Day: October 18, 2022

《Design, synthesis and biological activities of novel pleuromutilin derivatives with a substituted triazole moiety as potent antibacterial agents》 was written by Zhang, Zhe; Li, Kang; Zhang, Guang-Yu; Tang, You-Zhi; Jin, Zhen. Safety of 2-(Piperidin-4-yl)ethanol And the article was included in European Journal of Medicinal Chemistry in 2020. The article conveys some information:

A series of novel pleuromutilin derivatives possessing 1,2,3-triazole moieties, I (R1 = NEt2, 4-hydroxypiperidin-1-yl, pyrrolidin-1-yl, etc.) and II (R2 = Me, Ph, 2-ClC6H4, 3-FC6H4, etc.), were synthesized via click reactions under mild conditions. The in vitro antibacterial activities of these derivatives against four strains of S. aureus (MRSA ATCC 43300, ATCC 29213, AD 3, and 144) and one strain of E. coli (ATCC 25922) were tested by the broth dilution method. The majority of the synthesized derivatives displayed potent antibacterial activities against MRSA (MIC = 0.125-2μg/mL). It was also found that most compounds had no significant inhibitory effect on the proliferation of RAW264.7 cells at the concentration of 8μg/mL. Among these derivatives, compound I (R1 = NMe2) (III) (∼1.71 log10 CFU/g) containing dimethylamine group side chain displayed more effective activity than tiamulin (∼0.77 log10 CFU/g) at a dose of 20 mg/kg in reducing MRSA load in thigh infected mice. Addnl., compound III (survival rate was 50%) also displayed superior in vivo efficacy to that of tiamulin (survival rate was 20%) in the mouse systemic model. Structure-activity relationship (SAR) studies resulted in compound III with the most potent in vitro and in vivo antibacterial activity among the series. Moreover, compound III was evaluated in CYP450 inhibition assay and showed moderate in vitro inhibition of CYP3A4 (IC50 = 6.148μM).2-(Piperidin-4-yl)ethanol(cas: 622-26-4Safety of 2-(Piperidin-4-yl)ethanol) was used in this study.

2-(Piperidin-4-yl)ethanol(cas: 622-26-4) have been used as an intermediate in the synthetic preparation of cellular-active allosteric inhibitors of FAKSafety of 2-(Piperidin-4-yl)ethanol

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Hammock, Bruce D.; McReynolds, Cindy B.; Wagner, Karen; Buckpitt, Alan; Cortes-Puch, Irene; Croston, Glenn; Lee, Kin Sing Stephen; Yang, Jun; Schmidt, William K.; Hwang, Sung Hee published an article in 2021. The article was titled 《Movement to the Clinic of Soluble Epoxide Hydrolase Inhibitor EC5026 as an Analgesic for Neuropathic Pain and for Use as a Nonaddictive Opioid Alternative》, and you may find the article in Journal of Medicinal Chemistry.Reference of tert-Butyl 4-aminopiperidine-1-carboxylate The information in the text is summarized as follows:

This report describes the development of an orally active analgesic that resolves inflammation and neuropathic pain without the addictive potential of opioids. EC5026 (I) acts on the cytochrome P 450 branch of the arachidonate cascade to stabilize epoxides of polyunsaturated fatty acids (EpFA), which are natural mediators that reduce pain, resolve inflammation, and maintain normal blood pressure. EC5026 is a slow-tight binding transition-state mimic that inhibits the soluble epoxide hydrolase (sEH) at picomolar concentrations The sEH rapidly degrades EpFA; thus, inhibiting sEH increases EpFA in vivo and confers beneficial effects. This mechanism addresses disease states by shifting endoplasmic reticulum stress from promoting cellular senescence and inflammation toward cell survival and homeostasis. We describe the synthesis and optimization of EC5026 and its development through human Phase 1a trials with no drug-related adverse events. Addnl., we outline fundamental work leading to discovery of the analgesic and inflammation-resolving CYP450 branch of the arachidonate cascade. In addition to this study using tert-Butyl 4-aminopiperidine-1-carboxylate, there are many other studies that have used tert-Butyl 4-aminopiperidine-1-carboxylate(cas: 87120-72-7Reference of tert-Butyl 4-aminopiperidine-1-carboxylate) was used in this study.

tert-Butyl 4-aminopiperidine-1-carboxylate(cas: 87120-72-7) belongs to anime. Acylation is one of the most important reactions of primary and secondary amines; a hydrogen atom is replaced by an acyl group (a group derived from an acid, such as RCOOH or RSO3H, by removal of ―OH, such as RC(=O)―, RS(O)2―, and so on). Reagents may be acid chlorides (RCOC1, RSO2C1), anhydrides ((RCO)2O), or even esters (RCOOR′); the products are amides of the corresponding acids.Reference of tert-Butyl 4-aminopiperidine-1-carboxylate

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Srivastava, Vikash; Singh, Surya Pal published an article in 2021. The article was titled 《A facile and regioselective synthesis of t-butyl 4-(5-amino-6-methoxy-2H-indazol-2-yl)piperidine-1-carboxylates and their antiprotozoal activity》, and you may find the article in Chemistry & Biology Interface.Electric Literature of C10H20N2O2 The information in the text is summarized as follows:

Herein, a series of tert-Bu 4-(5-amino-6-methoxy-2H-indazol-2-yl)piperidine-1-carboxylate derivatives were synthesized and evaluated for antiprotozoal activity. Metronidazole and Albendazole were used as reference drugs and compounds I, II and III were found antagonistic to the three protozoa. Nevertheless, all the tested compounds exhibited potency as antiprotozoal agents, with metronidazole being superior to the drug of choice in almost all cases. The experimental part of the paper was very detailed, including the reaction process of tert-Butyl 4-aminopiperidine-1-carboxylate(cas: 87120-72-7Electric Literature of C10H20N2O2)

tert-Butyl 4-aminopiperidine-1-carboxylate(cas: 87120-72-7) belongs to anime. Amine, any member of a family of nitrogen-containing organic compounds that is derived, either in principle or in practice, from ammonia (NH3). Naturally occurring amines include the alkaloids, which are present in certain plants; the catecholamine neurotransmitters (i.e., dopamine, epinephrine, and norepinephrine); and a local chemical mediator, histamine, that occurs in most animal tissues.Electric Literature of C10H20N2O2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Yang, Xiao-Guang; Du, Feng-Huan; Li, Jun-Jie; Zhang, Chi published an article in 2022. The article was titled 《Late-Stage Dehydroxyazidation of Alcohols Promoted by Trifunctional Hypervalent Azido-Iodine(III) Reagents》, and you may find the article in Chemistry – A European Journal.Related Products of 109384-19-2 The information in the text is summarized as follows:

A practical method for dehydroxyazidation of alcs. via an SN2 pathway involving PPh3 and trifunctional benziodazolone-based hypervalent azido-iodine(III) reagents, which function as an electrophilic center, an azido source and a base was reported. This mild, chemoselective method was used for late-stage azidation of structurally complex alcs., as well as for a new synthetic route to the antiepileptic drug rufinamide. The reaction mechanism was also investigated both exptl. and computationally. The experimental process involved the reaction of tert-Butyl 4-hydroxypiperidine-1-carboxylate(cas: 109384-19-2Related Products of 109384-19-2)

tert-Butyl 4-hydroxypiperidine-1-carboxylate(cas:109384-19-2) is a 4-hydroxypyridine with a boc protecting group used in the preparation of neurologically active agents and other pharmaceutical compounds.Related Products of 109384-19-2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

In 2022,Nagarale, Rajaram. K.; Bavdane, Priyanka P.; Sreenath, Sooraj; Pawar, Chetan M.; Dave, Vidhiben; Satpati, A. K. published an article in Journal of Polymer Research. The title of the article was 《Polyaniline derivatized anion exchange membrane for acid recovery》.Related Products of 1445-73-4 The author mentioned the following in the article:

Herein we are demonstrating the utility of an aniline derivatized anion exchange membrane for acid recovery by diffusion dialysis. The membrane was synthesized by oxidative polymerization of N-Methyl-4-piperidone derivative and confirmed by detailed spectroscopic characterisations. Free-standing membranes M1 and M2 was obtained by addition of different amount of PVA. For the comparison purpose, PVA blend with neat polyaniline was synthesized. Excellent physicochem. properties coupled with outstanding chem. stability in bentonite mine effluent with total acid concentration of ∼ 8 M, drawn interest to use in acid recovery by diffusion dialysis. In a simulated solution containing 6% iron and 3.5 M HCl, calculated proton dialysis coefficient (UH+) was 31 x 10-3 m h-1 and iron dialysis coefficient (UFe2+) was 3 x 10-4 m h-1 for the best membrane M2. It corresponded to separation factor (S) of 103 units, which was comparable with literature known best membranes like Neosepta. For effluent solution obtained from a local bentonite mine, membrane M2 showed UH+ value of 37 x 10-3 m h-1 and UFe2+ value of 6 x 10-4 m h-1 suggesting its best utility in acid recovery. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-piperidone(cas: 1445-73-4Related Products 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.Related Products of 1445-73-4

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

COA of Formula: C10H20N2O2In 2022 ,《Design and synthesis of dual inhibitors targeting snail and histone deacetylase for the treatment of solid tumor cancer》 appeared in European Journal of Medicinal Chemistry. The author of the article were Cui, Hao; Huang, Jingkun; Lei, Yan; Chen, Quanwei; Hu, Zan; Niu, Jiaqi; Wei, Ran; Yang, Kang; Li, Hongmei; Lu, Tao; Zhu, Yong; Huang, Yatian. The article conveys some information:

In this work, a series of Snail/HDAC dual inhibitors I (R = H, F; R1 = (1H-pyrazol-3-yl)aminyl, [1-[(tert-butoxy)carbonyl]piperidin-4-yl]aminyl, morpholin-4-yl, [(4-fluorophenyl)methyl]aminyl, etc.) were synthesized. Compound I (R = F; R1 = (5-methyl-1H-pyrazol-3-yl)aminyl) displayed the most potent inhibitory activity against HDAC1 with an IC50 of 0.405μM, potent inhibition against Snail with a Kd of 0.180μM, and antiproliferative activity in HCT-116 cell lines with an IC50 of 0.0751μM. Compound I (R = F; R1 = (5-methyl-1H-pyrazol-3-yl)aminyl) showed a good inhibitory effect on NCI-H522 (GI50 = 0.0488μM), MDA-MB-435 (GI50 = 0.0361μM), and MCF7 (GI50 = 0.0518μM). Docking studies showed that compound I (R = F; R1 = (5-methyl-1H-pyrazol-3-yl)aminyl) can be well docked into the active binding sites of Snail and HDAC. Further studies showed that compound I (R = F; R1 = (5-methyl-1H-pyrazol-3-yl)aminyl) increased histone H4 acetylation in HCT-116 cells and decreased the expression of Snail protein to induce cell apoptosis. These findings highlight the potential for the development of Snail/HDAC dual inhibitors as anti-solid tumor cancer drugs. In the experiment, the researchers used tert-Butyl 4-aminopiperidine-1-carboxylate(cas: 87120-72-7COA of Formula: C10H20N2O2)

tert-Butyl 4-aminopiperidine-1-carboxylate(cas: 87120-72-7) belongs to anime. Examples of direct uses of amines and their salts are as corrosion inhibitors in boilers and in lubricating oils (morpholine), as antioxidants for rubber and roofing asphalt (diarylamines), as stabilizers for cellulose nitrate explosives (diphenylamine), as protectants against damage from gamma radiation (diarylamines), as developers in photography (aromatic diamines), as flotation agents in mining, as anticling and waterproofing agents for textiles, as fabric softeners, in paper coating, and for solubilizing herbicides.COA of Formula: C10H20N2O2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

《Synthesis and pharmacological evaluation of enantiomerically pure endo-configured KOR agonists with 2-azabicyclo[3.2.1]octane scaffold》 was published in Organic & Biomolecular Chemistry in 2021. These research results belong to Jonas, Hendrik; Aiello, Daniele; Frehland, Bastian; Lehmkuhl, Kirstin; Schepmann, Dirk; Koehler, Jens; Diana, Patrizia; Wuensch, Bernhard. Recommanded Product: (S)-1-tert-Butyl 2-ethyl 4-oxopiperidine-1,2-dicarboxylate The article mentions the following:

Conformationally restricted bicyclic KOR agonists 10 with an endo-configured amino moiety were synthesized to analyze the bioactive conformation of conformationally flexible KOR agonists such as 2-5. A seven-step synthesis starting with (S)-configured 4-oxopiperidine-2-carboxylate 13 was developed. cis- and trans-configured diesters 12 were obtained in a 3 : 1 ratio via hydrogenation of the α,β-unsaturated ester 14. After establishment of the bicyclic scaffold, a diastereoselective reductive amination of ketone 11 provided exclusively the endo-configured bicyclic amines 10a,b. The 3 : 1 mixtures of enantiomers were separated by chiral HPLC, resp., leading to enantiomerically pure KOR agonists (1S,5S,7R)-10a,b and (1R,5R,7S)-10a,b (ent-10a,b). The KOR affinity was determined in receptor binding studies with the radioligand [3H]U-69 593. The high KOR affinity of endo-configured amines 10a (Ki = 7 nM) and 10b (Ki = 13 nM) indicates that the dihedral angle of the KOR pharmacophoric element N(pyrrolidine)-C-C-N(phenylacetyl) of 42° is close to the bioactive conformation of more flexible KOR agonists. It should be noted that changing the configuration of potent and selective KOR agonists 10a and 10b led to potent and selective σ1 ligands (e.g. ent-10aKi(σ1) = 10 nM). The experimental process involved the reaction of (S)-1-tert-Butyl 2-ethyl 4-oxopiperidine-1,2-dicarboxylate(cas: 180854-44-8Recommanded Product: (S)-1-tert-Butyl 2-ethyl 4-oxopiperidine-1,2-dicarboxylate)

(S)-1-tert-Butyl 2-ethyl 4-oxopiperidine-1,2-dicarboxylate(cas: 180854-44-8) 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.Recommanded Product: (S)-1-tert-Butyl 2-ethyl 4-oxopiperidine-1,2-dicarboxylate

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Name: Piperidine-4-carboxamideOn March 10, 2022, Beuchel, Andreas; Robaa, Dina; Negatu, Dereje A.; Madani, Abdeldjalil; Alvarez, Nadine; Zimmerman, Matthew D.; Richter, Adrian; Mann, Lea; Hoenke, Sophie; Csuk, Rene; Dick, Thomas; Imming, Peter published an article in ACS Medicinal Chemistry Letters. The article was 《Structure-Activity Relationship of Anti-Mycobacterium abscessus Piperidine-4-carboxamides, a New Class of NBTI DNA Gyrase Inhibitors》. The article mentions the following:

Mycobacterium abscessus causes difficult-to-cure pulmonary infections. The bacterium is resistant to most anti-infective agents, including first line antituberculosis (anti-TB) drugs. MMV688844 (844) is a piperidine-4-carboxamide (P4C) with bactericidal properties against M. abscessus. We recently identified DNA gyrase as the mol. target of 844. Here, we present in silico docking and genetic evidence suggesting that P4Cs display a similar binding mode to DNA gyrase as gepotidacin. Gepotidacin is a member of the Novel Bacterial Topoisomerase Inhibitors (NBTIs), a new class of nonfluoroquinolone DNA gyrase poisons. Thus, our work suggests that P4Cs present a novel structural subclass of NBTI. We describe structure-activity relationship studies of 844 leading to analogs showing increased antibacterial activity. Selected derivatives were tested for their inhibitory activity against recombinant M. abscessus DNA gyrase. Further optimization of the lead structures led to improved stability in mouse plasma and increased oral bioavailability. The results came from multiple reactions, including the reaction of Piperidine-4-carboxamide(cas: 39546-32-2Name: Piperidine-4-carboxamide)

Piperidine-4-carboxamide(cas: 39546-32-2) belongs to anime. Acylation is one of the most important reactions of primary and secondary amines; a hydrogen atom is replaced by an acyl group (a group derived from an acid, such as RCOOH or RSO3H, by removal of ―OH, such as RC(=O)―, RS(O)2―, and so on). Reagents may be acid chlorides (RCOC1, RSO2C1), anhydrides ((RCO)2O), or even esters (RCOOR′); the products are amides of the corresponding acids.Name: Piperidine-4-carboxamide

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Safety of Piperidine-4-carboxamideOn May 1, 2020 ,《Translation of the copper/bipyridine-promoted Petasis reaction to solid phase-coupled DNA for encoded library synthesis》 appeared in Bioorganic & Medicinal Chemistry. The author of the article were Potowski, Marco; Esken, Robin; Brunschweiger, Andreas. The article conveys some information:

The Petasis three-component reaction gives rise to diverse substituted α-aryl glycines from readily available amines, boronic acids and glyoxalic acid. Thus, this reaction is highly attractive for DNA-encoded small mol. screening library synthesis. The Petasis reaction is for instance promoted by a potentially DNA damaging copper(I)/bipyridine reagent system in dry organic solvents. We found that solid phase-coupled DNA strands tolerated this reagent system at elevated temperature allowing for synthesis of diverse substituted DNA-tagged α-aryl glycines from DNA-conjugated secondary amines. The experimental part of the paper was very detailed, including the reaction process of Piperidine-4-carboxamide(cas: 39546-32-2Safety of Piperidine-4-carboxamide)

Piperidine-4-carboxamide(cas: 39546-32-2) belongs to anime. Left-handed and right-handed forms (mirror-image configurations, known as optical isomers or enantiomers) are possible when all the substituents on the central nitrogen atom are different (i.e., the nitrogen is chiral). With amines, there is extremely rapid inversion in which the two configurations are interconverted.Safety of Piperidine-4-carboxamide

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

SDS of cas: 59234-40-1On September 30, 2017 ,《Stereo-selective preparation of teneraic acid, trans-(2S,6S)-piperidine-2,6-dicarboxylic acid, via anodic oxidation and cobalt-catalyzed carbonylation》 was published in Chemical & Pharmaceutical Bulletin. The article was written by Amino, Yusuke; Nishi, Seiichi; Izawa, Kunisuke. The article contains the following contents:

Teneraic acid (piperidine-2,6-dicarboxylic acid) is a naturally occurring imino acid that comprises of three stereoisomers due to its two asym. centers at C2 and C6. The configuration of natural teneraic acid is reported to correspond to trans-(2S,6S). However, a few studies are focused on the stereospecific synthesis of trans-(2S,6S)-teneraic acid. The present study investigates a convenient synthetic method that includes regiospecific anodic oxidation and stereospecific cobalt-catalyzed carbonylation to obtain trans-(2S,6S)-teneraic acid. Me (S)-N-benzoyl-α-methoxypipecolate, the key intermediate that displays a structure that corresponds to an intermediate (N-α-hydroxyalkyl amide) of intramol. amidocarbonylation, was obtained via an anodic oxidation of Me (S)-N-benzoylpipecolate. Subsequently, cobalt-catalyzed carbonylation converted the Me (S)-N-benzoyl-α-methoxypipecolate to trans-(2S,6S)-N-benzoyl-teneraic acid di-Me ester in good optical purity (>95% enantiomeric excess (ee)) and modest yield (63%). Finally, de-protection occurred via acidic hydrolysis to obtain trans-(2S,6S)-teneraic acid. The stereochem. of synthesized teneraic acid was confirmed as corresponding to trans-(2S,6S) by comparing its phys. properties with those of a cis-meso-isomer and those of a trans-(2S,6S)-isomer that were reported in previous studies. In the experiment, the researchers used 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-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.SDS of cas: 59234-40-1

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem