Month: March 2022

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, Research Support, N.I.H., Extramural, Research Support, U.S. Gov’t, Non-P.H.S., Journal of Medicinal Chemistry called Discovery of a Novel and Brain-Penetrant O-GlcNAcase Inhibitor via Virtual Screening, Structure-Based Analysis, and Rational Lead Optimization, Author is Tawada, Michiko; Fushimi, Makoto; Masuda, Kei; Sun, Huikai; Uchiyama, Noriko; Kosugi, Yohei; Lane, Weston; Tjhen, Richard; Endo, Satoshi; Koike, Tatsuki, which mentions a compound: 4045-24-3, SMILESS is COC1CCNCC1, Molecular C6H13NO, Category: pyrrolines.

O-GlcNAcase (OGA) has received increasing attention as an attractive therapeutic target for tau-mediated neurodegenerative disorders; however, its role in these pathologies remains unclear. Therefore, potent chem. tools with favorable pharmacokinetic profiles are desirable to characterize this enzyme. Herein, we report the discovery of a potent and novel OGA inhibitor, compound 5i, comprising an aminopyrimidine scaffold, identified by virtual screening based on multiple methodologies combining structure-based and ligand-based approaches, followed by sequential optimization with a focus on ligand lipophilicity efficiency. This compound was observed to increase the level of O-GlcNAcylated protein in cells and display suitable pharmacokinetic properties and brain permeability. Crystallog. anal. revealed that the chem. series bind to OGA via characteristic hydrophobic interactions, which resulted in a high affinity for OGA with moderate lipophilicity. Compound 5i could serve as a useful chem. probe to help establish a proof-of-concept of OGA inhibition as a therapeutic target for the treatment of tauopathies.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

Formula: C6H13NO. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 4-Methoxypiperidine, is researched, Molecular C6H13NO, CAS is 4045-24-3, about An acid-catalyzed 1,4-addition isocyanide-based multicomponent reaction in neat water. Author is Lei, Jie; Li, Yong; Xu, Jia; Tang, Dian-Yong; Shao, Jing-Wei; Li, Hong-yu; Chen, Zhong-Zhu; Xu, Zhi-Gang.

A green 1,4-addition isocyanide-based three-component reaction was developed to synthesize chromanones via a facile, mild, and efficient one-pot protocol without a metal catalyst. The 1,4-addition of isocyanides occurred at the C-2 position of chromones instead of the Schiff base in neat water. The hydrogen bond can dictate the stereo-outcome of olefins and provided an effective method for the diastereomer-selective synthesis of this type of chromanone. The novel green synthetic protocol allowed the quick synthesis of complex chromanones in an environmentally friendly manner.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

Recommanded Product: 58081-05-3. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: (R)-4-Hydroxydihydrofuran-2(3H)-one, is researched, Molecular C4H6O3, CAS is 58081-05-3, about Synthesis of (S)- and (R)-3-hydroxy-4-butanolide and (2S,4S)-, (2R,4S)-, (2S,4R)-, and (2R,4R)-2-hydroxy-4-(hydroxymethyl)-4-butanolide and their satiety and hunger modulating activities. Author is Uchikawa, Osamu; Okukado, Nobuhisa; Sakata, Toshiie; Arase, Koichi; Terada, Kenji.

Two endogenous γ-lactones, 3-hydroxy-4-butanolide (I) and 2-hydroxy-4-hydrtoxymethyl-4-butanolide (II) have been identified as substances that enhance, resp., satiety and hunger by their effects on the feeding behavior and the central neurons of rats. All the stereoisomers of these two lactones were synthesized and their effects on the feeding behavior and humoral factors were assessed by infusion into the rat third cerebroventricle. Among four isomers, (2S,4S)-II was most effective in eliciting the feeding and caused potent hypoglycemia with hyperinsulinemia. (S)-I suppressed the food intake more potently than the antipode and caused humoral responses reciprocal to those of (2S,4S)-II. Thus, (S)-I and (2S,4S)-II are physiol. active forms for conveying intrinsic signals of satiety and hunger to neurons in the hypothalamus.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: 1-(Cyclopropanecarbonyl)indoline-5-sulfonyl chloride, is researched, Molecular C12H12ClNO3S, CAS is 879562-21-7, about Identification of Inhibitors of NOD1-Induced Nuclear Factor-κB Activation.Safety of 1-(Cyclopropanecarbonyl)indoline-5-sulfonyl chloride.

NOD1 (nucleotide-binding oligomerization domain 1) protein is a member of the NLR (NACHT and leucine rich repeat domain containing proteins) protein family, which plays a key role in innate immunity as a sensor of specific microbial components derived from bacterial peptidoglycans and induction of inflammatory responses. Mutations in NOD proteins have been associated with various inflammatory diseases that affect NF-κB (nuclear factor κB) activity, a major signaling pathway involved in apoptosis, inflammation, and immune response. A luciferase-based reporter gene assay was utilized in a high-throughput screening program conducted under the NIH-sponsored Mol. Libraries Probe Production Center Network program to identify the active scaffolds. Herein, we report the chem. synthesis, structure-activity relationship studies, downstream counterscreens, secondary assay data, and pharmacol. profiling of the 2-aminobenzimidazole lead, I, as a potent and selective inhibitor of NOD1-induced NF-κB activation.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 4-Methoxypiperidine( cas:4045-24-3 ) is researched.Electric Literature of C6H13NO.Du, Lifei; Wang, Xiaoyu; Cui, Guonan; Xu, Bailing published the article 《Design, synthesis and biological evaluation of novel thiazole-based derivatives as human Pin1 inhibitors》 about this compound( cas:4045-24-3 ) in Bioorganic & Medicinal Chemistry. Keywords: thiazole based derivative human Pin1 inhibitors; PPIase; Pin1; Pin1 inhibitor; Thiazole derivatives. Let’s learn more about this compound (cas:4045-24-3).

Pin1 is a peptidyl prolyl cis-trans isomerase (PPIase) and inhibiting Pin1 is a potential way for discovering anti-tumor agents. With an aim to find potent Pin1 inhibitors with a novel scaffold, a series of thiazole derivatives with an alicyclic heterocycles on the 2-position were designed, synthesized and tested against human Pin1. Compound 9p bearing a 2-oxa-6-azaspiro [3,3] heptane moiety on the thiazole scaffold was identified as the most potent Pin1 inhibitor of this series with an IC50 value of 0.95 μM. The structure-activity relationship (SAR) and mol. modeling study indicated that introducing an alicyclic ring with an H-bond acceptor would be a viable way to improve the binding affinity.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

Recommanded Product: (R)-4-Hydroxydihydrofuran-2(3H)-one. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: (R)-4-Hydroxydihydrofuran-2(3H)-one, is researched, Molecular C4H6O3, CAS is 58081-05-3, about Structural and stereoisomeric specificity of serum-borne sugar acids related to feeding control by rats.

Specificity of chem. structures and stereoisomers among serum-borne short-chain organic acids in rats were assessed for their effects on feeding behavior and humoral factors by infusion into the rat 3rd cerebroventricle. Infusion of glyceric acid (1.0 μmol), 3,4-dihydroxybutanoic acid γ-lactone (3,4-DB), or 3,4,5-trihydroxypentanoic acid γ-lactone (2.50 μmol) immediately before the dark phase decreased food intake for, at most, 24 h. These acids did not affect drinking or ambulation. Initial feeding, not necessarily accompanied by periprandial drinking, was induced after infusion of 2,4-dihydroxy-butanoic acid γ-lactone, 2,4,5-trihydroxypentanoic acid γ-lactone (2,4,5-TP), or exogenous 2,4,5,6-tetrahydroxyhexanoic acid γ-lactone (2.50 μmol) in the light phase. Of these acids, 3,4-DB most potently suppressed and 2,4,5-TP most potently enhanced feeding. Of these, the 2S,4S-isomer and the 3S-isomer were the most potent of 2,4,5-TP and 3,4-DB, resp. Only the 2S,4S-isomer of 2,4,5-TP induced hypoglycemia with hyperinsulinemia, whereas opposite effects were produced by the 3S-isomer of 3,4-DB. The positions of the hydroxyl groups on 4-butanolide and the S- and S,S-stereoisomers are important in modulating food intake through the hypothalamus.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Ishibashi, Fumito; Hayashita, Mami; Okazaki, Momotoshi; Shuto, Yoshihiro researched the compound: (R)-4-Hydroxydihydrofuran-2(3H)-one( cas:58081-05-3 ).Quality Control of (R)-4-Hydroxydihydrofuran-2(3H)-one.They published the article 《Improved procedure for the enantiomeric synthesis of 1-hydroxy/acetoxy-2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane lignans: total syntheses of (+)-paulownin, (+)-phrymarin I and (+)-phrymarin II》 about this compound( cas:58081-05-3 ) in Bioscience, Biotechnology, and Biochemistry. Keywords: lignan paulownin phrymarin enantiomeric synthesis photocyclization. We’ll tell you more about this compound (cas:58081-05-3).

Short enantiomeric syntheses of the 1-hydroxy/acetoxy-3,7-dioxabicyclo[3.3.0]octane lignans, (+)-paulownin (I, R1 = R2 = R3 = H), and (+)-phrymarin I (I, R1 = R2 = OMe, R3 = Ac) and II (I, R1 = OMe, R2 = H, R3 = Ac), were accomplished by starting from the chiral synthon, (R)-(+)-3-hydroxybutanolide, and employing photocyclization as the key step.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

Computed Properties of C4H6O3. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. 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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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: 2-Chloro-5-iodo-3-methylpyridine, is researched, Molecular C6H5ClIN, CAS is 59782-89-7, about Structure-Activity Studies and Analgesic Efficacy of N-(3-Pyridinyl)-Bridged Bicyclic Diamines, Exceptionally Potent Agonists at Nicotinic Acetylcholine Receptors.Recommanded Product: 59782-89-7.

A series of exceptionally potent agonists at neuronal nicotinic acetylcholine receptors (nAChRs) has been investigated. Several N-(3-pyridinyl) derivatives of bridged bicyclic diamines exhibit double-digit-picomolar binding affinities for the α4β2 subtype, placing them with epibatidine among the most potent nAChR ligands described to date. Structure-activity studies have revealed that substitutions, particularly hydrophilic groups in the pyridine 5-position, differentially modulate the agonist activity at ganglionic vs central nAChR subtypes, so that improved subtype selectivity can be demonstrated in vitro. Analgesic efficacy has been achieved across a broad range of pain states, including rodent models of acute thermal nociception, persistent pain, and neuropathic allodynia. Unfortunately, the hydrophilic pyridine substituents that were shown to enhance agonist selectivity for central nAChRs in vitro tend to limit CNS penetration in vivo, so that analgesic efficacy with an improved therapeutic window was not realized with those compounds

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 59782-89-7, is researched, SMILESS is CC1=CC(I)=CN=C1Cl, Molecular C6H5ClINJournal, Journal of Chemical and Engineering Data called Some 2,5- and 5,6-dihalonicotinic acids and their precursors. IV, Author is Setliff, Frank L.; Lane, Julie E., the main research direction is pyridinecarboxylic acid dihalo; nicotinic acid dihalo; oxidation picoline; chloropyridinecarboxylic acid.Name: 2-Chloro-5-iodo-3-methylpyridine.

The pyridinecarboxylic acids I (R = Cl, R1 = CO2H, R2 = Cl, iodo; R = Cl, R1 = Cl, iodo, R2 = CO2H) were prepared by oxidation of I (R = Cl, R1 = Me, R2 = Cl, iodo; R = Cl, R1 = Cl, iodo, R2 = Me; resp.), which were prepared by diazotization and substitution of I (R = Cl, R1 = Me, R2 = NH2; R = Cl, R1 = NH2, R2 = Me; resp.). I (R = R1 = Cl, R2 = CO2H) and NaI gave I (R = iodo, R1 = Cl, R2 = CO2H).

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Reference:
Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem