Tag: 200-300

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

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

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

The Witkop-Winterfeldt oxidation converts tetrahydropyridoindoles into pyrroloquinolones and cinnolines by an unprecedented scaffold rearrangement was written by Mentel, Matthias;Peters, Martin;Albering, Joerg;Breinbauer, Rolf. And the article was included in Tetrahedron in 2011.Application of 33439-27-9 This article mentions the following:

The Fischer indole reaction between phenylhydrazines and N-tosyl-4-piperidone furnishes tetrahydropyrido[4,3-b]indoles. In a Witkop-Winterfeldt oxidation using ozone, such indole derivatives are converted into medium-sized dicarbonyl ring systems, which cyclize to pyrroloquinolones. A detailed study of the reaction intermediates and the characterization of a cinnoline betaine side product formed by an unprecedented ring closure mechanism are reported. 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 saturated organic heteromonocyclic parent, an azacycloalkane, a secondary amine and a member of piperidines. 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 of 33439-27-9

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

6-Benzhydryl-4-amino-quinolin-2-ones as Potent Cannabinoid Type 1 (CB₁) Receptor Inverse Agonists and Chemical Modifications for Peripheral Selectivity was written by Zhang, Yue-Mei;Greco, Michael N.;Macielag, Mark J.;Teleha, Christopher A.;DesJarlais, Renee L.;Tang, Yuting;Ho, George;Hou, Cuifen;Chen, Cailin;Zhao, Shuyuan;Kauffman, Jack;Camacho, Raul;Qi, Jenson;Murray, William;Demarest, Keith;Leonard, James. And the article was included in Journal of Medicinal Chemistry in 2018.Application In Synthesis of 1-(Methylsulfonyl)piperidin-4-amine hydrochloride This article mentions the following:

A novel series of 6-benzhydryl-4-amino-quinolin-2-ones was discovered as cannabinoid type 1 receptor (CB₁R) inverse agonists based on the high-throughput screening hit, compound 1a. Structure-activity relationships were studied to improve in vitro/in vivo pharmacol. and restrict distribution to the peripheral circulation. We adopted several strategies such as increasing topol. polar surface area, incorporating discrete polyethylene glycol side chains, and targeting P-glycoprotein (P-gp) to minimize access to the brain. Compound 6a is a P-gp substrate and a potent and highly selective CB₁R inverse agonist, demonstrating excellent in vivo metabolic stability and a low brain to plasma ratio. However, brain receptor occupancy studies showed that compound 6a may accumulate in brain with repeat dosing. This was evidenced by compound 6a inhibiting food intake and inducing weight loss in diet-induced obese mice. Thus, a strategy based on P-gp efflux may not be adequate for peripheral restriction of the disclosed quinolinone series. In the experiment, the researchers used many compounds, for example, 1-(Methylsulfonyl)piperidin-4-amine hydrochloride (cas: 651057-01-1Application In Synthesis of 1-(Methylsulfonyl)piperidin-4-amine hydrochloride).

1-(Methylsulfonyl)piperidin-4-amine hydrochloride (cas: 651057-01-1) belongs to piperidine derivatives. The piperidine structural motif is present in numerous natural alkaloids. These include piperine, which gives black pepper its spicy taste. Piperidine derivatives bearing a masked aldehyde function in the ε-position are easily transformed into quinolizidine compounds through intramolecular reductive amination.Application In Synthesis of 1-(Methylsulfonyl)piperidin-4-amine hydrochloride

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Catalytic C(sp²)-C(sp³) Bond Formation of Methoxyarenes by the Organic Superbase t-Bu-P4 was written by Shigeno, Masanori;Hayashi, Kazutoshi;Nozawa-Kumada, Kanako;Kondo, Yoshinori. And the article was included in Organic Letters in 2020.COA of Formula: C13H16N2 This article mentions the following:

The organic superbase catalyst t-Bu-P4 achieves nucleophilic aromatic substitution of methoxyarenes with alkanenitrile pronucleophiles. A variety of functional groups [cyano, nitro, (non)enolizable ketone, chloride, and amide moieties] are allowed on methoxyarenes. Moreover, an array of alkanenitriles with/without an aryl moiety at the nitrile α-position can be employed. The system also features no requirement of a stoichiometric base, MeOH (not salt waste) formation as a byproduct, and the production of congested quaternary carbon centers. In the experiment, the researchers used many compounds, for example, 1-Benzylpiperidine-4-carbonitrile (cas: 62718-31-4COA of Formula: C13H16N2).

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. Piperidine derivatives bearing a masked aldehyde function in the ε-position are easily transformed into quinolizidine compounds through intramolecular reductive amination.COA of Formula: C13H16N2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Silyl enol etherification by a Tf₂NH/amine co-catalytic system for minimizing hazardous waste generation was written by Kurahashi, Kei;Yamaoka, Yousuke;Takemoto, Yoshiji;Takasu, Kiyosei. And the article was included in Reaction Chemistry & Engineering in 2018.Computed Properties of C12H15NO3S This article mentions the following:

A practical silyl enol etherification of ketones with allylsilanes catalyzed by a Tf₂NH-amine co-catalyst under mild conditions has been developed. The reaction generated only volatile isobutene gas as waste. Moreover, a multi-gram synthesis using a microfluidic system and a domino silyl enol etherification-(2 + 2) cycloaddition reaction were demonstrated. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Computed Properties of C12H15NO3S).

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. 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 C12H15NO3S

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Discovery of MAP855, an Efficacious and Selective MEK1/2 Inhibitor with an ATP-Competitive Mode of Action was written by Poddutoori, Ramulu;Aardalen, Kimberly;Aithal, Kiran;Barahagar, Sanjeev Surendranath;Belliappa, Charamanna;Bock, Mark;Chelur, Shekar;Gerken, Andrea;Gopinath, Sreevalsam;Gruenenfelder, Bjoern;Kiffe, Michael;Krishnaswami, Maithreyi;Langowski, John;Madapa, Sudharshan;Narayanan, Kishore;Pandit, Chetan;Panigrahi, Sunil Kumar;Perrone, Mark;Potakamuri, Ravi Kumar;Ramachandra, Murali;Ramanathan, Anuradha;Ramos, Rita;Sager, Emine;Samajdar, Susanta;Subramanya, Hosahalli S.;Thimmasandra, Devaraja Seethappa;Venetsanakos, Eleni;Mobitz, Henrik. And the article was included in Journal of Medicinal Chemistry in 2022.Formula: C9H19N3O2 This article mentions the following:

Mutations in MEK1/2 have been described as a resistance mechanism to BRAF/MEK inhibitor treatment. We report the discovery of a novel ATP-competitive MEK1/2 inhibitor with efficacy in wildtype (WT) and mutant MEK12 models. Starting from a HTS hit, we obtained selective, cellularly active compounds that showed equipotent inhibition of WT MEK1/2 and a panel of MEK1/2 mutant cell lines. Using a structure-based approach, the optimization addressed the liabilities by systematic anal. of mol. matched pairs (MMPs) and ligand conformation. Addition of only three heavy atoms to early tool compound 6 removed Cyp3A4 liabilities and increased the cellular potency by 100-fold, while reducing log P by 5 units. Profiling of MAP855, compound 30, in pharmacokinetic-pharmacodynamic and efficacy studies in BRAF-mutant models showed comparable efficacy to clin. MEK1/2 inhibitors. Compound 30 is a novel highly potent and selective MEK1/2 kinase inhibitor with equipotent inhibition of WT and mutant MEK1/2, whose drug-like properties allow further investigation in the mutant MEK setting upon BRAF/MEK therapy. 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. 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.Formula: C9H19N3O2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem