Tag: 189.2105

Highly Chemo- and Enantioselective Synthesis of 3-Allyl-3-aryl Oxindoles via the Direct Palladium-Catalyzed 伪-Arylation of Amides was written by Luan, Xinjun;Wu, Linglin;Drinkel, Emma;Mariz, Ronaldo;Gatti, Michele;Dorta, Reto. And the article was included in Organic Letters in 2010.Application In Synthesis of 1-Methyl-3-indoleacetic acid This article mentions the following:

Nonracemic cinnamyl imidazolidinylenepalladium complexes such as I (R = Et₂CH) are prepared as catalysts for the chemoselective and enantioselective arylation of N-(2-bromophenyl) allyl-substituted acetamides such as II (R¹ = Ph, 1-naphthyl, 2-naphthyl, 2-MeC₆H₄, 2-FC₆H₄, 2-MeOC₆H₄, 4-MeC₆H₄, 4-FC₆H₄, 4-F₃CC₆H₄, 4-PhC₆H₄, 3-MeC₆H₄, 3-FC₆H₄, 3-MeOC₆H₄, 3,5-Me₂C₆H₃, 1-Me-3-indolyl, Me; R² = H, Me; R³ = H, MeO) to give nonracemic (aryl)(allyl)oxindoles such as III (R¹ = Ph, 1-naphthyl, 2-naphthyl, 2-MeC₆H₄, 2-FC₆H₄, 2-MeOC₆H₄, 4-MeC₆H₄, 4-FC₆H₄, 4-F₃CC₆H₄, 4-PhC₆H₄, 3-MeC₆H₄, 3-FC₆H₄, 3-MeOC₆H₄, 3,5-Me₂C₆H₃, 1-Me-3-indolyl, Me; R² = H, Me; R³ = H, MeO) in 40-98% yields and in 4-91% ee (with all but three of the 21 examples in 69-91% ee) with none of the isomeric benzazepinone products formed in most cases. In the experiment, the researchers used many compounds, for example, 1-Methyl-3-indoleacetic acid (cas: 1912-48-7Application In Synthesis of 1-Methyl-3-indoleacetic acid).

1-Methyl-3-indoleacetic acid (cas: 1912-48-7) 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Application In Synthesis of 1-Methyl-3-indoleacetic acid

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

Decarboxylative Coupling Reaction of 2-(1H-indol-3-yl)acetic Acids with Indole, Azaindole, Benzimidazole and Indazole Derivatives was written by Pillaiyar, Thanigaimalai;Uzair, Muhammad;Ullah, Saif;Schnakenburg, Gregor;Mueller, Christa E.. And the article was included in Advanced Synthesis & Catalysis in 2019.Recommanded Product: 1912-48-7 This article mentions the following:

A new, mild and efficient copper(II)-promoted decarboxylative coupling reaction of 2-(1H-indol-3-yl)acetic acid derivatives I (R = H, 4-Cl, 5-OCH₃, 6-F, 5-Cl, 6-Cl; R¹ = H, CH₃) with a variety of (substituted) indoles II (R² = H, Ph, CO₂Et; R³ = H, CH₃; R⁴ = H, Me, F, Br, MeO, CHO; R⁵ = H, MeO, CHO, F; R⁶ = H, Cl, Br, MeO, Et, CN; R⁷ = H, Br; R⁶R⁷ = CH=CH-CH=CH) yielding (un)sym. substituted 3,3′-diindolylmethanes (DIMs) III have been reported. Reaction of 2-(1H-indol-3-yl)acetic acid I (R = R¹ = H) with 7-azaindole led to 3-((1H-indol-3-yl)methyl)-1H-pyrrolo[2,3-b]pyridine, while 4-, 5-, and 6-azaindoles and benzimidazole reacted at the N1-nitrogen atom. Reaction of I (R = R¹ = H) with 1H-indazole led to a mixture of 1-((1H-indol-3-yl)methyl)-1H-indazole and 2-((1H-indol-3-yl)methyl)-2H-indazole. The new method allows large-scale synthesis of biol. active DIMs. In the experiment, the researchers used many compounds, for example, 1-Methyl-3-indoleacetic acid (cas: 1912-48-7Recommanded Product: 1912-48-7).

1-Methyl-3-indoleacetic acid (cas: 1912-48-7) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Recommanded Product: 1912-48-7

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

Unique versatility of ionic liquids as clean decarboxylation catalyst cum solvent: a metal- and quinoline-free paradigm towards synthesis of indoles, styrenes, stilbenes and arene derivatives under microwave irradiation in aqueous conditions was written by Sharma, Abhishek;Kumar, Rakesh;Sharma, Naina;Kumar, Vinod;Sinha, Arun K.. And the article was included in Advanced Synthesis & Catalysis in 2008.HPLC of Formula: 1912-48-7 This article mentions the following:

Ionic liquids have been found to provide a new platform for metal- and quinoline-free decarboxylation of various N-heteroaryl and aryl carboxylic acids under microwave irradiation in aqueous condition. The method was found to possess a wide substrate scope towards the synthesis of various pharmacol. and industrially important aromatic compounds including indoles, styrenes, stilbenes, and nitro- or hydroxyarene derivatives The decarboxylation of indole and 伪-phenylcinnamic acids proceeded well without addition of any catalyst in neat 1-hexyl-3-methylimidazolium bromide ([hmim]Br) and 1-methylimidazolium p-toluenesulfonic acid ([Hmim]PTSA), resp., while addition of a mild base like aqueous sodium hydrogen carbonate to [hmim]Br further improved the decarboxylation of hydroxylated cinnamic and aromatic acid substrates. The developed methodol. not only precludes the usage of toxic metal/quinoline and harsh organic bases but also offers several inherent benefits like recyclability of reagent system, reduction in waste and hazards, short reaction time besides ease of product recovery. In the experiment, the researchers used many compounds, for example, 1-Methyl-3-indoleacetic acid (cas: 1912-48-7HPLC of Formula: 1912-48-7).

1-Methyl-3-indoleacetic acid (cas: 1912-48-7) 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.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: 1912-48-7

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

Mechanisms for increased pH-mediated amelioration of copper toxicity in Citrus sinensis leaves using physiology, transcriptomics and metabolomics was written by Zhang, Jiang;Chen, Xu-Feng;Huang, Wei-Tao;Chen, Huan-Huan;Lai, Ning-Wei;Yang, Lin-Tong;Huang, Zeng-Rong;Guo, Jiuxin;Ye, Xin;Chen, Li-Song. And the article was included in Environmental and Experimental Botany in 2022.Related Products of 830-96-6 This article mentions the following:

Limited data are available on the mol. and physiol. mechanisms for increased pH-mediated amelioration of copper (Cu) toxicity in plants. Citrus sinensis seedlings were fertilized with a nutrient solution at the Cu concentration of 300 (Cu toxicity) or 0.5渭M (control) and a pH of 3.0, 4.0, or 4.8 for 17 wk. Subsequently, we examined the interactive effects of low pH and Cu toxicity on transcriptomics, metabolomics, and some physiol. parameters in leaves. Our results demonstrated that increased pH reduced Cu toxicity-induced leaf Cu accumulation and oxidative damage by reducing reactive oxygen species (ROS) production and maintaining the homeostasis of sulfur (S)-containing compounds (reduced glutathione), ascorbate, and cell redox potential, thus mitigating Cu toxic effects on leaf chlorophyll biosynthesis, photosynthesis, and metabolisms of carbohydrates, lipids, amino acids, and secondary metabolites. The increased pH mitigated Cu toxicity-induced impairment of cell wall metabolism by reducing cell wall Cu concentration, thus improving leaf growth. Under low pH (pH 3.0), C. sinensis leaves also displayed some adaptive responses to Cu toxicity to meet the increased demand for the dissipation of excess light energy and the detoxification of Cu and ROS, including: (a) increased distribution of Cu in cell wall; (b) elevated photorespiration and thermal dissipation. And increased accumulation of nonstructural carbohydrates [fructose, glucose, starch, total nonstructural carbohydrates (the summation of fructose + glucose + sucrose + starch), maltotetraose and 1,1-kestotetraose] and upregulation of metabolism (glycolysis/gluconeogenesis, pyruvate metabolism and pentose phosphate pathway) related to energy production; (d) downregulation of phospholipid [LysoPC 18:3(2 n isomer)] and phosphate-containing compounds (2′-deoxycytidine-5′-monophosphate and AMP) and upregulation of -tryptophan metabolism and related amino acids (-tryptophan and 5-hydroxy–tryptophan); and (e) increased accumulation of some secondary metabolites [total phenolics, lignin, alkaloids (3-indoleacrylic acid, N-acetyl-5-hydroxytryptamine and Me nicotinate), plumerane (indole and 3-indolepropionic acid) and coumarins (isoscopoletin, scopoletin, skimming and scopolin)]. However, these adaptive responses could not protect low pH-treated leaves from Cu toxicity, as indicated by elevated malondialdehyde accumulation and electrolyte leakage and decreased photosynthesis and chlorophyll level in leaves as well as reduced leaf growth due to impaired cell metabolism Cu toxicity intensified the adverse effects of low pH on C. sinensis leaves. In the experiment, the researchers used many compounds, for example, 3-Indolepropionic acid (cas: 830-96-6Related Products of 830-96-6).

3-Indolepropionic acid (cas: 830-96-6) 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. 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.Related Products of 830-96-6

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 evaluation of the anti-proliferative activity of diaryl-3-pyrrolin-2-ones and fused analogs was written by Mowery, Patricia;Banales Mejia, Fernando;Franceschi, Courtney L.;Kean, Maeve H.;Kwansare, Deborah O.;Lafferty, Megan M.;Neerukonda, Namita D.;Rolph, Carly E.;Truax, Nathanyal J.;Pelkey, Erin T.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2017.Formula: C11H11NO2 This article mentions the following:

Analogs containing a central 3-pyrrolin-2-one core with different methoxyphenyl and/or indole substituents, e.g. I, were prepared and tested for anti-proliferative activity in U-937 cells. The most efficacious analogs were non-rigid, (non-fused) contained methoxyaryl groups located at the 4-position, and contained either methoxyaryl or indole groups located at the 3-position. Both the number of methoxy groups contained in the substituents and the particular location of the indole rings with respect to the lactam carbonyl had significant affects on anti-proliferative activity. This work provides a framework to better understand structure-activity relationships for inducing anti-proliferative activity in diaryl heterocyclic scaffolds. In the experiment, the researchers used many compounds, for example, 1-Methyl-3-indoleacetic acid (cas: 1912-48-7Formula: C11H11NO2).

1-Methyl-3-indoleacetic acid (cas: 1912-48-7) 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Formula: C11H11NO2

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 Chemo- and Enantioselective Synthesis of 3-Allyl-3-aryl Oxindoles via the Direct Palladium-Catalyzed α-Arylation of Amides was written by Luan, Xinjun;Wu, Linglin;Drinkel, Emma;Mariz, Ronaldo;Gatti, Michele;Dorta, Reto. And the article was included in Organic Letters in 2010.Application In Synthesis of 1-Methyl-3-indoleacetic acid This article mentions the following:

Nonracemic cinnamyl imidazolidinylenepalladium complexes such as I (R = Et₂CH) are prepared as catalysts for the chemoselective and enantioselective arylation of N-(2-bromophenyl) allyl-substituted acetamides such as II (R¹ = Ph, 1-naphthyl, 2-naphthyl, 2-MeC₆H₄, 2-FC₆H₄, 2-MeOC₆H₄, 4-MeC₆H₄, 4-FC₆H₄, 4-F₃CC₆H₄, 4-PhC₆H₄, 3-MeC₆H₄, 3-FC₆H₄, 3-MeOC₆H₄, 3,5-Me₂C₆H₃, 1-Me-3-indolyl, Me; R² = H, Me; R³ = H, MeO) to give nonracemic (aryl)(allyl)oxindoles such as III (R¹ = Ph, 1-naphthyl, 2-naphthyl, 2-MeC₆H₄, 2-FC₆H₄, 2-MeOC₆H₄, 4-MeC₆H₄, 4-FC₆H₄, 4-F₃CC₆H₄, 4-PhC₆H₄, 3-MeC₆H₄, 3-FC₆H₄, 3-MeOC₆H₄, 3,5-Me₂C₆H₃, 1-Me-3-indolyl, Me; R² = H, Me; R³ = H, MeO) in 40-98% yields and in 4-91% ee (with all but three of the 21 examples in 69-91% ee) with none of the isomeric benzazepinone products formed in most cases. In the experiment, the researchers used many compounds, for example, 1-Methyl-3-indoleacetic acid (cas: 1912-48-7Application In Synthesis of 1-Methyl-3-indoleacetic acid).

1-Methyl-3-indoleacetic acid (cas: 1912-48-7) 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Application In Synthesis of 1-Methyl-3-indoleacetic acid

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

Decarboxylative Coupling Reaction of 2-(1H-indol-3-yl)acetic Acids with Indole, Azaindole, Benzimidazole and Indazole Derivatives was written by Pillaiyar, Thanigaimalai;Uzair, Muhammad;Ullah, Saif;Schnakenburg, Gregor;Mueller, Christa E.. And the article was included in Advanced Synthesis & Catalysis in 2019.Recommanded Product: 1912-48-7 This article mentions the following:

A new, mild and efficient copper(II)-promoted decarboxylative coupling reaction of 2-(1H-indol-3-yl)acetic acid derivatives I (R = H, 4-Cl, 5-OCH₃, 6-F, 5-Cl, 6-Cl; R¹ = H, CH₃) with a variety of (substituted) indoles II (R² = H, Ph, CO₂Et; R³ = H, CH₃; R⁴ = H, Me, F, Br, MeO, CHO; R⁵ = H, MeO, CHO, F; R⁶ = H, Cl, Br, MeO, Et, CN; R⁷ = H, Br; R⁶R⁷ = CH=CH-CH=CH) yielding (un)sym. substituted 3,3′-diindolylmethanes (DIMs) III have been reported. Reaction of 2-(1H-indol-3-yl)acetic acid I (R = R¹ = H) with 7-azaindole led to 3-((1H-indol-3-yl)methyl)-1H-pyrrolo[2,3-b]pyridine, while 4-, 5-, and 6-azaindoles and benzimidazole reacted at the N1-nitrogen atom. Reaction of I (R = R¹ = H) with 1H-indazole led to a mixture of 1-((1H-indol-3-yl)methyl)-1H-indazole and 2-((1H-indol-3-yl)methyl)-2H-indazole. The new method allows large-scale synthesis of biol. active DIMs. In the experiment, the researchers used many compounds, for example, 1-Methyl-3-indoleacetic acid (cas: 1912-48-7Recommanded Product: 1912-48-7).

1-Methyl-3-indoleacetic acid (cas: 1912-48-7) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Recommanded Product: 1912-48-7

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

Unique versatility of ionic liquids as clean decarboxylation catalyst cum solvent: a metal- and quinoline-free paradigm towards synthesis of indoles, styrenes, stilbenes and arene derivatives under microwave irradiation in aqueous conditions was written by Sharma, Abhishek;Kumar, Rakesh;Sharma, Naina;Kumar, Vinod;Sinha, Arun K.. And the article was included in Advanced Synthesis & Catalysis in 2008.HPLC of Formula: 1912-48-7 This article mentions the following:

Ionic liquids have been found to provide a new platform for metal- and quinoline-free decarboxylation of various N-heteroaryl and aryl carboxylic acids under microwave irradiation in aqueous condition. The method was found to possess a wide substrate scope towards the synthesis of various pharmacol. and industrially important aromatic compounds including indoles, styrenes, stilbenes, and nitro- or hydroxyarene derivatives The decarboxylation of indole and α-phenylcinnamic acids proceeded well without addition of any catalyst in neat 1-hexyl-3-methylimidazolium bromide ([hmim]Br) and 1-methylimidazolium p-toluenesulfonic acid ([Hmim]PTSA), resp., while addition of a mild base like aqueous sodium hydrogen carbonate to [hmim]Br further improved the decarboxylation of hydroxylated cinnamic and aromatic acid substrates. The developed methodol. not only precludes the usage of toxic metal/quinoline and harsh organic bases but also offers several inherent benefits like recyclability of reagent system, reduction in waste and hazards, short reaction time besides ease of product recovery. In the experiment, the researchers used many compounds, for example, 1-Methyl-3-indoleacetic acid (cas: 1912-48-7HPLC of Formula: 1912-48-7).

1-Methyl-3-indoleacetic acid (cas: 1912-48-7) 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.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: 1912-48-7

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

Mechanisms for increased pH-mediated amelioration of copper toxicity in Citrus sinensis leaves using physiology, transcriptomics and metabolomics was written by Zhang, Jiang;Chen, Xu-Feng;Huang, Wei-Tao;Chen, Huan-Huan;Lai, Ning-Wei;Yang, Lin-Tong;Huang, Zeng-Rong;Guo, Jiuxin;Ye, Xin;Chen, Li-Song. And the article was included in Environmental and Experimental Botany in 2022.Related Products of 830-96-6 This article mentions the following:

Limited data are available on the mol. and physiol. mechanisms for increased pH-mediated amelioration of copper (Cu) toxicity in plants. Citrus sinensis seedlings were fertilized with a nutrient solution at the Cu concentration of 300 (Cu toxicity) or 0.5μM (control) and a pH of 3.0, 4.0, or 4.8 for 17 wk. Subsequently, we examined the interactive effects of low pH and Cu toxicity on transcriptomics, metabolomics, and some physiol. parameters in leaves. Our results demonstrated that increased pH reduced Cu toxicity-induced leaf Cu accumulation and oxidative damage by reducing reactive oxygen species (ROS) production and maintaining the homeostasis of sulfur (S)-containing compounds (reduced glutathione), ascorbate, and cell redox potential, thus mitigating Cu toxic effects on leaf chlorophyll biosynthesis, photosynthesis, and metabolisms of carbohydrates, lipids, amino acids, and secondary metabolites. The increased pH mitigated Cu toxicity-induced impairment of cell wall metabolism by reducing cell wall Cu concentration, thus improving leaf growth. Under low pH (pH 3.0), C. sinensis leaves also displayed some adaptive responses to Cu toxicity to meet the increased demand for the dissipation of excess light energy and the detoxification of Cu and ROS, including: (a) increased distribution of Cu in cell wall; (b) elevated photorespiration and thermal dissipation. And increased accumulation of nonstructural carbohydrates [fructose, glucose, starch, total nonstructural carbohydrates (the summation of fructose + glucose + sucrose + starch), maltotetraose and 1,1-kestotetraose] and upregulation of metabolism (glycolysis/gluconeogenesis, pyruvate metabolism and pentose phosphate pathway) related to energy production; (d) downregulation of phospholipid [LysoPC 18:3(2 n isomer)] and phosphate-containing compounds (2′-deoxycytidine-5′-monophosphate and AMP) and upregulation of -tryptophan metabolism and related amino acids (-tryptophan and 5-hydroxy–tryptophan); and (e) increased accumulation of some secondary metabolites [total phenolics, lignin, alkaloids (3-indoleacrylic acid, N-acetyl-5-hydroxytryptamine and Me nicotinate), plumerane (indole and 3-indolepropionic acid) and coumarins (isoscopoletin, scopoletin, skimming and scopolin)]. However, these adaptive responses could not protect low pH-treated leaves from Cu toxicity, as indicated by elevated malondialdehyde accumulation and electrolyte leakage and decreased photosynthesis and chlorophyll level in leaves as well as reduced leaf growth due to impaired cell metabolism Cu toxicity intensified the adverse effects of low pH on C. sinensis leaves. In the experiment, the researchers used many compounds, for example, 3-Indolepropionic acid (cas: 830-96-6Related Products of 830-96-6).

3-Indolepropionic acid (cas: 830-96-6) 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. 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.Related Products of 830-96-6

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