Month: April 2022

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: 1265884-98-7, is researched, Molecular C34H22NO2P, about Stereodivergent α-Allylation of Linear Aldehydes with Dual Iridium and Amine Catalysis, the main research direction is paroxetine aryl compound enantioselective synthesis diastereoselective synthesis; aldehyde allylic alc allylation Ir catalyst.Reference of 5-(11bR)-Dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-yl-5H-dibenz[b,f]azepine.

We describe the fully stereodivergent, dual catalytic α-allylation of linear aldehydes. The reaction proceeds via direct iridium-catalyzed substitution of racemic allylic alcs. with enamines generated in situ. The use of an Ir(P,olefin) complex and a diarylsilyl prolinol ether as catalysts in the presence of dimethylhydrogen phosphate as the promoter proved to be crucial for achieving high enantio- and diastereoselectivity (>99% ee, up to >20:1 dr). The utility of the method is demonstrated in a concise enantioselective synthesis of the antidepressant (-)-paroxetine.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

Formula: C12H15ClN2O2. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: H-Trp-OMe.HCl, is researched, Molecular C12H15ClN2O2, CAS is 7524-52-9, about Photochemical chemoselective alkylation of tryptophan-containing peptides. Author is Laroche, Benjamin; Tang, Xinjun; Archer, Gaetan; Di Sanza, Riccardo; Melchiorre, Paolo.

We report a photochem. method for the chemoselective radical functionalization of tryptophan (Trp)-containing peptides. The method exploits the photoactivity of an electron donor-acceptor complex generated between the tryptophan unit and pyridinium salts. Irradiation with weak light (390 nm) generates radical intermediates right next to the targeted Trp amino acid, facilitating a proximity-driven radical functionalization. This protocol exhibits high chemoselectivity for Trp residues over other amino acids and tolerates biocompatible conditions.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – 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 Convenient method for the synthesis of some novel chiral methyl 2-(2-oxo-2H-benzo[e][1,3]oxazin-3(4H)-yl)propanoate derivatives and biological evaluation of their antioxidant, cytotoxic, and molecular docking properties, published in 2021-02-28, which mentions a compound: 7524-52-9, Name is H-Trp-OMe.HCl, Molecular C12H15ClN2O2, Recommanded Product: 7524-52-9.

Ten chiral Me 2-(2-oxo-2H-benzo[e][1,3]oxazin-3(4H)-yl)propanoate derivatives, e.g. I, have been synthesized from optically pure amino Me phenols and 4-nitrophenyl chloroformate. Synthesized ester derivatives were screened for their in vitro antioxidant activity. Title compounds have exhibited comparable antioxidant activity with ascorbic acid as a standard Further, the in vitro cytotoxicity of these compounds were studied through MTT cell proliferation assay in addition the effect on LDH leakage and NO release. Among the derivatives, I showed extremely best activity and the IC50 value (12.54 ± 0.71μM) is very close to doxorubicin (7.2 ± 0.58μM) as a standard Also, mol. docking studies have been carried out with STAT-3 (PDB ID: 1BG1) and BCL-2 (PDB ID: 4AQ3) proteins against the four active compounds, e.g. I. The binding energies of the tested compounds were in the range of -7.76 to -8.41 kcal/mol, which is very close to doxorubicin (-8.53 kcal/mol) as a standard These mol. docking results are in good agreement with the in vitro studies.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

Zhao, Wei; Yan, Patrick K.; Radosevich, Alexander T. published the article 《A Phosphetane Catalyzes Deoxygenative Condensation of α-Keto Esters and Carboxylic Acids via PIII/PV=O Redox Cycling》. Keywords: phosphetane catalyst preparation oxygenative condensation ketoester carboxylic acid.They researched the compound: 4-Methyl-1-phenyl-2,3-dihydro-1H-phosphole 1-oxide( cas:707-61-9 ).COA of Formula: C11H13OP. 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:707-61-9) here.

A small-ring phosphacycle is found to catalyze the deoxygenative condensation of α-keto esters and carboxylic acids. The reaction provides a chemoselective catalytic synthesis of α-acyloxy ester products with good functional group compatibility. Based on both stoichiometric and catalytic mechanistic experiments, the reaction is proposed to proceed via catalytic PIII/PV=O cycling. The importance of ring strain in the phosphacyclic catalyst is substantiated by an observed temperature-dependent product selectivity effect. The results point to an inherent distinction in design criteria for organophosphorus-based catalysts operating via PIII/PV=O redox cycling as opposed to Lewis base (nucleophilic) catalysis.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

Application In Synthesis of H-Trp-OMe.HCl. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: H-Trp-OMe.HCl, is researched, Molecular C12H15ClN2O2, CAS is 7524-52-9, about Construction of thioamide peptide via sulfur-involved amino acids/amino aldehydes coupling. Author is Liao, Yanyan; Jiang, Xuefeng.

A sulfur-involved ligation for thioamide quasi-peptides was developed via amino acids and amino aldehydes coupling. The key to the transformation was the chelation of copper with imines for chiral activation and fixation. In this environment, linear polysulfur decreased the alkalinity of single sulfur anions to prevent racemization caused by the interaction between sulfur and sodium sulfide. Dipeptides, tripeptides, tetrapeptides, and the linkage between the drug and amino acids were successfully obtained.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – 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, Chemistry – A European Journal called N-Cyanation of Primary and Secondary Amines with Cyanobenziodoxolone (CBX) Reagent, Author is Chen, Zimin; Yuan, Weiming, which mentions a compound: 7524-52-9, SMILESS is N[C@@H](CC1=CNC2=CC=CC=C12)C(OC)=O.[H]Cl, Molecular C12H15ClN2O2, Recommanded Product: H-Trp-OMe.HCl.

An efficient electrophilic N-cyanation of amines e.g., pyrrolidine with a stable and less-toxic 1-cyano-1,2-benziodoxol-3-(1H)-one reagent towards the synthesis of cyanamides e.g., Pyrrolidine-1-carbonitrile was disclosed. This synthetically practicable strategy allows the construction of a wide variety of cyanamides under very mild and simple conditions with a broad functional group compatibility, and showcases a huge potential in late-stage modification of complex mols.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

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: 1265884-98-7, is researched, Molecular C34H22NO2P, about Enantioselective Iridium-Catalyzed α-Allylation with Aqueous Solutions of Acetaldehyde, the main research direction is unsaturated aldehyde enantioselective synthesis iridium catalyzed allylation allylic alc.COA of Formula: C34H22NO2P.

The enantioselective α-allylation of aqueous solutions of acetaldehyde using iridium- and amine-catalyzed substitution of racemic allylic alcs. is described. The method utilizes a readily available, safely handled aqueous solution of acetaldehyde and furnishes γ,δ-unsaturated aldehydes in good yields and greater than 99% enantiomeric excess. The synthetic potential of the method is demonstrated with the enantioselective formal syntheses of heliannuols C and E as well as heliespirones A and C.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – 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 Asymmetric γ-Allylation of α,β-Unsaturated Aldehydes by Combined Organocatalysis and Transition-Metal Catalysis, published in 2015, which mentions a compound: 1265884-98-7, mainly applied to aldehyde unsaturated regioselective enantioselective diastereoselective allylation allylic alc acetate; cyclic aldehyde dienoic asym synthesis; allylation; asymmetric catalysis; diastereodivergence; dual catalysis; regiodivergence, Application of 1265884-98-7.

The first asym. regio- and diastereodivergent γ-allylation of cyclic α,β-unsaturated aldehydes I (X = CH2, R1 = H, 7-F, 6-MeO, 5,7-Me2, etc.; X = O, S, R1 = H) with various allylic alcs. R2CH(OH)CH:CH2 (R2 = Ph, 2-MeC6H4, 4-MeOC6H4, 4-O2NC6H4, etc.) or allylic acetates R2CH:CHCH2OAc based on combined organocatalysis and transition-metal catalysis is disclosed. By combining an aminocatalyst with an iridium catalyst, both diastereomers of branched allylated products II can be obtained from I and allylic alcs. in moderate to good yields and excellent regio- and stereoselectivities. Furthermore, by replacing the iridium catalyst with a palladium catalyst, the linear allylated products III were formed in good yields and excellent regio- and enantioselectivities from I and allylic acetates. The developed method thus provides selective access to all six isomers of the γ-allylated product in a divergent fashion by choosing the appropriate combination of organocatalyst, transition-metal catalyst, and ligand.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

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.Samsawat, Tipparat; Jaramornburapong, Chanjira; Phutdhawong, Weerachai; Phutdhawong, Waya S.; Taechowisan, Thongchai researched the compound: H-Trp-OMe.HCl( cas:7524-52-9 ).Formula: C12H15ClN2O2.They published the article 《Evaluating the effect of amine-geldanamycin hybrids on anticancer activity》 about this compound( cas:7524-52-9 ) in Journal of Applied Pharmaceutical Science. Keywords: amine geldanamycin hybrid anticancer activity mol docking solubility. We’ll tell you more about this compound (cas:7524-52-9).

Three new geldanamycin (GDM) derivatives, 17-(S)-2-amino-3-(1H-indol-3-ylpropan-1-ol)-17- demethoxygeldanamycin (2), 17-((S)-2-amino-3-phenylpropan-1-ol)-17-demethoxygeldanamycin (3), and 17-((S)-4- (2-amino-3-hydroxypropyl)phenol)-17-demethoxygeldanamycin (4), were synthesized by nucleophilic substitution of GDM (1). The binding ability of these compounds at the N-terminal domain of heat shock protein [Protein Data Bank (PDB) ID: 1OSF] derived from the PDB was analyzed by ligand-protein docking. Hydrogen-bonding interactions of compounds 2 and 3 were equal to those of 17-dimethylamino-ethylamino-17-demethoxygeldanamycin (17-DMAG), with binding energies of -98.33 and -122.41 kcal/mol, resp. The solubility of the synthesized compounds was ascertained. The solubilities of compounds 2, 3, and 4 in water were 5.571 mM, 1.963 mM, and 1.918 mM, higher than that of compound 1 by approx. 36.65, 12.91, and 12.62 times, resp. The cytotoxicity activity of the synthesized compounds was also evaluated against cancer cell lines using a tetrazolium-based colorimetric assay. These compounds showed high anticancer activity against human cervical carcinoma cells cells, with inhibitory concentration (IC50) values in the range of 19.36-45.66 μg/mL, which were better than that of compound 1, with IC50 values of 110.46 μg/mL. Compound 3 also exhibited cytotoxic activity against human hepatocellular carcinoma cells cells, with an IC50 value of 24.62 μg/mL. These compounds were less active against MDA-MB-231 cells, compared with compound 1. Compound 2 also showed weak cytotoxic activity on Vero and LLC-MK2 cells, with IC50 values of 229.19 and 330.58 μg/mL, resp. The predicted results indicated that these compounds have similar absorption, distribution, metabolism, excretion, and toxicity parameters as well as structures predictive of hepatotoxicity. The results showed that some of the synthesized compounds revealed selective cytotoxicity toward some cancer cells. Therefore, further studies on the synthesized compounds could be helpful in the treatment of some cancers.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Inhibition of bacteria by 5-fluoronicotinic acid and other analogs of nicotinic acid》. Authors are Streigbtoff, Frank.The article about the compound:Methyl 5-fluoro-3-pyridinecarboxylatecas:455-70-9,SMILESS:COC(=O)C1=CC(F)=CN=C1).Synthetic Route of C7H6FNO2. Through the article, more information about this compound (cas:455-70-9) is conveyed.

Several compounds related to 5-fluoronicotinic acid (I) have been demonstrated to inhibit Streptococcus spp. (Viridans group), Staphylococcus aureus, Escherichia coli, and Lactobacillus plan- tarum. The most active compounds were I and 5-fluoronicotin- amide (II). The growth of Streptococcus spp. was inhibited more than 5% by 0.05 γ/ml. of I or 0.5 of II. The inhibition of Streptococcus from 1 part of I or II was reversed by 4 and 2 parts of nicotinic acid, resp. The inhibition of E. coli from 100 parts of I or II was reversed by I part of nicotinic acid. Inhibitions by most other active compounds could be reversed by nicotinic acid. In experiments with mice, 8 compounds related to I had activity against Streptococcus pyogenes; I, II, and 5-fluoro-N-dimethyl- aminomethylnicotinamide protected all mice at 83 mg./kg. The action of 200 mg./kg. I was reversed by 20 mg./kg. of nicotinic acid. The activity of I was not increased by modifica- tions at the number 3 or 5 positions on the pyridine ring or by any other structural changes.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem