Heterocyclic Building Blocks-Pyrrolines

In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Synthesis of nature product kinsenoside analogues with anti-inflammatory activity, published in 2021-01-01, which mentions a compound: 58081-05-3, Name is (R)-4-Hydroxydihydrofuran-2(3H)-one, Molecular C4H6O3, Recommanded Product: (R)-4-Hydroxydihydrofuran-2(3H)-one.

Kinsenoside (I) is a major bioactive component in herbal medicines that possesses a broad range of pharmacol. functions. Goodyeroside A (II), an epimer of kinsenoside, remains less explored. In this report, the authors chem. synthesized kinsenoside, goodyeroside A and their analogs with glycan variation, chirality inversion at chiral center(s), and bioisosteric replacement of lactone with lactam. Among these compounds, goodyeroside A and its mannosyl counterpart III demonstrated superior anti-inflammatory efficacy. Furthermore, goodyeroside A was found to suppress inflammation through inhibiting the NF-κB signal pathway effectively. The structure-activity relationship is also explored for further development of more promising kinsenoside analogs as drug candidates.

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Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 4045-24-3, is researched, Molecular C6H13NO, about Design, synthesis and biological evaluation of Tozadenant analogues as adenosine A2A receptor ligands, the main research direction is morpholinyl benzothiazolyl methylpiperidine carboxamide preparation adenosine receptor fluorine isotopologue; A(2A) adenosine Receptor; Autoradiography; Binding studies; Fluorinated analogues; Fluorine-18 isotopologues; Ligand synthesis.Product Details of 4045-24-3.

With the aim to obtain potent adenosine A2A receptor (A2AR) ligands, a series of eighteen derivatives of 4-hydroxy-N-(4-methoxy-7-morpholin-4-yl-1,3-benzo[d]thiazol-2-yl)-4-methylpiperidine-1-carboxamide were designed and synthesized. The target compounds were obtained by a chem. building block principle that involved reaction of the appropriate aminobenzothiazole Ph carbamates with either com. available or readily synthesized functionalized piperidines. Ki values for human A2AR ranged from 2.4 to 38 nM, with more than 120-fold selectivity over A1 receptors for all evaluated compounds except 4-Fluoro-4-(hydroxymethyl)-N-(4-methoxy-7-morpholinobenzo[d]thiazol-2-yl)piperidine-1-carboxamide which had a Ki of 361 nM and 18-fold selectivity. The most potent fluorine-containing derivatives exhibited Ki values of 4.9 nM, 3.6 nM and 2.8 nM for the human A2AR. Interestingly, the corresponding values for rat A2AR were found to be four to five times higher. Their binding to A2AR was further confirmed by radiolabeling with 18F and in vitro autoradiog. in rat brain slices, which showed almost exclusive striatal binding and complete displacement by the A2AR antagonist ZM 241385. Authors conclude that these compounds represent potential candidates for the visualization of the A2A receptor and open pathways to novel therapeutic treatments of neurodegenerative disorders or cancer.

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COA of Formula: C4H6O3. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: (R)-4-Hydroxydihydrofuran-2(3H)-one, is researched, Molecular C4H6O3, CAS is 58081-05-3, about Diastereoselective Synthesis of C2′-Fluorinated Nucleoside Analogues Using an Acyclic Approach. Author is Dostie, Starr; Prevost, Michel; Mochirian, Philippe; Tanveer, Kashif; Andrella, Nicholas; Rostami, Ariana; Tambutet, Guillaume; Guindon, Yvan.

Nucleoside analogs bearing a fluorine in the C2′-position have been synthesized by SN2-like cyclizations of acyclic thioaminal precursors. This strategy provides access to two scaffolds, D-1′,2′-cis-thiofuranosides and D-1′,2′-trans-furanosides, which are difficult to generate using the standard approach for nucleoside synthesis. The addition of silylated nucleobases onto model C2-fluorinated dithioacetal substrates resulted in 1,2-syn diastereoselectivity, which is consistent with the C2-F and S-alkyl moiety being in close proximity. A new series of analogs bearing a C3′ all-carbon quaternary center along with a C2′-F atom have also been synthesized using this approach and are being investigated as potential antimetabolites.

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Sakai, Holt A.; Liu, Wei; Le, Chi “Chip”; MacMillan, David W. C. published an article about the compound: 4-Chloro-2-fluoropyridine( cas:34941-92-9,SMILESS:ClC1=CC(=NC=C1)F ).COA of Formula: C5H3ClFN. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:34941-92-9) through the article.

Overcoming intrinsic limitations of C(sp3)-Cl bond activation, the development of a novel organosilane reagent Si(TMS)3(N)R1R2 (R1 = adamantyl, tert-Bu, i-Pr, n-Bu; R2 = H) that can participate in chlorine atom abstraction under mild photocatalytic conditions were reported. In particular, the application of this mechanism to a dual nickel/photoredox catalytic protocol that enables the first cross-electrophile coupling of unactivated alkyl chlorides R3Cl (R3 = cyclohexyl, oxan-4-yl, 4-cyanobutyl, etc.) and aryl chlorides R4Cl (R4 = pyridin-4-yl, quinolin-3-yl, 2-(methylsulfanyl)pyrimidin-5-yl, etc.) was described. Employing these low-toxicity, abundant, and com. available organochloride building blocks, this methodol. allows access to a broad array of highly functionalized C(sp2)-C(sp3) coupled adducts, e.g., I including numerous drug analogs.

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In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Transition-metal-free direct nucleophilic substitution of carboranyllithium and 2-halopyridines, published in 2019, which mentions a compound: 34941-92-9, Name is 4-Chloro-2-fluoropyridine, Molecular C5H3ClFN, HPLC of Formula: 34941-92-9.

A practical and efficient C(cage)-heteroarylation of carborane is presented, via direct nucleophilic substitution of carboranyllithium with 2-halopyridines. This reaction does not need the aid of any transition metal and utilizes readily available carboranyllithium nucleophiles, thereby avoiding transmetalation of carboranyllithium. The process exhibits a broad scope, and a vast array of 2-halopyridines have proven to be suitable substrates. The method serves as a complement to C(cage)-arylation reactions and may find wide applications in materials science and medicinal and coordination chem.

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Application In Synthesis of 4-Methoxypiperidine. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 4-Methoxypiperidine, is researched, Molecular C6H13NO, CAS is 4045-24-3, about Discovery of Novel Thiophene-arylamide Derivatives as DprE1 Inhibitors with Potent Antimycobacterial Activities. Author is Wang, Pengxu; Batt, Sarah M.; Wang, Bin; Fu, Lei; Qin, Rongfei; Lu, Yu; Li, Gang; Besra, Gurdyal S.; Huang, Haihong.

In this study, we report the design and synthesis of a series of novel thiophene-arylamide compounds derived from the noncovalent decaprenylphosphoryl-β-D-ribose 2′-epimerase (DprE1) inhibitor TCA1 through a structure-based scaffold hopping strategy. Systematic optimization of the two side chains flanking the thiophene core led to new lead compounds bearing a thiophene-arylamide scaffold with potent antimycobacterial activity and low cytotoxicity. Compounds I, II, III [X = H,F] exhibited potent in vitro activity against both drug-susceptible (min. inhibitory concentration (MIC) = 0.02-0.12μg/mL) and drug-resistant (MIC = 0.031-0.24μg/mL) tuberculosis strains while retaining potent DprE1 inhibition (half maximal inhibitory concentration (IC50) = 0.2-0.9μg/mL) and good intracellular antimycobacterial activity. In addition, these compounds showed good hepatocyte stability and low inhibition of the human ether-á-go-go related gene (hERG) channel. The representative compound III [X = H] with acceptable pharmacokinetic property demonstrated significant bactericidal activity in an acute mouse model of tuberculosis. Moreover, the mol. docking study of template compound I provides new insight into the discovery of novel antitubercular agents targeting DprE1.

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SDS of cas: 58081-05-3. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: (R)-4-Hydroxydihydrofuran-2(3H)-one, is researched, Molecular C4H6O3, CAS is 58081-05-3, about Production of (S)-4-chloro-3-hydroxybutyrate by microbial resolution using hydrolase from Rhizobium sp. DS-S-51. Author is Nakagawa, Atsushi; Suzuki, Takahiro; Kato, Ko; Shinmyo, Atsuhiko; Suzuki, Toshio.

(S)-4-Chloro-3-hydroxybutyrate (CHB) is essential for the synthesis of biol. and pharmacol. important compounds Rhizobium sp. DS-S-51 isolated from soil samples showed hydrolytic activity toward (R)-CHB in the racemate to (R)-3-hydroxy-γ-butyrolactone (HL) under a simple composition of the reaction. Residual (S)-CHB was obtained with high optical purity. The gene encoding the enzyme concerned, designated CHB hydrolase, was isolated from DS-S-51, and the gene was highly expressed in Escherichia coli JM109. When the resolution of racemic Me CHB (CHBM) as a substrate was performed using this recombinant cell, JM109 (pKK-R1), the hydrolytic activity was found to be 40-fold greater than that of DS-S-51, and the maximum concentration of the substrate added increased 2-fold. Moreover, (R)-HL was also obtained without decreasing the optical purity compared with that when (R)-CHBM was used as a substrate.

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In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Tetrahydrofuran-Based Transient Receptor Potential Ankyrin 1 (TRPA1) Antagonists: Ligand-Based Discovery, Activity in a Rodent Asthma Model, and Mechanism-of-Action via Cryogenic Electron Microscopy, published in 2021-04-08, which mentions a compound: 34941-92-9, mainly applied to AM0902 oxadiazolone azabicyclohexane THF synthesis TRPA1 inflammation asthma pain, Computed Properties of C5H3ClFN.

Transient receptor potential ankyrin 1 (TRPA1) is a nonselective calcium-permeable ion channel highly expressed in the primary sensory neurons functioning as a polymodal sensor for exogenous and endogenous stimuli and has generated widespread interest as a target for inhibition due to its implication in neuropathic pain and respiratory disease. Herein, we describe the optimization of a series of potent, selective, and orally bioavailable TRPA1 small mol. antagonists, leading to the discovery of a novel tetrahydrofuran-based linker. Given the balance of physicochem. properties and strong in vivo target engagement in a rat AITC-induced pain assay, compound (I) was progressed into a guinea pig ovalbumin asthma model where it exhibited significant dose-dependent reduction of inflammatory response. Furthermore, the structure of the TRPA1 channel bound to compound (II) was determined via cryogenic electron microscopy to a resolution of 3 Å, revealing the binding site and mechanism of action for this class of antagonists. Tetrahydrofurans

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In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called A novel generation of optically active ethyl 4-chloro-3-hydroxybutyrate as a C4 chiral building unit using microbial dechlorination, published in 1996-11-08, which mentions a compound: 58081-05-3, mainly applied to microbial stereoselective dechlorination chlorohydroxybutyrate, Category: pyrrolines.

A novel procedure for the generation of optically active Et 4-chloro-3-hydroxybutyrate using bacterial cells was developed. Et (S)-4-chloro-3-hydroxybutyrate was prepared by Pseudomonas sp. OS-K-29, which stereoselectively assimilates 2,3-dichloro-1-propanol. The reaction was based on its kinetic dehalogenation for both enantiomers using the resting cells. The obtained 4-chloro-3-hydroxybutyrate had high enantiomeric excess of >98% with a yield of 33% at the microbial resolution step. Moreover, several C4 compounds having the 4-chloro-3-hydroxyl function were also resolved and gave good enantiomeric purities (>95% ee). Et (R)-4-chloro-3-hydroxybutyrate was also obtained with high enantiomeric purity (>98% ee) using the cells of Pseudomonas sp DS-K-NR818.

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Related Products of 58081-05-3. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: (R)-4-Hydroxydihydrofuran-2(3H)-one, is researched, Molecular C4H6O3, CAS is 58081-05-3, about Identification of Novel Glycosidic Aroma Precursors in Saffron (Crocus sativus L.). Author is Straubinger, Markus; Bau, Brigitte; Eckstein, Susanne; Fink, Margit; Winterhalter, Peter.

The methanolic extract of saffron was separated with the aid of multilayer coil countercurrent chromatog. After purification by HPLC, the following seven novel carotenoid metabolites were identified on the basis of their spectral (UV, FTIR, MS, NMR, CD) data: (4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-enecarbaldehyde O-β-D-gentiobioside (1), (4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-enecarboxylic acid O-β-D-glucopyranoside (2), 6-hydroxy-3-(hydroxymethyl)-2,4,4-trimethylcyclohexa-2,5-dienone 6-O-β-D-glucopyranoside (3), (2Z)-3-methylpent-2-enedioic acid 1-[1-(2,4,4-trimethyl-3,6-dioxocyclohexenyloxy)-O-β-D-glucopyranosid-6-yl] ester (4), (5S)-5-hydroxy-7,7-dimethyl-4,5,6,7-tetrahydro-3H-isobenzofuran-1-one O-β-D-glucopyranoside (5), (1R,5S,6R)-5-(hydroxymethyl)-4,4,6-trimethyl-7-oxabicyclo[4.1.0]heptan-2-one O-β-D-glucopyranoside (6), and (1R)- 3,5,5-trimethylcyclohex-3-enol O-β-D-glucopyranoside (7).

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