Day: April 1, 2022

Receveur, Jean-Marie; Murray, Anthony; Linget, Jean-Michel; Norregaard, Pia K.; Cooper, Martin; Bjurling, Emelie; Nielsen, Peter Aadal; Hoegberg, Thomas published the article 《Conversion of 4-cyanomethyl-pyrazole-3-carboxamides into CB1 antagonists with lowered propensity to pass the blood-brain-barrier》. Keywords: CB1 receptor antagonist preparation pharmacokinetic structure activity lipophilicity; pyrazole carboxamide derivative preparation CB1 cannabinoid receptor antagonist.They researched the compound: 6-(Piperazin-1-yl)nicotinonitrile( cas:149554-29-0 ).Safety of 6-(Piperazin-1-yl)nicotinonitrile. 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:149554-29-0) here.

A series of amides, amidines and amidoximes have been made from the corresponding nitrile compounds, to provide potent antagonists and inverse agonists for the CB1 receptor with considerably lower lipophilicity, higher polar surface area and improved plasma/brain ratios compared to the centrally acting rimonabant. Extensive investigations of ADME and in vivo pharmacol. properties led to selection of the amide series and specifically the 4-(4-fluorophenyl)piperidin-4-ol derivative D4. A clear improvement in the peripheral profile over rimonabant was seen, although some contribution of central effect on the pronounced weight reduction in obese mice cannot be ruled out.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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: 3393-45-1, is researched, SMILESS is O=C1C=CCCO1, Molecular C5H6O2Journal, Article, Research Support, Non-U.S. Gov’t, Journal of the American Chemical Society called Radical Dehydroxylative Alkylation of Tertiary Alcohols by Ti Catalysis, Author is Xie, Hao; Guo, Jiandong; Wang, Yu-Quan; Wang, Ke; Guo, Peng; Su, Pei-Feng; Wang, Xiaotai; Shu, Xing-Zhong, the main research direction is alc alkene titanium radical dehydroxylative alkylation catalyst; alkane preparation.Related Products of 3393-45-1.

Deoxygenative radical C-C bond-forming reactions of alcs. are a long-standing challenge in synthetic chem., and the current methods rely on multistep procedures. Herein, we report a direct dehydroxylative radical alkylation reaction of tertiary alcs. This new protocol shows the feasibility of generating tertiary carbon radicals from alcs. and offers an approach for the facile and precise construction of all-carbon quaternary centers. The reaction proceeds with a broad substrate scope of alcs. and activated alkenes. It can tolerate a wide range of electrophilic coupling partners, including allylic carboxylates, aryl and vinyl electrophiles, and primary alkyl chlorides/bromides, making the method complementary to the cross-coupling procedures. The method is highly selective for the alkylation of tertiary alcs., leaving secondary/primary alcs. (benzyl alcs. included) and phenols intact. The synthetic utility of the method is highlighted by its 10-g-scale reaction and the late-stage modification of complex mols. A combination of experiments and d. functional theory calculations establishes a plausible mechanism implicating a tertiary carbon radical generated via Ti-catalyzed homolysis of the C-OH bond.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 4-(p-Tolyl)-2,2:6,2-terpyridine(SMILESS: CC1=CC=C(C2=CC(C3=NC=CC=C3)=NC(C4=NC=CC=C4)=C2)C=C1,cas:89972-77-0) is researched.Application of 2150-55-2. The article 《Structural modeling, in vitro antiproliferative activity, and the effect of substituents on the DNA fastening and scission actions of heteroleptic copper(II) complexes with terpyridines and naproxen》 in relation to this compound, is published in New Journal of Chemistry. Let’s take a look at the latest research on this compound (cas:89972-77-0).

A series of heteroleptic copper(II) complexes of the type [Cu(L1-6)(nap)Cl] (1-6) (L1-6 = 4′-(4-substituted)-2,2′:6′,2”-terpyridines, nap = naproxen) was synthesized and characterized. The single crystal analyses of complexes 1 and 6 show distorted octahedral geometry around the copper(II) ion. Structural parameters from the crystallog. and DFT studies are in good agreement with each other. HOMO-LUMO energy levels are constructed and the corresponding theor. frontier energy gaps understand the charge transfer occurring in the mol., and the lowering of the HOMO-LUMO band gap supports the bioactive properties of the mol. Electrochem. studies show a one-electron irreversible reduction process in the cathodic potential (Epc) region from -0.75 to -0.82 V. The obtained room-temperature magnetic moment values (1.82-1.93 μB), XRD and EPR spectral data support a distorted octahedral geometry for the copper(II) complexes. The binding studies of complexes 1, 5 and 6 with CT-DNA imply a groove mode of binding, and complex 5 exhibits a higher binding affinity than the other complexes. The binding results are further supported by mol. docking studies. The higher binding propensity of complex 5, containing R5, was proved by computationally derived factors such as chem. potential (μ), chem. hardness (η), electrophilicity (ω) and nuclease-independent chem. shift (NICS). All the complexes display pronounced nuclease activity against supercoiled pBR322 DNA. The in vitro antiproliferative activity ofplexes 1, 5 and 6 against human breast cancer cells (MCF-7) was assessed by MTT assay, which shows the potency of 1 and 5, with lower IC50 values than cisplatin and values comparable to doxorubicin. The complexes induce mitochondrial-mediated and caspase-dependent apoptosis with an increase in G0-G1 and subsequent arrest in the S phase in cell cycle evaluation.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

Safety of 4-(p-Tolyl)-2,2:6,2-terpyridine. 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: 4-(p-Tolyl)-2,2:6,2-terpyridine, is researched, Molecular C22H17N3, CAS is 89972-77-0, about Synthesis, characterization, and DFT investigation of IrIII tolylterpyridine complexes. Author is Yoshikawa, Naokazu; Yamabe, Shinichi; Kanehisa, Nobuko; Kai, Yasushi; Takashima, Hiroshi; Tsukahara, Keiichi.

Three new polypyridine Ir(III) complexes [IrIIICl(L)(tterpy)](PF6)2 {L = phen (1), dpphen (2), and dmbpy (3)} were prepared Reference complexes [IrIIICl(bpy)(tterpy)](PF6)2 (4) and [IrIII(L)2](PF6)3 {L = tterpy (5) and terpy (6)} were also prepared Abbreviations of the ligands used here are phen = 1,10-phenanthroline, dpphen = 4,7-diphenyl-1,10-phenanthroline, bpy = 2,2′-bipyridine, dmbpy = 4,4′-dimethyl-2,2′-bipyridine, tterpy = 4′-(4-tolyl)-2,2′:6′,2”-terpyridine, and terpy = 2,2′:6′,2”-terpyridine. The syntheses, which were accomplished in typical reaction times of fifteen minutes by using a microwave oven, were easier than a previous method. The complexes were characterized by electrospray mass spectrometry, UV/visible spectroscopy, and cyclic voltammetry (CV). The x-ray structures of the two complexes 5 and 6 were also obtained. Cyclic voltammograms of all the [IrIIICl(L)(tterpy)]2+ complexes showed that the 1st reduction occurred, at ∼-0.67 V, which is attributed to the reduction of the tterpy ligand in [IrIIICl(L)(tterpy)]2+. The electronic properties of complexes 5 and 6 were studied by using B3LYP functional calculations, and their optimized geometries were compared to those of the exptl. observed ones. Excited triplet and singlet states are also examined by using time-dependent d. functional theory (TDDFT). The calculated energies of the lowest singlet and triplet states in the two complexes are in good agreement with the exptl. absorption and phosphorescence spectra. [IrIIICl(L)(tterpy)]2+ emits an intense phosphorescence at room temperature Since the lowest unoccupied MOs (LUMOs) of all [IrIIICl(L)(tterpy)]2+ complexes are composed of the π*-system contribution of the tterpy ligand, the spectroscopic and electrochem. results are discussed comparatively.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 5,6-Dihydro-2H-pyran-2-one( cas:3393-45-1 ) is researched.Synthetic Route of C5H6O2.Gabriel, Pablo; Almehmadi, Yaseen A.; Wong, Zeng Rong; Dixon, Darren J. published the article 《A General Iridium-Catalyzed Reductive Dienamine Synthesis Allows a Five-Step Synthesis of Catharanthine via the Elusive Dehydrosecodine》 about this compound( cas:3393-45-1 ) in Journal of the American Chemical Society. Keywords: catharanthine synthesis reductive activation; isoquinuclidine preparation reductive activation. Let’s learn more about this compound (cas:3393-45-1).

A new reductive strategy for the stereo- and regioselective synthesis of functionalized isoquinuclidines has been developed. Pivoting on the chemoselective iridium(I)-catalyzed reductive activation of β,γ-unsaturated δ-lactams, the efficiently produced reactive dienamine intermediates readily undergo [4 + 2] cycloaddition reactions with a wide range of dienophiles, resulting in the formation of bridged bicyclic amine products. This new synthetic approach was extended to aliphatic starting materials, resulting in the efficient formation of cyclohexenamine products, and readily applied as the key step in the shortest (five-step) total synthesis of vinca alkaloid catharanthine to date, proceeding via its elusive biosynthetic precursor, dehydrosecodine.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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 Asymmetric [3+2] cycloaddition reaction of a chiral cyclic nitrone for the synthesis of new tropane alkaloids, published in 2020-01-03, which mentions a compound: 3393-45-1, Name is 5,6-Dihydro-2H-pyran-2-one, Molecular C5H6O2, Quality Control of 5,6-Dihydro-2H-pyran-2-one.

The 1,3-dipolar cycloaddition of a chiral nitrone with α,β-unsaturated lactones was carried out to give the corresponding isoxazolidines. Tetrahydro-1,3-oxazines with an oxa-tropane skeleton were obtained in one step by alkylation. The structures of several of these compounds were corroborated by X-ray diffraction and mol. modeling studies confirmed the results and proposed a mechanism for their formation.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

Abdel-Kader, Maged S.; Al-Taweel, Areej M.; El-Deeb, Kadriya S. published an article about the compound: (S)-5-(Hydroxymethyl)dihydrofuran-2(3H)-one( cas:32780-06-6,SMILESS:O=C1O[C@H](CO)CC1 ).Synthetic Route of C5H8O3. 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:32780-06-6) through the article.

Bioactivity guided phytochem. study of the petroleum ether and butanol extracts of Clematis hirsuta resulted in the isolation of 12 compounds Rat paw edema as a model of acute inflammation was used to evaluate the anti-inflammatory activity of the extracts and the chromatog. fractions. Five known sterols and triterpenes namely: β-amyrin (1), lupeol (2), β-sitosterol (3), oleanolic acid (4) and stigmasterol glycoside (5) were isolated from the petroleum ether extract The n-butanol extract afforded two compounds reported for the first time from natural source: (S)-(+)-dihydro-5-(hydroxymethyl)-2(3H)-furanone (7) and (S)-(-)-5-hydroxymethyl-2(5H)-furanone (8). In addition, anemonin (6), dihydro-4-hydroxy-5-(hydroxymethyl)-2(3H)-furanone (2-deoxy-D-ribono-1,4-lactone) (9), biophenol (cimidahurin) (10), glucose (11) and sucrose (12) were also identified. The structures were determined from spectroscopic data including 1D- and 2D-NMR experiments

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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: 89972-77-0, is researched, SMILESS is CC1=CC=C(C2=CC(C3=NC=CC=C3)=NC(C4=NC=CC=C4)=C2)C=C1, Molecular C22H17N3Journal, Indian Journal of Chemistry, Section A: Inorganic, Bio-inorganic, Physical, Theoretical & Analytical Chemistry called A two-component co-crystal of Cu(II) complex of p-tolyl-terpyridine, Author is Bhattacharya, Dibyendu, the main research direction is crystal structure copper tolyl terpyridine nitrate complex preparation.Computed Properties of C22H17N3.

A unique two-component co-crystal, [Cu(L)(NO3)2][Cu(L)(NO3)(CH3OH)](NO3)·H2O (L = p-tolyl-terpyridine) has been prepared in (1:1) water-methanol medium at room temperature and characterized by single-crystal x-ray diffraction anal. The compound crystallizes in the triclinic system (space group P1̅). The structure consists of two mononuclear Cu(II) moieties, one cationic and another neutral. In the asym. unit, one Cu(II) center furnishes a five-coordinated distorted square pyramidal geometry (CuN3O2), organized by three nitrogens of L ligand and one oxygen of a monodentate nitrate anion in the equatorial position and one methanol mol. in the apical position with geometry index τ5 = 0.15. The other Cu(II) center displays a four-coordinate distorted square planar geometry (CuN3O), framed by three nitrogens of ligand L and one oxygen of a monodentate nitrate anion with geometry index τ4 = 0.29 and the tetrahedral character parameter, THCDa/100 of -1.00.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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, Journal of Chemical Ecology called Bioactivity, synthesis, and chirality of the sex pheromone of currant stem girdler, Janus integer, Author is James, David G.; Petroski, Richard J.; Cosse, Allard A.; Zilkowski, Bruce W.; Bartelt, Robert J., which mentions a compound: 32780-06-6, SMILESS is O=C1O[C@H](CO)CC1, Molecular C5H8O3, Recommanded Product: 32780-06-6.

It was previously reported that females of the currant stem girdler, Janus integer Norton (Hymenoptera: Cephidae), produce a compound, (Z)-9-octadecen-4-olide (I), that is sensitively detected by the antennae of males only. These characteristics suggested a pheromonal function, and this has now been confirmed with behavioral tests. Field tests conducted during two seasons in a com. red currant field showed that synthetic racemic I is attractive to male J. integer under natural conditions. A clear dose-response was evident, with greatest numbers of girdlers caught in sticky traps baited with 10 mg of the pheromone (in rubber septa) and least in traps baited with 1 mg or less. During May 2002, 10, 5, 3, and 1 mg baited traps caught means of 41.4, 26.6, 6.7, and 2.7 males/trap/visit (3-5 day intervals), resp., with a maximum of 229 males caught in a single trap baited with 5 mg. A new synthetic method for racemic I is presented. The absolute configuration of natural I from the male sawflies was determined to be (R). The potential for using the sex pheromone of J. integer to improve management of this currant and gooseberry pest is discussed.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

Name: (S)-3-(Piperidin-2-yl)pyridine. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: (S)-3-(Piperidin-2-yl)pyridine, is researched, Molecular C10H14N2, CAS is 494-52-0, about A rapid LC-MS/MS method for simultaneous determination of nicotine and its key derivatives including hydroxylation isomers. Author is Shen, Yixiao; Zhang, Ning; Prinyawiwatkul, Witoon; Xu, Zhimin.

A rapid high pressure liquid chromatog. coupled with tandem mass spectrometry method (LC-MS/MS) was developed for simultaneously determining nicotine (NT) and its derivatives including cotinine (CT), trans-3-hydroxycotinine (HC), nornicotine (NNT), anatabine (AT), anabasine (AB) and amino ketone (4-(methylamino)-1-(3-pyridyl)1-butanone) (AK) as well as two important metabolites isomers 2-hydroxynicotine (2-HN) and 6-hydroxynicotine (6-HN) in tobacco leaves. Different from other methods, 2-HN and 6-HN isomers can be successfully separated and quantified through a combination of amide and C18 columns and optimized multiple reaction monitoring mode of tandem mass spectrometry. The limits of detections (LOD) and quantification (LOQ) of these compounds were 0.02 and 0.06 ng/mL for CT and HC, 0.05 and 0.15 ng/mL for AK and 6-HN, and 0.1 and 0.3 ng/mL for AB, NNT, AT, 2-HN and NT, resp. Their recoveries ranged from 86.1% for 2-HN to 102.2% for AK by using solvent extraction assisted with ultrasonication. The developed method was validated through determination of the compounds in different regular and genetically modified (for lowering nicotine) tobacco leaves. Conclusively, it is a robust and rapid method for simultaneous quantification of nicotine and its derivatives in tobacco products. The protocol of the method could also be applied in developing anal. method for tracking the toxic substances synthesis and metabolism in tobacco leaves or other herbal plants.

There is still a lot of research devoted to this compound(SMILES：C1(C=NC=CC=1)[C@@H]1CCCCN1)Name: (S)-3-(Piperidin-2-yl)pyridine, and with the development of science, more effects of this compound(494-52-0) can be discovered.

Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI