Month: January 2023

1-, 3- And 8-substituted-9-deazaxanthines as potent and selective antagonists at the human A_2B adenosine receptor. [Erratum to document cited in CA149:000438] was written by Stefanachi, Angela;Brea, Jose Manuel;Cadavid, Maria Isabel;Centeno, Nuria B.;Esteve, Cristina;Loza, Maria Isabel;Martinez, Ana;Nieto, Rosa;Ravina, Enrique;Sanz, Ferran;Segarra, Victor;Sotelo, Eddy;Vidal, Bernat;Carotti, Angelo. And the article was included in Bioorganic & Medicinal Chemistry in 2008.Synthetic Route of C12H17NO This article mentions the following:

In Tables 1 (pages 2855-2858), 2 (page 2859-2860), and 3 (page 2861), the second column heading, “R¹/R³“, was incorrectly given, and should read: “R³/R¹“. On page 2858, in Table 2, for compound 58, in the second column, “(CH₃)₂CHCH₂/Pr”, was incorrectly given, and should read “CH₃/(CH₃)₂CHCH₂“. On page 2861, in Table 3, for compound 87, in the second column, “CH₃/Pr” was incorrectly given, and should read “Pr/CH₃“. In the experiment, the researchers used many compounds, for example, 4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8Synthetic Route of C12H17NO).

4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8) belongs to piperidine derivatives. The piperidine ring can be found not only in more than half of the currently known structures of alkaloids, but also in many natural or synthetic compounds with interesting biological activities. 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.Synthetic Route of C12H17NO

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthesis of Bridged Azacycles and Propellanes via Nitrene/Alkyne Cascades was written by Wang, Qinxuan;May, Jeremy A.. And the article was included in Organic Letters in 2020.Safety of 1-Tosylpiperidin-4-one This article mentions the following:

A nitrene/alkyne cascade reaction terminating in C-H bond insertion to form functionalized bridged azacycles from carbonazidates is presented. Due to an initial Huisgen cyclization, all carbonazidates reacted with the alkyne in an exo mode in contrast to the use of sulfamate esters, which react predominately in an endo mode. Substrates with different ring sizes as well as different aryl and heteroaryl groups were also explored. Variation of the nitrene tether showed that 7-membered rings were the maximum ring size to be formed by nitrene attack on the alkyne. Examples incorporating stereocenters on the carbonazidate’s tether induced diasteroselectivity in the formation of the bridged ring and two new stereocenters. Addnl., propellanes containing aminals, hemiaminals, and thioaminals formed from the bridged azacycles in the same reaction via an acid-promoted rearrangement. 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. The piperidine moiety constitutes an important building block for the synthesis of a variety of bioactive natural products, alkaloids and other drugs. 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.Safety of 1-Tosylpiperidin-4-one

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Cyclic Alkenylsulfonyl Fluorides: Palladium-Catalyzed Synthesis and Functionalization of Compact Multifunctional Reagents was written by Lou, Terry Shing-Bong;Bagley, Scott W.;Willis, Michael C.. And the article was included in Angewandte Chemie, International Edition in 2019.HPLC of Formula: 33439-27-9 This article mentions the following:

A series of low-mol.-weight, compact, and multifunctional cyclic alkenylsulfonyl fluorides were efficiently prepared from the corresponding alkenyl triflates. Palladium-catalyzed sulfur dioxide insertion using the surrogate reagent DABSO effects sulfinate formation, before trapping with an F electrophile delivers the sulfonyl fluorides. A broad range of functional groups are tolerated, and a correspondingly large collection of derivatization reactions are possible on the products, including substitution at sulfur, conjugate addition, and N-functionalization. Together, these attributes suggest that this method could find new applications in chem. biol. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9HPLC of Formula: 33439-27-9).

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. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.HPLC of Formula: 33439-27-9

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Direct and enantioselective α-allylation of ketones via singly occupied molecular orbital (SOMO) catalysis was written by Mastracchio, Anthony;Warkentin, Alexander A.;Walji, Abbas M.;MacMillan, David W. C.. And the article was included in Proceedings of the National Academy of Sciences of the United States of America in 2010.Category: piperidines This article mentions the following:

The first enantioselective organocatalytic α-allylation of cyclic ketones was accomplished via singly occupied MO catalysis. Geometrically constrained radical cations, forged from the one-electron oxidation of transiently generated enamines, readily undergo allylic alkylation with a variety of com. available allylsilanes. A reasonable latitude in both the ketone and allylsilane components is readily accommodated in this new transformation. Moreover, three new oxidatively stable imidazolidinone catalysts have been developed that allow cyclic ketones to successfully participate in this transformation. The new catalyst platform has also been exploited in the first catalytic enantioselective α-oxoalkylation and α-arylalkylation of ketones. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Category: piperidines).

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. 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.Category: piperidines

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Design, synthesis and characterization of PROTACs targeting the androgen receptor in prostate and lung cancer models was written by Gockel, Lukas M.;Pfeifer, Vladlena;Baltes, Fabian;Bachmaier, Rafael D.;Wagner, Karl G.;Bendas, Gerd;Guetschow, Michael;Sosic, Izidor;Steinebach, Christian. And the article was included in Archiv der Pharmazie (Weinheim, Germany) in 2022.Formula: C10H20ClNO2 This article mentions the following:

Three subgroups of enzalutamide-based PROTACs was presented in which only the exit vector was modified. By recruiting cereblon, the potent degradation of AR in lung cancer cells was demonstrated. Furthermore, the initial evaluation enabled the design of an optimized PROTAC with a rigid linker that degraded AR with a DC₅₀ value in the nanomolar range. These results provide novel AR-directed PROTACs and a clear rationale for further investigating AR involvement in lung cancer models. In the experiment, the researchers used many compounds, for example, tert-Butyl piperidine-4-carboxylate hydrochloride (cas: 892493-65-1Formula: C10H20ClNO2).

tert-Butyl piperidine-4-carboxylate hydrochloride (cas: 892493-65-1) belongs to piperidine derivatives. The piperidine ring can be found not only in more than half of the currently known structures of alkaloids, but also in many natural or synthetic compounds with interesting biological activities. 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.Formula: C10H20ClNO2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Preparation of Indolenines via Nucleophilic Aromatic Substitution was written by Huber, Florian;Roesslein, Joel;Gademann, Karl. And the article was included in Organic Letters in 2019.Electric Literature of C13H16N2 This article mentions the following:

An unusual aromatic substitution to access indolenines is described. 2-(2-Methoxyphenyl)acetonitrile derivatives are reacted with various alkyl and aryl Li reagents to furnish the corresponding indolenine products, constituents of natural products, and cyanine dyes such as indocyanine green. This new method was used to synthesize 41 indolenines with large functional group tolerance, and selected examples were further converted to the corresponding indolenine dyes. Key experiments provide insight into the mechanism of this nucleophilic aromatic substitution. In the experiment, the researchers used many compounds, for example, 1-Benzylpiperidine-4-carbonitrile (cas: 62718-31-4Electric Literature of C13H16N2).

1-Benzylpiperidine-4-carbonitrile (cas: 62718-31-4) belongs to piperidine derivatives. Piperidine is a saturated organic heteromonocyclic parent, an azacycloalkane, a secondary amine and a member of piperidines. The piperidine and polyhydroxylated indolizidine derivatives have shown to be promising α-glucosidase inhibitors. The former are analogs of DNJ with an improved α-glucosidase inhibitory profile than that of DNJ. Boisson et al.Electric Literature of C13H16N2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Reactions with arenesulfonyl azides of some indoles with oxygen- and nitrogen-containing substituents was written by Bailey, A. Sydney;Birch, Christopher M.;Illingworth, David;Willmott, Janet C.. And the article was included in Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) in 1978.Application In Synthesis of 1-Tosylpiperidin-4-one This article mentions the following:

The pyridoindole I (X = NSO₂C₆H₄Me-4) with 4-RC₆H₄SO₂N₃ (II, R = O₂N) gave 34% spiro compound III. Pyranoindole I (X = O) with II (R = Cl) gave 89% spiro compound IV. Me 1,3-dimethylindole-2-carboxylate with II (R = O₂N) in pyridine was kepy 4 wk at 80° to give Me 1,3-dimethyl-2-(p-nitrophenylsulfonylimino)indoline-3-carboxylate by CO₂Me migration. Me 1,3-dimethyl-2-indoleacetate with II (R = O₂N, Cl) gave the resp. 2-(carbomethoxymethylene)-3-(benzenesulfonamido)indoline derivatives In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Application In Synthesis of 1-Tosylpiperidin-4-one).

1-Tosylpiperidin-4-one (cas: 33439-27-9) belongs to piperidine derivatives. Piperidine and its derivatives have become increasingly popular in many synthetic schemes. Piperidine prefers a chair conformation, similar to cyclohexane. Unlike cyclohexane, piperidine has two distinguishable chair conformations: one with the N–H bond in an axial position, and the other in an equatorial position.Application In Synthesis of 1-Tosylpiperidin-4-one

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Efficient and modular synthesis of new structurally diverse functionalized [n]paracyclophanes by a ring-distortion strategy was written by Krieger, Jean-Philippe;Ricci, Gino;Lesuisse, Dominique;Meyer, Christophe;Cossy, Janine. And the article was included in Angewandte Chemie, International Edition in 2014.Recommanded Product: 1-Tosylpiperidin-4-one This article mentions the following:

With the goal of synthesizing new [n]paracyclophanes, the expansion of the scope of a strategy originally disclosed by Winterfeldt et al., was investigated. This approach involves sequential Diels-Alder/retro-Diels-Alder reactions, the applications of which were constrained so far to steroid derivatives An efficient access to new functionalized [9]-, [10]-, and [16]paracyclophanes, including original cage architectures, was developed from readily available building blocks using thermal electrocyclization and a cycloaddition/cycloreversion sequence as the key steps. 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 and its derivatives have become increasingly popular in many synthetic schemes. The piperidine and polyhydroxylated indolizidine derivatives have shown to be promising α-glucosidase inhibitors. The former are analogs of DNJ with an improved α-glucosidase inhibitory profile than that of DNJ. Boisson et al.Recommanded Product: 1-Tosylpiperidin-4-one

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Structure and activity relationship of 2-(substituted benzoyl)-hydroxyindoles as novel CaMKII inhibitors was written by Komiya, Masafumi;Asano, Shigehiro;Koike, Nobuyuki;Koga, Erina;Igarashi, Junetsu;Nakatani, Shogo;Isobe, Yoshiaki. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2011.Product Details of 4045-22-1 This article mentions the following:

A series of novel 2-substituted-5-hydroxyindoles were synthesized and evaluated for their inhibitory activity against CaMKII. Structure and activity relationship results indicated that potent inhibitory activity could be achieved by modification at the para-position of the Ph ring of the high throughput screening hit compound I. Among the prepared compounds, we identified II as a novel CaMKII inhibitor with an activity stronger than that of KN-93, a known CaMKII inhibitor. In the experiment, the researchers used many compounds, for example, 1-(4-Hydroxypiperidin-1-yl)ethanone (cas: 4045-22-1Product Details of 4045-22-1).

1-(4-Hydroxypiperidin-1-yl)ethanone (cas: 4045-22-1) 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.Product Details of 4045-22-1

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

New μ-opioid receptor agonists with a phenoxyacetic acid moiety was written by Sato, Susumu;Komoto, Teruo;Kanamaru, Yoshihiko;Kawamoto, Noriyuki;Okada, Tomomi;Kaiho, Terurnitsu;Mogi, Kinichi;Morimoto, Shinichi;Umehara, Norimitsu;Koda, Tadayuki;Miyashita, Akira;Sakamoto, Takao;Niino, Yasuhiro;Oka, Tetsuo. And the article was included in Chemical & Pharmaceutical Bulletin in 2002.Synthetic Route of C12H17NO This article mentions the following:

New μ-opioid receptor (MOR) agonists containing 4-hydroxypiperidine, piperidine and piperazine moieties were synthesized and evaluated to find a peripheral opioid analgesic. Among the synthesized compounds, I showed the highest agonist potency on the MOR in an isolated guinea-pig ileum preparation, and it also had selectivity to the human MOR expressed in Chinese hamster ovary (CHO)-K1 cells compared with the same types of δ- and κ-opioid receptors. In addition, compound I showed 10 times more potent MOR agonist activity than loperamide. Furthermore, compound I showed a peripheral analgesic activity in the rat. In the experiment, the researchers used many compounds, for example, 4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8Synthetic Route of C12H17NO).

4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8) belongs to piperidine derivatives. Piperidine is a metabolite of cadaverine, a polyamine found in the human intestine. 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.Synthetic Route of C12H17NO

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem