Day: February 7, 2023

Synthesis of carbo- and heterocyclic aldehydes bearing an adjacent donor group. Ozonolysis versus OsO₄/KIO₄-oxidation was written by Mihovilovic, Marko D.;Spina, Markus;Mueller, Bernhard;Stanetty, Peter. And the article was included in Monatshefte fuer Chemie in 2004.Application of 33439-27-9 This article mentions the following:

The synthesis of carbo- and heterocyclic aldehydes bearing an ipso-methoxy group is investigated. The synthetic sequence is based on an initial Grignard addition of an olefin to a cyclic ketone followed by methylation of the resulting tertiary alc. The terminal olefin serves as precursor for the aldehyde functionality. Oxidation by ozonolysis turned out to depend significantly on the distance of the donor methoxy group. The observed side reactions could be circumvented by applying a one-pot OsO₄ mediated diol formation followed by Malaprade oxidation using KIO₄. A series of carbo- and heterocyclic precursors were successfully converted to the title products. 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 has a role as a reagent, a protic solvent, a base, a catalyst, a plant metabolite, a human metabolite and a non-polar solvent. 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

Preparation of 4-heteroaryl-4-cyanopiperidines via S_NAr substitution reactions was written by Chang, Ronald K.;Di Marco, Christina N.;Pitts, Daniel R.;Greshock, Thomas J.;Kuduk, Scott D.. And the article was included in Tetrahedron Letters in 2009.Category: piperidines This article mentions the following:

The scope and limitations of S_NAr substitution of metalated 4-cyanopiperidines with heterocyclic halides were explored. These facile reactions provide rapid access to a wide range of 4-hetaryl-4-cyanopiperidines and resulted in improved yields, faster reaction times, and lower temperatures than previously published methods. In the experiment, the researchers used many compounds, for example, 1-Benzylpiperidine-4-carbonitrile (cas: 62718-31-4Category: piperidines).

1-Benzylpiperidine-4-carbonitrile (cas: 62718-31-4) 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.Category: piperidines

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthesis and biological evaluation of phenyl piperidine derivatives as CCR2 antagonists was written by Xia, Mingde;Hou, Cuifen;Pollack, Scott;Brackley, James;DeMong, Duane;Pan, Meng;Singer, Monica;Matheis, Michele;Olini, Gil;Cavender, Druie;Wachter, Michael. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2007.Reference of 58333-75-8 This article mentions the following:

A series of Ph piperidine derivatives possessing potent and selective CCR2 antagonist activity is reported. Structure-activity relationship (SAR) studies have established that incorporation of a second ring system adjacent to the aryl piperidine plays an important role in determining the CCR2 potency. Both a second piperidine ring and a 1,3-substituted cyclopentylamine have been probed as linkers. For the cyclopentylamine series, the 1S,3R-configuration exhibits much higher affinity for hCCR2 than the 1R,3S-configuration. Compound (I) shows good selectivity over CCR1, CCR3, 5-HT and has an excellent P 450 profile. 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. 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. 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.Reference of 58333-75-8

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Successful reduction of off-target hERG toxicity by structural modification of a T-type calcium channel blocker was written by Choi, Yeon Jae;Seo, Jae Hong;Shin, Kye Jung. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2014.SDS of cas: 58333-75-8 This article mentions the following:

To obtain an optimized T-type calcium channel blocker with reduced off-target hERG toxicity, we modified the structure of the original compound by introducing a zwitterion and reducing the basicity of the nitrogen. Among the structurally modified compounds we designed, compounds 5 and 6, which incorporate amides in place of the original compound’s amines, most appreciably alleviated hERG toxicity while maintaining T-type calcium channel blocking activity. Notably, the benzimidazole amide 5 selectively blocked T-type calcium channels without inhibiting hERG (hERG/T-type ≥ 220) and L-type channels (L-type/T-type = 96), and exhibited an excellent pharmacokinetic profile in rats. 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. The piperidine moiety constitutes an important building block for the synthesis of a variety of bioactive natural products, alkaloids and other drugs. 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

Synthesis and NK₁/NK₂ binding activities of a series of diacyl-substituted 2-arylpiperazines was written by Blythin, David J.;Chen, Xiao;Piwinski, John J.;Shih, Neng-Yang;Shue, Ho-Jane;Anthes, John C.;McPhail, Andrew T.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2002.Application In Synthesis of tert-Butyl 4-aminopiperazine-1-carboxylate This article mentions the following:

The synthesis and binding affinity for hNK₁ and hNK₂ receptors of a series of diacyl substituted 2-aryl piperazines are described. SAR evaluation led to one racemic derivative as an apparent dual inhibitor. Chiral chromatog. separation of racemic derivative led to the observation that NK₁ activity was shown by one enantiomer and NK₂ activity was shown by the other enantiomer. X-ray crystallog. anal. of the crystalline di-BOC derivative of the NK₂ active piperazine showed that the 2R configuration was associated with NK₂ activity. Further derivatization indicated that dual NK₁/NK₂ activity could be built into the 2R series. In the experiment, the researchers used many compounds, for example, tert-Butyl 4-aminopiperazine-1-carboxylate (cas: 118753-66-5Application In Synthesis of tert-Butyl 4-aminopiperazine-1-carboxylate).

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 derivatives bearing a masked aldehyde function in the ε-position are easily transformed into quinolizidine compounds through intramolecular reductive amination.Application In Synthesis of tert-Butyl 4-aminopiperazine-1-carboxylate

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthesis and Application of N-Tosyl Piperidinyl-Containing α-Aminophosphonates was written by Jiang, Zhifu;Zhao, Jian;Gao, Beibei;Chen, Shuo;Qu, Wenyan;Mei, Xiangdong;Rui, Changhui;Ning, Jun;She, Dongmei. And the article was included in Phosphorus, Sulfur and Silicon and the Related Elements in 2013.Category: piperidines This article mentions the following:

A series of novel (4′-tosyl) piperidin-4-yl containing α-aminophosphonates were synthesized by a one-pot reaction, efficiently catalyzed by magnesium perchlorate, under solvent-free conditions from 1-tosylpiperidin-4-one, substituted aromatic amines, and di-Et phosphite (DEP). The synthesized compounds were characterized by IR, ¹H NMR, ¹³C NMR, ³¹P NMR, and HRMS spectroscopy. A single-crystal X-ray structure of di-Et 4-(2-chlorophenyl) amino-1-(4′-methylbezenesulfonyl) piperidin-4-yl-phosphonate was obtained, and some of the title compounds displayed insecticidal activities against Plutella xylostella. 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.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.Category: piperidines

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Facile and clean oxidation of alcohols in water using hypervalent iodine(III) reagents was written by Tohma, Hirofumi;Maegawa, Tomohiro;Takizawa, Shinobu;Kita, Yasuyuki. And the article was included in Advanced Synthesis & Catalysis in 2002.Formula: C12H15NO3S This article mentions the following:

The facile and efficient oxidation of various alcs. such as benzylic alcs., primary alcs., secondary alcs., and diols in water using the hypervalent iodine(III) reagent, iodosobenzene (PhI:O), with KBr is described. Electrospray ionization (ESI) mass spectrometric studies on the behavior of PhI:O-KBr in aqueous solution suggested that these reactions are induced by the formation of highly reactive iodine species [PhI(Br)_nO^–]. Further development to recyclable polymer-supported iodine(III) reagent extends the utility of this reaction to afford an environmentally benign method. 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 has a role as a reagent, a protic solvent, a base, a catalyst, a plant metabolite, a human metabolite and a non-polar solvent. 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: C12H15NO3S

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthesis of α-quaternary bicyclo[1.1.1]pentanes through synergistic organophotoredox and hydrogen atom transfer catalysis was written by Nugent, Jeremy;Sterling, Alistair J.;Frank, Nils;Mousseau, James J.;Anderson, Edward A.. And the article was included in Organic Letters in 2021.Quality Control of 1-Tosylpiperidin-4-one This article mentions the following:

Bicyclo[1.1.1]pentanes (BCPs) are of importance in drug design as sp3-rich bioisosteres of arenes and tert-Bu groups, however the preparation of BCPs with adjacent quaternary carbons is barely known. Authors report a facile synthesis of α-quaternary BCPs using organophotoredox and hydrogen atom transfer catalysis in which α-keto radicals, generated through oxidation of β-ketocarbonyls, underwent efficient addition to [1.1.1]propellane. The BCP products can be transformed into a variety of useful derivatives including enantioenriched BCPs featuring α-quaternary stereocenters. 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 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.Quality Control of 1-Tosylpiperidin-4-one

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

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