Month: October 2022

Quality Control of 1-Methyl-4-piperidoneIn 2021 ,《Synthesis, Biological Evaluation, and Molecular Docking Studies of Some Spiro-5-Cyanopyrimidine Derivatives》 was published in Russian Journal of Bioorganic Chemistry. The article was written by Goda Pankaja Kumar; Sekhar, Thuraka; Thriveni, Pinnu; Venkateswarlu, Annavarapu; Peddanna, Kotha; Reddy, Peduri Suresh; Krishna, Mypati Hari; Sreelatha, Tumma. The article contains the following contents:

A simple, convenient, environmentally benign method has been developed for the synthesis of spiro-5-cyanopyrimidines by multi-component condensation of cyclic ketones, malononitrile and urea/thiourea using potassium carbonate in aqueous medium. The simple work-up procedure and good yield in short time are important features of this protocol. The synthesized compounds were tested for antibacterial activity against Gram pos. and Gram neg. bacteria and some of the tested compounds were found to have good antibacterial activities. Furthermore, docking study has been performed against enzyme of bacteria that showed good binding interactions. In the experiment, the researchers used 1-Methyl-4-piperidone(cas: 1445-73-4Quality Control 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.Quality Control of 1-Methyl-4-piperidone

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

《Aryl-indolyl maleimides as inhibitors of CaMKIIδ. Part 2: SAR of the amine tether》 was written by Levy, Daniel E.; Wang, Dan-Xiong; Lu, Qing; Chen, Zheng; Perumattam, John; Xu, Yong-jin; Higaki, Jeffrey; Dong, Hanmin; Liclican, Albert; Laney, Maureen; Mavunkel, Babu; Dugar, Sundeep. COA of Formula: C13H16N2 And the article was included in Bioorganic & Medicinal Chemistry Letters on April 1 ,2008. The article conveys some information:

A family of aryl-substituted maleimides was prepared and studied for their activity against calmodulin-dependant kinase. Inhibitory activities against the enzyme ranged from 34 nM to >20 μM and were dependant upon both the nature of the aryl group and the tether joining the basic amine to the indolyl maleimide core. Key interactions with the kinase ATP site and hinge region, predicted by homol. modeling, were confirmed. The experimental part of the paper was very detailed, including the reaction process of 1-(Piperidin-4-yl)-1H-indole(cas: 118511-81-2COA of Formula: C13H16N2)

1-(Piperidin-4-yl)-1H-indole(cas: 118511-81-2) belongs to piperidines. Piperidine derivatives are also used in solid-phase peptide synthesis (SPPS) and many degradation reactions. COA of Formula: C13H16N2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

《GC-MS analysis of bioactive components and evaluation of in-vitro pancreatic lipase inhibitory activity of aqueous extracts of Pleurotus eryngii》 was published in International Journal of Chemical Studies in 2021. These research results belong to Entooru, Keshamma; Srinivasalu, Krishnaprasad Musalappa; Thimmaiah, Sridhar Bilagumba; Rangappa, Haleshappa; Nanjaiah, Shivakumara Kanchidoddi; Kolgi, Rajeev Ramachandra; Bopaiah, Roy Uddapanda. Reference of Triacetonamine The article mentions the following:

Present study was designed to conduct with main purpose to determine bioactive components and evaluation of aqueous extract of Pleurotus eryngii for in-vitro pancreatic lipase inhibitory activity. GC-MS anal. was carried out to determine the bioactive components and in-vitro pancreatic lipase inhibitory assay was carried out to determine IC50 values of aqueous extracts of Pleurotus eryngii. The results of the present study depicted that the aqueous extracts of Pleurotus eryngii possess in-vitro pancreatic lipase inhibitory activities at the concentration of 1-30μg/mL and this could be attributed to the prevailing compounds identified in the GC-MS anal. i.e., conhydrin, di-Et phthalate, phthalic acid-Bu hex-3-yl ester (alkaloids), ar-turmerone (sesquiterpenoid), palmitic acid, myristic acid, phenol and benzoic acid from ethanolic extract of Pleurotus eryngii. In conclusion, polyphenols, alkaloids terpenoids and Vitamin B class of secondary metabolites majorly identified in GC-MS anal. of aqueous extract of Pleurotus eryngii has been reported to possess the in-vitro pancreatic lipase inhibitory activities. Hence, further in-vivo studies in exptl. induced obese animal models could be recommended to access the safety and efficacy of aqueous extracts of Pleurotus eryngii to strongly recommend them as natural antiobesity agents in the formulations of natural antiobesity drugs. The experimental part of the paper was very detailed, including the reaction process of Triacetonamine(cas: 826-36-8Reference of Triacetonamine)

Triacetonamine(cas: 826-36-8) 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.Reference of Triacetonamine

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Recommanded Product: 118511-81-2On March 1, 2014, Yang, Shyh-Ming; Tang, Yuting; Rano, Thomas; Lu, Huajun; Kuo, Gee-Hong; Gaul, Michael D.; Li, Yaxin; Ho, George; Lang, Wensheng; Conway, James G.; Liang, Yin; Lenhard, James M.; Demarest, Keith T.; Murray, William V. published an article in Bioorganic & Medicinal Chemistry Letters. The article was 《4-Bicyclic heteroaryl-piperidine derivatives as potent, orally bioavailable stearoyl-CoA desaturase-1 (SCD1) inhibitors: Pyridazine-based analogs》. The article mentions the following:

Design, synthesis, and biol. evaluation of pyridazine-based, 4-bicyclic heteroaryl-piperidine derivatives as potent stearoyl-Co-A desaturase-1 (SCD1) inhibitors are described. In a chronic study of selected analog I in Zucker fa/fa (ZF) rat, dose-dependent decrease of body weight gain and plasma fatty acid desaturation index (DI) in both C16 and C18 are also demonstrated. The results indicate that the plasma fatty acid DI may serve as an indicator for direct target engagement and biomarker for SCD1 inhibition. The experimental process involved the reaction of 1-(Piperidin-4-yl)-1H-indole(cas: 118511-81-2Recommanded Product: 118511-81-2)

1-(Piperidin-4-yl)-1H-indole(cas: 118511-81-2) belongs to piperidines. Piperidine derivatives are also used in solid-phase peptide synthesis (SPPS) and many degradation reactions. Recommanded Product: 118511-81-2

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

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