Tag: 100-200

《Development of phenazine-2,3-diol-based photosensitizers: effect of formyl groups on singlet oxygen generation》 was published in Materials Chemistry Frontiers in 2021. These research results belong to Ohira, Kazuki; Imato, Keiichi; Ooyama, Yousuke. Category: piperidines The article mentions the following:

Phenazine-2,3-diol derivatives KO-0-3, which have zero to three formyl groups, resp., have been developed as photosensitizers (PSs) possessing the ability to generate singlet oxygen (1O2). The photoabsorption bands of KO-0-3 are significantly red-shifted compared to those of phenazine-2,3-MOM (methoxymethyl) derivatives 5-8, whose hydroxy and formyl groups are protected, and have onsets at around 600-650 nm. Furthermore, the fluorescence quantum yields (Φfl) of KO-0-3 (Φfl = 0.024-0.097) are lower than those of 5-8 (Φfl = 0.34-0.46) in solution To gain insight into the 1O2 generation properties of KO-0-3, we evaluated the 1O2 quantum yields (ΦΔ) and rate constants (kobs), and demonstrated that KO-1-3 possess a higher ability to generate 1O2 under visible light irradiation than those of 5-8. Moreover, it was found that the ΦΔ values of KO-0-3 increase in the order of KO-0 (0.036) < KO-1 (0.22) < KO-2 (0.33) < KO-3 (0.41) with increasing number of formyl groups. This result indicates that formyl groups facilitate the intersystem crossing (ISC) from the lowest singlet excited states of the PSs (S1) to the triplet excited states (Tn) according to El-Sayed′s rule. Consequently, this work provides useful knowledge in mol. design of efficient phenazine-2,3-diol-based PSs for photodynamic therapy (PDT). In the experimental materials used by the author, we found Triacetonamine(cas: 826-36-8Category: piperidines)

Triacetonamine(cas: 826-36-8) is a member of piperidine. 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. Hence, continuous efforts have been made to develop convenient methods to prepare piperidine derivatives.Category: piperidines

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

《A stochastic model for the synthesis and degradation of natural organic matter. Part III: Modeling Cu(II) complexation》 was written by Cabaniss, Stephen E.; Maurice, Patricia A.; Madey, Greg. Quality Control of Cis-piperidine-2,6-dicarboxylic acid And the article was included in Applied Geochemistry on August 31 ,2007. The article conveys some information:

An agent-based biogeochem. model has been developed which begins with biochem. precursor mols. and simulates the transformation and degradation of natural organic matter (NOM). This paper presents an empirical quant. structure activity relationship (QSAR) which uses the numbers of ligand groups, charge d. and heteroatom d. of a mol. to estimate Cu-binding affinity (K’Cu) at pH 7.0 and ionic strength 0.10 for the mols. in this model. Calibration of this QSAR on a set of 41 model compounds gives a root mean square error of 0.88 log units and r2 =0.93. Two simulated NOM assemblages, one beginning with small mols. (tannins, terpenoids, flavonoids) and one with biopolymers (protein, lignin), give markedly different distributions of log K’Cu. However, calculations based on these log K’Cu distributions agree qual. with published exptl. Cu(II) titration data from river and lake NOM samples. In the part of experimental materials, we found many familiar compounds, such as Cis-piperidine-2,6-dicarboxylic acid(cas: 59234-40-1Quality Control of Cis-piperidine-2,6-dicarboxylic acid)

Cis-piperidine-2,6-dicarboxylic acid(cas: 59234-40-1) is a member of piperidine. Piperidine is ubiquitous structural motif widely occurred in diverse synthetically and naturally occurring bioactive molecules. Piperidines are an immensely important class of compounds medicinally: the piperidine ring is the most common heterocyclic subunit among FDA approved drugs.Quality Control of Cis-piperidine-2,6-dicarboxylic acid

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

In 2022,Yang, Chaofu; Sun, Xianyu; Li, Zhan; Cheng, Yunyun; Lei, Yu; Lu, Liang; Liu, Xuan; Zhuang, Xiaomei; Wang, Tao; He, Xinhua published an article in Journal of Molecular Structure. The title of the article was 《The effect of benzenesulfonamide′s side chains on their human carbonic anhydrase I/II inhibitory activities》.Category: piperidines The author mentioned the following in the article:

Benzenesulfonamides are well-known potent carbonic anhydrase inhibitors (CAIs). They are usually composed of benzenesulfonamide heads and hydrophobic side chain tails. However, hydrophobic side chain tails contribute to poor water solubility, which is a major challenge in the development of CAIs. Herein, to elaborate whether benzenesulfonamides with hydrophilic/hydrophobic tails are effective against carbonic anhydrases (CAs), 12 benzenesulfonamides containing hydrophilic tails and 16 benzenesulfonamides containing hydrophobic tails were designed and synthesized. Benzenesulfonamides with hydrophilic tails including 4b, 4c, and 5b and benzenesulfonamides with hydrophobic tails including 2e, 4b, and 4c are potent carbonic anhydrase I/II dual inhibitors whose Ki to CA I and CA II were below 10 nM, and below 50 nM, resp. However, the water solubility of 4b, 4c, and 5b was 52, 148, and 71 mg/100 g of water, resp., which is much better than that of benzenesulfonamides with hydrophobic tails. In a hypoxic mouse model, compounds 4c and 5b extended the survival of mice by 34.46% and 28.23%, resp., compared to the blank control. Treatment with 4c and 5b extended survival better than acetazolamide treatment did (16.86%). Moreover, 5b also has better anti-convulsant effect than AAZ. Mol. docking anal. demonstrated that hydrogen bonds between the oxygen atoms in the hydrophilic tails of 4b, 4c, and 5b and H2O in hCA I and hCA II protein facilitated ligand-receptor binding. Therefore, considering the good water solubility and potent CA I/II inhibition, 4c and 5b are worth exploring as therapeutic options for acute mountain sickness. In conclusion, benzenesulfonamides containing hydrophilic tails could offer innovative opportunities for potent, water-soluble anti-AMS (Acute Mountain Sickness) compounds In addition to this study using 2-(Piperidin-4-yl)ethanol, there are many other studies that have used 2-(Piperidin-4-yl)ethanol(cas: 622-26-4Category: piperidines) was used in this study.

2-(Piperidin-4-yl)ethanol(cas: 622-26-4) can be used to synthese ursolic acid derivatives, spiroimidazolidinone NPC1L1 inhibitors, neurokinin-2 receptor antagonists, antagonists for inhibition of platelet aggregation.Category: piperidines

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

In 2022,Zeng, Minghao; Liu, Wenqi; Guo, Haikun; Li, Tingting; Li, Qijia; Zhao, Chengji; Li, Xiaojin; Li, Haolong published an article in ACS Applied Energy Materials. The title of the article was 《Polyoxometalate-Cross-Linked Proton Exchange Membranes with Post-Assembled Nanostructures for High-Temperature Proton Conduction》.Safety of 1-Methyl-4-piperidone The author mentioned the following in the article:

High-temperature proton exchange membranes (HT-PEMs) are key components in high-temperature energy storage and conversion technologies, which require excellent proton conductivity and mech. strength. However, it is difficult for HT-PEMs to balance their mech. and conductive properties. Here, we present a strategy to prepare HT-PEMs based on the combination of polyoxometalate (POM)-dominated noncovalent crosslinking and H3PO4 (PA)-induced post-assembly. Hybrid membranes containing polyvinylpyrrolidone (PVP), poly(terphenyl piperidine) (PTP), and H3PW12O40 (PW) are prepared, where the polymers are electrostatically cross-linked by PW and maintain certain mobility. When the membranes adsorb PA, the polarity difference between the PVP-PW-PA moieties and the PTP-PW-PA moieties increases, causing the chains to rearrange into bicontinuous structures via a post-assembly process. The resultant membranes show a break strength over 7 MPa and a proton conductivity of ~55 mS cm-1 at 160°C. The high-temperature supercapacitors based on such membranes exhibit a specific capacitance of 145.4 F g-1 and a capacitance retention of 80% after 3000 charge-discharge cycles at 150°C. Their H2/air fuel cells display a peak power of 273.6 mW cm-2 at 160°C. This work provides a paradigm for using POMs as dynamic cross-linkers to fabricate nanostructured PEMs, which paves a feasible route to developing high-performance electrolyte materials. The experimental process involved the reaction of 1-Methyl-4-piperidone(cas: 1445-73-4Safety of 1-Methyl-4-piperidone)

1-Methyl-4-piperidone(cas: 1445-73-4) is a member of piperidine. Piperidine is ubiquitous structural motif widely occurred in diverse synthetically and naturally occurring bioactive molecules. Piperidines are an immensely important class of compounds medicinally: the piperidine ring is the most common heterocyclic subunit among FDA approved drugs.Safety of 1-Methyl-4-piperidone

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

《Structure activity relationship analysis of antiproliferative cyclic C5-curcuminoids without DNA binding: Design, synthesis, lipophilicity and biological activity》 was published in Journal of Molecular Structure in 2020. These research results belong to Huber, Imre; Rozmer, Zsuzsanna; Gyongyi, Zoltan; Budan, Ferenc; Horvath, Peter; Kiss, Eszter; Perjesi, Pal. Product Details of 1445-73-4 The article mentions the following:

The chem. susceptibility of the β-diketone linker between the two aromatic rings in the structure of curcumin to hydrolysis and metabolism has made it crucial to investigate structurally modified analogs of curcumin without such shortcomings. The synthesis of twenty cyclic C5-curcuminoids, I (R = NO2, Cl, H, MeO, NMe2, X = CHMe, NH, NMe, CHOH), is described in this study in order to gain more insight into their anticancer structure-activity relationship (SAR). The design of their synthesis included four different cyclanones and five substituted aromatic aldehydes to form four, five-membered subgroups. These model compounds were evaluated in vitro for antiproliferative activity in an XTT cell viability assay against MCF-7 human non-invasive breast adenocarcinoma cancer cells and Jurkat human T lymphocyte leukemia cells in five different concentrations (10 nM, 100 nM, 1μM, 10μM and 20μM). The majority of the compounds investigated have shown remarkable cytotoxicity with IC50 values in the range of 120 nM and 2μM with very high relative toxicity values to curcumin. The SAR conclusions are drawn and summarized. A method was developed and applied in a TLC based exptl. logP measurement, which is new for such C5-curcuminoids. The logP data and structural modifications have shown a strong correlation. The correlation of these exptl. logP and the corresponding IC50 values of the model-compounds were calculated according to the Pearson and Kendall correlation coefficient and showed weak concordance. The physicochem. behaviors of the majority of these compounds are in good accordance with Lipinski’s rule. The most promising compound is I (R = NO2, X = NH), which is the most active (IC50 = 0.12-0.32μM) and most potent (80 times of curcumin) compound with the lowest lipophilicity (exptl. logP = 3.22), which is important also from a pharmacokinetic point of view. The anal. of exptl. logP and computed ClogP values have revealed good agreement. These cyclic C5-curcuminoids in contrast to curcumin do not bind to natural DNA based on their CD spectra. The results came from multiple reactions, including the reaction of 1-Methyl-4-piperidone(cas: 1445-73-4Product Details of 1445-73-4)

1-Methyl-4-piperidone(cas: 1445-73-4) is a member of piperidine. 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. Hence, continuous efforts have been made to develop convenient methods to prepare piperidine derivatives.Product Details of 1445-73-4

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

In 2018,Demuth, Jiri; Kucera, Radim; Kopecky, Kamil; Havlinova, Zuzana; Libra, Antonin; Novakova, Veronika; Miletin, Miroslav; Zimcik, Petr published 《Efficient synthesis of a wide-range absorbing azaphthalocyanine dark quencher and its application to dual-labeled oligonucleotide probes for quantitative real-time polymerase chain reactions》.Chemistry – A European Journal published the findings.Category: piperidines The information in the text is summarized as follows:

Unsym. dialkylamino-substituted zinc azaphthalocyanine (AzaPc) exhibits unique spectral and photophys. properties for dark quenchers of fluorescence in DNA hybridization probes. The panchromatic light absorption of AzaPc from 300 nm up to at least 700 nm and its lack of fluorescence make it an ideal candidate for a universal dark quencher. To prove this exptl., oligodeoxyribonucleotide probes were labeled at the 3′-end by this AzaPc and at the 5′-end by a fluorophore used in the polymerase chain reaction (PCR)-i.e., fluorescein, CAL Fluor Red 610, and Cy5. AzaPc showed a significantly higher quenching efficiency compared to the com. available dark quenchers (BHQ-1, BHQ-2, BBQ-650) in a developed model of TaqMan PCR assay. The AzaPc-labeled probe proved to also be useful in a practical PCR assay for the quantification of the SLCO2B1 transporter gene expression. The constructed calibration curves indicated linearity in the range from 102 to 107 of target copies. After reading the article, we found that the author used 2-(Piperidin-4-yl)ethanol(cas: 622-26-4Category: piperidines)

2-(Piperidin-4-yl)ethanol(cas: 622-26-4) can be used to synthese ursolic acid derivatives, spiroimidazolidinone NPC1L1 inhibitors, neurokinin-2 receptor antagonists, antagonists for inhibition of platelet aggregation.Category: piperidines

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Spivak, Charles E.; Waters, James A.; Aronstam, Robert S. published an article in Molecular Pharmacology. The title of the article was 《Binding of semirigid nicotinic agonists to nicotinic and muscarinic receptors》.COA of Formula: C8H15NO2 The author mentioned the following in the article:

Isoarecolone methiodide (1-methyl-4-acetyl-1,2,3,6-tetrahydropyridine methiodide) was previously shown to be among the most potent agonists tested at the frog neuromuscular junction. Because nicotinic receptors from different sources vary in their selectivities, isoarecolone methiodide as well as 19 addnl. congeners, most of which were also previously tested at the frog neuromuscular junction, were studied in binding assays. Torpedo nobiliana was the tissue source for nicotinic receptors. Two types of experiments were conducted. The first evaluated the affinities of the agonists (including acetylcholine and carbamylcholine) for the recognition site by allowing the agonists to compete for that site with 125I-α-bungarotoxin. The inhibition potencies obtained correlated strongly (Spearman’s correlation coefficient, -0.91) with the potency obtained at the frog neuromuscular junction. The second type of experiment evaluated the agonists for their ability to activate the receptor. The binding of [3H]perhydrohistrionicotoxin, which was employed as an indicator of the activation of the receptor, was measured in the presence of each of the agonists. Isoarecolone methiodide was the most potent of all. A few of the agonists (partial agonists) were incapable of fully enhancing this binding. For the full agonists, the concentration that produced half of the maximum binding of [3H]perhydrohistrionicotoxin was defined as the EC50. The correlation coefficient (Spearman’s) for EC50 vs. potency at the frog neuromuscular junction was -0.73, indicating innate differences between Torpedo and frog receptors. In addition, these compounds were treated for their affinity at muscarinic receptors from rat brain. Competition experiments were carried out using [3H]N-methylscopolamine. The affinity of isoarecolone methiodide was only about 7-fold lower than that of acetylcholine and less than 2-fold lower than that of carbamylcholine. In contrast, 1-methyl-4-acetylpiperazine methiodide was much more selective for nicotinic receptors. Its activity was similar to isoarecolone methiodide at the nicotinic receptor, but it was among the weakest compounds in its affinity for the muscarinic receptor. The experimental process involved the reaction of Methyl 1-methylpiperidine-3-carboxylate(cas: 1690-72-8COA of Formula: C8H15NO2)

Methyl 1-methylpiperidine-3-carboxylate(cas: 1690-72-8) is a member of piperidine. Piperidine-containing compounds are also frequently employed in synthesis as ligands or auxiliaries. Accordingly, many efforts have been devoted to the development of novel methods for the synthesis of these compounds over the years.COA of Formula: C8H15NO2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Safety of Methyl 2-(1-methylpiperidin-4-yl)acetateOn May 3, 1985 ,《Synthetic applications of 2-cyano-1,2,3,6-tetrahydropyridines. 2. Synthesis of isodasycarpidone and related systems, the ervitsine skeleton and its benzo analog》 appeared in Journal of Organic Chemistry. The author of the article were Bosch, Joan; Rubiralta, Mario; Domingo, Antonio; Bolos, Jordi; Linares, Ana; Minguillon, Cristina; Amat, Mercedes; Bonjoch, Josep. The article conveys some information:

The synthesis of isodasycarpidone (I, R = Me, R1 = Et, R2 = H) N-demethylisodasycaripdone (I, R = H, R1 = Et, R2 = H) and their epi derivatives I (R = Me, R1 = H, R2 = Et; R = R1 = H, R2 = Et) is described. The condensation of an appropriate 2-cyano-1,2,3,6-tetrahydropyridine with indole and the conjugate addition of diethylcopper(I) magnesium bromide to the resulting α,β-unsaturated esters constitute the key steps of this synthesis. A similar condensation from methyl-2-cyano-1-methyl-1,2,3,6-tetrahydropyridine-4-acetate and indolylmagnesium iodide or (m-methoxyphenyl)magnesium bromide, followed by catalytic hydrogenation, hydrolysis, and cyclization by polyphosphoric acid establishes synthetic routes to the tetracyclic framework (II) of the indole alkaloid ervitsine and its benzo analog III. The experimental process involved the reaction of Methyl 2-(1-methylpiperidin-4-yl)acetate(cas: 95533-25-8Safety of Methyl 2-(1-methylpiperidin-4-yl)acetate)

Methyl 2-(1-methylpiperidin-4-yl)acetate(cas: 95533-25-8) is a member of piperidine. 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. Hence, continuous efforts have been made to develop convenient methods to prepare piperidine derivatives.Safety of Methyl 2-(1-methylpiperidin-4-yl)acetate

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Quality Control of Cis-piperidine-2,6-dicarboxylic acidOn November 30, 1985 ,《The characterization of the specific binding of [3H]-N-acetylaspartylglutamate to rat brain membranes》 appeared in Journal of Neuroscience. The author of the article were Koller, Kerry J.; Coyle, Joseph T.. The article conveys some information:

3H-labeled N-acetylaspartylglutamate (NAAG) [3106-85-2] bound saturably and reversibly to rat brain crude synaptosomal membranes. Optimal binding occurred in Tris-HCl buffer, pH 7.2, at 37°, using previously frozen, preincubated membranes. Saturation experiments revealed an apparent dissociation constant of 383 nm and a Bmax of 31 pmol/mg protein. [3H]NAAG specific binding was displaceable by serine-O-sulfate  [626-69-7], quisqualate  [52809-07-1], ibotenate  [2552-55-8], and glutamate  [56-86-0], with Ki values in the nanomolar range, whereas the amino-phosphono analogs displaced [3H]NAAG in the micromolar range. No specific binding was found in peripheral tissues. Within the central nervous system, the thalamus exhibited the greatest amount of binding, whereas binding was lowest in cortex. Ca2+ enhanced the specific binding, whereas Na+ caused a concentration-dependent inhibition. It appears that [3H]NAAG labels an acidic amino acid receptor site designated A-4, which recognizes the antagonist, 2-amino-4-phosphonobutyric acid, and this receptor may mediate the neurophysiol. effects of endogenous NAAG. After reading the article, we found that the author used Cis-piperidine-2,6-dicarboxylic acid(cas: 59234-40-1Quality Control of Cis-piperidine-2,6-dicarboxylic acid)

Cis-piperidine-2,6-dicarboxylic acid(cas: 59234-40-1) is a member of piperidine. Piperidine-containing compounds are also frequently employed in synthesis as ligands or auxiliaries. Accordingly, many efforts have been devoted to the development of novel methods for the synthesis of these compounds over the years.Quality Control of Cis-piperidine-2,6-dicarboxylic acid

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

《Enzyme-catalyzed hydrolysis of N-benzyloxycarbonyl-cis-2,6-(acetoxymethyl)piperidine. A facile route to optically active piperidines》 was written by Chenevert, Robert; Dickman, Michael. SDS of cas: 59234-40-1 And the article was included in Tetrahedron: Asymmetry on August 31 ,1992. The article conveys some information:

The first enzymic asymmetrization of a piperidine system is reported. Hydrolysis of N-benzyloxycarbonyl-cis-2,6-(acetoxymethyl)piperidine in the presence of Aspergillus niger lipase gave the corresponding 2R,6S monoacetate in good chem. yield and very high optical purity (ee ≥ 98%). In the experiment, the researchers used many compounds, for example, Cis-piperidine-2,6-dicarboxylic acid(cas: 59234-40-1SDS of cas: 59234-40-1)

Cis-piperidine-2,6-dicarboxylic acid(cas: 59234-40-1) is a member of piperidine. Piperidine is ubiquitous structural motif widely occurred in diverse synthetically and naturally occurring bioactive molecules. Piperidines are an immensely important class of compounds medicinally: the piperidine ring is the most common heterocyclic subunit among FDA approved drugs.SDS of cas: 59234-40-1

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem