Tag: M.W=200-250

Chen, Yiding published the artcileDirect Copper-Catalyzed Three-Component Synthesis of Sulfonamides, SDS of cas: 132431-09-5, the main research area is aryl heteroaryl alkenyl sulfonamide preparation; copper catalyst coupling boronic acid amine DABSO; secondary cyclic acyclic amine aniline coupling boronic acid DABSO.

Sulfonamides such as N-(phenylsulfonyl)morpholine were prepared in one step by coupling of aryl-, heteroaryl-, and alkenylboronic acids such as phenylboronic acid with cyclic and acyclic alkyl secondary amines such as morpholine and primary anilines and the bis(sulfur dioxide) complex of DABCO (DABSO) in the presence of Cu(OTf)2 and 4,4′-dimethoxy-2,2′-bipyridine in DMSO. The method was used on gram scale and was used to prepare sulfonamides from drugs and drug fragments.

Journal of the American Chemical Society published new progress about Anilines Role: RCT (Reactant), RACT (Reactant or Reagent) (primary). 132431-09-5 belongs to class piperidines, name is Benzyl (piperidin-4-ylmethyl)carbamate, and the molecular formula is C14H20N2O2, SDS of cas: 132431-09-5.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Tang, Kai published the artcileStructure-based design, synthesis and biological evaluation of aminopyrazines as highly potent, selective, and cellularly active allosteric SHP2 inhibitors, Synthetic Route of 73874-95-0, the main research area is aminopyrazine preparation cellularly active allosteric SHP2 inhibitor; Aminopyrazines; Dephosphorylase; SHP2 inhibitor.

Src homol.-2-containing protein tyrosine phosphatase 2 (SHP2) encoded by the proto-oncogene PTPN11 is the first identified non-receptor protein tyrosine phosphatase. SHP2 dysregulation contributes to the pathogenesis of different cancers, making SHP2 a promising therapeutic target for cancer therapy. In this article, authors report the structure-guided design based on the well-characterized SHP2 inhibitor SHP099, extensive structure-activity relationship studies (SARs) of aminopyrazines, biochem. characterization and cellular potency. These medicinal chem. efforts lead to the discovery of the lead compound TK-453 I, which potently inhibits SHP2 (SHP2WT IC50 = 0.023μM, ΔTm = 7.01°C) in a reversible and noncompetitive manner. Compound I exhibits high selectivity over SHP2PTP, SHP1 and PTP1B, and may bind at the “”tunnel”” allosteric site of SHP2 as SHP099. As the key pharmacophore, the aminopyrazine scaffold not only reorganizes the cationic-π stacking interaction with R111 via the novel hydrogen bond interaction between the S atom of thioether linker and T219, but also mediates a hydrogen bond with E250. In vitro studies indicate that I inhibits proliferation of HeLa, KYSE-70 and THP-1 cells moderately and induces apoptosis of Hela cells. Further mechanistic studies suggest that I can decrease the phosphorylation levels of AKT and Erk1/2 in HeLa and KYSE-70 cells.

European Journal of Medicinal Chemistry published new progress about Arylboronic acids Role: RCT (Reactant), RACT (Reactant or Reagent). 73874-95-0 belongs to class piperidines, name is tert-Butyl piperidin-4-ylcarbamate, and the molecular formula is C10H20N2O2, Synthetic Route of 73874-95-0.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Zhou, Xueying published the artcileHaloamines as Bifunctional Reagents for Oxidative Aminohalogenation of Maleimides, Application of tert-Butyl piperidin-4-ylcarbamate, the main research area is chloro amino pyrroledione green preparation; maleimide haloamine oxidative aminohalogenation copper catalyst.

An unprecedented copper-catalyzed oxidative aminohalogenation of electron-deficient maleimides with secondary amines and NXS (X = Cl, Br, I) was developed to form pyrrole-2,5-diones I [R1 = Me, R2 = n-pentyl, Bn, CH2(4-ClC6H4), etc.; R1R2 = CH2CH2CH2, CH2CH2OCH2CH2, CH2(CH2)3CH2, etc.] in which the N-X bonds generated in situ were used as difunctionalized reagents. The distinctive features of this multicomponent reaction included a simple green catalytic system, a spectral substrate range and the late-stage modification of drug mols. Most importantly, this umpolung radical cascade strategy exploits the in situ formation of N-iodoamines that enabled efficient alkene aminoiodination.

Organic Letters published new progress about Aliphatic amines Role: RCT (Reactant), RACT (Reactant or Reagent). 73874-95-0 belongs to class piperidines, name is tert-Butyl piperidin-4-ylcarbamate, and the molecular formula is C10H20N2O2, Application of tert-Butyl piperidin-4-ylcarbamate.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Kim, WooChan published the artcileDiscovery of Novel Pyrimidine-Based Capsid Assembly Modulators as Potent Anti-HBV Agents, Recommanded Product: tert-Butyl piperidin-4-ylcarbamate, the main research area is pyrimidine preparation antiviral activity SAR pharmacokinetic study mol docking; structure property relationship.

In this study, novel potent pyrimidine derivatives I (R1 = SMe, SO2Me; R2 = [2-(pyridin-3-ylformamido)ethyl]aminyl, 3-Cl-4-FC6H3NH, 4-aminopiperidin-1-yl, etc.; R3 = [4-(morpholin-4-yl)phenyl]aminyl, C6H5NH, 3-Br-4-FC6H3NH, etc.) as core assembly modulators were synthesized and their antiviral effects were evaluated in in vitro and in vivo biol. experiments One of the synthesized derivatives, compound I (R1 = SO2Me; R2 = 4-aminopiperidin-1-yl; R3 = 3-Cl-4-F-C6H3NH) displayed potent inhibitory effects in the in vitro assays (52% inhibition in the protein-based assay at 100 nM and an IC50 value of 181 nM in the serum HBV DNA quantification assay). Moreover, treatment with compound I (R1 = SO2Me; R2 = 4-aminopiperidin-1-yl; R3 = 3-Cl-4-F-C6H3NH) for 5 wk significantly decreased serum levels of HBV DNA levels (3.35 log reduction) in a human liver-chimeric uPA/SCID mouse model, and these effects were significantly increased when I (R1 = SO2Me; R2 = 4-aminopiperidin-1-yl; R3 = 3-Cl-4-F-C6H3NH) was combined with tenofovir, a nucleotide analog inhibitor of reverse transcriptase used for the treatment of HBV infection.

Journal of Medicinal Chemistry published new progress about Acid chlorides Role: RCT (Reactant), RACT (Reactant or Reagent). 73874-95-0 belongs to class piperidines, name is tert-Butyl piperidin-4-ylcarbamate, and the molecular formula is C10H20N2O2, Recommanded Product: tert-Butyl piperidin-4-ylcarbamate.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Qian, Yuqing published the artcileDesign and synthesis of N-(1-(6-(substituted phenyl)-pyridazin-3-yl)-piperidine-3-yl)-amide derivatives as JMJD6 inhibitors, Quality Control of 73874-95-0, the main research area is pyridazinyl piperidinyl amide preparation antitumor inhibitor docking; Breast cancer, antitumor agent; JMJD6 inhibitor.

JMJD6 is a member of the JmjC domain-containing family and has been identified as a promising therapeutic target for treating estrogen-induced and triple-neg. breast cancer. To develop novel anti-breast cancer agents, a class of N-(1-(6-(substituted phenyl)-pyridazine-3-yl)-piperidine-3-yl)-amide derivatives I [R = 3-(pyridin-3-ylcarbonylamino), 4-(4-methoxyphenylcarbonylamino), 3-(4-methoxyphenylcarbonylamino), etc.; R1 = MeO, Cl, Et, NH2, NHBoc, NHMe] as potential JMJD6 inhibitors was synthesized. Among them, the anti-cancer compound I [R = 3-((4-methoxyphenyl)amidyl), etc.; R1 = NHMe] was an excellent JMJD6 binder (KD = 0.75 ± 0.08μM). It could upregulate the mRNA and protein levels of p53 and its downstream effectors p21 and PUMA by inhibiting JMJD6. Besides, compound I [R = 3-(4-methoxyphenylcarbonylamino); R1 = NHMe] displayed potent anti-proliferative activities against tested breast cancer cells by the induction of cell apoptosis and cell cycle arrest. Significantly, compound I [R = 3-(4-methoxyphenylcarbonylamino); R1 = NHMe] also promoted a remarkable reduction in tumor growth, with a TGI value of 66.6% (50 mg/kg, i.p.). Taken together, this findings suggest that compound I [R = 3-(4-methoxyphenylcarbonylamino); R1 = NHMe] is a potent JMJD6 inhibitor bearing a new scaffold acting as a promising drug candidate for the treatment of breast cancer.

Bioorganic Chemistry published new progress about Acid chlorides Role: RCT (Reactant), RACT (Reactant or Reagent). 73874-95-0 belongs to class piperidines, name is tert-Butyl piperidin-4-ylcarbamate, and the molecular formula is C10H20N2O2, Quality Control of 73874-95-0.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Zhang, Jin published the artcileDesign, synthesis and biological evaluation of 1H-pyrazolo [3,4-d]pyrimidine derivatives as PAK1 inhibitors that trigger apoptosis, ER stress and anti-migration effect in MDA-MB-231 cells, Synthetic Route of 73874-95-0, the main research area is pyrazolopyrimidine preparation PAK1 inhibitor mol docking; Apoptosis; Breast cancer; High-throughput screening; Migration; PAK1 inhibitor.

P21-activated kinase 1 (PAK1) is associated with cell proliferation, survival and migration. Deregulation of PAK1 activity is involved in various human diseases, including cancer, inflammation, and neurol. disorders. Using a high-throughput virtual screening, we identified the 1H-pyrazolo [3,4-d]pyrimidine scaffold as a promising lead for targeting PAK1. A novel potent PAK1 inhibitor, (I), was discovered, which presented an IC50 value of 174 nM with a good selectivity. In addition, compound Icould inhibit PAK1-ERK signaling to suppress MDA-MB-231 cells proliferation with an IC50 value of 3.48μM for 48 h. Subsequently, compound Iwas documented to induce cell apoptosis. Interestingly, according to the RNASeq-based analyses, substantiated that compound Iinduced significant ER-Stress, suppressed migration via FOXO3 activation, JNK1/2, ERK1/2 and AKT signaling inhibition. Together, these results demonstrate that compound Iis a novel PAK1 inhibitor triggering apoptosis, ER stress and anti-migration effect in MDA-MB-231 cells, which may provide a candidate lead for the development of novel potent inhibitors of PAK1.

European Journal of Medicinal Chemistry published new progress about Acid chlorides Role: RCT (Reactant), RACT (Reactant or Reagent). 73874-95-0 belongs to class piperidines, name is tert-Butyl piperidin-4-ylcarbamate, and the molecular formula is C10H20N2O2, Synthetic Route of 73874-95-0.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Yakukhnov, Sergey A. published the artcileCatalytic Transfer Hydrodebenzylation with Low Palladium Loading, Category: piperidines, the main research area is benzyl ester palladium catalyst hydrodebenzylation; ether benzyl palladium catalyst hydrodebenzylation; amine benzyl palladium catalyst hydrodebenzylation; aryl halide palladium catalyst hydrodehalogenation.

A highly-efficient catalytic system for hydrodebenzylation is described. The cleavage of O-benzyl and N-benzyl protecting groups was performed using an uncommonly low palladium loading (0.02-0.3 mol%; TON up to 5000) in a relatively short reaction time. This approach was used for a variety of substrates including pharmaceutically important precursors, and gram-scale deprotection was demonstrated. Transfer conditions and an easy-to-make Pd/C catalyst are key features of this debenzylation scheme.

Advanced Synthesis & Catalysis published new progress about Aromatic hydrocarbons Role: SPN (Synthetic Preparation), PREP (Preparation). 73874-95-0 belongs to class piperidines, name is tert-Butyl piperidin-4-ylcarbamate, and the molecular formula is C10H20N2O2, Category: piperidines.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Hayhow, Thomas G. published the artcileA Buchwald-Hartwig Protocol to Enable Rapid Linker Exploration of Cereblon E3-Ligase PROTACs**, Recommanded Product: tert-Butyl piperidin-4-ylcarbamate, the main research area is isoindolyl amine preparation; aryl bromide amine Buchwald Hartwig amination palladium catalyst; PEPPSI; PROTAC; amination; cereblon; drug discovery.

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.

Chemistry – A European Journal published new progress about Aryl bromides Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 73874-95-0 belongs to class piperidines, name is tert-Butyl piperidin-4-ylcarbamate, and the molecular formula is C10H20N2O2, Recommanded Product: tert-Butyl piperidin-4-ylcarbamate.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Song, Bichao published the artcilePd-Catalyzed Decarboxylative Olefination: Stereoselective Synthesis of Polysubstituted Butadienes and Macrocyclic P-glycoprotein Inhibitors, Application of tert-Butyl piperidin-4-ylcarbamate, the main research area is vinylethylene carbonate diazo ester palladium decarboxylative olefination catalyst; vinyloxazolidinone diazo ester palladium decarboxylative olefination catalyst; vinylbenzoxazinone diazo ester palladium decarboxylative olefination catalyst; butadiene polysubstituted stereoselective preparation.

The efficient and stereoselective synthesis of polysubstituted butadienes, especially the multifunctional butadienes, represents a great challenge in organic synthesis. Herein, we wish to report a distinctive Pd(0) carbene-initiated decarboxylative olefination approach that enables the direct coupling of diazo esters with vinylethylene carbonates (VECs), vinyl oxazolidinones, or vinyl benzoxazinones to afford alc.-, amine-, or aniline-containing 1,3-dienes in moderate to high yields and with excellent stereoselectivity. This protocol features operational simplicity, mild reaction conditions, a broad substrate scope, and gram-scalability. Notably, a structurally unique allylic Pd(II) intermediate was isolated and characterized. DFT calculation and control experiments demonstrated that a rare Pd(0) carbene intermediate could be involved in this reaction. Moreover, the polysubstituted butadienes as novel building blocks were unprecedentedly assembled into macrocycles, which efficiently inhibited the P-glycoprotein and dramatically reversed multidrug resistance in cancer cells by 190-fold.

Journal of the American Chemical Society published new progress about Allyl amines Role: SPN (Synthetic Preparation), PREP (Preparation). 73874-95-0 belongs to class piperidines, name is tert-Butyl piperidin-4-ylcarbamate, and the molecular formula is C10H20N2O2, Application of tert-Butyl piperidin-4-ylcarbamate.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Zhang, Xiangyu published the artcileDesign, synthesis and biological evaluation of novel benzofuran derivatives as potent LSD1 inhibitors, Synthetic Route of 73874-95-0, the main research area is cyanophenyl aminomethyl arylbenzofuran preparation; LSD1 cytochromep450 inhibition SAR antitumor cytotoxicity docking apoptosis induction; Anti-lung cancer; Benzofuran derivatives; LSD1; Molecular docking; Structure-activity relationships.

A series of benzofurans I [R = 3-aminopropylamino, pyrrolidin-3-ylamino, piperazin-1-yl, etc.; Ar = pyrimidin-5-yl, p-tolyl, 1-methylindazol-5-yl, etc.] were designed, synthesized and biochem. evaluated as LSD1 inhibitors based on scaffold hopping and conformational restriction strategy. Most of the compounds I potently suppressed the enzymic activities of LSD1 and potently inhibited tumor cells proliferation. In particular, the representative compound I [R = (3S)-3-amino-1-piperidyl; Ar = p-tolyl] exhibited excellent LSD1 inhibition at the mol. levels with IC50 = 0.065μM, as well as anti-proliferation against MCF-7, MGC-803, H460, A549 and THP-1 tumor cells with IC50 values of 2.90 ± 0.32, 5.85 ± 0.35, 2.06 ± 0.27, 5.74 ± 1.03 and 6.15 ± 0.49μM, resp. The binding modes of these compounds I were rationalized by mol. docking. Meanwhile, a preliminary druggability evaluation showed that compound I [R = (3S)-3-amino-1-piperidyl; Ar = p-tolyl] displayed favorable liver microsomal stability and weak inhibitory activity against CYPs at 10μM. Remarkably, H460 xenograft tumors studies revealed that compound I [R = (3S)-3-amino-1-piperidyl; Ar = p-tolyl] demonstrated robust in-vivo antitumor efficacy without significant side effects. All the results demonstrated that compound I [R = (3S)-3-amino-1-piperidyl; Ar = p-tolyl] could represent a promising lead for further development.

European Journal of Medicinal Chemistry published new progress about Antitumor agents. 73874-95-0 belongs to class piperidines, name is tert-Butyl piperidin-4-ylcarbamate, and the molecular formula is C10H20N2O2, Synthetic Route of 73874-95-0.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem