Category: piperidines

《Molecular Orientation and Dynamics of a Derivative of 2,2,6,6-Tetramethyl-1-Piperidinyloxyl Radical with a Large Substituent Group Dispersed in 1D-Nanochannels of 2,4,6-Tris(4-Chlorophenoxy)-1,3,5-Triazine Crystal》 was written by Kobayashi, Hirokazu; Odanaka, Yuki. Related Products of 826-36-8 And the article was included in Applied Magnetic Resonance on August 31 ,2020. The article conveys some information:

The mol. orientation and dynamics were examined for 4-acetamido-2,2,6,6-tetramethyl-1-piperidinyloxyl (4-acetamido-TEMPO) radicals, which have a larger substituent group than many other TEMPO radicals, dispersed in the one-dimensional (1D) nanochannel of 2,4,6-tris(4-chlorophenoxy)-1,3,5-triazine (CLPOT) with 4-substituted-2,2,6,6-tetramethylpiperidine (R-TEMP; R=OH or H). When TEMPOH (R=OH) was used as a spacer for dispersion in the CLPOT nanochannels, the mol. orientation of 4-acetamido-TEMPO in the CLPOT nanochannels was similar to that of other previously reported 4-substituted-TEMPO (4-X-TEMPO; X=OH, =O or OCH3) radicals. However, the activation energy for the rotational diffusion of 4-acetamido-TEMPO in the CLPOT nanochannels, estimated to be 11 kJ mol-1, was larger than that of other 4-X-TEMPO mols. (6-8 kJ mol-1). These results indicate that the mol. dynamics of 4-X-TEMPO in the CLPOT nanochannels can be controlled by the selection of a larger substituent X at the 4-position in 4-X-TEMPO (in this study, X=NHCOCH3), and also suggest an important concept for the design of new organic magnets. In addition to this study using Triacetonamine, there are many other studies that have used Triacetonamine(cas: 826-36-8Related Products of 826-36-8) was used in this study.

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.Related Products of 826-36-8

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

《A novel series of potent and selective ketone histone deacetylase inhibitors with antitumor activity in vivo》 was written by Jones, Philip; Altamura, Sergio; De Francesco, Raffaele; Gonzalez Paz, Odalys; Kinzel, Olaf; Mesiti, Giuseppe; Monteagudo, Edith; Pescatore, Giovanna; Rowley, Michael; Verdirame, Maria; Steinkuhler, Christian. Reference of 1-Methylpiperidine-2-carboxylic acid hydrochloride And the article was included in Journal of Medicinal Chemistry on April 24 ,2008. The article conveys some information:

Histone deacetylase (HDAC) inhibitors offer a promising strategy for cancer therapy, and the first generation HDAC inhibitors are currently in the clinic. Entirely novel ketone HDAC inhibitors have been developed from the cyclic tetrapeptide apicidin. These compounds show class I subtype selectivity and levels of cellular activity comparable to clin. candidates. A representative example has demonstrated tumor growth inhibition in a human colon HCT-116 carcinoma xenograft model comparable to known inhibitors. The experimental process involved the reaction of 1-Methylpiperidine-2-carboxylic acid hydrochloride(cas: 25271-35-6Reference of 1-Methylpiperidine-2-carboxylic acid hydrochloride)

1-Methylpiperidine-2-carboxylic acid hydrochloride(cas: 25271-35-6) 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.Reference of 1-Methylpiperidine-2-carboxylic acid hydrochloride

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Reference of 2-(Piperidin-4-yl)ethanolIn 2020 ,《Discovery of a Novel, Highly Potent, and Selective Thieno[3,2-d]pyrimidinone-Based Cdc7 Inhibitor with a Quinuclidine Moiety (TAK-931) as an Orally Active Investigational Antitumor Agent》 was published in Journal of Medicinal Chemistry. The article was written by Kurasawa, Osamu; Miyazaki, Tohru; Homma, Misaki; Oguro, Yuya; Imada, Takashi; Uchiyama, Noriko; Iwai, Kenichi; Yamamoto, Yukiko; Ohori, Momoko; Hara, Hideto; Sugimoto, Hiroshi; Iwata, Kentaro; Skene, Robert; Hoffman, Isaac; Ohashi, Akihiro; Nomura, Toshiyuki; Cho, Nobuo. The article contains the following contents:

In our pursuit of developing a novel, potent, and selective cell division cycle 7 (Cdc7) inhibitor, we optimized the previously reported thieno[3,2-d]pyrimidinone analog I showing time-dependent Cdc7 kinase inhibition and slow dissociation kinetics. These medicinal chem. efforts led to the identification of compound 3d, which exhibited potent cellular activity, excellent kinase selectivity, and antitumor efficacy in a COLO205 xenograft mouse model. However, the issue of formaldehyde adduct formation emerged during a detailed study of 3d, which was deemed an obstacle to further development. A structure-based approach to circumvent the adduct formation culminated in the discovery of compound 11b (TAK-931) possessing a quinuclidine moiety as a preclin. candidate. In this paper, the design, synthesis, and biol. evaluation of this series of compounds will be presented. In the experiment, the researchers used many compounds, for example, 2-(Piperidin-4-yl)ethanol(cas: 622-26-4Reference of 2-(Piperidin-4-yl)ethanol)

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 FAKReference of 2-(Piperidin-4-yl)ethanol

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Zhou, Yu; Li, Xiaoguang; Chen, Kerong; Ba, Qian; Zhang, Xu; Li, Jingquan; Wang, Jinfang; Wang, Hui; Liu, Hong published their research in European Journal of Medicinal Chemistry in 2021. The article was titled 《Structural optimization and biological evaluation for novel artemisinin derivatives against liver and ovarian cancers》.Application In Synthesis of 2-(Piperidin-4-yl)ethanol The article contains the following contents:

An increasing number of artemisinin (ARS) and its derivatives have been reported for their potential therapeutic value of human cancer. However, their therapeutic potencies are limited owing to their poor pharmacokinetic profiles. Our previous studies showed that lead compound I originated from incorporating the pharmacophore of the approved chemotherapeutic agent melphalan into the basic skeleton of artemisinin with a succinic linker exhibited an excellent toxicity to human ovarian cancer cells and low cytotoxicity to normal cells. The mechanism studies demonstrated that it inhibited the growth and proliferation of ovarian cancer cells and resulted in S-phase arrest, apoptosis and inhibition of migration. Meanwhile, it exhibited excellent antitumor activities in animal models. Herein, further structure optimization for this lead compound I was performed and nineteen novel derivatives were designed and synthesized. Several compounds demonstrated powerful cytotoxic effects against human liver cancer and ovarian cancer cell lines, with their IC50s below 0.86μM against Hep3B and A2780 cell lines, which are superior to that of I. Four compounds were selected to further evaluate their antitumor activities in in vitro and in vivo ovarian and liver cancer models; the results indicated that compound II exhibited the best therapeutic effect, not only effectively inhibiting the growth of 7404 xenograft and Huh7 xenograft, but also presenting a good dose-dependent inhibition toward the growth of A2780 xenograft. Overall, based on these pos. results, these novel chem. structures may provide a new inspiration for the discovery of novel antitumor agents originated from artemisinin scaffolds.2-(Piperidin-4-yl)ethanol(cas: 622-26-4Application In Synthesis of 2-(Piperidin-4-yl)ethanol) 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.Application In Synthesis of 2-(Piperidin-4-yl)ethanol

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Zhang, Zhuming; Connolly, Peter J.; Lim, Heng Keang; Pande, Vineet; Meerpoel, Lieven; Teleha, Christopher; Branch, Jonathan R.; Ondrus, Janine; Hickson, Ian; Bush, Tammy; Luistro, Leopoldo; Packman, Kathryn; Bischoff, James R.; Ibrahim, Salam; Parrett, Christopher; Chong, Yolanda; Gottardis, Marco M.; Bignan, Gilles published their research in Journal of Medicinal Chemistry in 2021. The article was titled 《Discovery of JNJ-63576253: A Clinical Stage Androgen Receptor Antagonist for F877L Mutant and Wild-Type Castration-Resistant Prostate Cancer (mCRPC)》.Related Products of 109384-19-2 The article contains the following contents:

Persistent androgen receptor (AR) activation drives therapeutic resistance to second-generation AR pathway inhibitors and contributes to the progression of advanced prostate cancer. One resistance mechanism is point mutations in the ligand binding domain of AR that can transform antagonists into agonists. The AR F877L mutation, identified in patients treated with enzalutamide or apalutamide, confers resistance to both enzalutamide and apalutamide. Compound 4 (JNJ-pan-AR) was identified as a pan-AR antagonist with potent activity against wild-type and clin. relevant AR mutations including F877L. Metabolite identification studies revealed a latent bioactivation pathway associated with 4. Subsequent lead optimization of 4 led to amelioration of this pathway and nomination of 5 (JNJ-63576253) as a clin. stage, next-generation AR antagonist for the treatment of castration-resistant prostate cancer (CRPC). The results came from multiple reactions, including 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

《A Buchwald-Hartwig Protocol to Enable Rapid Linker Exploration of Cereblon E3-Ligase PROTACs**》 was written by Hayhow, Thomas G.; Borrows, Rachel E. A.; Diene, Coura R.; Fairley, Gary; Fallan, Charlene; Fillery, Shaun M.; Scott, James S.; Watson, David W.. Product Details of 622-26-4 And the article was included in Chemistry – A European Journal in 2020. The article conveys some information:

A palladium-catalyzed Buchwald-Hartwig amination for lenalidomide-derived aryl bromides was optimized using high throughput experimentation (HTE) to afford isoindolyl amines I [R1 = H, Me; R2 = n-Bu, Ph, 2-MeC6H4, etc.; R1R2 = (CH2)2O(CH2)2, (CH2)2CH(CH2OH)(CH2)2, (CH2)2N(Boc)(CH2)2, etc.]. The substrate scope of the optimized conditions was evaluated for a range of alkyl- and aryl- amines and functionalised aryl bromides. The methodol. allowed access to new cereblon-based bifunctional proteolysis targeting chimeras with a reduced step count and improved yields. The results came from multiple reactions, including the reaction of 2-(Piperidin-4-yl)ethanol(cas: 622-26-4Product Details of 622-26-4)

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.Product Details of 622-26-4

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

《Highly Selective Sub-Nanomolar Cathepsin S Inhibitors by Merging Fragment Binders with Nitrile Inhibitors》 was published in Journal of Medicinal Chemistry in 2020. These research results belong to Schade, Markus; Merla, Beatrix; Lesch, Bernhard; Wagener, Markus; Timmermanns, Simone; Pletinckx, Katrien; Hertrampf, Torsten. Computed Properties of C10H19NO3 The article mentions the following:

Pharmacol. inhibition of cathepsin S (CatS) allows for a specific modulation of the adaptive immune system and many major diseases. Here, we used NMR fragment screening and crystal structure-aided merging to synthesize novel, highly selective CatS inhibitors with picomolar enzymic Ki values and nanomolar functional activity in human Raji cells. Noncovalent fragment hits revealed binding hotspots, while the covalent inhibitor structure-activity relationship enabled efficient potency optimization. In addition to this study using tert-Butyl 4-hydroxypiperidine-1-carboxylate, there are many other studies that have used tert-Butyl 4-hydroxypiperidine-1-carboxylate(cas: 109384-19-2Computed Properties of C10H19NO3) was used in this study.

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.Computed Properties of C10H19NO3

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

《Catalytic Transfer Hydrogenation of Arenes and Heteroarenes》 was published in Chemistry – A European Journal in 2020. These research results belong to Gelis, Coralie; Heusler, Arne; Nairoukh, Zackaria; Glorius, Frank. Category: piperidines The article mentions the following:

Transfer hydrogenation reactions are of great interest to reduce diverse mols. under mild reaction conditions. To date, this type of reaction has only been successfully applied to alkenes, alkynes and polarized unsaturated compounds such as ketones, imines, pyridines, etc. The reduction of benzene derivatives by transfer hydrogenation has never been described, which is likely due to the high energy barrier required to dearomatize these compounds In this context, a catalytic transfer hydrogenation reaction for the reduction of benzene derivatives and heteroarenes to form complex 3-dimensional scaffolds bearing various functional groups at room temperature without needing compressed hydrogen gas has been developed. In the experiment, the researchers used tert-Butyl 4-hydroxypiperidine-1-carboxylate(cas: 109384-19-2Category: piperidines)

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.Category: piperidines

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

《Discovery of Potent, Selective, and Orally Bioavailable Inhibitors of USP7 with In Vivo Antitumor Activity》 was published in Journal of Medicinal Chemistry in 2020. These research results belong to Leger, Paul R.; Hu, Dennis X.; Biannic, Berenger; Bui, Minna; Han, Xinping; Karbarz, Emily; Maung, Jack; Okano, Akinori; Osipov, Maksim; Shibuya, Grant M.; Young, Kyle; Higgs, Christopher; Abraham, Betty; Bradford, Delia; Cho, Cynthia; Colas, Christophe; Jacobson, Scott; Ohol, Yamini M.; Pookot, Deepa; Rana, Payal; Sanchez, Jerick; Shah, Niket; Sun, Michael; Wong, Steve; Brockstedt, Dirk G.; Kassner, Paul D.; Schwarz, Jacob B.; Wustrow, David J.. Safety of tert-Butyl 4-hydroxypiperidine-1-carboxylate The article mentions the following:

USP7 is a promising target for cancer therapy as its inhibition is expected to decrease function of oncogenes, increase tumor suppressor function, and enhance immune function. Using a structure-based drug design strategy, a new class of reversible USP7 inhibitors has been identified that is highly potent in biochem. and cellular assays and extremely selective for USP7 over other deubiquitinases. The succinimide was identified as a key potency-driving motif, forming two strong hydrogen bonds to the allosteric pocket of USP7. Redesign of an initial benzofuran-amide scaffold yielded a simplified ether series of inhibitors, utilizing acyclic conformational control to achieve proper amine placement. Further improvements were realized upon replacing the ether-linked amines with carbon-linked morpholines, a modification motivated by free energy perturbation (FEP+) calculations This led to the discovery of compound 41(I), a highly potent, selective, and orally bioavailable USP7 inhibitor. In xenograft studies, compound 41 demonstrated tumor growth inhibition in both p53 wildtype and p53 mutant cancer cell lines, demonstrating that USP7 inhibitors can suppress tumor growth through multiple different pathways.tert-Butyl 4-hydroxypiperidine-1-carboxylate(cas: 109384-19-2Safety of tert-Butyl 4-hydroxypiperidine-1-carboxylate) was used in this study.

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.Safety of tert-Butyl 4-hydroxypiperidine-1-carboxylate

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

The author of 《Structure overhaul affords a potent purine PI3Kδ inhibitor with improved tolerability》 were Methot, Joey L.; Zhou, Hua; Kattar, Sam D.; McGowan, Meredeth A.; Wilson, Kevin; Garcia, Yudith; Deng, Yongi; Altman, Michael; Fradera, Xavier; Lesburg, Charles; Fischmann, Thierry; Li, Chaomin; Alves, Steve; Shah, Sanjiv; Fernandez, Rafael; Goldenblatt, Peter; Hill, Armetta; Shaffer, Lynsey; Chen, Dapeng; Tong, Vince; McLeod, Robbie L.; Yu, Hongshi; Bass, Alan; Kemper, Ray; Gatto, Nicholas T.; LaFranco-Scheuch, Lisa; Trotter, Benjamin Wesley; Guzi, Timothy; Katz, Jason D.. And the article was published in Journal of Medicinal Chemistry in 2019. Product Details of 87120-72-7 The author mentioned the following in the article:

PI3Kδ catalytic activity is required for immune cell activation, and has been implicated in inflammatory diseases as well as hematol. malignancies in which the AKT pathway is overactive. A purine PI3Kδ inhibitor bearing a benzimidazolone-piperidine motif was found to be poorly tolerated in dog, which was attributed to diffuse vascular injury. Several strategies were implemented to mitigate this finding, including reconstruction of the benzimidazolone-piperidine selectivity motif. Structure-based design led to the identification of O- and N-linked heterocycloalkyls, with pyrrolidines being particularly ligand efficient and kinome selective, and having an improved safety pharmacol. profile. A representative was advanced into a dog tolerability study where it was found to be well tolerated, with no histopathol. evidence of vascular injury. In the experiment, the researchers used many compounds, for example, tert-Butyl 4-aminopiperidine-1-carboxylate(cas: 87120-72-7Product Details of 87120-72-7)

tert-Butyl 4-aminopiperidine-1-carboxylate(cas: 87120-72-7) belongs to anime. Large quantities of aliphatic amines are made synthetically. The most widely used industrial method is the reaction of alcohols with ammonia at a high temperature, catalyzed by metals or metal oxide catalysts (e.g., nickel or copper). Mixtures of primary, secondary, and tertiary amines are thereby produced.Product Details of 87120-72-7

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem