Heterocyclic Building Blocks-piperidine

Discovery and optimization of novel, non-steroidal glucocorticoid receptor modulators was written by Ray, Nicholas C.;Clark, Robin D.;Clark, David E.;Williams, Karen;Hickin, H. G.;Crackett, Peter H.;Dyke, Hazel J.;Lockey, Peter M.;Wong, Melanie;Devos, Rene;White, Anne;Belanoff, Joseph K.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2007.Reference of 58333-75-8 This article mentions the following:

A virtual screening approach comprising a 3-D similarity search based on known GR modulators was used to identify a novel series of non-steroidal glucocorticoid receptor (GR) antagonists. Optimization of the initial hit to provide potent compounds which exhibit good selectivity against other steroidal nuclear hormone receptors is described. In the experiment, the researchers used many compounds, for example, 4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8Reference of 58333-75-8).

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. Piperidine derivatives bearing a masked aldehyde function in the ε-position are easily transformed into quinolizidine compounds through intramolecular reductive amination.Reference of 58333-75-8

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Discovery of 2-(4-Pyridin-2-ylpiperazin-1-ylmethyl)-1H-benzimidazole (ABT-724), a Dopaminergic Agent with a Novel Mode of Action for the Potential Treatment of Erectile Dysfunction was written by Cowart, Marlon;Latshaw, Steven P.;Bhatia, Pramila;Daanen, Jerome F.;Rohde, Jeffrey;Nelson, Sherry L.;Patel, Meena;Kolasa, Teodozyi;Nakane, Masaki;Uchic, Marie E.;Miller, Loan N.;Terranova, Marc A.;Chang, Renjie;Donnelly-Roberts, Diana L.;Namovic, Marian T.;Hollingsworth, Peter R.;Martino, Brenda R.;Lynch, James J. III;Sullivan, James P.;Hsieh, Gin C.;Moreland, Robert B.;Brioni, Jorge D.;Stewart, Andrew O.. And the article was included in Journal of Medicinal Chemistry in 2004.Recommanded Product: 58333-75-8 This article mentions the following:

A new class of agents with potential utility for the treatment of erectile dysfunction has been discovered, guided by the hypothesis that selective D₄ agonists are erectogenic but devoid of the side effects typically associated with dopaminergic agents. The lead agent 2-(4-pyridin-2-ylpiperazin-1-ylmethyl)-1H-benzimidazole (1, ABT-724) was discovered by optimization of a series of benzimidazole arylpiperazines. This highly selective D₄ agonist was found to be very potent and efficacious in vivo, eliciting penile erections in rats at a dose of 0.03 μmol/kg, with a pos. response rate of 77% erectile incidence. Even at high doses, it was devoid of side effects in animal models of central nervous system behaviors, emesis, or nausea. The structure-activity relationship of the parent benzimidazole series leading to 1 is described, with the detailed in vitro and in vivo profiles described. Distinctive structural features were discovered that are associated with D₄ selective agonism in this series of analogs. In the experiment, the researchers used many compounds, for example, 4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8Recommanded Product: 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. Piperidine derivatives bearing a masked aldehyde function in the ε-position are easily transformed into quinolizidine compounds through intramolecular reductive amination.Recommanded Product: 58333-75-8

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthesis of metabolism-resistant substrates for the transport system for cationic amino acids. Their stimulation of the release of insulin and glucagon, and of the urinary loss of amino acids related to cystinuria was written by Christensen, Halvor N.;Cullen, Andrea M.. And the article was included in Biochimica et Biophysica Acta, Biomembranes in 1973.Recommanded Product: 33439-27-9 This article mentions the following:

Renal tubular transport (resorption) of citrulline [372-75-8] in rats did not occur by the same system serving for the basic amino acids or by the system serving for cystine [56-89-3], despite observed interactions in the resorption of these amino acids. Administration i.p. of the cationic arginine analog DL-1-guanyl-4-piperidineglycine (I) [41021-57-2] (5 mmoles/kg) selectively increased urinary excretion (i.e. inhibited resorption) of citrulline compared to that of basic amino acids (lysine [56-87-1], ornithine [70-26-8], arginine [74-79-3]). 4-Amino-1-guanylpiperidine-4-carboxylic acid (II) [31364-50-8] increased excretion of both citrulline and basic amino acids, and the citrulline analog 4-amino-1-carbamoylpiperidine-4-carboxylic acid (III) [40951-38-0], which did exist in cationic form, also increased the excretion of basic amino acids. I, II, and III increased cystine excretion, with I having the least effect. 4-Aminopiperidine-4-carboxylic acid (IV) [40951-39-1] and 4-piperidineglycine (V) [40951-40-4], like I, stimulated mainly citrulline excretion, and had little effect on excretion of basic amino acids or cystine. A mutual inhibitory interaction between citrulline and the basic amino acids not based on a shared transport route was postulated. Citrulline lost may thus be causally related to the loss of other amino acids in cystinuria. I, II, and homoarginine [156-86-5] mimicked the action of arginine and lysine and stimulated the release of insulin [9004-10-8] and glucagon [9007-92-5] from the pancreas in rats in vivo. II-V were metabolized slowly or not at all by the rat. Excretion of II-V was biphasic, with 43-63% of the dose lost during the 1st 6 hr and the hourly loss declining exponentially thereafter with a half-life varying from 10 hr for IV to 46 hr for II. Preparation of IV by the Strecker synthesis, its guanylation and carbamoylation to II and III, resp., and the radioactive labeling of several compounds were described, along with the synthesis of 1,4-diaminocyclohexane-1-carboxylic acid [40951-41-5], used in studies reported elsewhere. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Recommanded Product: 33439-27-9).

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. 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.Recommanded Product: 33439-27-9

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

The Banert cascade: A synthetic sequence to polyfunctional NH-1,2,3-triazoles was written by Loren, Jon C.;Sharpless, K. Barry. And the article was included in Synthesis in 2005.Quality Control of 1-Tosylpiperidin-4-one This article mentions the following:

A series of polyfunctional NH-1,2,3-triazoles, e.g., I, were prepared directly from propargyl halides and nucleophiles using a powerful, albeit little appreciated, synthetic sequence called the Banert cascade. Propargyl azides, prepared in situ from propargyl halides or sulfonates, underwent a thermal rearrangement sequence to triazafulvene intermediates, potent electrophiles, which were readily captured by diverse nucleophiles. Using this cascade, a series of racemic azidomethyl(hydroxymethyl)-NH-1,2,3-triazoles were prepared by a two-step protocol that commences with the addition of propargyl chloride to aldehydes and ketones. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Quality Control 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. Piperidine derivatives bearing a masked aldehyde function in the ε-position are easily transformed into quinolizidine compounds through intramolecular reductive amination.Quality Control of 1-Tosylpiperidin-4-one

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Design and characterization of cereblon-mediated androgen receptor proteolysis-targeting chimeras was written by Takwale, Akshay D.;Jo, Seung-Hyun;Jeon, Yeong Uk;Kim, Hyung Soo;Shin, Choong Hoon;Lee, Heung Kyoung;Ahn, Sunjoo;Lee, Chong Ock;Du Ha, Jae;Kim, Jeong-Hoon;Hwang, Jong Yeon. And the article was included in European Journal of Medicinal Chemistry in 2020.Computed Properties of C10H20ClNO2 This article mentions the following:

Proteolysis-targeting chimera (PROTAC)-mediated protein degradation is a rapidly emerging therapeutic intervention that induces the degradation of targeted proteins. Herein, we report the design and biol. evaluation of a series of androgen receptor (AR) PROTAC degraders for the treatment of metastatic castration-resistant prostate cancer. Predominantly, instead of thalidomide, we utilized the TD-106 scaffold, a novel cereblon (CRBN) binder that was identified in our previous study. Our results suggest that the linker position in the TD-106 CRBN binder is critical for the efficiency of AR degradation The compounds attached to the 6-position of TD-106 promoted better degradation of AR than those at the 5- and 7-positions. Among the synthesized AR PROTACs, the representative degrader 33c (TD-802) effectively induced AR protein degradation, with a degradation concentration 50% of 12.5 nM and a maximum degradation of 93% in LNCaP prostate cancer cells. Addnl., most AR PROTAC degraders, including TD-802, displayed good liver microsomal stability and in vivo pharmacokinetic properties. Finally, we showed that TD-802 effectively inhibited tumor growth in an in vivo xenograft study. In the experiment, the researchers used many compounds, for example, tert-Butyl piperidine-4-carboxylate hydrochloride (cas: 892493-65-1Computed Properties of C10H20ClNO2).

tert-Butyl piperidine-4-carboxylate hydrochloride (cas: 892493-65-1) belongs to piperidine derivatives. Piperidine is a metabolite of cadaverine, a polyamine found in the human intestine. Piperidine derivatives bearing a masked aldehyde function in the ε-position are easily transformed into quinolizidine compounds through intramolecular reductive amination.Computed Properties of C10H20ClNO2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Adventures in Scaffold Morphing: Discovery of Fused Ring Heterocyclic Checkpoint Kinase 1 (CHK1) Inhibitors was written by Yang, Bin;Vasbinder, Melissa M.;Hird, Alexander W.;Su, Qibin;Wang, Haixia;Yu, Yan;Toader, Dorin;Lyne, Paul D.;Read, Jon A.;Breed, Jason;Ioannidis, Stephanos;Deng, Chun;Grondine, Michael;De Grace, Nancy;Whitston, David;Brassil, Patrick;Janetka, James W.. And the article was included in Journal of Medicinal Chemistry in 2018.Quality Control of Benzyl 3-hydroxypiperidine-1-carboxylate This article mentions the following:

Checkpoint kinase 1 (CHK1) inhibitors are potential cancer therapeutics that can be utilized for enhancing the efficacy of DNA damaging agents. Multiple small mol. CHK1 inhibitors from different chem. scaffolds have been developed and evaluated in clin. trials in combination with chemotherapeutics and radiation treatment. Scaffold morphing of thiophene carboxamide ureas (TCUs), such as AZD7762 (1) and a related series of triazoloquinolines (TZQs), led to the identification of fused-ring bicyclic CHK1 inhibitors, 7-carboxamide thienopyridines (7-CTPs), and 7-carboxamide indoles. X-ray crystal structures reveal a key intramol. noncovalent sulfur-oxygen interaction in aligning the hinge-binding carboxamide group to the thienopyridine core in a coplanar fashion. An intramol. hydrogen bond to an indole NH was also effective in locking the carboxamide in the preferred bound conformation to CHK1. Optimization on the 7-CTP series resulted in the identification of lead compound 44, which displayed respectable drug-like properties and good in vitro and in vivo potency. In the experiment, the researchers used many compounds, for example, Benzyl 3-hydroxypiperidine-1-carboxylate (cas: 95798-22-4Quality Control of Benzyl 3-hydroxypiperidine-1-carboxylate).

Benzyl 3-hydroxypiperidine-1-carboxylate (cas: 95798-22-4) belongs to piperidine derivatives. Piperidine and its derivatives have become increasingly popular in many synthetic schemes. 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.Quality Control of Benzyl 3-hydroxypiperidine-1-carboxylate

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

A Conjugate Addition Approach to Diazo-Containing Scaffolds with β Quaternary Centers was written by Fang, Jian;Howard, Evan M.;Brewer, Matthias. And the article was included in Angewandte Chemie, International Edition in 2020.Recommanded Product: 33439-27-9 This article mentions the following:

Structurally complex diazo-containing scaffolds are formed by conjugate addition to vinyl diazonium salts. The electrophile, a little studied α-diazonium-α,β-unsaturated carbonyl compound, is formed at low temperature under mild conditions by treating β-hydroxy-α-diazo carbonyls with Sc(OTf)₃. Conjugate addition occurs selectively at the 3-position of indole to give α-diazo-β-indole carbonyls, and enoxy silanes react to give 2-diazo-1,4-dicarbonyl products. These reactions gave tertiary and quaternary centers, and give products that would be otherwise difficult to form. Importantly, the diazo functional group is retained within the mol. for future manipulation. Treating an α-diazo ester indole addition product with Rh₂(OAc)₄ caused a rearrangement to occur to give a 2-(1H-indol-3-yl)-2-enoate. In the case of diazo ketone compounds, this shift occurred spontaneously on prolonged exposure to the Lewis acidic reaction conditions. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Recommanded Product: 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. 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.Recommanded Product: 33439-27-9

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthesis and evaluation of anticancer and PDE 5 inhibitory activity of spiro-substituted quinazolin-4-ones was written by Ameen, Mohamed A.;Ahmed, Essam Kh.;Ramadan, Mohamed;Abd El-Naby, Hisham A.;Abdel-Haseeb, Asmaa A.. And the article was included in Monatshefte fuer Chemie in 2017.Formula: C12H15NO3S This article mentions the following:

A series of novel spiro-substituted 2,3-dihydroquinazolin-4(1H)-ones was synthesized and structurally confirmed by spectral anal., screened for their anticancer activity at a concentration of 10 μΜ against a panel of 56 cell lines derived from nine different types of cancers, including leukemia, melanoma, lung, colon, CNS, ovarian, renal, prostate, and breast cancers. The synthesized compounds screened for their PDE 5 inhibitory activity and it showed encouraged activity compared to sildenafil. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Formula: C12H15NO3S).

1-Tosylpiperidin-4-one (cas: 33439-27-9) belongs to piperidine derivatives. Piperidine is a saturated organic heteromonocyclic parent, an azacycloalkane, a secondary amine and a member of piperidines. 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.Formula: C12H15NO3S

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Titanium and Cobalt Bimetallic Radical Redox Relay for the Isomerization of N-Bz Aziridines to Allylic Amides was written by Wood, Devin P.;Guan, Weiyang;Lin, Song. And the article was included in Synthesis in 2021.HPLC of Formula: 33439-27-9 This article mentions the following:

Herein, a bimetallic radical redox-relay strategy is employed to generate alkyl radicals under mild conditions with titanium(III) catalysis and terminated via hydrogen atom transfer with cobalt(II) catalysis to enact base-free isomerizations of N-Bz aziridines I [R¹R³ = (CH₂)₃, R² = H; R¹R² = CH₂NTsCH₂CH₂, R³ = H; R¹ = MeO₂C(CH₂)₇, R² = R³ = H; etc] to N-Bz allylic amides II. This reaction provides an alternative strategy for the synthesis of allylic amides from alkenes via a three-step sequence to accomplish a formal transpositional allylic amination. 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. 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. 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.HPLC of Formula: 33439-27-9

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Ligand-Controlled Regioselective Copper-Catalyzed Trifluoromethylation To Generate (Trifluoromethyl)allenes was written by Ambler, Brett R.;Peddi, Santosh;Altman, Ryan A.. And the article was included in Organic Letters in 2015.Quality Control of 1-Tosylpiperidin-4-one This article mentions the following:

“Cu-CF₃” species have been used historically for a broad spectrum of nucleophilic trifluoromethylation reactions. Although recent advancements have employed ligands to stabilize and harness the reactivity of this key organometallic intermediate, the ability of a ligand to differentiate a regiochem. outcome of a Cu-CF₃-mediated or -catalyzed reaction has not been previously reported. Herein, we report the first example of a Cu-catalyzed trifluoromethylation reaction in which a ligand controls the regiochem. outcome. More specifically, we demonstrate the ability of bipyridyl-derived ligands to control the regioselectivity of the Cu-catalyzed nucleophilic trifluoromethylation reactions of propargyl electrophiles to generate (trifluoromethyl)allenes [e.g., I → II with 25:1 and 18:1 selectivity for allene using CuI, NaO₂CCF₂Br, KF, and 1,10-phenanthroline or terpyridine, resp.]. This method provides a variety of di-, tri-, and tetrasubstituted (trifluoromethyl)allenes, which can be further modified to generate complex fluorinated substructures. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Quality Control of 1-Tosylpiperidin-4-one).

1-Tosylpiperidin-4-one (cas: 33439-27-9) belongs to piperidine derivatives. Piperidine is a saturated organic heteromonocyclic parent, an azacycloalkane, a secondary amine and a member of piperidines. 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.Quality Control of 1-Tosylpiperidin-4-one

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem