Month: February 2023

The Piloty-Robinson reaction of N-substituted piperidin-4-one azines. A novel route for the synthesis of 3,6-diazacarbazole was written by Alekseyev, R. S.;Kurkin, A. V.;Yurovskaya, M. A.. And the article was included in Chemistry of Heterocyclic Compounds (New York, NY, United States) in 2011.Recommanded Product: 1-Tosylpiperidin-4-one This article mentions the following:

The possibility of preparing 1,2,3,4,6,7,8,9-octahydro-5H-pyrrolo[3,2-c:4,5-c’]dipyridines using the Piloty-Robinson reaction has been studied under various conditions. A novel method is proposed for the synthesis of the aromatic 3,6-diazacarbazole (5H-pyrrolo[3,2-c:4,5-c’]dipyridine) from 2,8-dibenzoyl-1,2,3,4,6,7,8,9-octahydro-5H-pyrrolo[3,2-c:4,5-c’]dipyridine obtained for the first time by the Piloty-Robinson method under thermal conditions. 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 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.Recommanded Product: 1-Tosylpiperidin-4-one

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Mild and selective boronic acid catalyzed 1,3-transposition of allylic alcohols and Meyer-Schuster rearrangement of propargylic alcohols was written by Zheng, Hongchao;Lejkowski, Michal;Hall, Dennis G.. And the article was included in Chemical Science in 2011.Category: piperidines This article mentions the following:

Boronic acid catalysis (BAC) was applied to the transposition of allylic alcs. and a related Meyer-Schuster rearrangement of propargylic alcs. using highly electron-deficient polyfluoroarylboronic acids as catalysts under mild metal-free conditions. A wide range of synthetically useful products was formed and the synthesis of the target compounds was achieved with E:Z selectivity superior to that of metal-catalyzed methods. A mechanism is proposed involving partial or full ionization into an allylic (or propargylic) carbocation and addnl. possibilities for multicatalytic tandem reactions are exemplified. 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 saturated organic heteromonocyclic parent, an azacycloalkane, a secondary amine and a member of piperidines. 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

Thioether acetamides as P3 binding elements for tetrahydropyrido-pyrazole cathepsin S inhibitors was written by Wiener, Danielle K.;Lee-Dutra, Alice;Bembenek, Scott;Nguyen, Steven;Thurmond, Robin L.;Sun, Siquan;Karlsson, Lars;Grice, Cheryl A.;Jones, Todd K.;Edwards, James P.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2010.SDS of cas: 58333-75-8 This article mentions the following:

A series of tetrahydropyrido-pyrazole cathepsin S (CatS) inhibitors with thioether acetamide functional groups were prepared with the goal of improving upon the cellular activity of amidoethylthioethers. This Letter describes altered amide connectivity, in conjunction with changes to other binding elements, resulting in improved potency, as well as increased knowledge of the relationship between this chemotype and human CatS activity. 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 structural motif is present in numerous natural alkaloids. These include piperine, which gives black pepper its spicy taste. 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.SDS of cas: 58333-75-8

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Crystallography-guided discovery of carbazole-based retinoic acid-related orphan receptor gamma-t (RORγt) modulators: insights into different protein behaviors with “short” and “long” inverse agonists was written by Yu, Ming-cheng;Yang, Feng;Ding, Xiao-yu;Sun, Nan-nan;Jiang, Zheng-yuan;Huang, Ya-fei;Yan, Yu-rong;Zhu, Chen;Xie, Qiong;Chen, Zhi-feng;Guo, Si-qi;Jiang, Hua-liang;Chen, Kai-xian;Luo, Cheng;Luo, Xiao-min;Chen, Shi-jie;Wang, Yong-hui. And the article was included in Acta Pharmacologica Sinica in 2021.Name: 1-(4-Hydroxypiperidin-1-yl)ethanone This article mentions the following:

A series of 6-substituted carbazole-based retinoic acid-related orphan receptor gamma-t (RORγt) modulators were discovered through 6-position modification guided by insights from the crystallog. profiles of the “short” inverse agonist 6. With the increase in the size of the 6-position substituents, the “short” inverse agonist 6 first reversed its function to agonists and then to “long” inverse agonists. The cocrystal structures of RORγt complexed with the representative “short” inverse agonist 6 (PDB: 6LOB), the agonist 7d (PDB: 6LOA) and the “long” inverse agonist 7h (PDB: 6LO9) were revealed by X-ray anal. However, minor differences were found in the binding modes of “short” inverse agonist 6 and “long” inverse agonist 7h. To further reveal the mol. mechanisms of different RORγt inverse agonists, we performed mol. dynamics simulations and found that “short” or “long” inverse agonists led to different behaviors of helixes H11, H11′, and H12 of RORγt. The “short” inverse agonist 6 destabilizes H11′ and dislocates H12, while the “long” inverse agonist 7h separates H11 and unwinds H12. The results indicate that the two types of inverse agonists may behave differently in downstream signaling, which may help identify novel inverse agonists with different regulatory mechanisms. In the experiment, the researchers used many compounds, for example, 1-(4-Hydroxypiperidin-1-yl)ethanone (cas: 4045-22-1Name: 1-(4-Hydroxypiperidin-1-yl)ethanone).

1-(4-Hydroxypiperidin-1-yl)ethanone (cas: 4045-22-1) belongs to piperidine derivatives. The piperidine structural motif is present in numerous natural alkaloids. These include piperine, which gives black pepper its spicy taste. 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.Name: 1-(4-Hydroxypiperidin-1-yl)ethanone

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthesis of novel 1,3-thiazin-4-ones by acetylene diester cyclization and their anticancer activities was written by Anand, Selvam Athavan Alias;Loganathan, Chandrasekaran;Thomas, Nisha Susan;Saravanan, Kuppusamy;Alphonsa, Antony Therasa;Kabilan, Senthamaraikannan. And the article was included in Phosphorus, Sulfur and Silicon and the Related Elements in 2016.Product Details of 33439-27-9 This article mentions the following:

A novel series of 1,3-thiazin-4-one derivatives containing a piperidyl ring I (R¹ = Ts, Boc; R² = H, Me; R³ = Me, Et), II (R¹ = Boc; R² = H, Me) were designed and synthesized efficiently by thioamide and acetylene diester cyclization reaction via aminolysis of the ester group and the elimination of an alc. mol. All the newly synthesized compounds were studied for their in vitro anticancer activity against human liver cancer cell lines Hep G2 using MTT assay. The IC₅₀ values of the tested compounds ranged between 7.48 +/- 0.71 and 56.57 +/- 1.37 μM. Further, the apoptosis evaluation by the mitochondrial membrane potential using JC-1 dye was carried out and the results are in good agreement with the cytotoxicity studies. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Product Details of 33439-27-9).

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. 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.Product Details of 33439-27-9

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

A radical chlorodifluoromethylation protocol for late-stage difluoromethylation and its application to an oncology candidate was written by Meng, Depei;Li, Lingchun;Brown, Adam;Desrosiers, Jean-Nicolas;Duan, Shengquan;Hayward, Cheryl M.;He, Zhengbiao;Hu, Jinbo;Makowski, Teresa;Maloney, Mark;Monfette, Sebastien;Perfect, Hahdi;Piper, Jared L.;Zhou, Min;Widlicka, Daniel W.. And the article was included in Cell Reports Physical Science in 2021.Related Products of 651057-01-1 This article mentions the following:

An efficient radical chlorodifluoromethylation protocol with sodium chlorodifluoromethanesulfinate, which is complementary to the existing late-stage difluoromethylation strategies has been described. CF₂Cl radical is a suitable surrogate for accessing the CF₂H group while possessing completely different electronic properties compared to the CF₂H radical. This method is chemoselective and regioselective for the chlorodifluoromethylation of (hetero)arenes RH [R = 2,4,6-trimethylphenyl, 2,3-dihydro-1,4-benzodioxin-5-yl, 4-oxo-1H,4H,5H-pyrazolo[3,4-d]pyrimidin-3-yl, etc.] and electron-rich alkenes R¹C(=CH₂)OAc (R¹ = Ph, 2-naphthyl, 2-thienyl, etc.) and shows good functionality, tolerance, and generality on scope. The preparation of the sodium chlorodifluoromethanesulfinate is thoroughly investigated and can be scaled up to hundreds of kilograms. The method is successfully implemented on the synthesis of an oncol. candidate compound I. In the experiment, the researchers used many compounds, for example, 1-(Methylsulfonyl)piperidin-4-amine hydrochloride (cas: 651057-01-1Related Products of 651057-01-1).

1-(Methylsulfonyl)piperidin-4-amine hydrochloride (cas: 651057-01-1) 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.Related Products of 651057-01-1

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

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