Day: February 22, 2023

Efficient copper-catalyzed cross-coupling of nitrogen nucleophiles with N,N-dibenzyl-4-iodobenzenesulfonamide and its application in the synthesis of Celecoxib intermediate was written by Yong, Fui-Fong;Azri, Miskal;Darrell Lim, Yong-En;Teo, Yong-Chua. And the article was included in Tetrahedron in 2020.Formula: C7H6N2 This article mentions the following:

A practical and efficient strategy has been developed for the cross-coupling of N,N-dibenzyl-4-iodobenzenesulfonamide with nitrogen nucleophiles using 0.5-20 mol% of CuI under ligand-free conditions. A variety of nitrogen nucleophiles including nitrogen heterocycles, sulfonamides and amides afforded the corresponding products in moderate to good yields (up to 98%) under the optimized conditions. The application of this catalytic system to the synthesis of Celecoxib intermediate was also successfully demonstrated. In the experiment, the researchers used many compounds, for example, 1H-Pyrrolo[2,3-b]pyridine (cas: 271-63-6Formula: C7H6N2).

1H-Pyrrolo[2,3-b]pyridine (cas: 271-63-6) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Formula: C7H6N2

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

Redox-triggered dearomative [5 + 1] annulation of indoles with O-alkyl ortho-oxybenzaldehydes for the synthesis of spirochromanes was written by Cao, Lianyi;Hu, Fangzhi;Sun, Hongmei;Zhang, Xiaomei;Li, Shuai-Shuai. And the article was included in Organic Chemistry Frontiers in 2022.HPLC of Formula: 1076-74-0 This article mentions the following:

The dearomative [5 + 1] annulation of 2-methylindoles I (R = H, 4-Me, 5-F, 6-OMe, etc.) with new five-membered synthons O-alkyl ortho-oxybenzaldehydes II (R¹ = t-Bu, propan-2-yl, butan-2-yl; R² = H, Me, t-Bu; R³ = Me, ethenyl, Ph, naphthalen-2-yl, etc.; R⁴ = H, Me) was developed unprecedentedly through cascade [1,5]-hydride transfer/dearomative cyclization in HFIP for the synthesis of spirochromanes III bearing the 2-methylindolenine skeleton. In addition, the dual alkylation of the Me group of 2-methylindolenines was achieved by sequential operation through the redox neutral [5 + 1] annulation with the second five-membered synthon N-alkyl ortho-aminobenzaldehydes IV (R⁵ = Me; R⁶ = Et; R⁵R⁶ = -(CH₂)₄-; R⁷ = H, Cl), providing the chromane and tetrahydroquinoline fused spiroindolenines V in good yields. Furthermore, the auxiliary group that facilitates the hydride transfer process could be simply removed. In the experiment, the researchers used many compounds, for example, 5-Methoxy-2-methyl-1H-indole (cas: 1076-74-0HPLC of Formula: 1076-74-0).

5-Methoxy-2-methyl-1H-indole (cas: 1076-74-0) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.HPLC of Formula: 1076-74-0

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

Hepatopathy following consumption of a commercially available blue-green algae dietary supplement in a dog was written by Bautista, Adrienne C.;Moore, Caroline E.;Lin, Yanping;Cline, Martha G.;Benitah, Noemi;Puschner, Birgit. And the article was included in BMC Veterinary Research in 2015.Category: indole-building-block This article mentions the following:

Background: Dietary supplement use in both human and animals to augment overall health continues to increase and represents a potential health risk due to the lack of safety regulations imposed on the manufacturers. Because there are no requirements for demonstrating safety and efficacy prior to marketing, dietary supplements may contain potentially toxic contaminants such as hepatotoxic microcystins produced by several species of blue-green algae. Case presentation: An 11-yr-old female spayed 8.95 kg Pug dog was initially presented for poor appetite, lethargy polyuria, polydipsia, and an inability to get comfortable. Markedly increased liver enzyme activities were detected with no corresponding abnormalities evident on abdominal ultrasound. A few days later the liver enzyme activities were persistently increased and the dog was coagulopathic indicating substantial liver dysfunction. The dog was hospitalized for further care consisting of oral S-adenosylmethionine, silybin, vitamin K, and ursodeoxycholic acid, as well as i.v. ampicillin sodium/sulbactam sodium, dolasetron, N-acetylcysteine, metoclopramide, and i.v. fluids. Improvement of the hepatopathy and the dog’s clin. status was noted over the next three days. Assessment of the dog’s diet revealed the use of a com. available blue-green algae dietary supplement for three-and-a-half weeks prior to hospitalization. The supplement was submitted for toxicol. testing and revealed the presence of hepatotoxic microcystins (MCs), MC-LR and MC-LA. Use of the supplement was discontinued and follow-up evaluation over the next few weeks revealed a complete resolution of the hepatopathy. Conclusions: To the authors’ knowledge, this is the first case report of microcystin intoxication in a dog after using a com. available blue-green algae dietary supplement. Veterinarians should recognize the potential harm that these supplements may cause and know that with intervention, recovery is possible. In addition, more prudent oversight of dietary supplement use is recommended for our companion animals to prevent adverse events/intoxications. In the experiment, the researchers used many compounds, for example, rel-(5s,6R,8r,9aS)-3-Oxooctahydro-1H-2,6-methanoquinolizin-8-yl 1H-indole-3-carboxylate (cas: 115956-12-2Category: indole-building-block).

rel-(5s,6R,8r,9aS)-3-Oxooctahydro-1H-2,6-methanoquinolizin-8-yl 1H-indole-3-carboxylate (cas: 115956-12-2) 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Category: indole-building-block

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

Amphetamine promotes cortical Up state: Role of adrenergic receptors was written by Shen, Guofang;Shi, Wei-Xing. And the article was included in Addiction Biology in 2021.Recommanded Product: (-)-1-(3-Hydroxypropyl)-5-[(2R)-2-[[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-2,3-di-hydro-1H-indole-7-carboxamide This article mentions the following:

We report that systemic injection of d-amphetamine produced similar effects. Our evidence further suggests that norepinephrine (NE) plays a major role in the effects of d-amphetamine since they were mimicked by the NE reuptake inhibitors tomoxetine and nisoxetine and completely blocked by the 伪1 receptor antagonist prazosin. The effects of d-amphetamine persisted, however, in the presence of 伪2 or 尾 receptor blockade. Experiments with 伪1 subtype-selective antagonists further suggest that d-amphetamines effects depend on activation of central, but not peripheral, 伪1A receptors. Unexpectedly, the putative 伪1 receptor agonist cirazoline failed to mimic the effects of d-amphetamine. Previous studies suggest that cirazoline is also an antagonist at 伪2 receptors. Furthermore, it is a partial, not full, agonist at 伪1B and 伪1D receptors. Whether or not these properties of cirazoline contribute to its failure to mimic d-amphetamines effects remains to be determined Methylphenidate and d-amphetamine are two most common medications for attention-deficit/hyperactivity disorder (ADHD). Both, however, are associated with adverse effects including abuse potential and psychotomimetic effects. Further understanding of their mechanisms of action will help develop safer treatments for ADHD and offer new insights into drug addiction and psychosis. In the experiment, the researchers used many compounds, for example, (-)-1-(3-Hydroxypropyl)-5-[(2R)-2-[[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-2,3-di-hydro-1H-indole-7-carboxamide (cas: 160970-54-7Recommanded Product: (-)-1-(3-Hydroxypropyl)-5-[(2R)-2-[[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-2,3-di-hydro-1H-indole-7-carboxamide).

(-)-1-(3-Hydroxypropyl)-5-[(2R)-2-[[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-2,3-di-hydro-1H-indole-7-carboxamide (cas: 160970-54-7) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Recommanded Product: (-)-1-(3-Hydroxypropyl)-5-[(2R)-2-[[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-2,3-di-hydro-1H-indole-7-carboxamide

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

One-Pot Synthesis of 纬-Azidobutyronitriles and Their Intramolecular Cycloadditions was written by Ivanov, Konstantin L.;Tukhtaev, Hamidulla B.;Tukhtaeva, Feruza O.;Bezzubov, Stanislav I.;Melnikov, Mikhail Ya.;Budynina, Ekaterina M.. And the article was included in Synthesis in 2020.Category: indole-building-block This article mentions the following:

Efficient gram-scale, one-pot approached to azidocyanobutyrates and their amidated or decarboxylated derivatives was developed, starting from com. available aldehydes and cyanoacetates. These techniques combine (1) Knoevenagel condensation, (2) Corey-Chaykovsky cyclopropanation and (3) nucleophilic ring opening of donor-acceptor cyclopropanes with the azide ion, as well as (4) Krapcho decarboxylation or (4′) amidation. The synthetic utility of the resulting 纬-azidonitriles was demonstrated by their transformation into tetrazoles via intramol. (3+2)-cycloaddition A condition-dependent activation effect of the 伪-substituent was revealed in that case. Thermally activated azide-nitrile interaction did not differentiate the presence of an 伪-electron-withdrawing substituent in 纬-azidonitriles, whereas the Lewis acid mediated (SnCl₄or TiCl₄) reaction proceeded much easier for azidocyanobutyrates. This allowed us to develop an efficient procedure for converting azidocyanobutyrates into the corresponding tetrazoles. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-indole-2-carbaldehyde (cas: 27421-51-8Category: indole-building-block).

1-Methyl-1H-indole-2-carbaldehyde (cas: 27421-51-8) 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. 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.Category: indole-building-block

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

Structure-Based design of Marine-derived Meridianin C derivatives as glycogen synthase kinase 3尾 inhibitors with improved oral bioavailability: From aminopyrimidyl-indoles to the sulfonyl analogues was written by Han, Shuwen;Zhou, Wei;Zhuang, Chunlin;Chen, Fener. And the article was included in Bioorganic Chemistry in 2022.Category: indole-building-block This article mentions the following:

Glycogen synthase kinase 3尾 (GSK-3尾) has become an attractive target for the treatment of diabetes. Compound I is an indole-based GSK-3尾 inhibitor designed from the Meridianin C, a marine natural product (MNP) isolated from Aplidium聽meridianum. However, this compound has a moderate inhibitory activity toward GSK-3尾 (IC₅₀ = 24.4 渭M), moderate glucose uptake (38%), and especially, a low oral bioavailability (F = 11.4%). In the present study, applying the structure-based design strategy, a series of derivatives modified on the indole moiety were synthesized based on the lead compound I, followed by evaluating their cytotoxic activity, antihyperglycemic activity, and kinase inhibitory activity. Among this series, compound 6x with a sulfonyl group displayed the highest glucose uptake (83.5%) in muscle L6 cells, showing much higher inhibitory activity against GSK-3尾 (IC₅₀ = 5.25 渭M). Mol. docking indicated that compound 6x was properly inserted into the ATP-binding binding pocket of GSK-3尾 with a higher docking score (-8.145 kcal/mol) compared with that of compound I (-6.950 kcal/mol), interpreting the higher kinase inhibitory activity toward GSK-3尾. Remarkably, compound 6x showed favorable drug-like properties, including significantly better oral bioavailability (F = 47.4%) and no two-week acute toxicity at a dose of 1g/kg. Our findings suggest that these MNP-derived sulfonyl indole derivatives could be used as lead compounds for the development of anti-hyperglycemic drugs. In the experiment, the researchers used many compounds, for example, 4-Nitroindole (cas: 4769-97-5Category: indole-building-block).

4-Nitroindole (cas: 4769-97-5) 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. 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). Category: indole-building-block

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

Highly Enantioselective Synthesis of (R)-3-Alkyl-3-hydroxyindolin-2-ones including Natural Product (R)-Convolutamydine A Catalyzed by a Primary Amine was written by Guo, Jun-Tao;Zhang, Bao-Qiang;Luo, Yuan;Guan, Zhi;He, Yan-Hong. And the article was included in Asian Journal of Organic Chemistry in 2017.HPLC of Formula: 20780-72-7 This article mentions the following:

An efficient strategy for constructing (R)-3-alkyl-3-hydroxyindolin-2-one derivatives I (R¹ = H, 4-Cl, 5-Br, etc.; R² = H, CH₃, Bn) catalyzed by a structurally simple and easily prepared primary amine catalyst under mild conditions has been developed. Various isatins and ketones were tolerated, and the desired products were obtained in up to 99 % yield and up to 99 % ee. The biol. active natural product (R)-convolutamydine A was synthesized in 96 % yield and 95 % ee. In the experiment, the researchers used many compounds, for example, 4-Bromoindoline-2,3-dione (cas: 20780-72-7HPLC of Formula: 20780-72-7).

4-Bromoindoline-2,3-dione (cas: 20780-72-7) 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. 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). HPLC of Formula: 20780-72-7

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

Interfacial polarization dominant CNTs/PyC hollow microspheres as a lightweight electromagnetic wave absorbing material was written by Kong, Luo;Luo, Sihan;Zhang, Guiqin;Xu, Hailong;Wang, Tong;Huang, Jianfeng;Fan, Xiaomeng. And the article was included in Carbon in 2022.Category: indole-building-block This article mentions the following:

For the non-magnetic materials, polarization and conductivity loss are the keys to affect the electromagnetic wave absorption properties. The heterogeneous interfacial polarization is an important scientific issue in research of electromagnetic wave absorbing materials. Carbon nanotubes/pyrolytic carbon hollow microspheres (CNTs/PyC HMs) are prepared by in-situ growth of CNTs growing on the surface of zero-dimensional PyC HMs carrier. A large number of heterogeneous interface between CNTs and PyC HMs are constructed. The crystallization degree of CNTs can be significantly regulated in a small temperature range. When the reaction temperature increases from 600 to 700掳C, CNTs gradually change from amorphous to crystalline state. The higher crystallization degree of CNTs leads to a greater conductivity differences in heterogeneous interfaces, which results in an enhancement of interfacial polarization intensity. CNTs/PyC HMs with special hollow structure and a large number of heterogeneous interfaces exhibit excellent dielec. loss capability. When the thickness is 2.3 mm and reaction temperature is 650掳C, the min. reflection coefficient is -56 dB and the effective absorption bandwidth reaches 4 GHz. The polarization loss induced by heterogeneous interfaces is an important avenue to enhance electromagnetic wave absorption properties, and a design strategy of interfacial polarization dominant electromagnetic wave absorbing material is explored. In the experiment, the researchers used many compounds, for example, 5,6-Dihydroxyindole (cas: 3131-52-0Category: indole-building-block).

5,6-Dihydroxyindole (cas: 3131-52-0) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Category: indole-building-block

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽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 photochromic properties of novel spiro[indoline-quinoline]oxazine derivatives was written by Zhou, Yan;Pang, Meili;Li, Jingjing;Li, Hong. And the article was included in Dyes and Pigments in 2014.Recommanded Product: 118-12-7 This article mentions the following:

A series of novel spirooxazine derivatives containing nitrogen heterocycles have been synthesized and characterized by ¹H NMR, ¹³C NMR, IR and HRMS in this paper, and the photochromic behaviors of the compounds have been studied in different solutions and the compounds were embedded into a poly(methylmethacrylate) and poly(vinyl butyral) matrix (PMMA, PVB). In solutions, they showed thermochromism and acidichromism. Embedded into polymeric films, the photochromic kinetics of the thermal decoloration of the compounds significantly changed and it was found that the decoloration curves fitted biexponential function. Detailed studies showed that representative compound 1 [1,3,3-trimethyl-6′-piperidino-spiro(indoline-2,3′-[3H]-quinolino[2,1-b][1,4]oxazine)] exhibited high fatigue resistance in poly(methylmethacrylate) and poly(vinyl butyral) matrix. In the experiment, the researchers used many compounds, for example, 1,3,3-Trimethyl-2-methyleneindoline (cas: 118-12-7Recommanded Product: 118-12-7).

1,3,3-Trimethyl-2-methyleneindoline (cas: 118-12-7) 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.Recommanded Product: 118-12-7

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

Indole-3-acetic acid in Fusarium graminearum: Identification of biosynthetic pathways and characterization of physiological effects was written by Luo, Kun;Rocheleau, Helene;Qi, Peng-Fei;Zheng, You-Liang;Zhao, Hui-Yan;Ouellet, Therese. And the article was included in Fungal Biology in 2016.SDS of cas: 879-37-8 This article mentions the following:

Fusarium graminearum is a devastating pathogenic fungus causing fusarium head blight (FHB) of wheat. This fungus can produce indole-3-acetic acid (IAA) and a very large amount of IAA accumulates in wheat head tissues during the first few days of infection by F. graminearum. Using liquid culture conditions, we have determined that F. graminearum can use tryptamine (TAM) and indole-3-acetonitrile (IAN) as biosynthetic intermediates to produce IAA. It is the first time that F. graminearum is shown to use the L-tryptophan-dependent TAM and IAN pathways rather than the indole-3-acetamide or indole-3-pyruvic acid pathways to produce IAA. Our experiments also showed that exogenous IAA was metabolized by F. graminearum. Exogenous IAA, TAM, and IAN inhibited mycelial growth; IAA and IAN also affected the hyphae branching pattern and delayed macroconidium germination. IAA and TAM had a small pos. effect on the production of the mycotoxin 15-ADON while IAN inhibited its production Our results showed that IAA and biosynthetic intermediates had a significant effect on F. graminearum physiol. and suggested a new area of exploration for fungicidal compounds In the experiment, the researchers used many compounds, for example, Indole-3-acetamide (cas: 879-37-8SDS of cas: 879-37-8).

Indole-3-acetamide (cas: 879-37-8) 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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.SDS of cas: 879-37-8

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