Tag: 200-300

Synthesis of nitrogen-containing heterocyclic compounds was written by de Stevens, George;Dughi, Marylou;Lukaszewski, Halina;Blatter, Herbert. And the article was included in Oesterreichische Chemiker-Zeitung in 1962.HPLC of Formula: 90271-86-6 This article mentions the following:

A new heterocyclic compound, 1,2,4,5-tetrahydro-3-methyl-1,3-benzodiazepine (I, R = H₂), pKa < 2, was synthesized from o-aminophenylacetic acid methylamide (II) and formaldehyde through I (R = O). Condensation of II with BzH in boiling diethylene glycol dimethyl ether produced only 3-benzylideneoxindole; however, a quant. yield of o-MeNHCOCH₂C₆H₄N:CHPh, λ 260 mμ (ε 15.760), and 320 mμ (ε 6450), was obtained by carrying out the condensation at 95°. New tetracyclic indoles were synthesized from 1-carbethoxymethyl-1,2,3,4-tetrahydro-β-carboline (III, R = EtO), which reacted with MeNH₂ to give a good yield of III (R = NHMe) (IV). IV condensed with formaldehyde in boiling ethanol gave 68% 3-methylaza-1,2,3,4,6,7,12,12boctahydro-2-oxoindolo[2,3-a]pyridocoline (V, R = Me). Condensation of IV with appropriate benzaldehyde gave V (R = Ph, p-ClC₆H₄, 3,4,5-(MeO)₃C₆H₂, and p-MeOC₆H₄). Reduction of the cyclic amides with LiAlH₄ resulted in loss of carbonyl group. Reduction of IV with LiAlH₄ gave the corresponding amino alcohol (VI), which with HCHO gave VII. Replacement of formaldehyde with benzaldehyde did not produce the expected oxazine but the dimeric compound (VIII). Condensation of indole-3-carboxaldehyde with nitropropane in presence of (NH₄)₂HPO₄, AcOH, and Ac₂O resulted in 3-cyanoindole, 60%, m. 178°. This method was extended to other aromatic aldehydes to give: 5-bromo-3-cyanoindole, 41%; 3-cyano-7-azaindole, 40%; p-dimethylaminobenzonitrile, 77%; p-chlorobenzonitrile, 50%; 3,4,5-trimethoxybenzonitrile, 74%; p-isopropylbenzonitrile, 30%. 20 references. In the experiment, the researchers used many compounds, for example, 5-Bromo-3-cyanoindole (cas: 90271-86-6HPLC of Formula: 90271-86-6).

5-Bromo-3-cyanoindole (cas: 90271-86-6) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.HPLC of Formula: 90271-86-6

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

External oxidant-free and selective thiofunctionalization of alkenes enabled by photoredox-neutral catalysis was written by Liang, Rong-Bin;Zhu, Can-Ming;Song, Pei-Qi;Zhao, Lei-Min;Tong, Qing-Xiao;Zhong, Jian-Ji. And the article was included in Organic Chemistry Frontiers in 2022.COA of Formula: C14H9NO2S This article mentions the following:

A simple photoredox-neutral approach is reported for the three-component thiohydroxylation, thioalkoxylation and thioamination of vinylarenes ArC(R)=CH₂ (Ar = Ph, 3-bromophenyl, 2H-1,3-benzodioxol-5-yl, etc.; R = H, Me, Ph, thien-2-yl, etc.) towards valuable vicinal S,O- and S,N-disubstituted mols. N-Phenyl-sulfenyl phthalimides I (R¹ = Ph, 2-chlorophenyl, naphthalen-2-yl, etc.), a commonly used sulfur electrophile, were demonstrated to act as a thiyl radical precursor and play a crucial role in this reaction. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4COA of Formula: C14H9NO2S).

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.COA of Formula: C14H9NO2S

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Development of Proneurogenic, Neuroprotective Small Molecules was written by MacMillan, Karen S.;Naidoo, Jacinth;Liang, Jue;Melito, Lisa;Williams, Noelle S.;Morlock, Lorraine;Huntington, Paula J.;Estill, Sandi Jo;Longgood, Jamie;Becker, Ginger L.;McKnight, Steven L.;Pieper, Andrew A.;De Brabander, Jef K.;Ready, Joseph M.. And the article was included in Journal of the American Chemical Society in 2011.Category: indole-building-block This article mentions the following:

Degeneration of the hippocampus is associated with Alzheimer’s disease and occurs very early in the progression of the disease. Current options for treating the cognitive symptoms associated with Alzheimer’s are inadequate, giving urgency to the search for novel therapeutic strategies. Pharmacol. agents that safely enhance hippocampal neurogenesis may provide new therapeutic approaches. We discovered the first synthetic mol., named P7C3, which protects newborn neurons from apopotic cell death, and thus promotes neurogenesis in mice and rats in the subgranular zone of the hippocampal dentate gyrus, the site of normal neurogenesis in adult mammals. We describe the results of a medicinal chem. campaign to optimize the potency, toxicity profile, and stability of P7C3. Systematic variation of nearly every position of the lead compound revealed elements conducive toward increases in activity and regions subject to modification. We have discovered compounds that are orally available, nontoxic, stable in mice, rats, and cell culture, and capable of penetrating the blood-brain barrier. The most potent compounds are active at nanomolar concentrations Finally, we have identified derivatives that may facilitate mode-of-action studies through affinity chromatog. or photo-crosslinking. In the experiment, the researchers used many compounds, for example, 5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5Category: indole-building-block).

5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5) belongs to indole derivatives. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Category: indole-building-block

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Synthesis and antimicrobial activity of tetrodecamycin partial structures was written by Paintner, Franz F.;Allmendinger, Lars;Bauschke, Gerd;Berns, Caroline;Heisig, Peter. And the article was included in Bioorganic & Medicinal Chemistry in 2003.SDS of cas: 14204-27-4 This article mentions the following:

An efficient synthetic approach to the core structure I (R = H) of the novel polyketide antibiotic tetrodecamycin was developed. This approach features the acid-catalyzed cyclization of a tert-butyldimethylsilyl protected Me α-(γ-hydroxyacyl) tetronate, leading to the novel tricyclic ring skeleton exhibited by I (R = H), and an efficient strategy for the parallel introduction of the cis-diol and exo-methylene function. In addition to I (R = H), a diastereomer of I (R = H), analog II, and several other derivatives were prepared and evaluated for their antibacterial activities against Staphylococcus aureus (including MRSA) and Enterococcus faecalis and for their cytotoxic activities against human leukemia cell lines (HL-60, Jurkat T-cells). While I (R = H) did not inhibit the growth of the Gram-pos. pathogens (MICs >128 μg mL^-1), analog II and 2-naphthoyl derivative I (R = 2-naphthoyl) showed promising antibacterial activities with MICs of 4-16 μg mL^-1. Remarkably, the antibacterial activity of these compounds was paralleled by cytotoxicity (IC₅₀ 10-23 μM). The reactive exo-methylene moiety was shown to be crucial, but not sufficient on its own, for both the antibacterial and the cytotoxic activities. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4SDS of cas: 14204-27-4).

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. Indole plays a fundamental role for QS in E. coli, being one of the signal molecules responsible for the transcription of a variety of genes (gabT, and tnaB ASTD). SDS of cas: 14204-27-4

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Synthesis of 4-bromo- and 6-bromoindoles and of 4-amino- and 6-aminoindoles and reactions of these compounds was written by Plieninger, Hans;Suehiro, T.;Suhr, K.;Decker, M.. And the article was included in Chemische Berichte in 1955.Synthetic Route of C9H6BrNO2 This article mentions the following:

Bromination of o-O₂NC₆H₄Me gives a mixture of 4,2- and 6,2-Br(O₂N)C₆H₃Me which with (CO₂Et)₂ in the presence of NaOEt yields a mixture of the Na salts of 4,2- (I) and 6,2-Br(O₂N)C₆H₃COCO₂H (II); on cooling the aqueous solution, the less soluble salt of I separates first, and with HCl gives I, m. 138-40°; the acidified mother liquor yields II, m. 117°. I and II can be reduced with Fe(OH)₂ to 4-bromo-2-carboxyindole (III), m. 263°, and the 6-Br isomer (IV), m. 220-4°, resp. Refluxed with Cu₂Br₂ and quinoline, these acids are decarboxylated to 4- and 6-bromoindoles, yellow oil and solid m. 94°, resp.; refluxing with Cu₂Cl₂ gives 4-and 6-chloroindoles, colorless oil, and solid m. 78-80°, resp. Refluxing III with a 15% solution of HCl in EtOH gives the Et ester, m. 161°; Et ester of IV, m. 186-7°. The Et ester of III with piperidine and 30% aqueous formalin in the presence of 60% aqueous AcOH produces 3-piperidinomethyl-4-bromo-2-carbethoxyindole (V), m. 148°; similarly, the Et ester of IV yields the 6-Br isomer (VI), m. 122-4°. 4-Bromoindole (VII), with pyridine, 30% aqueous formalin, and 60% aqueous AcOH yields 3-piperidinomethyl-4-bromoindole (VIII), m. 190°, on cooling, and methylation with Me₂SO₄ in EtOH and treatment with 1-carbethoxy-2-cyclohexanone and Na-OEt produces 1-(4-bromo-α-skatyl)-1-carbethoxy-2-cyclohexanone (IX), m. 160-5°. V similarly gives 1-(2-carbethoxy-4-bromo-α-skatyl)-1-carbethoxy-2-cyclohexanone (X), m. 201°, and VI gives the 6-bromo-α-skatyl isomer, m. 194-6°. VIII with BzOH, Me₂SO₄, and 1-carbobenzyloxy-2-cyclohexanone in the presence of BzOK gives 1-(4-bromo-α-skatyl)-1-carbobenzyloxy-2-cyclohexanone (XI), m. 116-17°. Attempts to cyclize IX in the presence of Mg in THF, Na in xylene, or Na in liquid NH₃, and to cyclize X in the presence of Na or Li under various conditions all failed. 1-Benzyl-4-bromoindole with MeMgI and solid CO₂ yields a complex which can be destroyed to give 1-benzyl-4-carboxyindole, m. 178-80°. III with concentrated NH₄OH gives 4-aminoindole, m. 108°; similarly IV yields 6-aminoindole, m. 68-70°, forming with Ac₂O and pyridine the N-Ac derivative, m. 169°. In the experiment, the researchers used many compounds, for example, 4-Bromo-1H-indole-2-carboxylic acid (cas: 16732-64-2Synthetic Route of C9H6BrNO2).

4-Bromo-1H-indole-2-carboxylic acid (cas: 16732-64-2) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings.Synthetic Route of C9H6BrNO2

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Reduction of Benzolactams to Isoindoles via an Alkoxide-Catalyzed Hydrosilylation was written by Ding, Guangni;Wu, Xiaoyu;Jiang, Lili;Zhang, Zhaoguo;Xie, Xiaomin. And the article was included in Organic Letters in 2017.Synthetic Route of C14H11NO This article mentions the following:

An alkoxide-catalyzed reduction of benzolactams to isoindoles with silanes was realized. With t-BuOK as the catalyst and Ph₂SiH₂ as the reductant, a series of benzolactams containing different functional groups were reduced to the corresponding isoindoles, which could be captured by N-Ph maleimide to form Diels-Alder products in moderate to good yields. Deuterium labeling studies and the hydrosilylation of benzolactam in DMF indicated that the deprotonation of benzolactams took place at C3 potion during the reduction In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Synthetic Route of C14H11NO).

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Synthetic Route of C14H11NO

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Inducer-specific regulators of tumor necrosis factor alpha production was written by Miyachi, Hiroyuki;Azuma, Akihiko;Hioki, Erika;Kobayashi, Yoshiro;Iwaski, Shiego;Hashimoto, Yuichi. And the article was included in Chemical & Pharmaceutical Bulletin in 1996.SDS of cas: 5388-42-1 This article mentions the following:

Novel potent regulators of tumor necrosis factor alpha (TNF-α) production by a human promyelocytic leukemia cell one, HL-60, were prepared All the compounds showed inducer-specific and bidirectional regulation of TNF-α production, i.e., they enhanced 12-O-tetradecanoylphorbol-13-acetate-induced TNF-α production, while they inhibited okadaic acid-induced one. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1SDS of cas: 5388-42-1).

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.SDS of cas: 5388-42-1

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

α-Angelica Lactone in a New Role: Facile Access to N-Aryl Tetrahydroisoquinolinones and Isoindolinones via Organocatalytic α-CH₂ Oxygenation was written by Thatikonda, Thanusha;Deepake, Siddharth K.;Das, Utpal. And the article was included in Organic Letters in 2019.Category: indole-building-block This article mentions the following:

A method for the direct oxidation of various N-aryl tetrahydroisoquinolines and isoindolines to the corresponding lactams using α-angelica lactone as a catalyst was developed. The utility of the method was further demonstrated by synthesis of indoprofen and indobufen. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Category: indole-building-block).

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Category: indole-building-block

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Electrochemical Direct Thiolation of Lactams with Mercaptans: An Efficient Access to N-Acylsulfenamides was written by Wei, Zhaoxin;Wang, Renjie;Zhang, Yonghong;Wang, Bin;Xia, Yu;Abdukader, Ablimit;Xue, Fei;Jin, Weiwei;Liu, Chenjiang. And the article was included in European Journal of Organic Chemistry in 2021.Recommanded Product: 14204-27-4 This article mentions the following:

An efficient and eco-friendly electrochem. methodol. for the oxidative cross coupling hydrogen evolution (CCHE) reactions of lactams with thiols was presented. Various electron deficient N-acylsulfenamides were smoothly produced in modest to excellent yields without using any external oxidant. Elementary mechanistic insight supported a possible free radical process and hydrogen was the only side product. The approach provided a safe, convenient, and economical preparation of synthetically important N-thiophthalimides on a gram scale. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Recommanded Product: 14204-27-4).

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) belongs to indole derivatives. Indole, first isolated in 1866, and it is commonly synthesized from phenylhydrazine and pyruvic acid, although several other procedures have been discovered. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Recommanded Product: 14204-27-4

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Molecular Structure of Monolayers from Thiol-Terminated Polyimide Model Compounds on Gold. 1. A Spectroscopic Investigation was written by Young, J. T.;Boerio, F. J.;Zhang, Z.;Beck, T. L.. And the article was included in Langmuir in 1996.Related Products of 14204-27-4 This article mentions the following:

The mol. orientation and/or packing for monolayers formed by adsorption of (4-mercaptophenyl)phthalimide (4-MPP), a thiol-terminated polyimide model compound, onto gold substrates, was determined using surface-enhanced Raman scattering (SERS), reflection-absorption IR spectroscopy (RAIR), XPS (XPS), ellipsometry, and electrochem. SERS, RAIR, and XPS showed that 4-MPP mols. were chemisorbed onto the gold surface through the thiol groups to form an oriented monolayer. For adsorption times less than about 2 h, the ellipsometric thickness of the films increased as a function of time, but for longer times the ellipsometric thickness reached a limiting value of about 11.5 Å. For adsorption times greater than about 2 h, the surface d. was about 5.2 × 10^-10 mol/cm², corresponding to a mol. area of 32 Ų/mol. Considering the size of the 4-MPP mol. compared to that of an alkanethiol mol., it was concluded that the adsorbed mols. were highly packed on the gold surface. The orientation of adsorbed 4-MPP mols. was determined quant. using IR spectroscopy. It was found that the mols. were oriented with a vertical configuration in which the mol. axes tilted away from the surface normal by about 21°. There was no preferred rotation angle for the imide ring in 4-MPP. The thickness and orientation determined by IR spectroscopy were in excellent agreement with results obtained from mol. dynamics, which are presented in the following paper. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Related Products of 14204-27-4).

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Related Products of 14204-27-4

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles