Heterocyclic Building Blocks-piperidine

Synthesis and antihypertensive activity of some new quinazoline derivatives was written by Honkanen, Erkki;Pippuri, Aino;Kairisalo, Pekka;Nore, Pentti;Karppanen, Heikki;Paakkari, Ilari. And the article was included in Journal of Medicinal Chemistry in 1983.Recommanded Product: 1-Benzylpiperidine-4-carbonitrile This article mentions the following:

A series of substituted 2-piperidino-4-amino-6,7-dimethoxyquinazolines I.HCl [R = Me, CH₂Ph, CH(OH)R¹ (R¹ = alkyl, cycloalkyl), COR² (R² = alkyl, cycloalkyl, alkoxy, amino)] was synthesized and screened as potential antihypertensive agents. At small doses, two of the new compounds I (R = 4-(cyclopentylcarbonyl), 4-Q], appeared to be somewhat less potent than prazosin,; but at the higher doses of 10-100 μmol/kg, they appeared to be even more efficacious antihypertensive agents than prazosin. Structure activity relationships were discussed. In the experiment, the researchers used many compounds, for example, 1-Benzylpiperidine-4-carbonitrile (cas: 62718-31-4Recommanded Product: 1-Benzylpiperidine-4-carbonitrile).

1-Benzylpiperidine-4-carbonitrile (cas: 62718-31-4) 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-Benzylpiperidine-4-carbonitrile

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthesis and biological evaluation of ethacrynic acid derivatives bearing sulfonamides as potent anti-cancer agents was written by El Abbouchi, Abdelmoula;El Brahmi, Nabil;Hiebel, Marie-Aude;Bignon, Jerome;Guillaumet, Gerald;Suzenet, Franck;El Kazzouli, Said. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2020.Recommanded Product: 651057-01-1 This article mentions the following:

A series of ethacrynic acid (2-[2,3-dichloro-4-(2-methylidenebutanoyl)phenoxy]acetic acid) (EA, Edecrin) containing sulfonamides linked via three types of linkers namely 1,2-ethylenediamine, piperazine and 4-aminopiperidine was synthesized and subsequently evaluated in vitro against HL60 and HCT116 cancer cell lines. All the EA analogs, excluding two derivs, showed anti-proliferative activity with IC_50s in the micromolar range (less than 4 uM). Three derivatives I–III were selected for their interesting dual activity on HL60 cell line in order to be further evaluated against a panel of cancer cell lines (HCT116, A549, MCF7, PC3, U87-MG and SKOV3) as well as on MRC5 as a normal cell line. These compounds displayed IC₅₀ values in nanomolar range against A549, MCF7, PC3 and HCT116 cell lines, deducing the discovery that piperazine or 4-aminopiperidine is the linker’s best choice to develop EA analogs with highly potent anti-proliferative activities own up to 24 nM. Besides, in terms of selectivity, those linkers are more suitable offering safety ratios of up to 63.8. In the experiment, the researchers used many compounds, for example, 1-(Methylsulfonyl)piperidin-4-amine hydrochloride (cas: 651057-01-1Recommanded Product: 651057-01-1).

1-(Methylsulfonyl)piperidin-4-amine hydrochloride (cas: 651057-01-1) 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. 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: 651057-01-1

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Application of chemical cytochrome P-450 model systems to studies on drug metabolism. IV. Mechanism of piperidine metabolism pathways via an iminium intermediate was written by Masumoto, Hiroshi;Ohta, Shigeru;Hirobe, Masaaki. And the article was included in Drug Metabolism and Disposition in 1991.COA of Formula: C12H18ClNO This article mentions the following:

Oxidations of the piperidine ring by chem. model and liver microsomal systems were investigated with a simple piperidine derivative, N-benzylpiperidine (BP), as the substrate in order to probe the generality and the mechanism of the biotransformation of the piperidine ring. The piperidine ring of BP as well as that of phencyclidine was suggested to be oxidized to a ketone at the β-position in the meso-tetraphenylporphinatoiron(III) chloride system, and the reaction was expected to occur in the liver microsomal system. The β-oxo formation was observed directly in the liver microsomal system, and found to be dependent on cytochrome P 450. Then it was suggested that the piperidine-β-oxo formation was a general oxidation pathway of the piperidine biotransformation. Hydrogen abstraction in the reaction was not a rate-determining step. Therefore, the authors presumed a possible mechanism of β-oxo formation via BP-iminium. From the comparative study on the reactivities of dipropylbenzylamine (DPB) and BP, and the stabilities of iminium (Im⁺) species of BP and DPB, it was suggested that BP-Im⁺ was relatively stable and was the most likely precursor of BP-β-oxo. BP-Im⁺ and its free base, enamine, afforded large amounts of BP-β-oxo as well as BP-α-oxo in the chem. model and the microsomal systems. This evidence supported the iminium-enamine mechanism. In the experiment, the researchers used many compounds, for example, 1-Benzyl-3-piperidinol hydrochloride (cas: 105973-51-1COA of Formula: C12H18ClNO).

1-Benzyl-3-piperidinol hydrochloride (cas: 105973-51-1) 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.COA of Formula: C12H18ClNO

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

A general method for the α-acyloxylation of carbonyl compounds was written by Beshara, Cory S.;Hall, Adrian;Jenkins, Robert L.;Jones, Kerri L.;Jones, Teyrnon C.;Killeen, Niall M.;Taylor, Paul H.;Thomas, Stephen P.;Tomkinson, Nicholas C. O.. And the article was included in Organic Letters in 2005.Name: 1-Tosylpiperidin-4-one This article mentions the following:

A simple, one-pot method for the α-acyloxylation of carbonyl compounds that proceeded at room temperature in the presence of both moisture and air has been developed. Treatment of a variety of aldehydes and both cyclic and acyclic ketones with N-methyl-O-benzoylhydroxylamine hydrochloride provided the α-functionalized product in good isolated yield. The transformation was tolerant of a wide range of functional groups and, significantly, was regiospecific in the discrimination of secondary over primary centers in the case of nonsym. substrates. 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. The piperidine structural motif is present in numerous natural alkaloids. These include piperine, which gives black pepper its spicy taste. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.Name: 1-Tosylpiperidin-4-one

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Morpholinosulfur Trifluoride (Morph-DAST)-Mediated Rearrangement in the Fluorination of Cyclic α,α-Dialkoxy Ketones toward 1,2-Dialkoxy-1,2-difluorinated Compounds was written by Surmont, Riccardo;Verniest, Guido;De Groot, Alex;Thuring, Jan Willem;De Kimpe, Norbert. And the article was included in Advanced Synthesis & Catalysis in 2010.Related Products of 33439-27-9 This article mentions the following:

The deoxofluorination of cyclic α,α-dialkoxy ketones with morpholinosulfur trifluoride gave title compounds, e.g. I (Z = BocN, CH₂, O, etc.). The reaction proceeds via a 1,2-alkoxy migration leading to mixtures of cis- and trans-isomers. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Related Products of 33439-27-9).

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. 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.Related Products of 33439-27-9

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Improved synthesis and radiolabeling of [¹¹C]MP4A, a suitable ligand for the investigation of the cholinergic system using PET was written by Carpinelli, A.;Magni, F.;Cattaneo, A.;Matarrese, M.;Turolla, E.;Todde, S.;Bosso, N.;Galli Kienle, M.;Fazio, F.. And the article was included in Applied Radiation and Isotopes in 2006.Category: piperidines This article mentions the following:

An improved synthesis of the precursor acetic acid-piperidine-4-yl ester by acetylation of 4-hydroxypiperidine hydrochloride in anhydrous chloroform was developed. A procedure for fast evaluation and characterization of products originated by acetylation of the 4-piperidinol using LC-APCI/MS with an acetonitrile-water gradient method on a Merck Purosphere RP-18 column was also developed. The highly purified precursor allowed the production of [¹¹C]MP4A for PET studies of acetylcholine neurotransmission system. The tracer was produced with >98% radiochem. purity, with yields ranging 20-60% (decay-corrected) from EOB. In the experiment, the researchers used many compounds, for example, 1-(4-Hydroxypiperidin-1-yl)ethanone (cas: 4045-22-1Category: piperidines).

1-(4-Hydroxypiperidin-1-yl)ethanone (cas: 4045-22-1) 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.Category: piperidines

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem