Heterocyclic Building Blocks-Pyridazine

Synthetic Route of C4H9ClFN. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: (R)-(-)-3-Fluoropyrrolidine Hydrochloride, is researched, Molecular C4H9ClFN, CAS is 136725-55-8, about PI-2620 Lead Optimization Highlights the Importance of Off-Target Assays to Develop a PET Tracer for the Detection of Pathological Aggregated Tau in Alzheimer′s Disease and Other Tauopathies. Author is Kroth, Heiko; Oden, Felix; Molette, Jerome; Schieferstein, Hanno; Gabellieri, Emanuele; Mueller, Andre; Berndt, Mathias; Sreenivasachary, Nampally; Serra, Andreia Monica; Capotosti, Francesca; Schmitt-Willich, Heribert; Hickman, David; Pfeifer, Andrea; Dinkelborg, Ludger; Stephens, Andrew.

The first candidate PI-2014 was tested in healthy controls and subjects with Alzheimer′s disease (AD). As PI-2014 displayed off-target binding to monoamine oxidase A (MAO-A), a new lead with improved binding to Tau and decreased MAO-A binding was required. For compound optimization, Tau binding assays based on both human AD brain homogenate and Tau-paired helical filaments were employed. Furthermore, two MAO-A screening assays based on (1) human-recombinant MAO-A and (2) displacement of 2-fluoro-ethyl-harmine from mouse brain homogenate were employed. Removing the N-Me group from the tricyclic core resulted in compounds displaying improved Tau binding. For the final round of optimization, the cyclic amine substituents were replaced by pyridine derivatives PI-2620 (2-(2-fluoropyridin-4-yl)-9H-pyrrolo[2,3-b:4,5-c′]dipyridine) emerged as a best candidate displaying high Tau binding, low MAO-A binding, high brain uptake, and fast and complete brain washout. Furthermore, PI-2620 showed Tau binding on brain sections from corticobasal degeneration, progressive supranuclear palsy, and Pick′s disease.

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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 Asymmetric organocatalytic N-alkylation of indole-2-carbaldehydes with α,β-unsaturated aldehydes: one-pot synthesis of chiral pyrrolo[1,2-a]indole-2-carbaldehydes, published in 2010, which mentions a compound: 21778-81-4, mainly applied to pyrroloindolecarbaldehyde asym preparation; indolecarbaldehyde unsaturated aldehyde Michael addition cyclization diphenylsilyloxymethylpyrrolidine, Quality Control of 5-Methoxy-1H-indole-2-carbaldehyde.

Diphenylprolinol trimethylsilyl ether-catalyzed asym. aza-Michael addition/aldol addition of indole-2-carboxaldehyde with unsaturated aldehydes is described. A series of chiral pyrrolo[1,2-a]indole-2-carbaldehydes were obtained in good yields with excellent stereoselectivities.

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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: 5-Methoxy-1H-indole-2-carbaldehyde, is researched, Molecular C10H9NO2, CAS is 21778-81-4, about Synthetic studies on mitomycins. Synthesis of aziridinopyrrolo[1,2-a]indoles.Reference of 5-Methoxy-1H-indole-2-carbaldehyde.

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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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.Lena, Gersande; Trapani, Joseph A.; Sutton, Vivien R.; Ciccone, Annette; Browne, Kylie A.; Smyth, Mark J.; Denny, William A.; Spicer, Julie A. researched the compound: 5-Methoxy-1H-indole-2-carbaldehyde( cas:21778-81-4 ).HPLC of Formula: 21778-81-4.They published the article 《Dihydrofuro[3,4-c]pyridinones as Inhibitors of the Cytolytic Effects of the Pore-Forming Glycoprotein Perforin》 about this compound( cas:21778-81-4 ) in Journal of Medicinal Chemistry. Keywords: furopyridinone dihydro arylmethylidene preparation inhibitor cytolytic effect glycoprotein perforin; pyrrolopyridinone arylmethylidene heteroarylmethylidene preparation inhibitor cytolytic effect glycoprotein perforin. We’ll tell you more about this compound (cas:21778-81-4).

Dihydrofuro[3,4-c]pyridinones are the first class of small mols. reported to inhibit the cytolytic effects of the lymphocyte toxin perforin. A lead structure was identified from a high throughput screen, and a series of analogs I (X = O, S; Y = O, NH; R = Ph, 4-FC6H4, 2-furyl, 5-methyl-2-thienyl, 3-thienyl, 2-benzofuryl, 3-benzothienyl, 3-indolyl, etc.) were designed and prepared to explore structure-activity relationships around the core bicyclic ring and pendant aryl(heteroaryl) ring. This resulted in the identification of a submicromolar inhibitor of the perforin-induced lysis of Jurkat T-lymphoma cells.

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The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 5-Methoxy-1H-indole-2-carbaldehyde(SMILESS: O=CC(N1)=CC2=C1C=CC(OC)=C2,cas:21778-81-4) is researched.Reference of 4-Aminopyrimidine. The article 《One-Step Synthesis of 2-Amino-5H-pyrimido[5,4-b]indoles, Substituted 2-(1,3,5-triazin-2-yl)-1H-indoles, and 1,3,5-Triazines from Aldehydes》 in relation to this compound, is published in European Journal of Organic Chemistry. Let’s take a look at the latest research on this compound (cas:21778-81-4).

An efficient one-step synthesis of 2-amino-5H-pyrimido[5,4-b]indoles through a copper-catalyzed cascade reaction between 3-haloindole-2-carbaldehydes and guanidine hydrochloride is described. In contrast, the base-mediated reactions of either 3-haloindole-2-carbaldehydes or substituted indole-2-carbaldehydes with substituted amidine hydrochlorides in DMSO result in the formation of 2-(1,3,5-triazin-2-yl)-1H-indole derivatives in one step in excellent yields. Studies toward exploring the utility of the method demonstrate that even substituted benzaldehydes undergo a similar reaction to efficiently yield 2,4,6-trisubstituted 1,3,5-triazines. A plausible mechanism for the formation of substituted 1,3,5-triazines identifies the role of DMSO as an oxidant during the reaction.

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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.Varghese, Swapna; Rahmani, Raphael; Russell, Stephanie; Deora, Girdhar Singh; Ferrins, Lori; Toynton, Arthur; Jones, Amy; Sykes, Melissa; Kessler, Albane; Eufrasio, Amanda; Cordeiro, Artur Torres; Sherman, Julian; Rodriguez, Ana; Avery, Vicky M.; Piggott, Matthew; Baell, Jonathan B. researched the compound: (R)-(-)-3-Fluoropyrrolidine Hydrochloride( cas:136725-55-8 ).HPLC of Formula: 136725-55-8.They published the article 《Discovery of Potent N-Ethylurea Pyrazole Derivatives as Dual Inhibitors of Trypanosoma brucei and Trypanosoma cruzi》 about this compound( cas:136725-55-8 ) in ACS Medicinal Chemistry Letters. Keywords: ethylurea pyrazole derivative preparation Trypanosoma brucei cruzi Chagas. We’ll tell you more about this compound (cas:136725-55-8).

Trypanosoma brucei (T. brucei) and Trypanosoma cruzi (T. cruzi) are causative agents of parasitic diseases known as human African trypanosomiasis and Chagas disease, resp. Together, these diseases affect 68 million people around the world. Current treatments are unsatisfactory, frequently associated with intolerable side-effects, and generally inadequate in treating all stages of disease. In this paper, we report the discovery of N-ethylurea pyrazoles that potently and selectively inhibit the viability of T. brucei and T. cruzi. Sharp and logical SAR led to the identification of 54 as the best compound, with an in vitro IC50 of 9 nM and 16 nM against T. b. brucei and T. cruzi, resp. Compound 54 demonstrates favorable physicochem. properties and was efficacious in a murine model of Chagas disease, leading to undetectable parasitemia within 6 days when CYP metabolism was inhibited.

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Pyridazine – Wikipedia,
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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, Non-U.S. Gov’t, Journal of Medicinal Chemistry called 2-[N-Acylamino(C1-C3)alkyl]indoles as MT1 melatonin receptor partial agonists, antagonists, and putative inverse agonists, Author is Spadoni, Gilberto; Balsamini, Cesarino; Bedini, Annalida; Diamantini, Giuseppe; Di Giacomo, Barbara; Tontini, Andrea; Tarzia, Giorgio; Mor, Marco; Plazzi, Pier Vincenzo; Rivara, Silvia; Nonno, Romolo; Pannacci, Marilou; Lucini, Valeria; Fraschini, Franco; Stankov, Bojidar Michaylov, which mentions a compound: 21778-81-4, SMILESS is O=CC(N1)=CC2=C1C=CC(OC)=C2, Molecular C10H9NO2, Category: pyridazine.

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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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: 2-(2-Bromoethoxy)tetrahydro-2H-pyran, is researched, Molecular C7H13BrO2, CAS is 17739-45-6, about Chitosan-based multi-liposomal complexes: Synthesis, biodegradability and cytotoxicity.Application of 17739-45-6.

Anionic liposomes were electrostatically adsorbed onto the surface of cationic chitosan particles crosslinked by sulfate anions, forming multi-liposomal containers (MLCs) for encapsulation and delivery of bioactive substances. An increase in mol. mass of chitosan from 30 to 300 kDa results in a size increase of chitosan particles, from 200 to 400 nm. Being saturated by liposomes, chitosan particles give MLCs of 320-540 nm. Each chitosan particle carries between 60 and 200 liposomes. The proteolytic complex Morikrase, a mixture of enzymes with various specificities, induces degradation of MLCs down to particles of size 10-15 nm; the higher the mol. mass of chitosan, the slower the enzyme-induced MLCs′ degradation pH variation within 5.5-7 and cholesterol incorporation into the liposomal membrane both have a minor effect on the rate of MLCs′ biodegradation Both the MLCs and the products of their biodegradation show low cytotoxicity. These results are of interest for constructing biodegradable capacious carriers of bioactive substances.

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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 Rapid and selective access to three distinct sets of indole-based heterocycles from a single set of Ugi-adducts under microwave heating. Author is Zhang, Lei; Zhao, Fei; Zheng, Mingyue; Zhai, Yun; Liu, Hong.

Three distinct sets of indole-based heterocycles, e.g. I, II and III, were rapidly and selectively synthesized from the same set of Ugi-adducts, e.g. IV, under microwave heating in a reaction-condition-controlled manner. Notably, an unprecedented metal-free intramol. sp3-hybridized C-H arylation using only cesium carbonate was discovered.

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Pyridazine – Wikipedia,
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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.Tsotinis, Andrew; Afroudakis, Pandelis A.; Davidson, Kathryn; Prashar, Anjali; Sugden, David researched the compound: 5-Methoxy-1H-indole-2-carbaldehyde( cas:21778-81-4 ).Quality Control of 5-Methoxy-1H-indole-2-carbaldehyde.They published the article 《Design, Synthesis, and Melatoninergic Activity of New Azido- and Isothiocyanato-Substituted Indoles》 about this compound( cas:21778-81-4 ) in Journal of Medicinal Chemistry. Keywords: indole azido isothiocyanato preparation melatoninergic. We’ll tell you more about this compound (cas:21778-81-4).

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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Reference:
Pyridazine – Wikipedia,
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