Day: October 11, 2022

Quality Control of 4-Amino-1-benzylpiperidine-4-carbonitrileOn May 1, 2007 ,《Identification of a novel class of succinyl-nitrile-based Cathepsin S inhibitors》 appeared in Bioorganic & Medicinal Chemistry Letters. The author of the article were Bekkali, Younes; Thomson, David S.; Betageri, Raj; Emmanuel, Michel J.; Hao, Ming-Hong; Hickey, Eugene; Liu, Weimin; Patel, Usha; Ward, Yancey D.; Young, Erick R. R.; Nelson, Richard; Kukulka, Alison; Brown, Maryanne L.; Crane, Kathy; White, Della; Freeman, Dorothy M.; Labadia, Mark E.; Wildeson, Jessi; Spero, Denice M.. The article conveys some information:

The synthesis and in vitro activities of a series of succinyl-nitrile-based inhibitors of Cathepsin S I [R1 = cyclohexyl, 4-methylcyclohexyl, 2-indanyl, etc.; R2 = H, R3 = PhCH2CH2, PhCH2OCH2, 4-ClC6H4CH2OCH2; R2R3 = CH2CH2, (CH2)2N(cyclo-C6H11)CH2, (CH2)2NMe(CH2)2, etc.] are described. Several members of this class show nanomolar inhibition of the target enzyme as well as cellular potency. The inhibitors displaying the greatest potency contain N-alkyl-substituted piperidine and pyrrolidine rings spiro-fused to the α-carbon of the P1 residue. In the part of experimental materials, we found many familiar compounds, such as 4-Amino-1-benzylpiperidine-4-carbonitrile(cas: 136624-42-5Quality Control of 4-Amino-1-benzylpiperidine-4-carbonitrile)

4-Amino-1-benzylpiperidine-4-carbonitrile(cas: 136624-42-5) belongs to anime. The reaction of alkyl halides, R―X, where X is a halogen, or analogous reagents with ammonia (or amines) is useful with certain compounds. Not all alkyl halides are effective reagents; the reaction is sluggish with secondary alkyl groups and fails with tertiary ones. Its usefulness is largely confined to primary alkyl halides (those having two hydrogen atoms on the reacting site).Quality Control of 4-Amino-1-benzylpiperidine-4-carbonitrile

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Pasqualetto, Gaia; Pileggi, Elisa; Schepelmann, Martin; Varricchio, Carmine; Rozanowska, Malgorzata; Brancale, Andrea; Bassetto, Marcella published their research in European Journal of Medicinal Chemistry on December 15 ,2021. The article was titled 《Ligand-based rational design, synthesis and evaluation of novel potential chemical chaperones for opsin》.Electric Literature of C6H12N2O The article contains the following contents:

Inherited blinding diseases retinitis pigmentosa (RP) and a subset of Leber’s congenital amaurosis (LCA) are caused by the misfolding and mistrafficking of rhodopsin mols., which aggregate and accumulate in the endoplasmic reticulum (ER), leading to photoreceptor cell death. One potential therapeutic strategy to prevent the loss of photoreceptors in these conditions is to identify opsin-binding compounds that act as chem. chaperones for opsin, aiding its proper folding and trafficking to the outer cell membrane. Aiming to identify novel compounds with such effect, a rational ligand-based approach was applied to the structure of the visual pigment chromophore, 11-cis-retinal, and its locked analog 11-cis-6mr-retinal. Following mol. docking studies on the main chromophore binding site of rhodopsin, 49 novel compounds, e.g., I, were synthesized according to optimized one-to seven-step synthetic routes. These agents were evaluated for their ability to compete for the chromophore binding site of opsin, and their capacity to increase the trafficking of the P23H opsin mutant from the ER to the cell membrane. Different new mols. displayed an effect in at least one assay, acting either as chem. chaperones or as stabilizers of the 9-cis-retinal-rhodopsin complex. These compounds could provide the basis to develop novel therapeutics for RP and LCA. In the experiment, the researchers used many compounds, for example, Piperidine-4-carboxamide(cas: 39546-32-2Electric Literature of C6H12N2O)

Piperidine-4-carboxamide(cas: 39546-32-2) belongs to anime. Halogenation, in which one or more hydrogen atoms of an amine is replaced by a halogen atom, occurs with chlorine, bromine, and iodine, as well as with some other reagents, notably hypochlorous acid (HClO). With primary amines the reaction proceeds in two stages, producing N-chloro- and N,N-dichloro-amines, RNHCl and RNCl2, respectively. With tertiary amines, an alkyl group may be displaced by a halogen.Electric Literature of C6H12N2O

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

The author of 《Preparation and chiral recognition of new chiral stationary phases derived from cellulose microspheres》 were Jin, Fenfen; Zhang, Juan; Chen, Wei; Fan, Qingchun; Bai, Zhengwu. And the article was published in Wuhan University Journal of Natural Sciences in 2012. Name: (R)-N-(2,6-Dimethylphenyl)-1-propylpiperidine-2-carboxamide hydrochloride The author mentioned the following in the article:

A new way to prepare cellulose-type chiral stationary phases (CSPs) was established. Cellulose microspheres with a volume-average diameter of 11.5 m were prepared by an emulsion-solidification method. Three new CSPs were obtained by crosslinking the cellulose microspheres with terephthaloyl chloride (TPC), and then modifying the crosslinked microspheres with 4-methylbenzoyl chloride, 3,5-dimethylbenzoyl chloride and 3,5-dichlorobenzoyl chloride, resp. The microspheres and the CSPs were characterized by FTIR, element anal. and scanning electronic microscopy (SEM). The chiral recognition ability of the CSPs was evaluated with HPLC. The chromatog. results demonstrate that the CSP prepared from 3,5-dichlorobenzoyl chloride possesses better chiral recognition ability compared with two other CSPs. In addition to this study using (R)-N-(2,6-Dimethylphenyl)-1-propylpiperidine-2-carboxamide hydrochloride, there are many other studies that have used (R)-N-(2,6-Dimethylphenyl)-1-propylpiperidine-2-carboxamide hydrochloride(cas: 112773-90-7Name: (R)-N-(2,6-Dimethylphenyl)-1-propylpiperidine-2-carboxamide hydrochloride) was used in this study.

(R)-N-(2,6-Dimethylphenyl)-1-propylpiperidine-2-carboxamide hydrochloride(cas: 112773-90-7) belongs to piperidines. Piperidine derivatives are also used in solid-phase peptide synthesis (SPPS) and many degradation reactions. Name: (R)-N-(2,6-Dimethylphenyl)-1-propylpiperidine-2-carboxamide hydrochloride

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

In 2019,European Journal of Medicinal Chemistry included an article by Volodina, Yulia L.; Dezhenkova, Lyubov G.; Tikhomirov, Alexander S.; Tatarskiy, Victor V.; Kaluzhny, Dmitry N.; Moisenovich, Anastasia M.; Moisenovich, Mikhail M.; Isagulieva, Alexandra K.; Shtil, Alexander A.; Tsvetkov, Vladimir B.; Shchekotikhin, Andrey E.. Formula: C10H20N2O2. The article was titled 《New anthra[2,3-b]furancarboxamides: A role of positioning of the carboxamide moiety in antitumor properties》. The information in the text is summarized as follows:

The synthesis and antitumor properties of a series of new anthra[2,3-b]furan-2-carboxamides was presented. Vast majority of new derivatives were similarly cytotoxic to wild type tumor cell lines and their isogenic sublines with P-glycoprotein overexpression and/or p53 inactivation. Comparison of structurally close derivatives varying in their position relative to the furan moiety, i.e., furan-3-carboxamide vs furan-2-carboxamides, revealed fundamental differences in the cytotoxicity profiles, formation of drug-DNA complexes, efficacy of topoisomerase 1 inhibition and mechanisms of tumor cell death. Together with previous SAR data on the role of individual substituents, these results provided evidence that regioisomerization of anthra[2,3-b]furancarboxamides generated the practically perspective derivatives whose properties varied significantly.tert-Butyl 4-aminopiperidine-1-carboxylate(cas: 87120-72-7Formula: C10H20N2O2) was used in this study.

tert-Butyl 4-aminopiperidine-1-carboxylate(cas: 87120-72-7) 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.Formula: C10H20N2O2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

《Diverse functionalization of strong alkyl C-H bonds by undirected borylation》 was published in Science (Washington, DC, United States) in 2020. These research results belong to Oeschger, Raphael; Su, Bo; Yu, Isaac; Ehinger, Christian; Romero, Erik; He, Sam; Hartwig, John. COA of Formula: C10H19NO3 The article mentions the following:

In the presence of a catalyst generated from [Ir(cod)(OMe)]2 and 2-methyl-1,10-phenanthroline, alkanes (including alcs., ethers, and protected amines) and cycloalkanes, cyclic ethers, and protected nitrogen heterocycles underwent undirected and regioselective borylation with B2(pin)2 (at primary C-H bonds in alkanes with unblocked primary C-H bonds, at secondary C-H bonds in cycloalkanes, and at secondary bonds β to heteroatoms in cyclic ethers and nitrogen heterocycles) in cyclooctane to yield alkyl, cycloalkyl, and heterocyclyl boronates. The product boronates were used in a variety of post-functionalization reactions; the method allows functionalization of organic mols. at positions inaccessible by previous methods. The mechanism and kinetics of the borylation was studied through kinetic isotope effect experiments using deuterated substrates and partially deuterated methylphenanthrolines and by determination of the kinetics of borylation of various substrates using 1,10-phenanthroline ligands. The results came from multiple reactions, including the reaction of tert-Butyl 4-hydroxypiperidine-1-carboxylate(cas: 109384-19-2COA of Formula: C10H19NO3)

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.COA of Formula: C10H19NO3

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Bessieres, Maxime; Plebanek, Elzbieta; Chatterjee, Payel; Shrivastava-Ranjan, Punya; Flint, Mike; Spiropoulou, Christina F.; Warszycki, Dawid; Bojarski, Andrzej J.; Roy, Vincent; Agrofoglio, Luigi A. published an article in 2021. The article was titled 《Design, synthesis and biological evaluation of 2-substituted-6-[(4-substituted-1-piperidyl)methyl]-1H-benzimidazoles as inhibitors of ebola virus infection》, and you may find the article in European Journal of Medicinal Chemistry.Recommanded Product: tert-Butyl 4-hydroxypiperidine-1-carboxylate The information in the text is summarized as follows:

Novel 2-substituted-6-[(4-substituted-1-piperidyl)methyl]-1H-benzimidazoles were designed and synthesized as Ebola virus inhibitors. The proposed structures of the new prepared benzimidazole-piperidine hybrids were confirmed based on their spectral data and CHN analyses. The target compounds were screened in vitro for their anti-Ebola activity. Among tested mols., compounds 26a (EC50 = 0.93μM, SI = 10) and 25a (EC50 = 0.64μM, SI = 20) were as potent as and more selective than Toremifene reference drug (EC50 = 0.38μM, SI = 7) against cell line. Probably the mechanism by which 25a and 26a block EBOV infection is through the inhibition of viral entry at the level of NPC1. Also, a docking study revealed that several of the NPC1 amino acids that participate in binding to GP are involved in the binding of the most active compounds 25a and 26a. Finally, in silico ADME prediction indicates that 26a is an idealy drug-like candidate. The authors’ results could enable the development of small mol. drug capable of inhibiting Ebola virus, especially at the viral entry step. In the experiment, the researchers used tert-Butyl 4-hydroxypiperidine-1-carboxylate(cas: 109384-19-2Recommanded Product: tert-Butyl 4-hydroxypiperidine-1-carboxylate)

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.Recommanded Product: tert-Butyl 4-hydroxypiperidine-1-carboxylate

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Name: 2-(Piperidin-4-yl)ethanolIn 2020 ,《Discovery of 2-(4-(2-fluoroethoxy)piperidin-1-yl)-9-methyl-9H-pyrrolo[2,3-b:4,5-c’]dipyridine ([18F]PI-2014) as PET tracer for the detection of pathological aggregated tau in Alzheimer’s disease and other tauopathies》 appeared in European Journal of Medicinal Chemistry. The author of the article were Gabellieri, Emanuele; Capotosti, Francesca; Molette, Jerome; Sreenivasachary, Nampally; Mueller, Andre; Berndt, Mathias; Schieferstein, Hanno; Juergens, Tanja; Varisco, Yvan; Oden, Felix; Schmitt-Willich, Heribert; Hickman, David; Dinkelborg, Ludger; Stephens, Andrew; Pfeifer, Andrea; Kroth, Heiko. The article conveys some information:

The compound screening was initiated with a direct staining assay to identify compounds binding to Tau aggregates and not Abeta plaques using human brain sections derived from late stage Alzheimer’s disease donors. The binding of Tau aggregate selective compounds was then quant. assessed with human brain derived paired helical filaments utilizing the label-free Back Scattering Interferometry assay. In vivo biodistribution experiments of selected fluorine-18 labeled compounds were performed in mice to assess brain uptake, brain washout, and defluorination. Compound 11 emerged as the most promising candidate, displaying high in vitro binding affinity and selectivity to neurofibrillary tangles. Fluorine-18 labeled compound 11 showed high brain uptake and rapid washout from the mouse brain with no observed bone uptake. Furthermore, compound 11 was able to detect Tau aggregates in tauopathy brain sections from corticobasal degeneration, progressive supranuclear palsy, and Pick’s disease donors. Thus, 2-(4-(2-fluoroethoxy)piperidin-1-yl)-9-methyl-9H-pyrrolo[2,3-b:4,5-c’]dipyridine (PI-2014, compound 11) was selected for characterization in a first-in-human study. 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: 622-26-4Name: 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 FAKName: 2-(Piperidin-4-yl)ethanol

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

《Piperidine-4-carboxamides target DNA gyrase in Mycobacterium abscessus》 was written by Negatu, Dereje Abate; Beuchel, Andreas; Madani, Abdeldjalil; Alvarez, Nadine; Chen, Chao; Aragaw, Wassihun Wedajo; Zimmerman, Matthew D.; Laleu, Benoit; Gengenbacher, Martin; Dartois, Veronique; Imming, Peter; Dicka, Thomas. SDS of cas: 39546-32-2 And the article was included in Antimicrobial Agents and Chemotherapy on August 31 ,2021. The article conveys some information:

New, more-effective drugs for the treatment of lung disease caused by nontuberculous mycobacteria (NTM) are needed. Among NTM opportunistic pathogens, Mycobacterium abscessus is the most difficult to cure and intrinsically multidrug resistant. In a whole-cell screen of a compound collection active against Mycobacterium tuberculosis, we previously identified the piperidine-4-carboxamide (P4C) MMV688844 (844) as a hit against M. abscessus. Here, we identified a more potent analog of 844 and showed that both the parent and improved analog retain activity against strains representing all three subspecies of the M. abscessus complex. Furthermore, P4Cs showed bactericidal and antibiofilm activity. Spontaneous resistance against the P4Cs emerged at a frequency of 10-8/CFU and mapped to gyrA and gyrB encoding the subunits of DNA gyrase. Biochem. studies with recombinant M. abscessus DNA gyrase showed that P4Cs inhibit the wild-type enzyme but not the P4C-resistant mutant. P4C-resistant strains showed limited cross-resistance to the fluoroquinolone moxifloxacin, which is in clin. use for the treatment of macrolide-resistant M. abscessus disease, and no cross-resistance to the benzimidazole SPR719, a novel DNA gyrase inhibitor in clin. development for the treatment of mycobacterial diseases. Analyses of P4Cs in recA promoter-based DNA damage reporter strains showed induction of recA promoter activity in the wild type but not in the P4C-resistant mutant background. This indicates that P4Cs, similar to fluoroquinolones, cause DNA gyrase-mediated DNA damage. Together, our results show that P4Cs present a novel class of mycobacterial DNA gyrase inhibitors with attractive antimicrobial activities against the M. abscessus complex. After reading the article, we found that the author used Piperidine-4-carboxamide(cas: 39546-32-2SDS of cas: 39546-32-2)

Piperidine-4-carboxamide(cas: 39546-32-2) belongs to anime. Amines characteristically form salts with acids; a hydrogen ion, H+, adds to the nitrogen. With the strong mineral acids (e.g., H2SO4, HNO3, and HCl), the reaction is vigorous. Salt formation is instantly reversed by strong bases such as NaOH. Neutral electrophiles (compounds attracted to regions of negative charge) also react with amines; alkyl halides (R′X) and analogous alkylating agents are important examples of electrophilic reagents.SDS of cas: 39546-32-2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

《Synthesis, characterization and antimicrobial activity of piperidine derivatives》 was published in Journal of the Chemical Society of Pakistan in 2019. These research results belong to Zafar, Shaista; Akhtar, Shamim; Ali, Syed Imran; Mushtaq, Nausheen; Naeem, Sabahat; Ali, Mohsin. Product Details of 39546-32-2 The article mentions the following:

Synthesis of various piperidine derivatives having important biol. and pharmacol. potentials has been discussed in the past. In present study we reported the synthesis of benzoyl and sulfonyl derivatives by taking Piperidine-4-carboxamide as principal mol. These compounds were characterized by various spectroscopic techniques such as NMR, FTIR and Mass spectrometry. Elemental composition was explored using CHN analyzer. Antimicrobial activity study of the synthesized compounds was performed using disk diffusion method. Dissociation constant (pKa) of the synthesized compounds were determined by potentiometric titration method. In addition The findings of the study predicted good absorption of these newly synthesized compounds Besides, compound III showed good antifungal activity which can be helpful in pharmacokinetics and pharmacodynamics approaches of antibiotics. In the experiment, the researchers used Piperidine-4-carboxamide(cas: 39546-32-2Product Details of 39546-32-2)

Piperidine-4-carboxamide(cas: 39546-32-2) belongs to anime. Amines have a free lone pair with which they can coordinate to metal centers. Amine–metal bonds are weaker because amines are incapable of backbonding, but they are still important for sensing applications.While stronger than hydrogen bonds, amine–metal bonds are still weaker than both covalent and ionic bonds.Product Details of 39546-32-2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Product Details of 194726-40-4On May 10, 2018 ,《Strategic Approaches to Overcome Resistance against Gram-Negative Pathogens Using β-Lactamase Inhibitors and β-Lactam Enhancers: Activity of Three Novel Diazabicyclooctanes WCK 5153, Zidebactam (WCK 5107), and WCK 4234》 appeared in Journal of Medicinal Chemistry. The author of the article were Papp-Wallace, Krisztina M.; Nguyen, Nhu Q.; Jacobs, Michael R.; Bethel, Christopher R.; Barnes, Melissa D.; Kumar, Vijay; Bajaksouzian, Saralee; Rudin, Susan D.; Rather, Philip N.; Bhavsar, Satish; Ravikumar, Tadiparthi; Deshpande, Prasad K.; Patil, Vijay; Yeole, Ravindra; Bhagwat, Sachin S.; Patel, Mahesh V.; van den Akker, Focco; Bonomo, Robert A.. The article conveys some information:

Limited treatment options exist to combat infections caused by multidrug-resistant (MDR) Gram-neg. bacteria possessing broad-spectrum β-lactamases. The design of novel β-lactamase inhibitors is of paramount importance. Here, three novel diazabicyclooctanes (DBOs), WCK 5153, zidebactam (WCK 5107), and WCK 4234 (compounds 1-3, resp.), were synthesized and biochem. characterized against clin. important bacteria. Compound 3 inhibited class A, C, and D β-lactamases with unprecedented k2/K values against OXA carbapenemases. Compounds 1 and 2 acylated class A and C β-lactamses rapidly but not the tested OXAs. Compounds 1-3 formed highly stable acyl-complexes as demonstrated by mass spectrometry. Crystallog. revealed that 1-3 complexed with KPC-2 adopted a “”chair conformation”” with the sulfate occupying the carboxylate binding region. The cefepime-2 and meropenem-3 combinations were effective in murine peritonitis and neutropenic lung infection models caused by MDR Acinetobacter baumannii. Compounds 1-3 are novel β-lactamase inhibitors that demonstate potent cross-class inhibition, and clin. studies targeting MDR infections are warranted. In the part of experimental materials, we found many familiar compounds, such as (R)-1-tert-Butyl 3-ethyl piperidine-1,3-dicarboxylate(cas: 194726-40-4Product Details of 194726-40-4)

(R)-1-tert-Butyl 3-ethyl piperidine-1,3-dicarboxylate(cas: 194726-40-4) 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.Product Details of 194726-40-4

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem