Month: January 2023

Molecular determinants for recognition of RU 24696 analogs at central 5-hydroxytryptamine recognition sites: use of a bilinear function and substituent volumes to describe steric fit was written by Taylor, Ethan Will;Nikam, Sham S.;Lambert, Georgina;Martin, Arnold R.;Nelson, David L.. And the article was included in Molecular Pharmacology in 1988.Reference of 33439-27-9 This article mentions the following:

The putative serotonin (5-HT) agonist RU 24969 (I) has been extensively used in the study and classification of 5-HT receptors. To study mol. determinants for recognition of 1,2,3,6-tetrahydropyridin-4-ylindoles (THP) at central 5-HT recognition sites, about 25 addnl. THP derivatives were synthesized, incorporating, among others, 16 different indole-5-substituents and 3 different pyridine-N substituents in various combinations. Two saturated derivatives (piperidin-4-ylindoles) and 2 2-Me analogs were also included. Binding affinities at 5-HT_1A, 5-HT₂, and total 5-HT₁ sites were obtained and the data were incorporated in quant. structure-activity relations (QSARs) using a combined linear free energy/mol. modeling approach. The QSAR analyses suggest distinct differences in the structural features that determine optimal potency at 5-HT_1A sites vs. those directing optima potency for 5-HT₂ sites. The parameter of the indole-5 substituent that almost exclusively determines potency for 5-HT_1A sites is volume, the optimal size being about 24 cubic angstroms (calculated by fitting the activity vs. volume data to a bilinear function). This is approx. the size of a carboxamide group. In contrast, at the 5-HT₂ site both volume and hydrophobicity play a major but opposing roles for the 5-substituent. A balance between the smallest possible volume and the greatest possible hydrophobicity is required for maximal 5-HT₂ potency. Benzyl groups on the indole-1 or pyridyl-1 positions also favor potency at the 5-HT₂ site (probably largely due to increased hydrophobic binding) while decreasing potency at the 5-HT_1A site. A minor electronic contribution to the QSARs involving the charge on the indole 5-carbon is of opposite sign for 5-HT_1A vs. 5-HT₂ sites and thus may also be useful for selective drug design. The data are consistent with the possibility that the indole and pyridyl rings are in a coplanar configuration when binding at both 5-HT_1A and 5-HT₂ sites, because the indole-2-Me substituent, which provides a large energy barrier to the coplanar configuration, greatly reduces the potency of THP at both binding sites. Similarities in analog selectivity patterns suggest that the indole portion of these compounds binds similarly to that of other indole derivatives such as tryptamines; thus, it is possible that optimally selective substituents predicted by these QSARs may be extrapolated to tryptamines and other indoles. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Reference of 33439-27-9).

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 bearing a masked aldehyde function in the ε-position are easily transformed into quinolizidine compounds through intramolecular reductive amination.Reference of 33439-27-9

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Electrochemical Deprotection of para-Methoxybenzyl Ethers in a Flow Electrolysis Cell was written by Green, Robert A.;Jolley, Katherine E.;Al-Hadedi, Azzam A. M.;Pletcher, Derek;Harrowven, David C.;De Frutos, Oscar;Mateos, Carlos;Klauber, David J.;Rincon, Juan A.;Brown, Richard C. D.. And the article was included in Organic Letters in 2017.Related Products of 33439-27-9 This article mentions the following:

Electrochem. deprotection of p-methoxybenzyl (PMB) ethers was performed in an undivided electrochem. flow reactor in MeOH solution, leading to the unmasked alc. and p-methoxybenzaldehyde di-Me acetal as a byproduct. The electrochem. method removes the need for chem. oxidants, and added electrolyte (BF₄NEt₄) can be recovered and reused. The method was applied to 17 substrates with high conversions in a single pass, yields up to 92%, and up to 7.5 g h^-1 productivity. The PMB protecting group was also selectively removed in the presence of some other common alc. protecting groups. 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. 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.Related Products of 33439-27-9

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

1-(1,3-Benzodioxol-5-ylmethyl)-3-[4-(1H-imidazol-1-yl)phenoxy]-piperidine analogs as potent and selective inhibitors of nitric oxide formation was written by Wei, Robert G.;Adler, Marc;Davey, David;Ho, Elena;Mohan, Raju;Polokoff, Mark;Tseng, Jih-Lie;Whitlow, Marc;Xu, Wei;Yuan, Shendong;Phillips, Gary. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2007.Formula: C12H18ClNO This article mentions the following:

A new series of 1-(1,3-benzodioxol-5-ylmethyl)-3-[4-(1H-Imidazol-1-yl)phenoxy]-piperidine analogs were designed and identified as potent and selective inhibitors of NO formation based both on the crystal structure of a murine iNOS Δ114 monomer domain/ inhibitor complex and inhibition of the NO formation in human A172 cell assays. Compound 12S showed high potency and high iNOS selectivity vs. nNOS and eNOS. In the experiment, the researchers used many compounds, for example, 1-Benzyl-3-piperidinol hydrochloride (cas: 105973-51-1Formula: C12H18ClNO).

1-Benzyl-3-piperidinol hydrochloride (cas: 105973-51-1) belongs to piperidine derivatives. Piperidine and its derivatives have become increasingly popular in many synthetic schemes. 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.Formula: C12H18ClNO

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Tertiary Amine Mediated Tandem Cross-Rauhut-Currier/Acetalization Reactions: Access to Functionalized Spiro-3,4-Dihydropyrans was written by Yao, Weijun;Wu, Yihua;Wang, Gang;Zhang, Yiping;Ma, Cheng. And the article was included in Angewandte Chemie, International Edition in 2009.Synthetic Route of C12H15NO3S This article mentions the following:

Spiro-3,4-dihydropyrans, e.g. I (R¹ = Ph,, R² = Me, Et; R¹ = 4-FC₆H₄, 4-MeC₆H₄, R² = Me; R¹ = 3-O₂NC₆H₄, 4-MeOC₆H₄, 2-furyl, N-tosylindol-3-yl, R² = Et), were prepared by DBU-mediated cross-Rauhut-Currier/acetalization of cyclic β-haloenals, e.g. II, with β,γ-unsaturated α-ketoesters, e.g. (E)-R¹CH:CHCOCO₂R², followed by oxidation In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Synthetic Route of C12H15NO3S).

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. 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.Synthetic Route of C12H15NO3S

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

C-H Insertion via Ruthenium Catalyzed gem-Hydrogenation of 1,3-Enynes was written by Peil, Sebastian;Gutierrez Gonzalez, Alejandro;Leutzsch, Markus;Fuerstner, Alois. And the article was included in Journal of the American Chemical Society in 2022.Electric Literature of C12H15NO3S This article mentions the following:

Gem-Hydrogenation of an internal alkyne with the aid of [Cp*RuCl]₄ as the precatalyst is a highly unorthodox transformation, in which one C atom of the triple bond is transformed into a methylene group, whereas the second C atom gets converted into a ruthenium carbene. In the case of 1,3-enynes bearing a propargylic steering substituent as the substrates, the reaction occurs regioselectively, giving rise to vinyl carbene complexes that adopt interconverting η¹/η³-binding modes in solution; a prototypical example of such a reactive intermediate was characterized in detail by spectroscopic means. Although both forms are similarly stable, only the η³-vinyl carbene proved kinetically competent to insert into primary, secondary, or tertiary C-H bonds on the steering group itself or another suitably placed ether, acetal, orthoester, or (sulfon)amide substituent. The ensuing net hydrogenative C-H insertion reaction is highly enabling in that it gives ready access to spirocyclic as well as bridged ring systems of immediate relevance as building blocks for medicinal chem. Moreover, the reaction scales well and lends itself to the formation of partly or fully deuterated isotopologues. Labeling experiments in combination with PHIP NMR spectroscopy (PHIP = parahydrogen induced polarization) confirmed that the reactions are indeed triggered by gem-hydrogenation, whereas kinetic data provided valuable insights into the very nature of the turnover-limiting transition state of the actual C-H insertion step. 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 metabolite of cadaverine, a polyamine found in the human intestine. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.Electric Literature of C12H15NO3S

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Visible-light photoredox synthesis of internal alkynes containing quaternary carbons was written by Gao, Chang;Li, Jingjing;Yu, Jipan;Yang, Haijun;Fu, Hua. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2016.Application of 406235-30-1 This article mentions the following:

A novel and efficient visible-light photoredox method for the synthesis of internal alkynes RCCAr (R = tert-Bu, 1-methylcyclohexyl, 1-methylcycloheptyl, etc.; Ar = C₆H₅, thiophen-2-yl, naphthalen-1-yl, etc.) containing quaternary carbons has been developed via coupling reactions of N-phthalimidoyl oxalates of tert-alcs. I with 1-(2-(arylsulfonyl)ethynyl)benzenes ArCCS(O)₂C₆H₅. The reactions proceeded well at room temperature with good functional group tolerability. In the experiment, the researchers used many compounds, for example, 1-Boc-4-Hydroxy-4-methylpiperidine (cas: 406235-30-1Application of 406235-30-1).

1-Boc-4-Hydroxy-4-methylpiperidine (cas: 406235-30-1) 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. 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.Application of 406235-30-1

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Indoline derivatives. Synthesis and factor Xa (FXa) inhibitory activities was written by Noguchi, Tetsuji;Tanaka, Naoki;Nishimata, Toyoki;Goto, Riki;Hayakawa, Miho;Sugidachi, Atsuhiro;Ogawa, Taketoshi;Asai, Fumitoshi;Matsui, Yumi;Fujimoto, Koichi. And the article was included in Chemical & Pharmaceutical Bulletin in 2006.Formula: C7H13NO2 This article mentions the following:

A series of bisamidine derivatives each having a ring structure in the center of the mol. was synthesized and their Factor Xa (FXa) inhibitory activities were evaluated. Among them, some indoline derivatives showed potent inhibitory activities in vitro. In particular, compound (I) having an (R)-configuration at the 2-position of the indoline ring exhibited the most potent FXa inhibitory activity in vitro, more potent than DX-9065a. Furthermore, I exhibited more potent anticoagulant activity than DX-9065a. The authors also succeeded in obtaining an x-ray crystal structure of FXa bound with I. In the experiment, the researchers used many compounds, for example, 1-(4-Hydroxypiperidin-1-yl)ethanone (cas: 4045-22-1Formula: C7H13NO2).

1-(4-Hydroxypiperidin-1-yl)ethanone (cas: 4045-22-1) 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. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.Formula: C7H13NO2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Total synthesis of balanol: a potent protein kinase C inhibitor of fungal origin was written by Adams, C. P.;Fairway, S. M.;Hardy, C. J.;Hibbs, D. E.;Hursthouse, M. B.;Morley, A. D.;Sharp, B. W.;Vicker, N.;Warner, I.. And the article was included in Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry in 1995.Product Details of 33439-27-9 This article mentions the following:

The total synthesis of the fungal metabolite balanol, a potent inhibitor of protein kinase C, is described. The synthesis includes a novel synthesis of 3-amino-4-hydroxyazepanes via a directed ring expansion of 3-bromopiperidin-4-ones. 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. The piperidine moiety constitutes an important building block for the synthesis of a variety of bioactive natural products, alkaloids and other drugs. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.Product Details of 33439-27-9

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Catalytic Asymmetric Homologation of 4-Substituted Cyclohexanones with CF₃CHN₂: Enantioselective Synthesis of α-Trifluoromethyl Cycloheptanones was written by Li, Shu-Sen;Sun, Shuo;Wang, Jianbo. And the article was included in Angewandte Chemie, International Edition in 2022.Computed Properties of C12H15NO3S This article mentions the following:

A catalytic asym. trifluoromethylation of cyclic ketones via a ScIII/chiral bisoxazoline-catalyzed homologation reaction by employing 2,2,2-trifluorodiazoethane (CF₃CHN₂) as the CF₃ source was reported. This desymmetrization process was highly efficient and generates two chiral centers with excellent diastereoselectivity and enantioselectivity, affording chiral α-trifluoromethyl cyclic ketones in a straightforward manner. 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 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 C12H15NO3S

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

2-Phenylpyrroles as conformationally restricted benzamide analogs. A new class of potential antipsychotics. 2 was written by Van Wijngaarden, Ineke;Kruse, Chris G.;Van der Heyden, Jan A. M.;Tulp, Martin T. M.. And the article was included in Journal of Medicinal Chemistry in 1988.Synthetic Route of C12H17NO This article mentions the following:

A series of 2-phenylpyrrole Mannich bases I (R = H, 4-F, 4-CF₃, 4-CHMe₂, 3-Cl, 2-OMe, 2,6-F₂; R¹ = H, Me, Ph, CF₂CF₂CF₃, CH₂CH₂OH) and II (R² = H, F; X = NC₆H₄CF₃-3, NC₆H₄F-4, CHPh, CHC₆H₄OMe-2, etc.) was synthesized and screened in pharmacol. models for antipsychotic activity and extrapyramidal effects. Structure modifications of I (R¹ = 4-F, R² = H), the prototype of a new class of sodium-independent atypical dopamine D-2 antagonists, resultes in II (R² = F, X = imino-7-benzofuranyl) (III), which was an even more potent and selective D-2 antagonist than the parent compound The excellent oral activity in the apomorphine-induced climbing behavior and the conditioned avoidance response tests and the absence of catalepsy make III particularly promising as a potential antipsychotic with a low propensity to induce acute extrapyramidal side effects. 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. Piperidine is a saturated organic heteromonocyclic parent, an azacycloalkane, a secondary amine and a member of piperidines. 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.Synthetic Route of C12H17NO

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem