Month: April 2022

Application In Synthesis of 5-Methoxy-1H-indole-2-carbaldehyde. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 5-Methoxy-1H-indole-2-carbaldehyde, is researched, Molecular C10H9NO2, CAS is 21778-81-4, about Catalytic Asymmetric [3 + 2] Annulation via Indolyl Copper-Allenylidene Intermediates: Diastereo- and Enantioselective Assembly of Pyrrolo[1,2-a]indoles. Author is Zhang, Jian; Ni, Tao; Yang, Wu-Lin; Deng, Wei-Ping.

A catalytic asym. decarboxylative [3 + 2] annulation via indolyl copper-allenylidene amphiphilic intermediates has been developed. This protocol offers a straightforward method for the synthesis of biol. important pyrrolo[1,2-a]indoles bearing contiguous quaternary and tertiary stereogenic centers with excellent diastereo- and enantioselectivities (up to >20:1 dr and >99% ee). In addition, the diversity-oriented synthesis of pyrrolo[1,2-a]indoles was achieved via versatile transformations of the alkyne-containing cycloadducts.

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Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 5-Methoxy-1H-indole-2-carbaldehyde( cas:21778-81-4 ) is researched.COA of Formula: C10H9NO2.Kuwano, Satoru; Suzuki, Takumi; Yamanaka, Masahiro; Tsutsumi, Ryosuke; Arai, Takayoshi published the article 《Catalysis based on C-I···π halogen bonds: electrophilic activation of 2-alkenylindoles by cationic halogen-bond donors for [4+2] cycloadditions》 about this compound( cas:21778-81-4 ) in Angewandte Chemie, International Edition. Keywords: alkenylindole iodoimidazolium triflate catalyst diastereoselective cycloaddition; indolyl tetrahydrocarbazole preparation; cycloaddition; density-functional calculations; halogen bonding; heterocycles; noncovalent bonds. Let’s learn more about this compound (cas:21778-81-4).

Homo- and cross-[4+2] cycloadditions of 2-alkenylindoles catalyzed by cationic halogen-bond donors were developed. Under mild reaction conditions, 3-indolyl-substituted tetrahydrocarbazole derivatives were obtained in good to excellent yields. Exptl. and quantum calculation studies revealed that the electrophilic activation of 2-alkenylindoles was achieved by C-I···π halogen bonds.

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Pyridazine – Wikipedia,
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Product Details of 136725-55-8. 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)-(-)-3-Fluoropyrrolidine Hydrochloride, is researched, Molecular C4H9ClFN, CAS is 136725-55-8, about Enantiomorphic Perovskite Ferroelectrics with Circularly Polarized Luminescence. Author is Gao, Ji-Xing; Zhang, Wan-Ying; Wu, Zheng-Guang; Zheng, You-Xuan; Fu, Da-Wei.

Materials with circularly polarized luminescence (CPL) activity have immense potential applications in mol. switches, optical sensors, information storage, asym. photosynthesis, 3D optical displays, biol. probe, and spintronic devices. However, the achiral architectures of most of the luminophores severely limit their practical needs. Within this context, mol. ferroelecs. with striking chem. variability and structure-property flexibility bring light to the assembly of CPL-active ferroelec. materials. Herein, we report organic-inorganic perovskite enantiomorphic ferroelecs., (R)- and (S)-3-(fluoropyrrolidinium)MnBr3, undergoing a 222F2-type ferroelec. phase transition at 273 K. Their mirror relationships are verified by both single-crystal X-ray diffraction and vibrational CD (VCD). Furthermore, the corresponding Cotton effect for two chiral crystals was captured by mirror CPL activity. This may be assigned to the inducing interaction between the achiral luminescent perovskite framework and chiral organic components. As far as we know, this is the first mol. ferroelec. with CPL activity. Accordingly, this will inspire intriguing research in mol. ferroelecs. with CPL activity and holds great potential for the development of new optoelectronic devices.

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Pyridazine – Wikipedia,
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The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 5-Methoxy-1H-indole-2-carbaldehyde, is researched, Molecular C10H9NO2, CAS is 21778-81-4, about Synthesis of indole-2-carbaldehydes, 2-(2-aminoethyl) – and 2-(2-aminopropyl)indoles, the main research direction is indolecarboxaldehydes aminoalkyl; aminoalkyl indolecarboxaldehydes.Application In Synthesis of 5-Methoxy-1H-indole-2-carbaldehyde.

Et indole-2-carboxylate derivatives (e.g. I) were reduced by LiAlH4 to indole-2-methanol derivatives (e.g. II). These were oxidized by MnO2 to indole-2-carboxaldehyde derivatives (e.g. III), which were also prepared from the indole-2-carboxylates by the McFadyen-Stevens reaction. The aldehydes reacted with MeNO2 and EtNO2, and the condensation products (e.g. IV and V) were reduced by LiAlH4 to 2-(2-aminoethyl)indoles (e.g. VI) and 2-(2-aminopropyl)indoles (e.g. VII), resp.

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Pyridazine – Wikipedia,
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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: 136725-55-8, is researched, Molecular C4H9ClFN, about Discovery and Characterization of Selective and Ligand-Efficient DYRK Inhibitors, the main research direction is DYRK inhibitor ligand efficient.Reference of (R)-(-)-3-Fluoropyrrolidine Hydrochloride.

Dual-specificity tyrosine-regulated kinase 1A (DYRK1A) regulates the proliferation and differentiation of neuronal progenitor cells during brain development. Consequently, DYRK1A has attracted interest as a target for the treatment of neurodegenerative diseases, including Alzheimer′s disease (AD) and Down′s syndrome. Recently, the inhibition of DYRK1A has been investigated as a potential treatment for diabetes, while DYRK1A′s role as a mediator in the cell cycle has garnered interest in oncol. indications. Structure-activity relationship (SAR) anal. in combination with high-resolution X-ray crystallog. leads to a series of pyrazolo[1,5-b]pyridazine inhibitors with excellent ligand efficiencies, good physicochem. properties, and a high degree of selectivity over the kinome. Compound 11 (I) exhibited good permeability and cellular activity without P-glycoprotein liability, extending the utility of 11 in an in vivo setting. These pyrazolo[1,5-b]pyridazines are a viable lead series in the discovery of new therapies for the treatment of diseases linked to DYRK1A function.

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Pyridazine – Wikipedia,
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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: 21778-81-4, is researched, Molecular C10H9NO2, about Coupling Catalytic Alkene Hydroacylation and α-Arylation: Enantioselective Synthesis of Heterocyclic Ketones with α-Chiral Quaternary Stereocenters, the main research direction is alkene intramol hydroacylation enantioselective arylation nickel NHC catalyst; heterocyclic ketone chiral quaternary stereocenter stereoselective preparation.HPLC of Formula: 21778-81-4.

We report a strategy that combines alkene hydroacylation and enantioselective α-(hetero)arylation reactions to form a wide variety of nitrogen-containing heterocyclic ketones bearing α-chiral quaternary stereogenic centers. Exo-selective, intramol. Ni-catalyzed hydroacylations of N-homoallylindole- and N-homoallylpyrrole-2-carboxaldehydes form α-substituted six-membered heterocyclic ketones in up to 95% yield, while N-heterocyclic carbene (NHC) catalyzed hydroacylations of N-allylindole- and N-allylpyrrole-2-carboxaldehydes form α-substituted five-membered heterocyclic ketones in up to 99% yield. The racemic five- and six-membered products of Ni- and NHC-catalyzed hydroacylation reactions are readily transformed into heterocyclic ketones containing an α-chiral quaternary stereogenic center by enantioselective Ni-catalyzed α-arylation and α-heteroarylation reactions. The chiral, nonracemic products formed through a combination of alkene hydroacylation and α-(hetero)arylation reactions are formed in moderate to high yields (44-99%) with excellent enantioselectivities (typically >95% ee). The identity of the precatalyst for Ni-catalyzed α-(hetero)arylation is dictated by the identity of the α-substituted heterocyclic ketone starting material. α-(Hetero)arylations of six-membered heterocyclic ketones occur at 65-85 °C in the presence of a catalyst generated in situ from Ni(COD)2 and (R)-BINAP or (R)-DIFLUORPHOS. α-(Hetero)arylation of five-membered heterocyclic ketones must be conducted at room temperature in the presence of an [((R)-BINAP)Ni(η2-NC-Ph)] precatalyst or a catalyst generated in situ from Ni(COD)2, (R)-DIFLUORPHOS, and benzonitrile.

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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 2-(2-Bromoethoxy)tetrahydro-2H-pyran, is researched, Molecular C7H13BrO2, CAS is 17739-45-6, about Multifunctional nanoassemblies target bacterial lipopolysaccharides for enhanced antimicrobial DNA delivery, the main research direction is Escherichia macrophage lipopolysaccharide POPC cardiolipin antimicrobial; Antibiotic resistance; Biomimetic membranes; Giant unilamellar vesicles; Nanomedicine; Transcription factor decoys.Quality Control of 2-(2-Bromoethoxy)tetrahydro-2H-pyran.

The development of new therapeutic strategies against multidrug resistant Gram-neg. bacteria is a major challenge for pharmaceutical research. Here, we explore the multifunctional therapeutic potential of nanostructured self-assemblies from a cationic bolaamphiphile, which target bacterial lipopolysaccharides (LPSs) and associates with an anti-bacterial nucleic acid to form nanoplexes with therapeutic efficacy against Gram-neg. bacteria. To understand the mechanistic details of these multifunctional antimicrobial-anti-inflammatory properties, we performed a fundamental study, comparing the interaction of these nanostructured therapeutics with synthetic biomimetic bacterial membranes and live bacterial cells. Combining a wide range of exptl. techniques (Confocal Microscopy, Fluorescence Correlation Spectroscopy, Microfluidics, NMR, LPS binding assays), we demonstrate that the LPS targeting capacity of the bolaamphiphile self-assemblies, comparable to that exerted by Polymixin B, is a key feature of these nanoplexes and one that permits entry of therapeutic nucleic acids in Gram-neg. bacteria. These findings enable a new approach to the design of efficient multifunctional therapeutics with combined antimicrobial and anti-inflammatory effects and have therefore the potential to broadly impact fundamental and applied research on self-assembled nano-sized antibacterials for antibiotic resistant infections.

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Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Hirata, Tadashi; Yamada, Yasuhiro; Matsui, Masanao published an article about the compound: 5-Methoxy-1H-indole-2-carbaldehyde( cas:21778-81-4,SMILESS:O=CC(N1)=CC2=C1C=CC(OC)=C2 ).Computed Properties of C10H9NO2. 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:21778-81-4) through the article.

Conversion of the nitro compounds 2,4,5-Me(R1O)R2C6H2NO2 (R1, R2 = Me, H; Me, Me; PhCH2O, H; PhCH2O, Me) by a modified Reissert indole synthesis gave the esters I (R3 = CO2Et), m. 155-6, – , – , 141-2°, resp., reduced by LiAlH4 to the alcs. I (R3 = CH2OH), m. 83.5-5.0, 139-40, 103-4, 100-3°, resp., oxidized in turn by KMnO4 in Me2CO with poor yields (10-20%) or with yields up to 90% by CrO3-C5H5N of the corresponding aldehydes I (R3 = CHO), m. 136-7, 172-3, 178-9, 172-5°, resp. The aldehydes treated with NaH and H2C:CHPPh3Br in tetrahydrofuran (THF) gave 80-8% yields of 9H-pyrrolo[1,2-a]indoles (II) (R1, R2 = Me, H; PhCH2O, H; PhCH2O, Me), m. 80-1, 88-9, 88-9°, resp., with structures supported by uv and N.M.R. spectra. Acylation of II with KOCMe3 and Me2CO3 afforded 60-80% 3H-pyrrolo-[1,2-a]indoles (III) (R4 = OMe), m. 121-3, 122-3, 139-41°, resp. Similarly acylation with HCO2Et gave III (R4 = H; R1, R2 = Me, H; PhCH2O, Me), m. 135-41 (decomposition), and 138-42°, with structures supported by ir, uv, and N.M.R. spectra. Functionalization of the vinylic double bond of III for attachment of the aziridine moiety was achieved by iodine-azide addition giving 74-5% yields of iodo-azides (IV, R1, R2 = Me, H; PhCH2O, Me), m. 93.8-4.5, and 171-9°, ir, uv, and N.M.R. spectral data given. Catalytic hydrogenation of IV over Pd-C in MeOH containing HCl gave 60-90% yields of the corresponding iodo-amine hydrochlorides, m. >300, >300°, yielding the expected iodoamines, m. indefinite, 135-41° (decomposition), resp., ir bands (Nujol) given. Protection of the amine group with ClCO2Me furnished the iodo carbamates (V) (R5 = H; R1, R2 = Me, H; PhCH2O, Me) (VI, VII), m. 160-2 and 183-4°, resp. Cyclization with NaOMe in (MeOCH2)2 or THF gave VIII (R5 = H; R1 = Me, R2 = H), m. 210.5-14.5°, with structure confirmed by spectroscopic data, and VIII (R5 = H, R1 = PhCH2O, R2 = Me), m. 219.5-21.5°. Nitration of VI and VII gave the 8-nitro derivatives V (R5 = NO2, R1, R2 = Me, H; PhCH2O, Me), m. indefinite and 192-9°, resp. The location of the NO2 group was elucidated by N.M.R. spectral anal. The ring closure of the 8-nitro derivatives similarly gave the corresponding aziridines, VIII (R5 = NO2; R1, R2 = Me, H; PhCH2O, Me), m. 242-6, and 232-3.5°.

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Reference:
Pyridazine – Wikipedia,
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Application In Synthesis of 5-Methoxy-1H-indole-2-carbaldehyde. 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: 5-Methoxy-1H-indole-2-carbaldehyde, is researched, Molecular C10H9NO2, CAS is 21778-81-4, about Modulation of the antitumor activity by methyl substitutions in the series of 7H-pyridocarbazole monomers and dimers. Author is Leon, P.; Garbay-Jaureguiberry, C.; Barsi, M. C.; Le Pecq, J. B.; Roques, Bernard P..

The structure of the dimeric antitumor drug ditercalinium (NSC 366241) [2,2′-([4,4′-bipiperidine]-1,1′-diyldi-2,1-ethanediyl)bis[10-methoxy-7H-pyrido[4,3-c]carbazolium] tetramethanesulfonate] was modified by introduction of Me groups in various positions of the aromatic ring. Methylation of 7H-pyridocarbazoles on position 7 was performed by reaction with NaH followed by MeI addition methylation at the 5- or 6-position required a total synthesis of the pyridocarbazole ring, including photocyclization of the appropriately substituted indolylpyridylethylene. Thus, 7H-pyridocarbazole monomers, e.g., 5-Me derivative I, and dimers, e.g. 6-Me derivative II, were prepared Monomeric analogs with the nitrogen atom of the pyridine ring in different positions have also been synthesized. Pharmacol. properties and DNA interactions of the new compounds are reported. In contrast with the monomeric analog of ditercalinium, which was inactive, Me substitutions on the 10-methoxy-7H-pyrido[4,3-c]carbazolium in positions 6 or 7 led to monomers endowed with small but significant activity. Dimerization of the methyl-substituted pyridocarbazoles yielded DNA bisintercalators with affinity slightly higher than that of the unsubstituted parent compounds These dimers, characterized by a relatively better therapeutic index, have the same mechanism of action as ditercalinium. Otherwise, in monomeric and dimeric series, Me substitution in position 4 or 5 provided inactive compounds unable to intercalate into DNA. All these results are in agreement with the previously proposed geometry for the complex of ditercalinium with DNA.

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Reference:
Pyridazine – Wikipedia,
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Application of 17739-45-6. 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: 2-(2-Bromoethoxy)tetrahydro-2H-pyran, is researched, Molecular C7H13BrO2, CAS is 17739-45-6, about Regioselective Tandem C-H Alkylation/Coupling Reaction of ortho-Iodophenylethylenes via C,C-Pallada(II)cycles.

Five-membered C,C-pallada(II)cycles are a unique class of diorganopalladium species with favorable stability and an electron-rich nature, leading to efficient sequential reactions with diverse electrophiles and nucleophiles. Specifically, the development of aryl-alkenyl-palladacycle-based transformations could provide an attractive approach with regio- and stereocontrol for the construction of multifunctionalized arylethylenes. However, currently, the C,C-pallada(II)cycle formation relies on a rigid skeleton or steric congestion in the backbone to promote cyclopalladation, and the formation of aryl-alkenyl-palladacycle without an α-substituent has not been achieved. Furthermore, reactions that could discriminate between the two sp2 carbon centers of such C(sp2),C(sp2)-palladacycle remain elusive. Herein, a regioselective three-component tandem alkylation/coupling reaction applicable for a variety of non-, α-, or β-substituted and α,β-disubstituted ortho-iodophenylethylenes is reported. Electron-rich 2-pyridone ligands are employed to enable the cyclopalladation process leading to aryl-alkenyl-palladacycle intermediates, of which the two C-Pd bonds are discriminated toward alkylation by their inherent steric and electronic differences. Good linear free-energy relationships between regio-/chemoselectivities and Hammett σ values are observed

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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem