Month: January 2023

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

One-Pot Synthesis of 2,5-Disubstituted Pyrimidines from Nitriles was written by Frutos, Rogelio P.;Wei, Xudong;Patel, Nitinchandra D.;Tampone, Thomas G.;Mulder, Jason A.;Busacca, Carl A.;Senanayake, Chris H.. And the article was included in Journal of Organic Chemistry in 2013.Computed Properties of C13H16N2 This article mentions the following:

A practical, one-step process for the synthesis of 2,5-disubstituted pyrimidines is presented. The protocol proved to be general for the synthesis of a variety of pyrimidine-containing compounds bearing an assortment of functional groups. In the experiment, the researchers used many compounds, for example, 1-Benzylpiperidine-4-carbonitrile (cas: 62718-31-4Computed Properties of C13H16N2).

1-Benzylpiperidine-4-carbonitrile (cas: 62718-31-4) 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.Computed Properties of C13H16N2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

σ Ligands with Subnanomolar Affinity and Preference for the σ₂ Binding Site. 1. 3-(ω-Aminoalkyl)-1H-indoles was written by Perregaard, Jens;Moltzen, Ejner K.;Meier, Eddi;Sanchez, Connie. And the article was included in Journal of Medicinal Chemistry in 1995.SDS of cas: 58333-75-8 This article mentions the following:

A series of 4-(1H-indol-3-yl)-1-butyl-substituted 4-phenylpiperidines, 4-phenyl-1,2,3,6-tetrahydropyridines, and 4-phenylpiperazines was synthesized. The Ph group was optionally substituted with 4-fluoro or 2-methoxy substituents. High affinity for both σ₁ and σ₂ binding sites was achieved with these compounds Addnl., these compounds had relatively high affinity for serotonin 5-HT_1A and 5-HT_2A, dopamine D₂, and adrenergic α₁ receptors. Introduction of a 4-fluorophenyl substituent at the indole nitrogen atom rendered very selective σ₂ ligands with subnanomolar affinity for the σ₂ binding site. The prototype of such a compound was I. This compound had the following binding affinities: IC₅₀ (σ₁) = 16 nM, IC₅₀ (σ₂) = 0.27 nM, IC₅₀ (5-HT_1A) = 22 000 nM, IC₅₀ (5-HT_2A) = 270 nM, IC₅₀ (D₂) = 4200 nM, IC₅₀ (α₁) = 220 nM. Spiro-joining of the Ph and the piperidine rings into a spiro[isobenzofuran-1(3H),4′-piperidine] ring system resulted in even more selective compounds Variations of the 1-substituent at the indole and of the chain length of the alkylene spacer group were studied. The optimal compound was the spiro analog of I. This compound (II) had the binding affinities: IC₅₀ (σ₁) = 17 nM, IC₅₀ (σ₂) = 0.12 nM, IC₅₀ (5-HT_1A) = 21 000 nM, IC₅₀ (5-HT_2A) = 2000 nM, IC₅₀ (D₂) = 800 nM, IC₅₀ (α₁) = 330 nM. However, the most selective σ₂ vs. σ₁ ligand was the tropane derivative (III). This compound had the following binding affinities: IC₅₀ (σ₁) = 1200 nM, IC₅₀ (σ₂) = 2.5 nM. Potent anxiolytic activity in the black/white box exploration test in rats was found with the two most prominent σ₂ ligands Lu 29-253 and Lu 28-179. Good penetration into the CNS was documented both after s.c. and peroral administration of Lu 28-179 by ex vivo binding studies. Long duration of action was demonstrated both in ex vivo binding (T_1/2 ∼ 20 h) and in the black/white box exploration test. In the experiment, the researchers used many compounds, for example, 4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8SDS of cas: 58333-75-8).

4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8) belongs to piperidine derivatives. Piperidine is a metabolite of cadaverine, a polyamine found in the human intestine. 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.SDS of cas: 58333-75-8

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Catalytic reductive ring opening of epoxides enabled by zirconocene and photoredox catalysis was written by Aida, Kazuhiro;Hirao, Marina;Funabashi, Aiko;Sugimura, Natsuhiko;Ota, Eisuke;Yamaguchi, Junichiro. And the article was included in Chem in 2022.Name: 1-Boc-4-Hydroxy-4-methylpiperidine This article mentions the following:

Herein, an unprecedented zirconocene-catalyzed ring opening of epoxides enabled by photoredox catalysis is reported. Compared with the conventional ring-opening methods, the present protocol exhibits reverse regioselectivity to afford more substituted alcs. via putative less-stable radicals. This reaction is remarkably mild and smoothly cleaves C-O bonds in mols. with a variety of functional groups, including natural products. The finding that changes the metal center in metallocene influences the energy profile of ring opening is a significant advance and provides a new perspective in radical chem. with group IV metals. In the experiment, the researchers used many compounds, for example, 1-Boc-4-Hydroxy-4-methylpiperidine (cas: 406235-30-1Name: 1-Boc-4-Hydroxy-4-methylpiperidine).

1-Boc-4-Hydroxy-4-methylpiperidine (cas: 406235-30-1) belongs to piperidine derivatives. Piperidine and its derivatives have become increasingly popular in many synthetic schemes. 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.Name: 1-Boc-4-Hydroxy-4-methylpiperidine

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Stereo-complementary bioreduction of saturated N-heterocyclic ketones was written by Li, Chao;Liu, Yan;Pei, Xiao-Qiong;Wu, Zhong-Liu. And the article was included in Process Biochemistry (Oxford, United Kingdom) in 2017.COA of Formula: C13H17NO3 This article mentions the following:

The asym. bioreduction of several saturated N-heterocyclic ketones such as 1-benzylpyrrolidin-3-one, 1-benzylpiperidin-3-one, 1-benzylazepan-3-one, etc. is demonstrated in a stereo-complementary fashion using the ketoreductases READH and ChKRED20 for the production of (S)- and (R)-alcs. such as 1-benzylpyrrolidin-3-ol, 1-benzylpiperidin-3-ol, 1-benzylazepan-3-ol, etc. resp. The reaction accepts substrates with a five-, six- or seven-membered ring, and exhibits excellent stereoselectivity when using 2-propanol as both the ultimate reducing agent and cosolvent and achieves >99% ee in the majority of cases for both enantiomers. In the experiment, the researchers used many compounds, for example, Benzyl 3-hydroxypiperidine-1-carboxylate (cas: 95798-22-4COA of Formula: C13H17NO3).

Benzyl 3-hydroxypiperidine-1-carboxylate (cas: 95798-22-4) 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.COA of Formula: C13H17NO3

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthesis and Antibacterial Activity of Ketolides (6-O-Methyl-3-oxoerythromycin Derivatives): A New Class of Antibacterials Highly Potent Against Macrolide-Resistant and -Susceptible Respiratory Pathogens was written by Agouridas, Constantin;Denis, Alexis;Auger, Jean-Michel;Benedetti, Yannick;Bonnefoy, Alain;Bretin, Francois;Chantot, Jean-Francois;Dussarat, Arlette;Fromentin, Claude;D’Ambrieres, Solange Gouin;Lachaud, Sylvette;Laurin, Patrick;Martret, Odile Le;Loyau, Veronique;Tessot, Nicole. And the article was included in Journal of Medicinal Chemistry in 1998.Category: piperidines This article mentions the following:

In the search for new antibiotics active against macrolide-resistant pneumococci and Haemophilus influenzae, we synthesized a new class of 3-oxo-6-O-methylerythromycin derivatives, so-called “ketolides”. A keto function was introduced in position 3 after removal of L-cladinose, a sugar which has long been thought essential. Further modifications of the macrolactone backbone allowed us to obtain three different series of 9-oxime, 11,12-carbamate, and 11,12-hydrazonocarbamate ketolides. These compounds were found to be very active against penicillin/erythromycin-resistant pneumococci and noninducers of MLS_B resistance. The 11,12-substituted ketolide 61 (HMR 3004) demonstrated a potent activity against multiresistant pneumococci associated with a well-balanced activity against all bacteria involved in respiratory infections including H. influenzae, Mycoplasma catarrhalis, group A streptococci, and atypical bacteria. In addition HMR 3004 displayed high therapeutic activity in animals infected by all major strains, irresp. of their resistance phenotype. In the experiment, the researchers used many compounds, for example, Benzyl 3-hydroxypiperidine-1-carboxylate (cas: 95798-22-4Category: piperidines).

Benzyl 3-hydroxypiperidine-1-carboxylate (cas: 95798-22-4) 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.Category: piperidines

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Design and Synthesis of Novel Spiro Derivatives as Potent and Reversible Monoacylglycerol Lipase (MAGL) Inhibitors: Bioisosteric Transformation from 3-Oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl Moiety was written by Ikeda, Shuhei;Sugiyama, Hideyuki;Tokuhara, Hidekazu;Murakami, Masataka;Nakamura, Minoru;Oguro, Yuya;Aida, Jumpei;Morishita, Nao;Sogabe, Satoshi;Dougan, Douglas R.;Gay, Sean C.;Qin, Ling;Arimura, Naoto;Takahashi, Yasuko;Sasaki, Masako;Kamada, Yusuke;Aoyama, Kazunobu;Kimoto, Kouya;Kamata, Makoto. And the article was included in Journal of Medicinal Chemistry in 2021.Recommanded Product: 183170-69-6 This article mentions the following:

The therapeutic potential of monoacylglycerol lipase (MAGL) inhibitors in central nervous system-related diseases has attracted attention worldwide. However, the availability of reversible-type inhibitor is still limited to clarify the pharmacol. effect. Herein, we report the discovery of novel spiro chem. series as potent and reversible MAGL inhibitors with a different binding mode to MAGL using Arg57 and His121. Starting from hit compound 1 and its co-crystal structure with MAGL, structure-based drug discovery (SBDD) approach enabled us to generate various spiro scaffolds like 2a (azetidine-lactam), 2b (cyclobutane-lactam), and 2d (cyclobutane-carbamate) as novel bioisosteres of 3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl moiety in 1 with higher lipophilic ligand efficiency (LLE). Optimization of the left hand side afforded 4f (I) as a promising reversible MAGL inhibitor, which showed potent in vitro MAGL inhibitory activity (IC₅₀ 6.2 nM), good oral absorption, blood-brain barrier penetration, and significant pharmacodynamic changes (2-arachidonoylglycerol increase and arachidonic acid decrease) at 0.3-10 mg/kg, po. in mice. In the experiment, the researchers used many compounds, for example, tert-Butyl 4-(1-hydroxyethyl)piperidine-1-carboxylate (cas: 183170-69-6Recommanded Product: 183170-69-6).

tert-Butyl 4-(1-hydroxyethyl)piperidine-1-carboxylate (cas: 183170-69-6) belongs to piperidine derivatives. Piperidine is a saturated organic heteromonocyclic parent, an azacycloalkane, a secondary amine and a member of piperidines. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.Recommanded Product: 183170-69-6

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem