Day: January 5, 2023

Expedient Access to 2,3-Dihydropyridines from Unsaturated Oximes by Rh(III)-Catalyzed C-H Activation was written by Romanov-Michailidis, Fedor;Sedillo, Kassandra F.;Neely, Jamie M.;Rovis, Tomislav. And the article was included in Journal of the American Chemical Society in 2015.Quality Control of 1-Tosylpiperidin-4-one This article mentions the following:

α,β-Unsaturated oxime pivalates are proposed to undergo reversible C(sp²)-H insertion with cationic Rh(III) complexes to furnish five-membered metallacycles. In the presence of 1,1-disubstituted olefins, these species participate in irreversible migratory insertion to give, after reductive elimination, 2,3-dihydropyridine products in good yields. Catalytic hydrogenation can then be used to convert these mols. into piperidines, which are important structural components of numerous pharmaceuticals. Thus, e.g., heterocyclization of unsaturated oxime pivalate I with alkene II in presence of [Rh(MeCN)₃(C₅Me₄CF₃)](SbF₆)₂ afforded dihydropyridine III (99%). 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 key saturated heterocyclic scaffold found in several of the top-selling small molecule pharmaceuticals and natural alkaloids, with a diverse range of 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.Quality Control of 1-Tosylpiperidin-4-one

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

New Pyrimido[5,4-b]indoles as Ligands for α₁-Adrenoceptor Subtypes was written by Romeo, Giuseppe;Materia, Luisa;Manetti, Fabrizio;Cagnotto, Alfredo;Mennini, Tiziana;Nicoletti, Ferdinando;Botta, Maurizio;Russo, Filippo;Minneman, Kenneth P.. And the article was included in Journal of Medicinal Chemistry in 2003.Recommanded Product: 58333-75-8 This article mentions the following:

Tricyclic 5H-pyrimido[5,4-b]indoles I (R¹ = H, Me, Et; n = 2, 3; R² = 2-MeO, 2-EtO, 4-Me₂CH, 4-Me₃C) and II (R³ = NCCH₂, Me₂CH, Bu, Me₃C, EtCHMe, cyclohexyl) bearing a piperazine moiety connected through an alkyl chain were designed as structural analogs of the α₁-AR ligand RN5. I and II were synthesized and tested in binding assays on human α_1A-AR, α_1B-AR, and α_1D-AR subtypes expressed in HEK293 cells, with many of the new mols. showing a preferential affinity for the α_1D-AR subtype. Some compounds, including II (R³ = Me₂CH, Me₃C), displayed substantial α_1D-AR selectivity with respect to α_1A-AR, α_1B-AR, serotonergic 5-HT_1A, 5-HT_1B, 5-HT_2A, and dopaminergic D₁ and D₂ receptors. Two conformationally rigid analogs of RN5, useful for studying the architecture of the receptor/ligand complex, were also prepared and tested. A subset of the new compounds was then used to evolve a preliminary pharmacophore model for α_1D-AR antagonists, based on a more generalized model developed for α₁-AR antagonists. This new model rationalized the relationships between structural properties and biol. data of the pyrimido[5,4-b]indole compounds, as well as other compounds 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 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: 58333-75-8

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Design and synthesis of 4-(heterocyclic substituted amino)-1H-pyrazole-3-carboxamide derivatives and their potent activity against acute myeloid leukemia (AML) was written by Zhi, Yanle;Wang, Zhijie;Yao, Chao;Li, Baoquan;Heng, Hao;Cai, Jiongheng;Xiang, Li;Wang, Yue;Lu, Tao;Lu, Shuai. And the article was included in International Journal of Molecular Sciences in 2019.Synthetic Route of C9H19N3O2 This article mentions the following:

Fms-like receptor tyrosine kinase 3 (FLT3) has been emerging as an attractive target for the treatment of acute myeloid leukemia (AML). By modifying the structure of FN-1501, a potent FLT3 inhibitor, 24 novel 1H-pyrazole-3-carboxamide derivatives I [R = Ph, pyridin-4-yl, 1-(tert-butoxycarbonyl)piperidine-4-yl, piperidin-4-yl] and II [R¹ = H, (morpholin-4-yl)carbonyl, (4-methylpiperazin-1-yl)carbonyl, piperazin-1-yl, etc.; R² = H, 4-methyl-1,4-diazepan-1-yl; X = CH, N; R³ = thieno[2,3-d]pyrimidin-4-yl, 7H-pyrrolo[2,3-d]pyrimidin-4-yl, etc.] were designed and synthesized. Compound II [R¹ = piperazin-1-yl, R² = H, X = CH, R³ = 7-thia-9,11-diazatricyclo[6.4.0.0(2,6)]dodeca-1(8),2(6),9,11-tetraen-12-yl (III)] showed strong activity against FLT3 (IC⁵⁰: 0.089 nM) and CDK2/4 (IC⁵⁰: 0.719/0.770 nM), which is more efficient than FN-1501(FLT3, IC⁵⁰: 2.33 nM; CDK2/4, IC⁵⁰: 1.02/0.39 nM). Compound III also showed excellent inhibitory activity against a variety of FLT3 mutants (IC⁵⁰ >5 nM), and potent anti-proliferative effect within the nanomolar range on acute myeloid leukemia (MV4-11, IC⁵⁰: 1.22 nM). In addition, compound III significantly inhibited the proliferation of most human cell lines of NCI60 (GI⁵⁰ < 1μ M for most cell lines). Taken together, these results demonstrated the potential of III as a novel compound for further development into a kinase inhibitor applied in cancer therapeutics. In the experiment, the researchers used many compounds, for example, tert-Butyl 4-aminopiperazine-1-carboxylate (cas: 118753-66-5Synthetic Route of C9H19N3O2).

tert-Butyl 4-aminopiperazine-1-carboxylate (cas: 118753-66-5) 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 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.Synthetic Route of C9H19N3O2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Antagonists of the human CCR5 receptor as anti-HIV-1 agents. Part 3: A proposed pharmacophore model for 1-[N-(methyl)-N-(phenylsulfonyl)amino]-2-(phenyl)-4-[4-(substituted)piperidin-1-yl]butanes was written by Finke, P. E.;Meurer, L. C.;Oates, B.;Shah, S. K.;Loebach, J. L.;Mills, S. G.;MacCoss, M.;Castonguay, L.;Malkowitz, L.;Springer, M. S.;Gould, S. L.;DeMartino, J. A.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2001.Recommanded Product: 4-(2-Methoxyphenyl)piperidine This article mentions the following:

Structure-activity relationship studies directed toward the optimization of (2S)-2-(3-chlorophenyl)-1-[N-(methyl)-N-(phenylsulfonyl)amino]-4-[4-(substituted)piperidin-1-yl]butanes as CCR5 antagonists resulted in the synthesis of the spiro-indanone derivative I (IC₅₀=5 nM). These and previous results are summarized in a proposed pharmacophore model for this class of CCR5 antagonist. In the experiment, the researchers used many compounds, for example, 4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8Recommanded Product: 4-(2-Methoxyphenyl)piperidine).

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 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: 4-(2-Methoxyphenyl)piperidine

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Au-Catalyzed Formation of Functionalized Quinolines from 2-Alkynyl Arylazide Derivatives was written by Gronnier, Colombe;Boissonnat, Guillaume;Gagosz, Fabien. And the article was included in Organic Letters in 2013.SDS of cas: 33439-27-9 This article mentions the following:

A new method for converting 2-alkynyl arylazide derivatives into functionalized polysubstituted quinolines following a gold-catalyzed 1,3-acetoxy shift/cyclization/1,2-group shift sequence has been developed (e.g., I → II). This transformation proceeds under mild reaction conditions, is efficient, and tolerates a large variety of functional groups. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9SDS of cas: 33439-27-9).

1-Tosylpiperidin-4-one (cas: 33439-27-9) belongs to piperidine derivatives. Piperidine and its derivatives have become increasingly popular in many synthetic schemes. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.SDS of cas: 33439-27-9

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

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