Category: 21778-81-4

Lorton, Charlotte; Voituriez, Arnaud published the article 《Phosphine-Promoted Synthesis of 9H-Pyrrolo[1,2-a]indole Derivatives via an γ-Umpolung Addition/Intramolecular Wittig Reaction》. Keywords: pyrroloindole synthesis phoshine promoted Michael intramol Wittig indolecarbaldehyde allenoate.They researched the compound: 5-Methoxy-1H-indole-2-carbaldehyde( cas:21778-81-4 ).Application of 21778-81-4. 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:21778-81-4) here.

The synthesis of substituted 9H-pyrrolo[1,2-a]indole products from 1H-indole-2-carbaldehydes and allenoates is described, using a phosphine-promoted Michael addition/intramol. Wittig reaction. This halide- and base-free methodol. provides an efficient access to different tricyclic nitrogen-containing heterocycles (18 examples, 32-88% isolated yields).

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Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – 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, ACS Catalysis called Enantioselective Synthesis of Polycyclic Indole Derivatives Based on aza-Morita-Baylis-Hillman Reaction, Author is Gao, Yuning; Xu, Qin; Shi, Min, which mentions a compound: 21778-81-4, SMILESS is O=CC(N1)=CC2=C1C=CC(OC)=C2, Molecular C10H9NO2, COA of Formula: C10H9NO2.

A chiral phosphine-catalyzed asym. aza-Morita-Baylis-Hillman reaction between indole-derived sulfonyl imines and bis(3-chlorophenyl)methyl acrylate has been developed, giving the desired adducts in good yields and enantiomeric excess values along with the further transformations to polycyclic indoles such as dihydropyrido[1,2-a]indole and dihydropyrazino[1,2-a]indole skeleton.

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Pyridazine – Wikipedia,
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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 4-Phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione Inhibitors of the Checkpoint Kinase Wee1. Structure-Activity Relationships for Chromophore Modification and Phenyl Ring Substitution, published in 2006-08-10, which mentions a compound: 21778-81-4, Name is 5-Methoxy-1H-indole-2-carbaldehyde, Molecular C10H9NO2, Category: pyridazine.

High-throughput screening has identified a novel class of inhibitors of the checkpoint kinase Wee1, which have potential for use in cancer chemotherapy. These inhibitors, e.g. I (R = H, 2-FC6H4, 3-NCC6H4, 2,6-Br2C6H3, 2-thienyl, 3-pyrrolyl, 3-pyridyl, etc.), are based on a 4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione template and have been shown by X-ray crystallog. to bind at the ATP site of the enzyme. An extensive study of the effects of substitution around this template has been carried out, which has identified substituents which lead to improvements in potency and selectivity for Wee1. While retention of the maleimide ring and pendant 4-Ph group is necessary for potency, replacement of the carbazole nitrogen by oxygen is well tolerated and results in improved Wee1 selectivity against the related checkpoint kinase Chk1. Wee1 potency and selectivity are also enhanced by the incorporation of lipophilic functionality at the 2′-position of the 4-Ph ring, and Wee1 selectivity against Chk1 is favored by C3-C5 alkyl substitution of the carbazole nitrogen. These studies provide a basis for the design of active analogs of the pyrrolocarbazole lead with improved phys. properties.

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Safety 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 Synthesis and Biological Evaluation of Indolyl-Pyridinyl-Propenones Having Either Methuosis or Microtubule Disruption Activity. Author is Trabbic, Christopher J.; Overmeyer, Jean H.; Alexander, Evan M.; Crissman, Emily J.; Kvale, Heather M.; Smith, Marcie A.; Erhardt, Paul W.; Maltese, William A..

Methuosis is a form of nonapoptotic cell death characterized by an accumulation of macropinosome-derived vacuoles with eventual loss of membrane integrity. Small mols. inducing methuosis could offer significant advantages compared to more traditional anticancer drug therapies that typically rely on apoptosis. Herein we further define the effects of chem. substitutions at the 2- and 5-indolyl positions on our lead compound I. We have identified a number of compounds that induce methuosis at similar potencies, including an interesting analog having a hydroxypropyl substituent at the 2-position. In addition, we have discovered that certain substitutions on the 2-indolyl position redirect the mode of cytotoxicity from methuosis to microtubule disruption. This switch in activity is associated with an increase in potency as large as 2 orders of magnitude. These compounds appear to represent a new class of potent microtubule-active anticancer agents.

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Pyridazine | C4H4N2 – PubChem

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 Pd-catalyzed cascade allylic alkylation and dearomatization reactions of indoles with vinyloxirane, published in 2016, which mentions a compound: 21778-81-4, Name is 5-Methoxy-1H-indole-2-carbaldehyde, Molecular C10H9NO2, Recommanded Product: 21778-81-4.

A palladium-catalyzed cascade allylic alkylation reaction of di-Me malonate tethered indoles with vinyloxirane was developed through intramol. nucleophilic ring-opening of vinyloxirane followed by subsequent intramol. Friedel-Crafts type allylic alkylation or allylic dearomatization. This protocol provided an efficient method to synthesize structurally diverse tetrahydrocarbolines e.g., I, and spiroindolenine derivatives e.g., II, under mild conditions.

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Quality Control 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 Concise synthesis of carbazole-1,4-quinones and evaluation of their antiproliferative activity against HCT-116 and HL-60 cells. Author is Nishiyama, Takashi; Hatae, Noriyuki; Yoshimura, Teruki; Takaki, Sawa; Abe, Takumi; Ishikura, Minoru; Hibino, Satoshi; Choshi, Tominari.

A convenient synthesis of carbazole-1,4-quinone alkaloid koeniginequinones A and B using a tandem ring-closing metathesis with the dehydrogenation reaction sequence under an O2 atmosphere as an important step is reported. Using this method, carbazole-1,4-quinones substituted at the 5-, 6-, 7-, and/or 8-positions I (R1 = R2 = H, CH3; R3 = H, 6-OCH3, 5,6-(OCH3)2, 7-CH3, 6-NO2, etc.; R4 = H, MOM) have been synthesized. Moreover, 24 compounds, including koeniginequinones A and B, have been evaluated for their antiproliferative activity against HCT-116 and HL-60 cells, and the 6-nitro analog exhibited the most potent activity against both tumor cell types.

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Tsotinis, Andrew; Afroudakis, Pandelis A.; Davidson, Kathryn; Prashar, Anjali; Sugden, David published the article 《Design, Synthesis, and Melatoninergic Activity of New Azido- and Isothiocyanato-Substituted Indoles》. Keywords: indole azido isothiocyanato preparation melatoninergic.They researched the compound: 5-Methoxy-1H-indole-2-carbaldehyde( cas:21778-81-4 ).Synthetic Route of C10H9NO2. 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:21778-81-4) here.

To develop irreversibly binding ligands for the melatonin receptor(s) as tools for tracing the primary melatonin binding site, novel melatoninergic azido- and isothiocyanato-substituted indoles were designed and synthesized. All active compounds were partial agonists or antagonists in the Xenopus melanophore assay, the most potent being 3-(2-azidoethyl)-5-methoxyindole and 3-(2-isothiocyanatoethyl)-5-methoxyindole.

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Pyridazine – Wikipedia,
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Computed Properties of C10H9NO2. 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 Rhodium(II)-catalyzed intramolecular annulation of 1-sulfonyl-1,2,3-triazoles with indoles: facile synthesis of functionalized tetrahydro-β-carbolines. Author is Shang, Hai; Tian, Yu; Luo, Jun; Li, Lingyu; Tang, Yefeng; Zou, Zhongmei.

A novel rhodium(II)-catalyzed intramol. annulation of 1-sulfonyl-1,2,3-triazoles with indoles was developed, which enabled the facile synthesis of various 4-functionalized tetrahydro-β-carbolines as well as relevant scaffolds from readily available starting materials.

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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: 21778-81-4, is researched, SMILESS is O=CC(N1)=CC2=C1C=CC(OC)=C2, Molecular C10H9NO2Journal, ACS Catalysis called Coupling Catalytic Alkene Hydroacylation and α-Arylation: Enantioselective Synthesis of Heterocyclic Ketones with α-Chiral Quaternary Stereocenters, Author is Ghosh, Avipsa; Walker, James A.; Ellern, Arkady; Stanley, Levi M., the main research direction is alkene intramol hydroacylation enantioselective arylation nickel NHC catalyst; heterocyclic ketone chiral quaternary stereocenter stereoselective preparation.SDS of cas: 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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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 2-[N-Acylamino(C1-C3)alkyl]indoles as MT1 melatonin receptor partial agonists, antagonists, and putative inverse agonists, published in 1998-09-10, which mentions a compound: 21778-81-4, mainly applied to melatonin receptor antagonist agonist, Product Details of 21778-81-4.

The synthesis of several novel indole melatonin analogs substituted at the 2-position with acylaminomethyl, acylaminoethyl, or acylaminopropyl side chains is reported. Using a novel in vitro functional assay (specific binding of [35S]GTPγS), the authors showed that several of these compounds exhibited partial agonist, antagonist, and inverse agonist activity. Binding and functional assays were performed on cloned human MT1 receptor. Structure-activity relation considerations indicate that N-[1-aryl-2-(4-methoxy-1H-indol-2-yl)(C1-C2)alkyl]alkanamides represent a lead structure for this type of ligands.

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Reference:
Pyridazine – Wikipedia,
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