Month: February 2023

Rapid synthesis of 4-benzyl-4-aminopiperidines by addition of Grignard reagents to N-(1-Boc-piperidin-4-ylidene)-tert-butanesulfinyl imine was written by Caldwell, John J.;Collins, Ian. And the article was included in Synlett in 2006.Application In Synthesis of 1-Tosylpiperidin-4-one This article mentions the following:

Two concise methods for the synthesis of aryl-substituted 4-benzyl-4-aminopiperidines by the addition of benzyl Grignard reagents to sulfinyl imines were developed. The hydration-prone tert-butylsulfinyl imine derived from N-Boc-piperidin-4-one was trapped as a stable 浼?sulfinylamino nitrile, which underwent displacement of the nitrile on treatment with Grignard reagents. Alternatively, benzyl and allyl Grignards added to the sulfinyl imine in situ in a one-pot procedure. Acid deprotection provided various substituted 4-benzyl-4-aminopiperidines. 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 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閳ユ弻 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

Design, Synthesis, and Structure-Activity Relationships of Novel Bicyclic Azole-amines as Negative Allosteric Modulators of Metabotropic Glutamate Receptor 5 was written by Burdi, Douglas F.;Hunt, Rachel;Fan, Lei;Hu, Tao;Wang, Jun;Guo, Zihong;Huang, Zhiqiang;Wu, Chengde;Hardy, Larry;Detheux, Michel;Orsini, Michael A.;Quinton, Maria S.;Lew, Robert;Spear, Kerry. And the article was included in Journal of Medicinal Chemistry in 2010.Synthetic Route of C12H15NO3S This article mentions the following:

A novel series of diaryl bicyclic azole-amines that are potent selective neg. modulators of metabotropic glutamate receptor 5 (mGluR5) were identified through rational design. An initial hit compound, I, of modest potency (IC₅₀ = 1.2 娓璏) was synthesized. Evaluation of structure-activity relationships (SAR) on the left-hand side of the mol. revealed a preference for a 2-substituted pyridine group linked directly to the central heterocycle. Variation of the central azolo-amine portion of the mol. revealed a preference for the [4,5-c]-oxazoloazepine scaffold, while right-hand side variants showed a preference for ortho- and meta-substituted benzene rings linked directly to the tertiary amine of the saturated heterocycle. These iterations led to the synthesis of II, a potent (IC₅₀ = 16 nM) and selective neg. modulator that showed good brain penetrance, high receptor occupancy, and a duration of action greater than 1 h in rat when administered i.p. Formal PK studies in rat and Rhesus monkey revealed a short half-life that was attributable to high first-pass clearance. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Synthetic Route of C12H15NO3S).

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 钄?position are easily transformed into quinolizidine compounds through intramolecular reductive amination.Synthetic Route of C12H15NO3S

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Design, Synthesis, and Pharmacological Characterization of Heterobivalent Ligands for the Putative 5-HT_2A/mGlu₂ Receptor Complex was written by Poulie, Christian B. M.;Liu, Na;Jensen, Anders A.;Bunch, Lennart. And the article was included in Journal of Medicinal Chemistry in 2020.Reference of 58333-75-8 This article mentions the following:

Herein, the synthesis of the first series of heterobivalent ligands targeting the putative heteromeric 5-HT_2A/mGlu₂ receptor complex, based on the 5-HT_2A antagonist MDL-100,907 and the mGlu₂ ago-PAM JNJ-42491293, are reported. The functional properties of monovalent and heterobivalent ligands were characterized in 5-HT_2A-, mGlu₂/Gqo5-, 5-HT_2A/mGlu₂-, and 5-HT_2A/mGlu₂/Gqo5-expressing HEK293 cells using a Ca²⁺ imaging assay and a [³H]ketanserin binding assay. Pronounced functional crosstalk was observed between the two receptors in 5-HT_2A/mGlu₂ and 5-HT_2A/mGlu₂/Gqo5 cells. While the synthesized monovalent ligands retained the 5-HT_2A antagonist and mGlu₂ ago-PAM functionalities, the seven bivalent ligands inhibited 5-HT-induced responses in 5-HT_2A/mGlu₂ cells and both 5-HT- and Glu-induced responses in 5-HT_2A/mGlu₂/Gqo5 cells. However, no definitive correlation between the functional potency and spacer length of the ligands was observed, an observation substantiated by the binding affinities exhibited by the compounds in 5-HT_2A, 5-HT_2A/mGlu₂, and 5-HT_2A/mGlu₂/Gqo5 cells. In conclusion, while functional crosstalk between 5-HT2A and mGlu2 was demonstrated, it remains unclear how these heterobivalent ligands interact with the putative receptor complex. 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 structural motif is present in numerous natural alkaloids. These include piperine, which gives black pepper its spicy taste. Piperidine derivatives bearing a masked aldehyde function in the 钄?position are easily transformed into quinolizidine compounds through intramolecular reductive amination.Reference of 58333-75-8

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

An Old Story in the Parallel Synthesis World: An Approach to Hydantoin Libraries was written by Bogolubsky, Andrey V.;Moroz, Yurii S.;Savych, Olena;Pipko, Sergey;Konovets, Angelika;Platonov, Maxim O.;Vasylchenko, Oleksandr V.;Hurmach, Vasyl V.;Grygorenko, Oleksandr O.. And the article was included in ACS Combinatorial Science in 2018.Recommanded Product: 1-(Methylsulfonyl)piperidin-4-amine hydrochloride This article mentions the following:

An approach to the parallel synthesis of hydantoin libraries by reaction of in situ generated 2,2,2-trifluoroethylcarbamates and 浼?amino esters was developed. To demonstrate utility of the method, a library of 1158 hydantoins designed according to the lead-likeness criteria (MW 200-350, cLogP 1-3) was prepared The success rate of the method was analyzed as a function of physicochem. parameters of the products, and it was found that the method can be considered as a tool for lead-oriented synthesis. A hydantoin-bearing submicromolar primary hit acting as an Aurora kinase A inhibitor was discovered with a combination of rational design, parallel synthesis using the procedures developed, in silico and in vitro screenings. In the experiment, the researchers used many compounds, for example, 1-(Methylsulfonyl)piperidin-4-amine hydrochloride (cas: 651057-01-1Recommanded Product: 1-(Methylsulfonyl)piperidin-4-amine hydrochloride).

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

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

A Noncoordinating Acid-Base Catalyst for the Mild and Nonreversible tert-Butylation of Alcohols and Phenols was written by Fandrick, Keith R.;Patel, Nitinchandra D.;Radomkit, Suttipol;Chatterjee, Arindom;Braith, Stefan;Fandrick, Daniel R.;Busacca, Carl A.;Senanayake, Chris H.. And the article was included in Journal of Organic Chemistry in 2021.Electric Literature of C11H21NO3 This article mentions the following:

A mild and nonreversible tert-butylation of alcs. and phenols can be achieved in high yields using the noncoordinating acid-base catalyst [bis(trifluoromethane)sulfonimide and 2,6-lutidine] with a tert-butylation reagent, tert-Bu 2,2,2-trichloroacetimidate. This method allows the use of substrates containing acid sensitive groups such as ketal, Boc, and boronate esters. In the experiment, the researchers used many compounds, for example, 1-Boc-4-Hydroxy-4-methylpiperidine (cas: 406235-30-1Electric Literature of C11H21NO3).

1-Boc-4-Hydroxy-4-methylpiperidine (cas: 406235-30-1) belongs to piperidine derivatives. The piperidine structural motif is present in numerous natural alkaloids. These include piperine, which gives black pepper its spicy taste. 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.Electric Literature of C11H21NO3

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Irradiation-Induced Heck Reaction of Unactivated Alkyl Halides at Room Temperature was written by Wang, Guang-Zu;Shang, Rui;Cheng, Wan-Min;Fu, Yao. And the article was included in Journal of the American Chemical Society in 2017.Category: piperidines This article mentions the following:

The palladium-catalyzed Mizoroki-Heck reaction is arguably one of the most significant carbon-carbon bond-construction reactions to be discovered in the last 50 years, with a tremendous number of applications in the production of chems. This Nobel-Prize-winning transformation has yet to overcome the obstacle of its general application in a range of alkyl electrophiles, especially tertiary alkyl halides that possess eliminable 灏?hydrogen atoms. Whereas most palladium-catalyzed cross-coupling reactions utilize the ground-state reactivity of palladium complexes under thermal conditions and generally apply a single ligand system, authors report that the palladium-catalyzed Heck reaction proceeds smoothly at room temperature with a variety of tertiary, secondary, and primary alkyl bromides upon irradiation with blue light-emitting diodes in the presence of a dual phosphine ligand system. Also rationalized that this unprecedented transformation is achieved by utilizing the photoexcited-state reactivity of the palladium complex to enhance oxidative addition and suppress undesired 灏?hydride elimination. In the experiment, the researchers used many compounds, for example, 1-Boc-4-Hydroxy-4-methylpiperidine (cas: 406235-30-1Category: piperidines).

1-Boc-4-Hydroxy-4-methylpiperidine (cas: 406235-30-1) 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. Piperidine prefers a chair conformation, similar to cyclohexane. Unlike cyclohexane, piperidine has two distinguishable chair conformations: one with the N閳ユ弻 bond in an axial position, and the other in an equatorial position.Category: piperidines

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Development of the Scope of a Co-Mediated O閳墫 Rearrangement Reaction was written by Meek, Simon J.;Pradaux, Fabienne;Carbery, David R.;Demont, Emmanuel H.;Harrity, Joseph P. A.. And the article was included in Journal of Organic Chemistry in 2005.Application of 33439-27-9 This article mentions the following:

An Al-promoted, Co-mediated O閳墫 rearrangement reaction of cyclic enol ethers is described. This process delivers functionalized cyclohexanones with good to excellent levels of diastereo control, whereby the product stereochem. is dependent on the E/Z-stereochem. of the starting enol ether. The rearrangement process also permits access to highly substituted 浼?spirocyclic cyclohexanones as well as cyclopentanones. The latter rearrangement appears to proceed via an unusual 5-(enol-endo)-exo-trig cyclization process. 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.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. 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.Application of 33439-27-9

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Development of a Suzuki Cross-Coupling Reaction between 2-Azidoarylboronic Pinacolate Esters and Vinyl Triflates To Enable the Synthesis of [2,3]-Fused Indole Heterocycles was written by Jana, Navendu;Nguyen, Quyen;Driver, Tom G.. And the article was included in Journal of Organic Chemistry in 2014.Recommanded Product: 33439-27-9 This article mentions the following:

The scope and limitations of a Suzuki reaction between 2-azidoarylboronic acid pinacolate esters and vinyl triflates are reported. This cross-coupling reaction enables the regioselective synthesis of indoles, e.g., I, after a subsequent Rh^II₂-catalyzed sp²-C-H bond amination reaction. 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. 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: 33439-27-9

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Donepezil-butylated hydroxytoluene (BHT) hybrids as Anti-Alzheimer’s disease agents with cholinergic, antioxidant, and neuroprotective properties was written by Cai, Pei;Fang, Si-Qiang;Yang, Hua-Li;Yang, Xue-Lian;Liu, Qiao-Hong;Kong, Ling-Yi;Wang, Xiao-Bing. And the article was included in European Journal of Medicinal Chemistry in 2018.Quality Control of 1-Benzylpiperidine-4-carbonitrile This article mentions the following:

The multifactorial nature of Alzheimer’s disease (AD) calls for the development of multitarget agents addressing key pathogenic processes. A novel family of donepezil-butylated hydroxytoluene (BHT) hybrids were designed, synthesized and evaluated as multifunctional ligands against AD. The optimal compound I displayed a balanced multifunctional profile covering an intriguing acetylcholinesterase (AChE) inhibition (IC_50, 0.075 娓璏 for eeAChE and 0.75 娓璏 for hAChE) and Monoamine oxidase B (MAO-B) inhibition (IC₅₀, 7.4 娓璏 for hMAO-B), excellent antioxidant activity (71.7 娓璏 of IC₅₀ by DPPH method, 0.82 and 1.62 trolox equivalent by ABTS method and ORAC method resp.), and inhibitory effects on self-induced, hAChE-induced A灏?aggregation. Moreover, I possessed neuroprotective potency against H₂O₂-induced oxidative damage on PC12 cells and Lipopolysaccharides (LPS)-stimulated inflammation on BV2 cells. Compound I was capable of penetrating BBB and presented good liver microsomal metabolic stability. Importantly, compound I could dose-dependently reverse scopolamine-induced memory deficit in mice without acute toxicity. Taken together, those outstanding results highlight the donepezil-BHT hybrid I as a promising prototype in the research of innovative compound for AD. In the experiment, the researchers used many compounds, for example, 1-Benzylpiperidine-4-carbonitrile (cas: 62718-31-4Quality Control of 1-Benzylpiperidine-4-carbonitrile).

1-Benzylpiperidine-4-carbonitrile (cas: 62718-31-4) 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. Piperidine prefers a chair conformation, similar to cyclohexane. Unlike cyclohexane, piperidine has two distinguishable chair conformations: one with the N閳ユ弻 bond in an axial position, and the other in an equatorial position.Quality Control of 1-Benzylpiperidine-4-carbonitrile

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Design, synthesis and biological activity of N-(amino)piperazine-containing benzothiazinones against Mycobacterium tuberculosis was written by Wang, Apeng;Xu, Shijie;Chai, Yun;Xia, Guimin;Wang, Bin;Lv, Kai;Ma, Chao;Wang, Dan;Wang, Aoyu;Qin, Xiaoyu;Liu, Mingliang;Lu, Yu. And the article was included in European Journal of Medicinal Chemistry in 2021.Computed Properties of C9H19N3O2 This article mentions the following:

A series of novel benzothiazinone derivatives containing a N-(amino)piperazine moiety I (R₁ = H, Me, iso-Bu, etc.; R₂ = cyclohexyl, 4-(methoxyimino)cyclohexyl, 4-F₃CC₆H₄, etc.), II (R = cyclohexylmethyl, 4-trifluoromethoxybenzyl, cyclohexanecarbonyl, pyridin-4-ylmethyl) based on the structure of WAP-1902 discovered, were designed and synthesized as new anti-TB agents. Many of the compounds exhibited excellent in vitro activity against both drug-sensitive MTB strain H37Rv and multidrug-resistant clin. isolates (MIC: < 0.016娓璯/mL), and good safety index (CC₅₀: >64娓璯/mL). Especially compound I (R₁ = Me; R₂ = 4-(methoxyimino)cyclohexyl) displayed low hERG cardiac toxicity and acceptable oral pharmacokinetic profiles, indicating its promising potential to be a lead compound for future antitubercular drug discovery. In the experiment, the researchers used many compounds, for example, tert-Butyl 4-aminopiperazine-1-carboxylate (cas: 118753-66-5Computed Properties of C9H19N3O2).

tert-Butyl 4-aminopiperazine-1-carboxylate (cas: 118753-66-5) belongs to piperidine derivatives. Piperidine and its derivatives have become increasingly popular in many synthetic schemes. 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.Computed Properties of C9H19N3O2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem