Category: 21778-81-4

Meyer, Michael D.; Kruse, Lawrence I. published the article 《Ergoline synthons: Synthesis of 3,4-dihydro-6-methoxybenz[cd]indol-5(1H)-one (6-methoxy-Uhle’s ketone) and 3,4-dihydrobenz[cd]indol-5(1H)-one (Uhle’s ketone) via a novel decarboxylation of indole-2-carboxylates》. Keywords: rhodium complex decarbonylation catalyst; Uhle ketone methoxy; benzindolone; ergoline synthon methoxybenzindolone; indolecarboxaldehyde decarbonylation catalyst.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.

An efficient synthesis of a new substituted ergoline synthon 3,4-dihydro-6-methoxybenz[cd]indol-5(1H)-one (I, R = MeO) is described. The general synthetic strategy was also applied to the preparation of the known Uhle’s ketone [I (R = H)]. The key step, a formal decarboxylation of intermediate 2-carboxy-3,4-dihydrobenz[cd]indol-5(1H)-one, is accomplished by reduction of the Et ester to the indole-2-carboxaldehyde followed by catalytic decarbonylation to the parent indole using in situ generated Rh[1,3-bis(biphenylphosphino)propane]2+Cl- catalyst. The catalytic decarbonylation was extended to several other indole-2-carboxaldehydes and appears to be a general reaction of indole aldehydes.

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Application of 21778-81-4. 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: 5-Methoxy-1H-indole-2-carbaldehyde, is researched, Molecular C10H9NO2, CAS is 21778-81-4, about Convenient synthesis of tetrahydro-γ-carbolines and tetrahydroquinolines through a chemo- and regioselectivity switch by a Bronsted acid catalyzed, one-pot, multicomponent reaction.

An efficient, one-pot, multicomponent reaction of aldehydes, p-methoxyaniline, and 2-vinylindoles was developed. This approach provides a practical approach to synthetically and biol. significant tetrahydro-γ-carboline and tetrahydroquinoline derivatives in good yields through a chemo- and regioselectivity switch, which can be tuned by simply changing the substituent on the indole component under identical reaction conditions.

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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 5-Substituted analogs of 3-hydroxymethyl-5-aziridinyl-1-methyl-2-[1H-indole-4,7-dione]prop-2-en-1-ol (EO9, NSC 382459) and their regioisomers as hypoxia-selective agents: structure-cytotoxicity in vitro, published in 1998-03-31, which mentions a compound: 21778-81-4, Name is 5-Methoxy-1H-indole-2-carbaldehyde, Molecular C10H9NO2, Computed Properties of C10H9NO2.

A series of regioisomeric analogs of 3-hydroxymethyl-5-aziridinyl-1-methyl-2-[1H-indole-4,7-dione]prop-2-en-1-ol (EO9, NSC 382459) with the hydroxymethyl and hydroxypropenyl substituents situated at either the 2- or the 3-position of the indole ring were synthesized. The compound lacking the 2-hydroxypropenyl substituent had similar properties to EO9 under both aerobic and hypoxic conditions against V79 cells and was more potent against a human tumor cell line (A549) than EO9. It was reduced by human DT-diaphorase (DTD) at more than double the rate of EO9, thus implicating the importance of the enzyme activation step. The compound lacking the 3-hydroxymethyl substituent was a better substrate for human DTD than EO9, yet exhibited lesser toxicity under both aerobic and hypoxic conditions. The toxicity of EO9 was attributed to a combination of the aziridinyl group and the leaving group properties of the 3-hydroxymethyl substituent. In general, compounds with a 5-methylaziridinyl moiety, such as EO8, exhibited substantially better hypoxia-selectivity due to much slower reduction by DTD (20-fold), thus reducing aerobic potency. All compounds had similar electron affinities, as indicated by their one-electron reduction potentials.

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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 Amide-Amine Replacement in Indole-2-carboxamides Yields Potent Mycobactericidal Agents with Improved Water Solubility, published in 2021-05-13, which mentions a compound: 21778-81-4, mainly applied to methylamine carboxamide benzothiophene benzoselenophene preparation antimycobacterial lipophilicity, Product Details of 21778-81-4.

Indolecarboxamides are potent but poorly soluble mycobactericidal agents. Here, it was found that modifying the incipient scaffold by amide-amine substitution and replacing the indole ring with benzothiophene or benzoselenophene led to striking (10-20-fold) improvements in solubility Potent activity could be achieved without the carboxamide linker but not in the absence of the indole ring. The indolylmethylamine, N-cyclooctyl-6-trifluoromethylindol-2-ylmethylamine (MIC90Mtb 0.13μM, MBC99.9Mtb 0.63μM), exemplifies a promising member that is more soluble and equipotent to its carboxamide equivalent It is also an inhibitor of the mycolate transporter MmpL3, a property shared by the methylamines of benzothiophene and benzoselenophene.

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Category: pyridazine. 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: 5-Methoxy-1H-indole-2-carbaldehyde, is researched, Molecular C10H9NO2, CAS is 21778-81-4, about Asymmetric construction of polycyclic indole derivatives with different ring connectivities by an organocatalysis triggered two-step sequence.

An organocatalysis triggered highly regio- and stereoselective two-step sequence between hemiacetals and indole-containing nitroolefins was developed. The key to the success of this sequence was the intramol. oxocarbenium ion induced collective alkylation at the C3, C2, or N1-position of the indole moiety, resp., providing biol. important polycyclic indole derivatives with different ring connectivities. An unexpected epimerization was observed during the C3-alkylation process, which generated products with different relative configurations compared with the C2- and N1-alkylation products.

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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.Category: pyridazine. The article 《Design, Synthesis, and Melatoninergic Activity of New Azido- and Isothiocyanato-Substituted Indoles》 in relation to this compound, is published in Journal of Medicinal Chemistry. Let’s take a look at the latest research on 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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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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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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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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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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