolidinone-quinolone hybrids, which combine the pharmacophores of a quinolone and an oxazolidinone, were synthesized and shown to be active against a variety of susceptible and resistant Gram-pos. and Gram-neg. bacteria. The nature of the spacer greatly influences the antibacterial activity by directing the mode of action, that is quinolone- and/or oxazolidinone-like activity. The best compounds in this series have a balanced dual mode of action and overcome all types of resistance, including resistance to quinolones and linezolid, in clin. relevant Gram-pos. pathogens. In the experiment, the researchers used many compounds, for example, Benzyl 3-hydroxypiperidine-1-carboxylate (cas: 95798-22-4Synthetic Route of C13H17NO3).

Benzyl 3-hydroxypiperidine-1-carboxylate (cas: 95798-22-4) belongs to piperidine derivatives. Piperidine has a role as a reagent, a protic solvent, a base, a catalyst, a plant metabolite, a human metabolite and a non-polar solvent. The piperidine and polyhydroxylated indolizidine derivatives have shown to be promising 浼?glucosidase inhibitors. The former are analogs of DNJ with an improved 浼?glucosidase inhibitory profile than that of DNJ. Boisson et al.Synthetic Route of C13H17NO3

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthetic Approach toward Enantiopure Cyclic Sulfinamides was written by Jersovs, Glebs;Bojars, Matiss;Donets, Pavel A.;Suna, Edgars. And the article was included in Organic Letters in 2022.Application of 33439-27-9 This article mentions the following:

A synthetic approach toward densely substituted enantiopure cyclic sulfinamides possessing up to four consecutive stereogenic centers has been developed based on a completely diastereoselective SN₂‘ cyclization/tert-Bu cleavage sequence. Diastereospecific transformation of the obtained scaffold into chiral S^VI derivatives such as sulfoximines and sulfonimidamides is demonstrated. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Application of 33439-27-9).

1-Tosylpiperidin-4-one (cas: 33439-27-9) belongs to piperidine derivatives. The piperidine structural motif is present in numerous natural alkaloids. These include piperine, which gives black pepper its spicy taste. Industrially, piperidine is produced by the hydrogenation of pyridine, usually over a molybdenum disulfide catalyst. Pyridine can also be reduced to piperidine via a modified Birch reduction using sodium in ethanol.Application of 33439-27-9

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Metallaphotoredox-enabled deoxygenative arylation of alcohols was written by Dong, Zhe;MacMillan, David W. C.. And the article was included in Nature (London, United Kingdom) in 2021.Computed Properties of C11H21NO3 This article mentions the following:

Metal-catalyzed cross-couplings are a mainstay of organic synthesis and are widely used for the formation of C-C bonds, particularly in the production of unsaturated scaffolds1. However, alkyl cross-couplings using native sp3-hybridized functional groups such as alcs. remain relatively underdeveloped2. In particular, a robust and general method for the direct deoxygenative coupling of alcs. would have major implications for the field of organic synthesis. A general method for the direct deoxygenative cross-coupling of free alcs. must overcome several challenges, most notably the in situ cleavage of strong C-O bonds3, but would allow access to the vast collection of com. available, structurally diverse alcs. as coupling partners4. Authors report herein a metallaphotoredox-based cross-coupling platform in which free alcs. are activated in situ by N-heterocyclic carbene salts for carbon-carbon bond formation with aryl halide coupling partners. This method is mild, robust, selective and most importantly, capable of accommodating a wide range of primary, secondary and tertiary alcs. as well as pharmaceutically relevant aryl and heteroaryl bromides and chlorides. The power of the transformation has been demonstrated in a number of complex settings, including the late-stage functionalization of Taxol and a modular synthesis of Januvia, an antidiabetic medication. This technol. represents a general strategy for the merger of in situ alc. activation with transition metal catalysis. In the experiment, the researchers used many compounds, for example, 1-Boc-4-Hydroxy-4-methylpiperidine (cas: 406235-30-1Computed Properties of C11H21NO3).

1-Boc-4-Hydroxy-4-methylpiperidine (cas: 406235-30-1) belongs to piperidine derivatives. Piperidine is a metabolite of cadaverine, a polyamine found in the human intestine. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.Computed Properties of C11H21NO3

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthesis and Antimalarial-Activity Evaluation of Tetraoxane-Triazine Hybrids and Spiro[piperidine-4,3′-tetraoxanes] was written by Kumar, Nitin;Khan, Shabana I.;Rawat, Diwan S.. And the article was included in Helvetica Chimica Acta in 2012.Recommanded Product: 1-Tosylpiperidin-4-one This article mentions the following:

A series of tetraoxane-triazine hybrids and spiro[piperidine-4,3′-tetraoxanes] have been synthesized, and all the compounds were screened for in vitro antimalarial activity against chloroquine-sensitive (D6) and chloroquine-resistant (W2) strains of Plasmodium falciparum. Most of the spiro[piperidine-4,3′-tetraoxanes] exhibited moderate to good antimalarial activities, and two compounds I and II have shown good antimalarial activity with IC₅₀ values in the range of 0.30 to 0.70 μM against both the strains with a high selectivity index and no cytotoxicity towards mammalian kidney cell line. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Recommanded Product: 1-Tosylpiperidin-4-one).

1-Tosylpiperidin-4-one (cas: 33439-27-9) belongs to piperidine derivatives. Piperidine is a metabolite of cadaverine, a polyamine found in the human intestine. Several piperidine alkaloids isolated from natural herbs, were found to exhibit antiproliferation and antimetastatic effects on various types of cancers both in vitro and in vivo for example Piperine, Evodiamine, Matrine, Berberine and Tetrandine.Recommanded Product: 1-Tosylpiperidin-4-one

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

New xanthine derivatives with potent and long lasting anti-bronchoconstrictive activity was written by Regnier, Gilbert L.;Guillonneau, Claude G.;Duhault, Jacques L.;Tisserand, Francoise P.;Saint-Romas, Guy;Holstorp, Sophie M.. And the article was included in European Journal of Medicinal Chemistry in 1987.Synthetic Route of C7H13NO2 This article mentions the following:

Twenty-nine new derivatives of 8-aminoalkyl-substituted xanthine [e.g. I, R¹ = H, Me, Et; R² = Me, iso-Pr, Ph, etc.; R³ = H, Me, 2,3-dihydroxypropyl, etc.; R⁴ = H or F; and X = CH(OH)CH₂, (CH₂)_n; n = 1-3] were synthesized. All I demonstrated a potent anti-bronochoconstrictive effect in the guinea pig and some had a very long duration of action (> 48h). II was selected for clin. trials in asthmatic patients because of its long duration of action, its lack of central nervous system-stimulating effects and its inhibiting action on mast cell degranulation and phosphodiesterse activity. Structure-activity relationships are discussed. In the experiment, the researchers used many compounds, for example, 1-(4-Hydroxypiperidin-1-yl)ethanone (cas: 4045-22-1Synthetic Route of C7H13NO2).

1-(4-Hydroxypiperidin-1-yl)ethanone (cas: 4045-22-1) belongs to piperidine derivatives. The piperidine moiety constitutes an important building block for the synthesis of a variety of bioactive natural products, alkaloids and other drugs. Fluorinated piperidines are also the subject of continued interest in medicinal chemistry, for example in the synthesis of selective dipeptidyl peptidase II (DPP II) inhibitors. Piperidine derivatives are also used in solid-phase peptide synthesis (SPPS) and many degradation reactions.Synthetic Route of C7H13NO2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthesis of quinoxaline analogues was written by Chang, Meng-Yang;Lee, Tein-Wei;Hsu, Ru-Ting;Yen, Tzu-Lin. And the article was included in Synthesis in 2011.Name: 1-Tosylpiperidin-4-one This article mentions the following:

Substituted tricyclic or tetracyclic quinoxalines, tricyclic pyridoquinoxalines and bis-quinoxalines were synthesized in high yields starting from cyclic ketones by the α-bromination of cyclic ketones with N-bromosuccinimide (NBS) followed by condensation of the resulting α-bromo ketones with 1,2-diaminobenzene, 3,4-diaminopyridine, or 3,3′-diaminobenzidine. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Name: 1-Tosylpiperidin-4-one).

1-Tosylpiperidin-4-one (cas: 33439-27-9) belongs to piperidine derivatives. Piperidine has a role as a reagent, a protic solvent, a base, a catalyst, a plant metabolite, a human metabolite and a non-polar solvent. Piperidine derivatives are being utilized in different ways as anticancer, antiviral, antimalarial, antimicrobial, antifungal, antihypertension, analgesic, anti-inflammatory, anti-Alzheimer, antipsychotic and/or anticoagulant agents.Name: 1-Tosylpiperidin-4-one

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Discovery of Novel Spiroindoline Derivatives as Selective Tankyrase Inhibitors was written by Shirai, Fumiyuki;Tsumura, Takeshi;Yashiroda, Yoko;Yuki, Hitomi;Niwa, Hideaki;Sato, Shin;Chikada, Tsubasa;Koda, Yasuko;Washizuka, Kenichi;Yoshimoto, Nobuko;Abe, Masako;Onuki, Tetsuo;Mazaki, Yui;Hirama, Chizuko;Fukami, Takehiro;Watanabe, Hirofumi;Honma, Teruki;Umehara, Takashi;Shirouzu, Mikako;Okue, Masayuki;Kano, Yuko;Watanabe, Takashi;Kitamura, Kouichi;Shitara, Eiki;Muramatsu, Yukiko;Yoshida, Haruka;Mizutani, Anna;Seimiya, Hiroyuki;Yoshida, Minoru;Koyama, Hiroo. And the article was included in Journal of Medicinal Chemistry in 2019.Related Products of 58333-75-8 This article mentions the following:

The canonical WNT pathway plays an important role in cancer pathogenesis. Inhibition of poly(ADP-ribose) polymerase catalytic activity of the tankyrases (TNKS/TNKS2) has been reported to reduce the Wnt/β-catenin signal by preventing poly ADP-ribosylation dependent degradation of AXIN, a neg. regulator of Wnt/β-catenin signaling. With the goal of investigating the effects of tankyrase and Wnt pathway inhibition on tumor growth, we set out to find small mol. inhibitors of TNKS/TNKS2 with suitable drug-like properties. Starting from 1a(I), a high-throughput screening hit, the spiroindoline derivative 40c(II) (RK-287107) was discovered as a potent TNKS/TNKS2 inhibitor with >7,000-fold selectivity against the PARP1 enzyme, which inhibits WNT-responsive TCF reporter activity and proliferation of human colorectal cancer cell line COLO-320DM. II also demonstrated dose-dependent tumor growth inhibition in a mouse xenograft model. These observations suggest that II is a promising lead compound for the development of novel tankyrase inhibitors as anticancer agents. In the experiment, the researchers used many compounds, for example, 4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8Related Products of 58333-75-8).

4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8) belongs to piperidine derivatives. Piperidine is a saturated organic heteromonocyclic parent, an azacycloalkane, a secondary amine and a member of piperidines. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.Related Products of 58333-75-8

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Optimization of biaryloxazolidinone as promising antibacterial agents against antibiotic-susceptible and antibiotic-resistant gram-positive bacteria was written by Wu, Yachuang;Ding, Xiudong;Yang, Yifeng;Li, Yingxiu;Qi, Yinliang;Hu, Feng;Qin, Mingze;Liu, Yajing;Sun, Lu;Zhao, Yanfang. And the article was included in European Journal of Medicinal Chemistry in 2020.Formula: C9H19N3O2 This article mentions the following:

Herein, novel biaryloxazolidinone analogs I [X = O, S, NMe, etc.; Y = N, CH, CHOH, etc.; Z = N, CH] were designed and synthesized to improve the chem. and metabolic stability. Compounds I [X = S, NMe, SO₂; Y = N, CHOH; Z = CH] showed significant antibacterial activity against the tested Gram-pos. bacteria as compared to radezolid and linezolid. Further studies indicated that most of them exhibited improved water solubility and chem. stability. Compound I [X = SO₂; Y = N; Z = CH] had MIC values of 0.125-0.25 μg/mL against all tested Gram-pos. bacteria, and showed excellent antibacterial activity against clin. isolates of antibiotic-susceptible and antibiotic-resistant bacteria. Moreover, it was stable in human liver microsome. From a safety viewpoint, it showed non-cytotoxic activity against hepatic cell and exhibited lower inhibitory activity against human MAO-A compared to linezolid. The potent antibacterial activity and all these improved drug-likeness properties and safety profile suggested that compound I [X = SO₂; Y = N; Z = CH] might be a promising drug candidate for further investigation. In the experiment, the researchers used many compounds, for example, tert-Butyl 4-aminopiperazine-1-carboxylate (cas: 118753-66-5Formula: C9H19N3O2).

tert-Butyl 4-aminopiperazine-1-carboxylate (cas: 118753-66-5) belongs to piperidine derivatives.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. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.Formula: C9H19N3O2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem