Heterocyclic Building Blocks-Pyridazine

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, Research Support, U.S. Gov’t, P.H.S., Journal of Medicinal Chemistry called 5-Amino-1-(chloromethyl)-1,2-dihydro-3H-benz[e]indoles: Relationships between Structure and Cytotoxicity for Analogues Bearing Different DNA Minor Groove Binding Subunits, Author is Atwell, Graham J.; Milbank, Jared J. B.; Wilson, William R.; Hogg, Alison; Denny, William A., which mentions a compound: 21778-81-4, SMILESS is O=CC(N1)=CC2=C1C=CC(OC)=C2, Molecular C10H9NO2, Recommanded Product: 5-Methoxy-1H-indole-2-carbaldehyde.

A series of 5-amino-seco-CBI compounds, designed for use as effectors for prodrugs, were prepared to study structure-activity relationships for the cytotoxicity of side chain analogs. Compounds were prepared by coupling 1-(chloromethyl)-5-nitro-1,2-dihydro-3H-benz[e]indole to appropriate carboxylic acids, followed by nitro group reduction, or by coupling suitable 5-amino-protected indolines to α,β-unsaturated acids, followed by deblocking. These AT-specific DNA alkylating agents were evaluated for cytotoxicity in a series of tumor cell lines (AA8, UV4, EMT6, SKOV3). For those analogs bearing an indolecarbonyl side chain, the 5′-methoxy derivative was the most cytotoxic (IC50 1.3 nM in AA8 cells, 4 h exposure), comparable to that of the parent CBI-TMI (5′,6′,7′-trimethoxyindole) derivative (IC50 0.46 nM in the above assay). A subset of solubilized derivatives bearing O(CH2)2NMe2 substituents were about 10-fold less potent. For compounds containing an acryloyl linker in the side chain, the 4′-methoxycinnamoyl derivative proved the most cytotoxic (IC50 0.09 nM in the above assay). A number of these 5-amino-seco-CBI-TMI analogs (including the solubilized compounds) are of interest both as cytotoxins and as components of amine-based prodrugs designed for tumor-specific activation.

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Das, Tapas; Kayet, Anirban; Mishra, Ruchika; Singh, Vinod K. 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 ).Application of 21778-81-4. 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.

A metal-free route to highly fluorescent 1,2-dihydropyrimido[1,6-α]indole derivatives I (R = H, OCH3, CH3, Br; Ar = C6H5, naphth-1-yl, furan-2-yl, etc.) has been developed via base catalyzed aldol followed by the Mannich reaction of indole-2-carboxaldehydes II with Et N-arylideneglycinates ArHC=NCH2COOEt at room temperature This transformation consists of the sequential formation of two new bonds to afford highly functionalized pyrimidoindole derivatives under mild reaction conditions.. Photophys. properties of the products have also been reported.

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Tan, Yu Jia; Li, Ming; Gunawan, Gregory Adrian; Nyantakyi, Samuel Agyei; Dick, Thomas; Go, Mei-Lin; Lam, Yulin 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 ).Recommanded Product: 5-Methoxy-1H-indole-2-carbaldehyde. 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.

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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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, International Journal of Systematic and Evolutionary Microbiology called Description of the bacterial RNA polymerase inhibitor GE23077-producer Actinomadura sp. NRRL B-65521T as Actinomadura lepetitiana sp. nov, Author is Dalmastri, Claudia; Gastaldo, Luciano; Berini, Francesca; Marinelli, Flavia; Marcone, Giorgia Letizia, which mentions a compound: 17739-45-6, SMILESS is BrCCOC1CCCCO1, Molecular C7H13BrO2, Synthetic Route of C7H13BrO2.

The filamentous actinomycete that produces the antibiotic GE23077 was isolated by the Lepetit Research Group from a soil sample collected in Thailand, and it was classified as a member of the genus Actinomadura on the basis of its morphol. and cell-wall composition Phylogenetic anal. based on 16S rRNA gene sequences indicated that this strain formed a distinct monophyletic line within the genus Actinomadura, and it was most closely related to Actinomadura bangladeshensis DSM 45347T (99.31% similarity) and Actinomadura mexicana DSM 44485T (98.94%). The GE23077-producing strain formed an extensively branched, non-fragmented vegetative mycelium; no pseudosporangia were formed and the arthrospores were organized in slightly twisted chains. The cell wall contained meso-2,6-diaminopimelic acid and the diagnostic sugar was madurose. The predominant menaquinone was MK-9(H6), with minor amounts of MK-9(H8) and MK-9(H4). The diagnostic phospholipids were phosphatidylinositol and diphosphatidylglycerol. The major cellular fatty acids were C16:0 and tuberculostearic acid (10-methyloctadecanoic acid), followed by minor amounts of C18:1ω9c, C16:1ω7c and 10-methylheptadecanoic acid. The genomic DNA G + C content was 71.77 mol%. Significant differences in the morphol., chemotaxonomic and biochem. data, and the low DNA-DNA relatedness between the GE23077-producing strain and closely related type strains clearly demonstrate that it represents a novel species of the genus Actinomadura, for which the name Actinomadura lepetitiana sp. nov. is proposed. The type strain is NRRL B-65521T(= LMG 31258T = DSM 109019T).

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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.Name: 5-Methoxy-1H-indole-2-carbaldehyde.

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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Category: pyridazine. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 2-(2-Bromoethoxy)tetrahydro-2H-pyran, is researched, Molecular C7H13BrO2, CAS is 17739-45-6, about Towards an Improved Design of MRI Contrast Agents: Synthesis and Relaxometric Characterisation of Gd-HPDO3A Analogues. Author is Tear, Louise R.; Carrera, Carla; Gianolio, Eliana; Aime, Silvio.

The properties of LnIII-HPDO3A complexes as relaxation enhancers and paraCEST agents are essentially related to the hydroxylpropyl moiety. A series of three HPDO3A derivatives, with small modifications to the hydroxyl arm, were herein studied to understand how heightened control can be gained over the parameters involved in the design of these agents. A full 1H and 17O-NMR relaxometric anal. was conducted and demonstrated that increasing the length of the OH group from the lanthanide center significantly enhanced the water exchange rate of the gadolinium complex, but with a subsequent reduction in kinetic stability. Alternatively, the introduction of an addnl. Me group, which increased the steric bulk around the OH moiety, gave almost exclusively the TSAP isomer (95 %) as identified by 1H-NMR of the europium complex. The gadolinium analog of this complex also exhibited a very fast water exchange rate, but with no detectable loss of kinetic stability. This complex therefore demonstrates a notable improvement over Gd-HPDO3A.

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HPLC of Formula: 21778-81-4. 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 Efficient selective synthesis of 2-substituted indoles from complex-base-promoted arynic cyclizations. Author is Kuehn-Caubere, Catherine; Rodriguez, Ivan; Pfeiffer, Bruno; Renard, Pierre; Caubere, Paul.

Indoles I [R = 5-MeO, 5-Me, 5-F, 7-Me, 5-MeO, 5-Cl, H; R1 = H, MeO; R2 = n-Pr, i-Pr, allyl, (CH2)2NEt2, (CH2)2NMe2, (CH2)2OEt, MeO] were efficiently obtained by selective arynic cyclization of halogenated aryl imines, e.g. 3,4-Cl(MeO)C6H3N:CMeCH2CH2CH2Me, in the presence of the complex-base NaNH2-Me3CONa. (Mercaptopropyl)indoles II (R = 5-OH, 7-OH; R3 = H, Me, CH2Ph, CH2CO2Et) were prepared by PhCH2SH-AlCl3 promoted opening of tetrahydrothiopyranoindoles which were also obtained from arynic cyclization of imines.

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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.Xie, Chao-Chao; Tan, Rui; Liu, Yan-Kai researched the compound: 5-Methoxy-1H-indole-2-carbaldehyde( cas:21778-81-4 ).Category: pyridazine.They published the article 《Asymmetric construction of polycyclic indole derivatives with different ring connectivities by an organocatalysis triggered two-step sequence》 about this compound( cas:21778-81-4 ) in Organic Chemistry Frontiers. Keywords: polycyclic indole preparation regioselective stereoselective; hemiacetal indole nitroolefin tandem Michael addition alkylation organocatalysis. We’ll tell you more about this compound (cas:21778-81-4).

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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Subba Rami Reddy, S. R.; Suryanarayana Rao, V.; Subba Narayana, Kanchana 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 ).Quality Control of 5-Methoxy-1H-indole-2-carbaldehyde. 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.

Objective of this research was to synthesize and characterize indole derivatives Indole nucleus has antimicrobial activities. Different kind of indole ring derivatives were synthesized such as 3-((E)-2-nitrovinyl)-1H-indole, 2-(1H-indol-3-yl)ethanamine, N-(2-(1H-indol-3-yl)ethyl)benzamide, Me 2-(3-(2-(benzamido)ethyl)-1H-indol-1-yl)acetate, 2-(3-(2-(benzamido)ethyl)-1H-indol-1-yl)acetic acid, N-(2-(1-((2,3-dihydro-1H-inden-5-yl-carbamoyl)methyl)-1H-indol-3-yl)ethyl)benzamide, e.g., I [R = 4-indanyl, 5-indanyl]. Antifungal activity of compounds I [R = 4-indanyl, 5-indanyl] were also studied.

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Category: pyridazine. Aromatic compounds can be divided into two categories: single heterocycles and fused 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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