Tag: 200-300

Ni-catalyzed cross-electrophile coupling between vinyl/aryl and alkyl sulfonates: synthesis of cycloalkenes and modification of peptides was written by Duan, Jicheng;Du, Yun-Fei;Pang, Xiaobo;Shu, Xing-Zhong. And the article was included in Chemical Science in 2019.Application of 33439-27-9 This article mentions the following:

The coupling reactions between vinyl/aryl and alkyl C-O electrophiles that can be derived from chem. feedstocks and naturally occurring functional groups was reported. This method provided an efficient approach to the synthesis of a wide range of functionalized, and/or secondary alkyl substituted cycloalkenes that are difficult to synthesize by conventional methods. The reaction proceeded with broad substrate scope, and tolerated various functional groups such as alc., aldehyde, ketone, ester, amide, alkene, alkyne, heterocycles, organotin and organosilicon compounds The synthetic utility of this method was demonstrated by providing facile access to important building blocks. The possibility to apply this method for late-stage modification of peptides was also demonstrated. A broad range of functionalized alkyl groups was selectively introduced into tyrosine in peptides via C-C bond formation, which was a challenge to the existing procedures. 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 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.Application of 33439-27-9

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Functionally Biased D2R Antagonists: Targeting the β-Arrestin Pathway to Improve Antipsychotic Treatment was written by Weiwer, Michel;Xu, Qihong;Gale, Jennifer P.;Lewis, Michael;Campbell, Arthur J.;Schroeder, Frederick A.;Van de Bittner, Genevieve C.;Walk, Michelle;Amaya, Aldo;Su, Ping;Dordevic, Luka;Sacher, Joshua R.;Skepner, Adam;Fei, David;Dennehy, Kelly;Nguyen, Shannon;Faloon, Patrick W.;Perez, Jose;Cottrell, Jeffrey R.;Liu, Fang;Palmer, Michelle;Pan, Jen Q.;Hooker, Jacob M.;Zhang, Yan-Ling;Scolnick, Edward;Wagner, Florence F.;Holson, Edward B.. And the article was included in ACS Chemical Biology in 2018.Formula: C11H21NO3 This article mentions the following:

Schizophrenia is a severe neuropsychiatric disease that lacks completely effective and safe therapies. As a polygenic disorder, genetic studies have only started to shed light on its complex etiol. To date, the pos. symptoms of schizophrenia are well-managed by antipsychotic drugs, which primarily target the dopamine D2 receptor (D2R). However, these antipsychotics are often accompanied by severe side effects, including motoric symptoms. At D2R, antipsychotic drugs antagonize both G-protein dependent (Gα_i/o) signaling and G-protein independent (β-arrestin) signaling. However, the relevant contributions of the distinct D2R signaling pathways to antipsychotic efficacy and on-target side effects (motoric) are still incompletely understood. Recent evidence from mouse genetic and pharmacol. studies point to β-arrestin signaling as the major driver of antipsychotic efficacy and suggest that a β-arrestin biased D2R antagonist could achieve an addnl. level of selectivity at D2R, increasing the therapeutic index of next generation antipsychotics. Here, we characterize BRD5814, a highly brain penetrant β-arrestin biased D2R antagonist. BRD5814 demonstrated good target engagement via PET imaging, achieving efficacy in an amphetamine-induced hyperlocomotion mouse model with strongly reduced motoric side effects in a rotarod performance test. This proof of concept study opens the possibility for the development of a new generation of pathway selective antipsychotics at D2R with reduced side effect profiles for the treatment of schizophrenia. In the experiment, the researchers used many compounds, for example, 1-Boc-4-Hydroxy-4-methylpiperidine (cas: 406235-30-1Formula: 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. 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.Formula: C11H21NO3

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Flow Photo-Nazarov Reactions of 2-Furyl Vinyl Ketones: Cyclizing a Class of Traditionally Unreactive Heteroaromatic Enones was written by Ashley, William L.;Timpy, Evan L.;Coombs, Thomas C.. And the article was included in Journal of Organic Chemistry in 2018.COA of Formula: C12H15NO3S This article mentions the following:

Nazarov reactions of 2-furyl vinyl ketones and related heteroaromatic enones, to produce furan-fused cyclopentanones using a flow photochem. approach, are described. Compounds possessing this connectivity between heterocycle and ketone (2-furyl, 2-benzofuryl, 2-thiophene-yl, and 2-benzothiophene-yl) have traditionally proven difficult or impossible to cyclize with typical Bronsted and Lewis acid mediated methods. Using mild flow photochem. conditions and acetic acid (AcOH) or hexafluoroisopropanol (HFIP) as solvent, these compounds were found to cyclize in 45-97% yields, with typical UV exposure times of 3.4-6.8 min. In all cases, 2-furyl and 2-thiophene-yl enones cyclized, whereas 2-benzofuryl and 2-benzothiophene-yl enones exhibited divergent properties with reactivity patterns tied to the identity of the vinyl group. This report discloses the first photo-Nazarov reactions of tetrahydropyridine-substituted 2-furyl ketones, providing a direct approach to the corresponding fused heterocyclic motifs built around a central cyclopentanone. These motifs constitute the core structures of biol. active natural products, including the marine alkaloid nakadomarin A. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9COA of Formula: C12H15NO3S).

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. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.COA of Formula: C12H15NO3S

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Photocatalytic Oxyamination of Alkenes: Copper(II) Salts as Terminal Oxidants in Photoredox Catalysis was written by Reed, Nicholas L.;Herman, Madeline I.;Miltchev, Vladimir P.;Yoon, Tehshik P.. And the article was included in Organic Letters in 2018.Computed Properties of C12H15NO3S This article mentions the following:

A photocatalytic method for the oxyamination of alkenes using simple nucleophilic nitrogen atom sources in place of prefunctionalized electrophilic nitrogen atom donors is reported. Copper(II) is an inexpensive, practical, and uniquely effective terminal oxidant for this process. In contrast to oxygen, peroxides, and similar oxidants commonly utilized in non-photochem. oxidative methods, the use of copper(II) as a terminal oxidant in photoredox reactions avoids the formation of reactive heteroatom-centered radical intermediates that can be incompatible with electron-rich functional groups. As a demonstration of the generality of this concept, it has been shown that diamination and deoxygenation reactions can also be accomplished using similar photooxidative conditions. 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. Piperidine and its derivatives have become increasingly popular in many synthetic schemes. 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.Computed Properties of C12H15NO3S

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthetic bacteriochlorins with integral spiro-piperidine motifs was written by Reddy, Kanumuri Ramesh;Lubian, Elisa;Pavan, M. Phani;Kim, Han-Je;Yang, Eunkyung;Holten, Dewey;Lindsey, Jonathan S.. And the article was included in New Journal of Chemistry in 2013.Electric Literature of C12H15NO3S This article mentions the following:

A new mol. design incorporates a spiro-piperidine unit in each pyrroline ring of synthetic bacteriochlorins, thereby (1) replacing the previous geminal di-Me group with a functionally equivalent motif to suppress adventitious dehydrogenation, (2) enabling tailoring of the bacteriochlorin by nitrogen derivatization, and (3) leaving the β-pyrrolic positions available for introduction of auxochromes to tune the spectral properties. Conversion of an N-protected 4-piperidone to the N-protected α,β-unsaturated ketone, Michael reaction with 4-(ethoxycarbonyl)-3-ethyl-2-(2-nitroethyl)pyrrole (I), and subsequent reductive cyclization provided the spiro-piperidine-1-methyldihydrodipyrrin (II; R = Ts, Boc; R¹ = H, Me). Treatment with SeO₂ followed by tri-Me orthoformate under acid catalysis converted the 1-Me group to a 1-(1,1-dimethoxymethyl) motif. Self-condensation of the resulting spiro-piperidine-dihydrodipyrrin-acetal afforded the 5-methoxy- or 5-unsubstituted bacteriochlorins III (R = Ts, Boc; R² = H, OMe), each bearing two spiro-piperidine units. The spiro-piperidine units were derivatized at the nitrogens by methylation, sulfonylation, acylation, or quaternization; the latter with Me iodide afforded two dicationic, hydrophilic bacteriochlorins. Altogether, eight spiro-piperidine-bacteriochlorins were prepared Spectroscopic characterization was carried out in DMF (and in water for the quaternized, 5-methoxybacteriochlorin). Compared to the 5-unsubstituted analog, the quaternized, 5-methoxybacteriochlorin has in DMF a shorter wavelength of the intense near-IR absorption band (733 vs. 752 nm) and fluorescence band (739 vs. 760 nm), modestly greater fluorescence yield (0.15 vs. 0.08) and modestly longer lifetime of the lowest singlet excited state (4.7 vs. 3.3 ns). In general, the spiro-piperidinyl moiety does not significantly alter the rate constants or yields of the decay pathways (fluorescence, intersystem crossing, internal conversion) of the lowest singlet excited state of the bacteriochlorin. Taken together, the results describe a new mol. design for tailoring the polarity of near-IR absorbers. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Electric Literature of C12H15NO3S).

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.Electric Literature of C12H15NO3S

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Rearrangement of Hydroxylated Pinene Derivatives to Fenchone-Type Frameworks: Computational Evidence for Dynamically-Controlled Selectivity was written by Blumel, Marcus;Nagasawa, Shota;Blackford, Katherine;Hare, Stephanie R.;Tantillo, Dean J.;Sarpong, Richmond. And the article was included in Journal of the American Chemical Society in 2018.Related Products of 33439-27-9 This article mentions the following:

An acid-catalyzed Prins/semipinacol rearrangement cascade reaction of hydroxylated pinene derivatives that leads to tricyclic fenchone-type scaffolds in very high yields and diastereoselectivity has been developed. Quantum chem. anal. of the selectivity-determining step provides support for the existence of an extremely flat potential energy surface around the transition state structure. This transition state structure appears to be ambimodal, i.e., the fenchone-type tricyclic scaffolds are formed in preference to the competing formation of a bornyl (camphor-type) skeleton under dynamic control via a post-transition state bifurcation (PTSB). In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Related Products of 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. 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.Related Products of 33439-27-9

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthesis of aryl (alkyl) ketones of the piperidine series was written by Kuroyan, R. A.;Markosyan, A. I.;Snkhchyan, G. M.;Vartanyan, S. A.. And the article was included in Armyanskii Khimicheskii Zhurnal in 1983.COA of Formula: C13H16N2 This article mentions the following:

Alkyl (aryl) piperidinyl ketones I [R = PhCH₂, R¹ = H, R² = C_1-5 n-alkyl, (un)substituted Ph, PhCH₂; R = R¹ = Me, R² = (un)substituted Ph, PhCH₂] were prepared from the corresponding piperidinecarboxaldehyde by oximation, dehydration to the nitrile and Grignard reaction with R²X (X = undefined halo). 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 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.COA of Formula: C13H16N2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

A convenient synthesis of functionalized 8- and 9-aza-1-oxaspiro[5.5]undecanes was written by Apostolopoulos, Costas D.;Haroutounian, Serkos A.. And the article was included in Journal of Heterocyclic Chemistry in 1995.Application of 95798-22-4 This article mentions the following:

2-Hydroxy-8-(or 9-)aza-1-oxaspiro[5.5]undec-3-en-5-ones derived from their corresponding 2-furfuryl alcs. were used as key intermediates for the convenient synthesis of several novel 8- and 9-aza-1-oxaspiro[5.5]undecane derivatives In the experiment, the researchers used many compounds, for example, Benzyl 3-hydroxypiperidine-1-carboxylate (cas: 95798-22-4Application of 95798-22-4).

Benzyl 3-hydroxypiperidine-1-carboxylate (cas: 95798-22-4) 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. 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.Application of 95798-22-4

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthesis of substituted 3-azabicyclo[3.3.1]nonanes was written by Speckamp, W. N.;Dijkink, J.;Dekkers, A. W. J. D.;Huisman, H. O.. And the article was included in Tetrahedron in 1971.Computed Properties of C12H15NO3S This article mentions the following:

The synthesis of 3-azabicyclo[3.3.1]nonanes is described via the addition of α-(bromomethyl)acrylate to N-tosylpiperidone enamine and subsequent transformation of these adducts. NMR investigation showed a fair correlation between structure and conformation of the adducts and the observed chem. shifts of CH-CO2R and N-CH2 protons. 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. Piperidine is a metabolite of cadaverine, a polyamine found in the human intestine. 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

Improved Ca_v2.2 Channel Inhibitors through a gem-Dimethylsulfone Bioisostere Replacement of a Labile Sulfonamide was written by Shao, Pengcheng P.;Ye, Feng;Chakravarty, Prasun K.;Herrington, James B.;Dai, Ge;Bugianesi, Randal M.;Haedo, Rodolfo J.;Swensen, Andrew M.;Warren, Vivien A.;Smith, McHardy M.;Garcia, Maria L.;McManus, Owen B.;Lyons, Kathryn A.;Li, Xiaohua;Green, Mitchell;Jochnowitz, Nina;McGowan, Erin;Mistry, Shruti;Sun, Shu-Yu;Abbadie, Catherine;Kaczorowski, Gregory J.;Duffy, Joseph L.. And the article was included in ACS Medicinal Chemistry Letters in 2013.HPLC of Formula: 183170-69-6 This article mentions the following:

The investigation of sulfonamide-derived Ca_v2.2 inhibitors to address drug-metabolism liabilities with this lead class of analgesics is reported. Modification of the benzamide substituent provided improvements in both potency and selectivity. However, it was discovered that formation of the persistent 3-(trifluoromethyl)benzenesulfonamide metabolite was an endemic problem in the sulfonamide series and that the replacement of the center aminopiperidine scaffold failed to prevent this metabolic pathway. This issue was eventually addressed by application of a bioisostere strategy. The new gem-di-Me sulfone series, e.g., I (IC₅₀ = 0.51 μM), retained Ca_v2.2 potency without the liability of the circulating sulfonamide metabolite. In the experiment, the researchers used many compounds, for example, tert-Butyl 4-(1-hydroxyethyl)piperidine-1-carboxylate (cas: 183170-69-6HPLC of Formula: 183170-69-6).

tert-Butyl 4-(1-hydroxyethyl)piperidine-1-carboxylate (cas: 183170-69-6) 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.HPLC of Formula: 183170-69-6

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem