Month: January 2023

Tetrahydro-isoquinoline-Based Factor Xa Inhibitors was written by Kucznierz, Ralf;Grams, Frank;Leinert, Herbert;Marzenell, Klaus;Engh, Richard A.;von Saal, Wolfgang. And the article was included in Journal of Medicinal Chemistry in 1998.Synthetic Route of C7H13NO2 This article mentions the following:

(Amidinotetrahydroisoquinolinyloxy)phenylacetic acids were prepared as inhibitors of Factor Xa (fXa). The compounds were prepared using 15 synthetic steps on average The most potent compounds I (R = H, Et) and II (R = H, Et; R¹ = Me, 4-MeOC₆H₄, Et) display inhibition constants of K_i = 21-55 nM but do not inhibit thrombin and only weakly inhibit trypsin. They bear a second basic moiety, e.g., substituted 1-(iminomethyl)piperidines, which is linked to C-4 of the Ph group via an oxygen atom. The inhibition constants of these compounds are almost independent of the size of the (iminomethyl)piperidine substituent. Due to the fact that fXa displays two cation binding sites, namely, the S1 and S4 sites, in principle two binding modes are conceivable for the novel dibasic fXa inhibitors. Mol. modeling experiments based on the X-ray structures of uninhibited fXa and the DX-9065a/fXa complex were carried out. The results, taken together with the inhibition constants, favor one binding mode: the tetrahydro-isoquinoline fills the S1 pocket even better than the naphthalene moiety of DX-9065a, and the (iminomethyl)piperidine residues occupy the S4 site. In the experiment, the researchers used many compounds, for example, 1-(4-Hydroxypiperidin-1-yl)ethanone (cas: 4045-22-1Synthetic Route of C7H13NO2).

1-(4-Hydroxypiperidin-1-yl)ethanone (cas: 4045-22-1) 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 C7H13NO2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Cyano phosphate: an efficient intermediate for the chemoselective conversion of carbonyl compounds to nitriles was written by Yoneda, Ryuji;Harusawa, Shinya;Kurihara, Takushi. And the article was included in Journal of Organic Chemistry in 1991.Application In Synthesis of 1-Benzylpiperidine-4-carbonitrile This article mentions the following:

Cyanohydrin di-Et phosphates, readily obtained from various ketones and aldehydes by reaction with di-Et phosphorocyanidate and lithium cyanide, reacted chemoselectively with SmI₂ in THF to give the corresponding nitriles in excellent yields. This method was also found applicable to α,β-unsaturated carbonyl compounds via cyano phosphates to give β,γ-unsaturated nitriles, not obtainable by standard methods, without isomerization of the double bonds. In the experiment, the researchers used many compounds, for example, 1-Benzylpiperidine-4-carbonitrile (cas: 62718-31-4Application In Synthesis of 1-Benzylpiperidine-4-carbonitrile).

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. 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 In Synthesis of 1-Benzylpiperidine-4-carbonitrile

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Discovery of 3-Methyl-N-(1-oxy-3′,4′,5′,6′-tetrahydro-2’H-[2,4′-bipyridine]-1′-ylmethyl)benzamide (ABT-670), an Orally Bioavailable Dopamine D₄ Agonist for the Treatment of Erectile Dysfunction was written by Patel, Meena V.;Kolasa, Teodozyj;Mortell, Kathleen;Matulenko, Mark A.;Hakeem, Ahmed A.;Rohde, Jeffrey J.;Nelson, Sherry L.;Cowart, Marlon D.;Nakane, Masaki;Miller, Loan N.;Uchic, Marie E.;Terranova, Marc A.;El-Kouhen, Odile F.;Donnelly-Roberts, Diana L.;Namovic, Marian T.;Hollingsworth, Peter R.;Chang, Renjie;Martino, Brenda R.;Wetter, Jill M.;Marsh, Kennan C.;Martin, Ruth;Darbyshire, John F.;Gintant, Gary;Hsieh, Gin C.;Moreland, Robert B.;Sullivan, James P.;Brioni, Jorge D.;Stewart, Andrew O.. And the article was included in Journal of Medicinal Chemistry in 2006.Category: piperidines This article mentions the following:

The goal of this study was to identify a structurally distinct D₄-selective agonist with superior oral bioavailability to our first-generation clin. candidate 1a (ABT-724) for the potential treatment of erectile dysfunction. Arylpiperazines such as (heteroarylmethyl)piperazine 1a, benzamide 2, and acetamides such as 3a,b exhibit poor oral bioavailability. Structure-activity relationship (SAR) studies with the arylpiperidine template provided potent partial agonists such as 4d and 5k that demonstrated no improvement in oral bioavailability. Further optimization with the (N-oxy-2-pyridinyl)piperidine template led to the discovery of compound 6b (ABT-670), which exhibited excellent oral bioavailability in rat, dog, and monkey (68%, 85%, and 91%, resp.) with comparable efficacy, safety, and tolerability to 1a. The N-oxy-2-pyridinyl moiety not only provided the structural motif required for agonist function but also reduced metabolism rates. The SAR study leading to the discovery of 6b is described herein. In the experiment, the researchers used many compounds, for example, 4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8Category: piperidines).

4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8) 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 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

Development of Human Calcitonin Gene-Related Peptide (CGRP) Receptor Antagonists. Potent and Selective Small Molecule CGRP Antagonists. 1-[N²-[3,5-Dibromo-N-[[4-(3,4-dihydro-2(1H)-oxoquinazolin-3-yl)-1- piperidinyl]carbonyl]-D-tyrosyl]-L-lysyl]-4-(4-pyridinyl)piperazine: The First CGRP Antagonist for Clinical Trials in Acute Migraine was written by Rudolf, Klaus;Eberlein, Wolfgang;Engel, Wolfhard;Pieper, Helmut;Entzeroth, Michael;Hallermayer, Gerhard;Doods, Henri. And the article was included in Journal of Medicinal Chemistry in 2005.Recommanded Product: 58333-75-8 This article mentions the following:

Although the triptans have greatly improved the acute treatment of migraine headache, there are yet many shortcomings. Therefore, new strategies for the treatment of migraine are needed which offer advantages over current therapy, e.g. triptans. Our novel approach was based on the hypothesis that the release of calcitonin gene-related peptide (CGRP) could play a causative role in migraine headache. Thus the authors initiated a program aimed at the design and synthesis of small mol. CGRP receptor antagonists. High throughput screening led to the identification of (R)-Tyr-(S)-Lys dipeptide-like compounds that showed weak but unequivocal binding to the human CGRP receptor. Lead optimization afforded highly potent CGRP antagonists, the prototype being compound (I) (BIBN4096). This compound exhibiting a favorable biol. profile was selected for initial clin. trials. A proof of concept study indicated that i.v. application of I was effective in the treatment of acute migraine headache. This finding strongly supports our initial working hypothesis that CGRP plays an important role in the pathophysiol. of migraine. In the experiment, the researchers used many compounds, for example, 4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8Recommanded Product: 58333-75-8).

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. 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: 58333-75-8

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthesis and investigation of the nonlinear optical properties of various p-aminophenyl sulfone oligomers was written by Mitchell, Michael A.;Tomida, Masayuki;Padias, Anne Buyle;Hall, H. K. Jr.;Lackritz, Hilary S.;Robello, Douglas R.;Willand, Craig S.;Williams, David J.. And the article was included in Chemistry of Materials in 1993.Safety of 1-(4-Hydroxypiperidin-1-yl)ethanone This article mentions the following:

A series of p-aminophenyl sulfone oligomers (monomers, dimers, and trimers) was synthesized with the purpose of studying the effect of several consecutive dipolar units on their second-order nonlinear optical (NLO) characteristics. Three classes of oligomers were synthesized, namely with a hexamethylene, dimethylene, or piperidine spacer. The dipole moments of these oligomers and the μβ_z value, as measured by EFISH (elec. field induced second harmonic generation), are reported. The results show that these compounds, despite their head-to-tail arrangement, lack the structural features needed to display enhancement of the hyperpolarizability. In the experiment, the researchers used many compounds, for example, 1-(4-Hydroxypiperidin-1-yl)ethanone (cas: 4045-22-1Safety of 1-(4-Hydroxypiperidin-1-yl)ethanone).

1-(4-Hydroxypiperidin-1-yl)ethanone (cas: 4045-22-1) 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.Safety of 1-(4-Hydroxypiperidin-1-yl)ethanone

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthesis of hetero-aryl-piperazines and hetero-aryl-bipiperidines with a restricted side chain and their affinities for 5-HT_1A receptor was written by Yoo, Kyung Ho;Choi, Hyun Sik;Kim, Dong Chan;Shin, Kye Jung;Kim, Dong Jin;Song, Yun Seon;Jin, Changbae. And the article was included in Archiv der Pharmazie (Weinheim, Germany) in 2003.Reference of 33439-27-9 This article mentions the following:

Heteroarylpiperazine and heteroarylbipiperidine derivatives, bearing a 4-piperidine ring instead of an alkylamino side chain to give the semi-rigidity, were prepared and evaluated for their abilities to displace [³H]-8-OH-DPAT binding to the rat hippocampal synaptic membranes. These compounds showed low to moderate affinities for 5-HT_1A receptor, with Ki values ranging from 6912 nM to 232 nM. Of these compounds, I and II exhibited the best affinities for 5-HT_1A receptor with Ki values of 232 nM and 338 nM, resp. 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 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 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

New CNS agent precursors. A simple and efficient route for synthesis of 6-aminomethyl-4,5,6,7-tetrahydrobenzofuran-4-ones as conformationally constrained butyrophenone analogs was written by Casariego, Isabel;Masaguer, Christian F.;Ravina, Enrique. And the article was included in Tetrahedron Letters in 1997.Application In Synthesis of 4-(2-Methoxyphenyl)piperidine This article mentions the following:

Starting from 3,4,5-trimethoxybenzoic acid, we described a practical and efficient five-step synthesis of 6-aminomethyl-4,5,6,7-tetrahydrobenzofuran-4-ones as new CNS agent precursors in an overall yield of 20%. In the experiment, the researchers used many compounds, for example, 4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8Application In Synthesis of 4-(2-Methoxyphenyl)piperidine).

4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8) 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 In Synthesis of 4-(2-Methoxyphenyl)piperidine

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Heterocycle-derived β-S-enals as bifunctional linchpins for the catalytic synthesis of saturated heterocycles was written by Niu, Jingze;Willis, Michael C.. And the article was included in Organic Chemistry Frontiers in 2016.Application of 33439-27-9 This article mentions the following:

We demonstrated how heterocycle-derived β-S-enals can be employed as bifunctional substrates in a cascade of two rhodium-catalyzed C-C bond forming reactions to deliver substituted heterocyclic products. A single rhodium-catalyst, generated in situ from a com. salt and ligand combination, was used to promote both an initial alkene or alkyne hydroacylation reaction, and then a Suzuki-type cross-coupling, resulting in a three-component assembly of the targeted heterocycles. Substrates based on N-, O- and S-heterocycles were included, as were a range of alkenes, alkynes and boronic acid derivatives 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 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.Application of 33439-27-9

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Heteroatom-Directed Alkylcyanation of Alkynes was written by Nakao, Yoshiaki;Yada, Akira;Hiyama, Tamejiro. And the article was included in Journal of the American Chemical Society in 2010.HPLC of Formula: 62718-31-4 This article mentions the following:

Alkanenitriles having a heteroatom such as nitrogen, oxygen, and sulfur at the γ-position add across alkynes stereo- and regioselectively by nickel/Lewis acid catalysis to give highly substituted acrylonitriles. The heteroatom functionalities likely coordinate to the nickel center to make oxidative addition of the C-CN bonds of the alkyl cyanides kinetically favorable, forming a five-membered nickelacycle intermediate and, thus, preventing β-hydride elimination to allow the alkylcyanation reaction. In the experiment, the researchers used many compounds, for example, 1-Benzylpiperidine-4-carbonitrile (cas: 62718-31-4HPLC of Formula: 62718-31-4).

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. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.HPLC of Formula: 62718-31-4

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Umpolung Difunctionalization of Carbonyls via Visible-light Photoredox Catalytic Radical-Carbanion Relay was written by Wang, Shun;Cheng, Bei-Yi;Srsen, Matea;Koenig, Burkhard. And the article was included in Journal of the American Chemical Society in 2020.SDS of cas: 33439-27-9 This article mentions the following:

The combination of photoredox catalysis with the Wolff-Kishner (WK) reaction allows the difunctionalization of carbonyl groups by a radical-carbanion relay sequence (photo-Wolff-Kishner reaction). Photoredox initiated radical addition to N-sulfonylhydrazones yields α-functionalized carbanions following WK-type mechanism. With sulfur-centered radicals, the carbanions were further functionalized by reaction with electrophiles including CO₂ and aldehydes to gave phenylthio aryl acetic acids R¹C(SR²)(CO₂H)R³ [R¹ = 4-MeC₆H₃, 2-thienyl, Bn, etc.; R² = Ph, cyclohexyl, CH₂CH₂Ph, etc.; R³ = H, Me, cyclopropyl, etc.] and phenylthio aryl ethanols (R³)(R⁴)C(SPh)CH(OH)R⁵ [R³ = H, Me; R⁴ = Ph, 2-thienyl, 4-PhC₆H₄; R⁵ = H, Et, Ph, etc.], whereas CF₃ radical addition furnished a wide range of gem-difluoroalkenes R⁶R⁷C=CF₂ [R⁶ = Ph, CH₂C(O)NHPh, 4-PhC₆H₄CH₂; R⁷ = H, Me, Bn, etc.; R⁶R⁷ = CH₂N(Ts)CH₂, CH₂CH₂N(Ts)CH₂CH₂, CH₂CH₂N(Boc)CH₂CH₂, CH₂CH₂CH(t-Bu)CH₂CH₂, (CH₂)₁₁] through β-fluoride elimination of the generated α-CF₃ carbanions. More than 80 substrate examples demonstrated the broad applicability of this reaction sequence. A series of investigations including radical inhibition, deuterium labeling, fluorescence quenching, cyclic voltammetry and control experiments support the proposed radical-carbanion relay mechanism. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9SDS of cas: 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. 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.SDS of cas: 33439-27-9

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem