Heterocyclic Building Blocks-Pyrrolines

Computed Properties of C9H9NO2. 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: (2-Methylbenzo[d]oxazol-5-yl)methanol, is researched, Molecular C9H9NO2, CAS is 136663-38-2, about Palladium-Catalyzed Direct Hydroxymethylation of Aryl Halides and Triflates with Potassium Acetoxymethyltrifluoroborate. Author is Murai, Norio; Yonaga, Masahiro; Tanaka, Keigo.

Suzuki-Miyaura cross-coupling reactions of aryl halides and triflates with potassium acetoxymethyltrifluoroborate afforded the corresponding aryl and heteroaryl methanol products in moderate to excellent yields.

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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.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. researched the compound: 1-(Cyclopropanecarbonyl)indoline-5-sulfonyl chloride( cas:879562-21-7 ).Formula: C12H12ClNO3S.They published the article 《Identification of Inhibitors of NOD1-Induced Nuclear Factor-κB Activation》 about this compound( cas:879562-21-7 ) in ACS Medicinal Chemistry Letters. Keywords: indoline tetrahydroisoquinoline aminobenzimidazole preparation; structure activity relationship pharmacokinetics NOD1 induced NFkappaB activation inhibitor. We’ll tell you more about this compound (cas:879562-21-7).

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

Product Details of 58081-05-3. 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 A novel generation of optically active ethyl 4-chloro-3-hydroxybutyrate as a C4 chiral building unit using microbial dechlorination. Author is Suzuki, Toshio; Idogaki, Hideaki; Kasai, Naoya.

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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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

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 Pheromone synthesis. XXIV. Synthesis of optically active forms of ipsdienol and ipsenol. The pheromone components of Ips bark beetles, published in 1979, which mentions a compound: 58081-05-3, mainly applied to ipsdienol ipsenol pheromone chiral preparation; Ips terpene pheromone, Safety of (R)-4-Hydroxydihydrofuran-2(3H)-one.

(R)-(-)- And (S)-(+)-ipsdienol (I) [(R)-(-)- and (S)-(+)-Me2C:CH(OH)CH2C(:CH2)CH:CH2, resp.] were prepared from (R)-(+)-glyceraldehyde acetonide and (R)-(+)-malic acid, resp., via the intermediate epoxide II and its enantiomer, resp. I is the naturally occurring form of this pheromone. Treating (S)- and (R)-isobutylethylene oxide with CH2:C(MgCl)CH:CH2 gave 32 and 50% (S)-(-)- and (R)-(+)-Me2CHCH2CH(OH)CH2C(:CH2)CH:CH2, resp.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

Application In Synthesis of 4-Methoxypiperidine. 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: 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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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: 4-Chloro-2-fluoropyridine, is researched, Molecular C5H3ClFN, CAS is 34941-92-9, about Access to Highly Substituted 7-Azaindoles from 2-Fluoropyridines via 7-Azaindoline Intermediates.Related Products of 34941-92-9.

A versatile synthesis of 7-azaindoles e. g., I, from substituted 2-fluoropyridines is described. C3-metalation and 1,4-addition to nitroolefins provide substituted 2-fluoro-3-(2-nitroethyl)pyridines. A facile oxidative Nef reaction/reductive amination/intramol. SNAr sequence furnishes 7-azaindolines. Finally, optional regioselective electrophilic C5-substitution (e.g., bromination or nitration) and subsequent in situ oxidation delivers highly functionalized 7-azaindoles in high overall efficiency.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

Reference of 4-Methoxypiperidine. 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 Photoredox B-H functionalization to selective B-N(sp3) coupling of nido-carborane with primary and secondary amines. Author is Huang, Ronghui; Zhao, Weijia; Xu, Shengwen; Xu, Jingkai; Li, Chunxiao; Lu, Changsheng; Yan, Hong.

Access to nido-carborane site-selective B-N(sp3) coupling by photoredox catalyzed B-H activation has been achieved for the first time, which leads to the synthesis of a series of nitrogen-containing nido-carboranes with moderate to good yields. This protocol is applicable to primary and secondary amines containing alkyl, or heteroaryl groups as well as sulfonamides. Furthermore, the open to air and metal-free conditions with excellent site-selectivity represent a significant improvement for B-H functionalization of nido-carboranes with organic functionalities.

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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: 4-Methoxypiperidine, is researched, Molecular C6H13NO, CAS is 4045-24-3, about Three-component radical homo Mannich reaction.Safety of 4-Methoxypiperidine.

By employing a radical process, enolizable aldehydes were utilized as substrates in the three-component radical homo-Mannich reaction for the streamlined synthesis of γ-amino-carbonyl compounds. The electrophilic radicals were generated from thiols HSCHR1C(O)R2 (R1 = H, Me; R2 = Me, EtO, PhCH2O, 1-adamantyl, Et2N, etc.) via the desulfurization process facilitated by visible-light, and then added to the electron-rich double bonds of enamines, formed in-situ from aldehydes or ketones R3CH2C(O)R4 [R3 = H, Et, MeSCH2, Ph, PhCH2, etc., R4 = H; R3 = H, R4 = Ph, 3-FC6H4, etc.; R3R4 = (CH2)5, CH2CHPhCH2CH2, CH2N(CH2Ph)CH2CH2, etc.] and amines R5NHR6 [R5 = Me, R6 = H2C:CHCH2, PhCH2, cyclohexyl, etc.; R5 = PhCH2, R6 = PhCH2, EtO2CCH2, etc.; R5R6 = (CH2)4, CHPh(CH2)3, etc.] to provide the products I in a single step. The broad scope, mild conditions, high functional group tolerance, and modularity of this metal-free approach for the synthesis of complex tertiary amine scaffolds will likely be of great utility to chemists in both academia and industry.

If you want to learn more about this compound(4-Methoxypiperidine)Safety of 4-Methoxypiperidine, you may wish to communicate with the author of the article,or consult the relevant literature related to this compound(4045-24-3).

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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.Liu, Qing; Liu, Zhen-Ling; Tian, Jing; Shi, Wei; Liu, Yin-Qian researched the compound: (R)-4-Hydroxydihydrofuran-2(3H)-one( cas:58081-05-3 ).SDS of cas: 58081-05-3.They published the article 《The semisynthetic spin-labelled derivatives of 3-hydroxybutanolide as potential oxidative stress inhibitors》 about this compound( cas:58081-05-3 ) in Natural Product Research. Keywords: hydroxybutanolide spin labeled antioxidant oxidative stress inhibitor; 3-hydroxybutanolide; antioxidant activity; spin-labelled; synthesis. We’ll tell you more about this compound (cas:58081-05-3).

To obtain more accessible oxidative stress inhibitors, a series of novel spin-labeled derivatives of 3-hydroxybutanolide with the natural active compound (kinsenoside) as the lead compound were designed, synthesized from nitroxide free radical piperidines and pyrrolines and the main structural unit of kinsenoside: 3-hydroxybutanolide. Antioxidant activity screening of these derivatives was performed using MTT method on rat pheochromocytoma PC12 cells. The antioxidative stress effect was further investigated on the changes of the important antioxidant enzyme activities and intracellular reactive oxygen species production Some of the derivatives showed comparable or superior antioxidative stress activity to kinsenoside. Also, most of the tested derivatives displayed obvious antioxidative ability in concentrations Cytotoxic assay simultaneously indicated that all compounds had very low toxicity to normal cells. Based on the observed results, the structure-activity relationship of these derivatives was discussed.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

Reference of 2,6-Dichloro-3-fluoropyridine. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 2,6-Dichloro-3-fluoropyridine, is researched, Molecular C5H2Cl2FN, CAS is 52208-50-1, about 2,6-Di(arylamino)-3-fluoropyridine Derivatives as HIV Non-Nucleoside Reverse Transcriptase Inhibitors. Author is Sergeyev, Sergey; Yadav, Ashok Kumar; Franck, Philippe; Michiels, Johan; Lewi, Paul; Heeres, Jan; Vanham, Guido; Arien, Kevin K.; Vande Velde, Christophe M. L.; De Winter, Hans; Maes, Bert U. W..

New non-nucleoside reverse transcriptase inhibitors (NNRTI), which are similar in structure to earlier described di(arylamino)pyrimidines but featuring a 2,6-di(arylamino)-3-fluoropyridine, 2,4-di(arylamino)-5-fluoropyrimidine, or 1,3-di(arylamino)-4-fluorobenzene moiety instead of a 2,4-disubstituted pyrimidine moiety, are reported. The short and practical synthesis of novel NNRTI relies on two sequential Pd-catalyzed aminations as the key steps. It is demonstrated through direct comparison with reference compounds that the presence of a fluorine atom increases the in vitro anti-HIV activity, both against the wild type virus and drug-resistant mutant strains. Three compounds, e.g., I, were found to display E50 close to 1.0 nM and a very high selectivity index (>40000).

Here is a brief introduction to this compound(52208-50-1)Reference of 2,6-Dichloro-3-fluoropyridine, if you want to know about other compounds related to this compound(52208-50-1), you can read my other articles.

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