Month: April 2022

Siddappa, S.; Bhat, G. A. published the article 《Synthesis of indole-2-carbaldehydes, 2-(2-aminoethyl) – and 2-(2-aminopropyl)indoles》. Keywords: indolecarboxaldehydes aminoalkyl; aminoalkyl indolecarboxaldehydes.They researched the compound: 5-Methoxy-1H-indole-2-carbaldehyde( cas:21778-81-4 ).Category: pyridazine. 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.

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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Reference:
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, Article, Journal of Medicinal Chemistry called 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, which mentions a compound: 136725-55-8, SMILESS is Cl.F[C@@H]1CCNC1, Molecular C4H9ClFN, Quality Control of (R)-(-)-3-Fluoropyrrolidine Hydrochloride.

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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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

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 Synthesis of 9H-Pyrrolo[1,2-a]indole and 3H-Pyrrolizine Derivatives via a Phosphine-Catalyzed Umpolung Addition/Intramolecular Wittig Reaction. Author is Saleh, Nidal; Voituriez, Arnaud.

The first umpolung addition/intramol. Wittig reaction, catalytic in phosphine, is described. The in situ phosphine oxide reduction was accomplished by the use of silane and a catalytic amount of bis(4-nitrophenyl)phosphate. This catalytic protocol is applicable to the synthesis of a wide range of functionalized 9H-pyrrolo[1,2-a]indoles and pyrrolizines (18 examples, 70-98% yields).

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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

SDS of cas: 885272-25-3. 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-(5-Methoxy-2-oxoindolin-3-yl)acetic acid, is researched, Molecular C11H11NO4, CAS is 885272-25-3, about Mechanistic study of reversible solid-state melt isomerization of 2-oxindoles to 2-quinolinones and its occurrence in a mass spectrometer.

An eco-friendly equilibrated rearrangement of a series of 2-oxo-3-indolyl acetic acids (1) with 2-oxo-1,2,3,4-tetrahydroquinoline-4-carboxylic acid derivatives (2) was investigated through a solid state melt reaction (SSMR). Mechanistic insight into the thermal rearrangement is provided by 13C-isotopic labeling. The standard mass spectra of 1 and 2 were virtually identical preventing their reliable identification. Reversible interconversion of 1 and 2 was evidenced to occur in the inlet system of a mass spectrometer under electron impact conditions. Relative abundances of fragment ions were found to be a function of temperature

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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Recommanded Product: 21778-81-4. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 5-Methoxy-1H-indole-2-carbaldehyde, is researched, Molecular C10H9NO2, CAS is 21778-81-4, about 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..

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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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Zheng, Yu; Ashizawa, Minoru; Zhang, Song; Kang, Jiheong; Nikzad, Shayla; Yu, Zhiao; Ochiai, Yuto; Wu, Hung-Chin; Tran, Helen; Mun, Jaewan; Zheng, Yu-Qing; Tok, Jeffrey B.-H.; Gu, Xiaodan; Bao, Zhenan published an article about the compound: 2-(2-Bromoethoxy)tetrahydro-2H-pyran( cas:17739-45-6,SMILESS:BrCCOC1CCCCO1 ).COA of Formula: C7H13BrO2. 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:17739-45-6) through the article.

Conjugation breakers (CBs) with different H-bonding chemistries and linker flexibilities are designed and incorporated into a diketopyrrolopyrrole (DPP)-based conjugated polymer backbone. The effects of H-bonding interactions on polymer semiconductor morphol., mech. properties, and elec. performance are systematically investigated. We observe that CBs with an H-bonding self-association constant >0.7 or a denser packing tendency are able to induce higher polymer chain aggregation and crystallinity in as-casted thin films, resulting in a higher modulus and crack on-set strain. Addnl., the rDoC (relative degree of crystallinity) of the stretched thin film with the highest crack on-set strain only suffers a small decrease, suggesting the main energy dissipation mechanism is the breakage of H-bonding interactions. By contrast, other less stretchable polymer films dissipate strain energy through the breakage of crystalline domains, indicated by a drastic decrease in rDoC. Furthermore, we evaluate their elec. performances under mech. strain in fully stretchable field-effect transistors. The polymer with the highest crack on-set strain has the least degradation in mobility as a function of strain. Overall, these observations suggest that we can aptly tune the mech. properties of a polymer semiconductor by modulating intermol. interactions, such as H-bonding chem. and linker flexibility. Such understanding provides mol. design guidelines for future stretchable semiconductors.

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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

HPLC of Formula: 136725-55-8. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: (R)-(-)-3-Fluoropyrrolidine Hydrochloride, is researched, Molecular C4H9ClFN, CAS is 136725-55-8, about Fluorine in medicinal chemistry: β-fluorination of peripheral pyrrolidines attached to acridine ligands affects their interactions with G-quadruplex DNA. Author is Campbell, Nancy H.; Smith, Daniel L.; Reszka, Anthony P.; Neidle, Stephen; O’Hagan, David.

Comparative X-ray structure studies reveal that C-F bond incorporation into the peripheral pyrrolidine moieties of the G-quadruplex DNA binding ligand BSU6039 leads to a distinct pyrrolidine ring conformation, relative to the non-fluorinated analog, and with a different binding mode involving reversal of the pyrrolidinium N+-H orientation.

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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Related Products of 136725-55-8. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: (R)-(-)-3-Fluoropyrrolidine Hydrochloride, is researched, Molecular C4H9ClFN, CAS is 136725-55-8, about Novel Human Neutral Sphingomyelinase 2 Inhibitors as Potential Therapeutics for Alzheimer’s Disease. Author is Sala, Michal; Hollinger, Kristen R.; Thomas, Ajit G.; Dash, Ranjeet P.; Tallon, Carolyn; Veeravalli, Vijayabhaskar; Lovell, Lyndah; Kogler, Martin; Hrebabecky, Hubert; Prochazkova, Eliska; Nesuta, Ondrej; Donoghue, Amanda; Lam, Jenny; Rais, Rana; Rojas, Camilo; Slusher, Barbara S.; Nencka, Radim.

Neutral sphingomyelinase 2 (nSMase2) catalyzes the cleavage of sphingomyelin to phosphorylcholine and ceramide, an essential step in the formation and release of exosomes from cells that is critical for intracellular communication. Chronic increase of brain nSMase2 activity and related exosome release has been implicated in various pathol. processes, including the progression of Alzheimer’s disease (AD), making nSMase2 a viable therapeutic target. Recently, we identified phenyl(R)-(1-(3-(3,4-dimethoxyphenyl)-2,6-dimethylimidazo[1,2-b] pyridazin-8-yl) pyrrolidin-3-yl)-carbamate 1 (PDDC)(I), the first nSMase2 inhibitor which possesses both favorable pharmacodynamics and pharmacokinetic (PK) parameters, including substantial oral bioavailability, brain penetration and significant inhibition of exosome release from the brain in vivo. Herein we demonstrate efficacy of 1 (PDDC) in a mouse model of AD and detail extensive structure-activity relationship (SAR) studies with 70 analogs, unveiling several that exert similar or higher activity against nSMase2 with favorable pharmacokinetic properties.

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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

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 Rapid Generation of Privileged Substructure-Based Compound Libraries with Structural Diversity and Drug-Likeness, published in 2014-04-14, which mentions a compound: 21778-81-4, mainly applied to indolecarboxaldehyde amine carboxylic acid isonitrile Ugi intramol arylation cyclization; heterocyclic compound library preparation structural diversity drug likeness, Category: pyridazine.

A library of privileged-substructure-based, heterocyclic compounds was constructed by a sequence of Ugi four-component reactions incorporating the indole motif and microwave-assisted cyclizations in branched pathways. Cheminformatic anal. confirmed that the library exhibited a high degree of structural diversity and good drug-likeness.

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Reference:
Pyridazine – Wikipedia,
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 Discovery of Potent N-Ethylurea Pyrazole Derivatives as Dual Inhibitors of Trypanosoma brucei and Trypanosoma cruzi, published in 2020-03-12, which mentions a compound: 136725-55-8, Name is (R)-(-)-3-Fluoropyrrolidine Hydrochloride, Molecular C4H9ClFN, Recommanded Product: (R)-(-)-3-Fluoropyrrolidine Hydrochloride.

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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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem