Heterocyclic Building Blocks-Pyrrolines

Name: (R)-4-Hydroxydihydrofuran-2(3H)-one. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: (R)-4-Hydroxydihydrofuran-2(3H)-one, is researched, Molecular C4H6O3, CAS is 58081-05-3, about Magnesium ethoxide mediated lactone aminolysis with aminoheterocycles. Author is Mercado-Marin, Eduardo V.; Chheda, Pratik Rajesh; Faulkner, Andrea; Carrera, Diane.

A mild method for the aminolysis of lactones with aminoheterocycles in the presence of magnesium ethoxide was described. A wide range of electronically diverse aminoheterocycles and substituted lactones successfully participated in this transformation to furnish the resulting amido-alc. products. Further application of this method to the synthesis of chiral α-amino amides derivatives was also described.

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

Khan, Pasha M.; Correa, Ricardo G.; Divlianska, Daniela B.; Peddibhotla, Satyamaheshwar; Sessions, E. Hampton; Magnuson, Gavin; Brown, Brock; Suyama, Eigo; Yuan, Hongbin; Mangravita-Novo, Arianna; Vicchiarelli, Michael; Su, Ying; Vasile, Stefan; Smith, Layton H.; Diaz, Paul W.; Reed, John C.; Roth, Gregory P. published the article 《Identification of Inhibitors of NOD1-Induced Nuclear Factor-κB Activation》. Keywords: indoline tetrahydroisoquinoline aminobenzimidazole preparation; structure activity relationship pharmacokinetics NOD1 induced NFkappaB activation inhibitor.They researched the compound: 1-(Cyclopropanecarbonyl)indoline-5-sulfonyl chloride( cas:879562-21-7 ).Application In Synthesis of 1-(Cyclopropanecarbonyl)indoline-5-sulfonyl chloride. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:879562-21-7) here.

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

Formula: C4H6O3. 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, X-ray Analysis, and Biological Evaluation of a New Class of Stereopure Lactam-Based HIV-1 Protease Inhibitors. Author is Wu, Xiongyu; Oehrngren, Per; Joshi, Advait A.; Trejos, Alejandro; Persson, Magnus; Arvela, Riina K.; Wallberg, Hans; Vrang, Lotta; Rosenquist, Aasa; Samuelsson, Bertil B.; Unge, Johan; Larhed, Mats.

In an effort to identify a new class of druglike HIV-1 protease inhibitors, stereopure β-hydroxy γ-lactam-containing inhibitors I (X = CH2, CH2CH2; R = H, Br, 2-pyridyl, 3-pyridyl, 4-pyridyl) have been synthesized and biol. evaluated. Three of these compounds were also cocrystd. with HIV-1 protease. The impact of the tether length of the central spacer (two or three carbons) was investigated. The compound I (X = CH2; R = Br) with a shorter tether and (3R,4S) absolute configuration exhibited high activity with a Ki of 2.1 nM and an EC50 of 0.64 μM. Further optimization by decoration of the P1′ side chain furnished an even more potent HIV-1 protease inhibitor (3R,4S)-I (X = CH2; R = 3-pyridyl) (Ki = 0.8 nM, EC50 = 0.04 μM). According to X-ray anal., this new class of inhibitors did not fully succeed in forming two sym. hydrogen bonds to the catalytic aspartates. The crystal structures of the complexes further explain the difference in potency between the shorter inhibitors (two-carbon spacer) and the longer inhibitors (three-carbon spacer).

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Reference:
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: (R)-4-Hydroxydihydrofuran-2(3H)-one( cas:58081-05-3 ) is researched.Synthetic Route of C4H6O3.Panek, James S.; Masse, Craig E. published the article 《Total Synthesis of (+)-Mycotrienol and (+)-Mycotrienin I》 about this compound( cas:58081-05-3 ) in Journal of Organic Chemistry. Keywords: mycotrienin I mycotrienol synthesis convergent asym; chiral allylsilane bond construction; Stille coupling macrocyclization triene incorporation. Let’s learn more about this compound (cas:58081-05-3).

A highly convergent asym. synthesis of the ansamycin antibiotics (+)-mycotrienin I (I) (R = cyclohexylcarbonyl-D-Ala) and (+)-mycotrienol (I) (R = H) (II) has been achieved through the synthesis and coupling of the C9-C16 subunit (III) and the aromatic subunit (IV). All four stereogenic centers were introduced using chiral allylsilane bond construction methodol. A key feature of the synthetic scheme includes the incorporation of the (E, E, E)-triene unit with simultaneous macrocyclization via a Stille-type coupling-macrocyclization.

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

Category: pyrrolines. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: 2-Chloro-5-iodo-3-methylpyridine, is researched, Molecular C6H5ClIN, CAS is 59782-89-7, about First identification of boronic species as novel potential inhibitors of the Staphylococcus aureus NorA efflux pump. Author is Fontaine, Fanny; Hequet, Arnaud; Voisin-Chiret, Anne-Sophie; Bouillon, Alexandre; Lesnard, Aurelien; Cresteil, Thierry; Jolivalt, Claude; Rault, Sylvain.

Overexpression of efflux pumps is an important mechanism of bacterial resistance that results in the extrusion of antimicrobial agents outside the bacterial cell. Inhibition of such pumps appears to be a promising strategy that could restore the potency of existing antibiotics. The NorA efflux pump of Staphylococcus aureus confers resistance to a wide range of unrelated substrates, such as hydrophilic fluoroquinolones, leading to a multidrug-resistance phenotype. Here, 150 heterocyclic boronic species were evaluated for their activity against susceptible and resistant strains of S. aureus. Twenty-four hit compounds, although inactive when tested alone, were found to potentiate ciprofloxacin activity by a 4-fold increase at concentrations ranging from 0.5 to 8 μg/mL against S. aureus 1199B, which overexpresses NorA. Boron-free analogs showed no biol. activity, thus revealing that the boron atom is crucial for biol. activity. This work describes the first reported efflux pump inhibitory activity of boronic acid derivatives

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

Du, Xiao-Ming; Sun, Ning-Yi; Irino, Nobuto; Shoyama, Yukihiro published an article about the compound: (R)-4-Hydroxydihydrofuran-2(3H)-one( cas:58081-05-3,SMILESS:O=C1OC[C@H](O)C1 ).HPLC of Formula: 58081-05-3. 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:58081-05-3) through the article.

The glycosidic constituents of whole plants of Anoectochilus formosanus propagated by tissue culture were investigated. A new compound, 2-(β-D-glucopyranosyloxymethyl)-5-hydroxymethylfuran, along with the known compounds, 3-(R)-3-β-D-glucopyranosyloxybutanolide (kinsenoside), 3-(R)-3-β-D-glucopyranosyloxy-4-hydroxybutanoic acid, 1-O-isopropyl-β-D-glucopyranoside, (R)-(+)-3,4-dihydroxybutanoic acid γ-lactone, 4-(β-D-glucopyranosyloxy)benzyl alc., (6R,9S)-9-hydroxy-megastigma-4,7-dien-3-one-9-O-β-D-glucopyranoside, and corchoionoside C were isolated.

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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: 58081-05-3, is researched, SMILESS is O=C1OC[C@H](O)C1, Molecular C4H6O3Journal, Article, Research Support, Non-U.S. Gov’t, Molecules called Efficient synthesis of kinsenoside and goodyeroside A by a chemo-enzymatic approach, Author is Zhang, Yang; Xia, Yihong; Lai, Yongji; Tang, Fang; Luo, Zengwei; Xue, Yongbo; Yao, Guangmin; Zhang, Yonghui; Zhang, Jinwen, the main research direction is kinsenoside chemoenzymic synthesis; goodyeroside chemoenzymic synthesis.Electric Literature of C4H6O3.

Kinsenoside (1) and goodyeroside A (2), two naturally occurring stereoisomers with diverse biol. activities, have been synthesized efficiently by a chemo-enzymic approach with a total yield of 12.7%. The aglycons, (R)- and (S)-3-hydroxy-γ-butyrolactone, were prepared from d- and l-malic acid by a four-step chem. approach with a yield of 75%, resp. These butyrolactones were then successfully glycosidated using β-D-glucosidase as a catalyst in a homogeneous organic-water system. Under the optimized enzymic conditions, the yields of kinsenoside and goodyeroside A in the enzymic steps both reached 16.8%.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

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, Non-U.S. Gov’t, Chemistry & Biology (Oxford, United Kingdom) called Honaucins A-C, Potent Inhibitors of Inflammation and Bacterial Quorum Sensing: Synthetic Derivatives and Structure-Activity Relationships, Author is Choi, Hyukjae; Mascuch, Samantha J.; Villa, Francisco A.; Byrum, Tara; Teasdale, Margaret E.; Smith, Jennifer E.; Preskitt, Linda B.; Rowley, David C.; Gerwick, Lena; Gerwick, William H., which mentions a compound: 58081-05-3, SMILESS is O=C1OC[C@H](O)C1, Molecular C4H6O3, Electric Literature of C4H6O3.

Honaucins A-C were isolated from the cyanobacterium Leptolyngbya crossbyana which was found overgrowing corals on the Hawaiian coast. Honaucin A consists of (S)-3-hydroxy-γ-butyrolactone and 4-chlorocrotonic acid, which are connected via an ester linkage. Honaucin A and its two natural analogs exhibit potent inhibition of both bioluminescence, a quorum-sensing-dependent phenotype, in Vibrio harveyi BB120 and lipopolysaccharide-stimulated nitric oxide production in the murine macrophage cell line RAW264.7. The decrease in nitric oxide production was accompanied by a decrease in the transcripts of several proinflammatory cytokines, most dramatically interleukin-1β. Synthesis of honaucin A, as well as a number of analogs, and subsequent evaluation in anti-inflammation and quorum-sensing inhibition bioassays revealed the essential structural features for activity in this chem. class and provided analogs with greater potency in both assays.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

Formula: 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 Stereoselective Cobalt-Catalyzed Cross-Coupling Reactions of Arylzinc Chlorides with α-Bromolactones and Related Derivatives. Author is Hofmayer, Maximilian S.; Sunagatullina, Alisa; Broesamlen, Daniel; Mauker, Philipp; Knochel, Paul.

α-Bromolactones bearing a substituent in the β-position undergo a highly trans-diastereoselective arylation with arylzinc chlorides in the presence of 10-20% CoCl2 and 10-20% PPh3 in THF under mild conditions (25°C, 16 h) leading to optically enriched α-arylated lactones and protected aldol products (99% ee) in 52-96% yield. The synthetic utility of this arylation was demonstrated by the stereoselective preparation of an artificial rotenoid MOM-protected munduserol derivative

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

Recommanded Product: 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 Chemoselective CaO-Mediated Acylation of Alcohols and Amines in 2-Methyltetrahydrofuran. Author is Pace, Vittorio; Hoyos, Pilar; Alcantara, Andres R.; Holzer, Wolfgang.

Calcium oxide is proposed as an innocuous acid scavenger for the chemoselective synthesis of amide- and ester-type compounds Although these mols. have wide spread applications in organic and pharmaceutical chem., and a large number of routes have been designed for their synthesis, the development of more efficient and environmentally friendly acylation strategies remains an ongoing challenge. The use of CaO allows for the stoichiometric acylation of primary alcs. in the presence of phenols or tertiary alcs.; amines can also be subjected to acylation reactions in the presence of hydroxyl groups. Chirality is obtained through acylation if the starting material is an optically pure alc. or if a chiral acylating agent is used. Furthermore, the use of 2-methyltetrahydrofuran (2-MeTHF), a more ecofriendly solvent, leads to maximized yields. This protocol is successfully applied to the synthesis of an interesting N-aryloxazolidin-2-one intermediate for the preparation of linezolid-type compounds

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