February 2023 - Page 30 of 117 - Indole Building Blocks

Hu, Miao et al. published their research in New Journal of Chemistry in 2021 | CAS: 16096-32-5

4-Methyl-1H-indole (cas: 16096-32-5) 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 was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.COA of Formula: C9H9N

Nickel-catalyzed C3-alkylation of indoles with alcohols via a borrowing hydrogen strategy was written by Hu, Miao;Jiang, Yong;Sun, Nan;Hu, Baoxiang;Shen, Zhenlu;Hu, Xinquan;Jin, Liqun. And the article was included in New Journal of Chemistry in 2021.COA of Formula: C9H9N This article mentions the following:

An efficient method for the Ni-catalyzed C3-alkylation of indoles using readily available alcs. as the alkylating reagents had developed to obtain alkylated indole I [R = H, Me, Ph; R¹ = n-Bu, Ph, Bn, etc.; R² = H, 4-MeC₆H₄, 6-FC₆H₄, etc.]. The alkylation was addressed with an air and moisture-stable binuclear nickel complex ligated by tetrahydroquinolin-8-one as the effective pre-catalyst. The newly developed transformation could accommodate a broad substrate scope including primary/secondary benzylic and aliphatic alcs. and substituted indoles. Mechanistic studies suggested that the reaction proceeded through a borrowing hydrogen pathway. In the experiment, the researchers used many compounds, for example, 4-Methyl-1H-indole (cas: 16096-32-5COA of Formula: C9H9N).

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

Pramanik, Subhendu et al. published their research in Organic Letters in 2022 | CAS: 27421-51-8

1-Methyl-1H-indole-2-carbaldehyde (cas: 27421-51-8) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Quality Control of 1-Methyl-1H-indole-2-carbaldehyde

Palladium-Catalyzed Benzannulations of 1-(Indol-2-yl)but-3-yn-1-ols: Easy Access to Functionalized Carbazoles was written by Pramanik, Subhendu;Chatterjee, Sarat;Banerjee, Rumjhum;Chowdhury, Chinmay. And the article was included in Organic Letters in 2022.Quality Control of 1-Methyl-1H-indole-2-carbaldehyde This article mentions the following:

An atom economic direct synthesis of carbazoles having aryl and keto-aryl groups has been achieved through Pd(II)-catalyzed cascade reactions between 1-(indol-2-yl)-3-butyn-1-ols and aldehydes. The reaction proceeds through alkyne-carbonyl metathesis, an uncommon pathway using palladium catalyst, and constitutes a fast intermol. assembly through four carbon-carbon bond formations in one-pot. Absence of the aldehyde substrate resulted in the formation of C1-aryl substituted carbazoles. The reaction is amenable to the synthesis of bis-carbazole derivatives In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-indole-2-carbaldehyde (cas: 27421-51-8Quality Control of 1-Methyl-1H-indole-2-carbaldehyde).

Wang, Ruo-Nan et al. published their research in Organic Chemistry Frontiers in 2022 | CAS: 61220-51-7

5-Chlorotryptophol (cas: 61220-51-7) 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. 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). Recommanded Product: 5-Chlorotryptophol

Acid-promoted formal [3+2] cyclization/N,O-ketalization of in-situ generated ortho-alkynyl quinone methides: access to bridged 2,3-cyclopentanoindoline skeletons was written by Wang, Ruo-Nan;Ma, Yan-Hua;Su, Qing-Qiang;Fan, Ya-Xin;Lv, Yong-Zheng;Zhang, Xiang-Zhi;Wang, Yan-Lan;Huang, Hong-Li;Du, Ji-Yuan. And the article was included in Organic Chemistry Frontiers in 2022.Recommanded Product: 5-Chlorotryptophol This article mentions the following:

An acid-catalyzed formal [3+2] cyclization/N,O-ketalization of in-situ formed ortho-alkynyl quinone methides (o-AQMs) and tryptophol derivatives was developed. With this method, a series of functionalized 2,3-cyclopentanoindoline derivatives were effectively synthesized in good yields with excellent diastereoselectivities under mild conditions. In this reaction, o-AQMs formally serves as synthetic equivalent of the 1,3-dipole, and the process involves a tandem 1,4-addition/dearomatization/1,2-shift/aromatization sequence of tryptophol. In the experiment, the researchers used many compounds, for example, 5-Chlorotryptophol (cas: 61220-51-7Recommanded Product: 5-Chlorotryptophol).

Kobayashi, Junichi et al. published their research in International Journal of Peptide & Protein Research in 1981 | CAS: 2382-80-1

Ethyl acetyl-L-tryptophanate (cas: 2382-80-1) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Category: indole-building-block

Nuclear magnetic resonance study on solvent dependence of side chain conformations of tyrosine and tryptophan derivatives was written by Kobayashi, Junichi;Higashijima, Tsutomu;Sekido, Sachiko;Miyazawa, Tatsuo. And the article was included in International Journal of Peptide & Protein Research in 1981.Category: indole-building-block This article mentions the following:

The stereoselectively 尾-deuterated species of Ac-X-NHMe, Ac-X-OH, and Ac-X-OEt (X = Tyr, Trp) and H-Trp-NHMe were synthesized. 270-MHz ¹H NMR spectra of the normal and deuterated species of these aromatic amino acid derivatives were analyzed. For most of the tyrosine and tryptophan derivatives in various polar and nonpolar solvents, the lower-field and higher-field 尾-proton signals were due to the pro-S and pro-R protons, resp. However, the alternative assignments apply for H-Trp-NHMe in aqueous solution and for Ac-Tyr-NHMe and Ac-Trp-NHMe in nonpolar solvents. Such alternative assignments of 尾-proton signals were also found for H-Phe-NHMe, Ac-Phe-NMe₂, and Ac-Phe-OtBu. From the analyses of the ¹H NMR spectra of tyrosine and tryptophan derivatives, the vicinal coupling constants and rotamer populations about the C_伪-C_尾 bond were determined in various solvents. The rotamer populations of H-Trp-NHMe, Ac-X-NHMe, Ac-X-OH and Ac-X-OEt depend significantly on solvent polarity. Each of these four types of derivatives exhibits specific solvent-polarity dependences of rotamer populations which were substantially reduced on replacement of 伪-carbonyl group by a methylene group, suggesting the effect of this carbonyl group in the solvent dependence of rotamer populations. In the experiment, the researchers used many compounds, for example, Ethyl acetyl-L-tryptophanate (cas: 2382-80-1Category: indole-building-block).

Jiang, Guangbin et al. published their research in New Journal of Chemistry in 2021 | CAS: 16096-32-5

4-Methyl-1H-indole (cas: 16096-32-5) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Electric Literature of C9H9N

Palladium-catalyzed sequential acylation/annulation of indoles with acyl chlorides using primary amine as the directing group was written by Jiang, Guangbin;Yang, Guang;Liu, Xinqiang;Wang, Shoucai;Ji, Fanghua. And the article was included in New Journal of Chemistry in 2021.Electric Literature of C9H9N This article mentions the following:

An convenient strategy for the direct acylation/annulation of indoles was developed using Pd(0) as an efficient catalyst. The main feature of this protocol was the use of acyl chlorides as the acylating agents with the primary amine as the directing group. A variety of indolo[1,2-a]quinoxalines were readily obtained in reasonable efficiency and satisfactory yields with good functional group tolerance. Based on control experiments, a tentative catalytic mechanism was proposed. In the experiment, the researchers used many compounds, for example, 4-Methyl-1H-indole (cas: 16096-32-5Electric Literature of C9H9N).

Li, Yuguo et al. published their research in Chemosphere in 2022 | CAS: 16096-32-5

4-Methyl-1H-indole (cas: 16096-32-5) 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. 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.HPLC of Formula: 16096-32-5

Comprehensive chemical characterization of dissolved organic matter in typical point-source refinery wastewaters was written by Li, Yuguo;Wu, Baichun;He, Chen;Nie, Fan;Shi, Quan. And the article was included in Chemosphere in 2022.HPLC of Formula: 16096-32-5 This article mentions the following:

In petroleum refineries, the elec. desalting, distillation, and stripping processes could generate large amounts of wastewaters that contain toxic substances. In this study, eight wastewater samples were collected from the three typical refining processes for comprehensive chem. characterization of the dissolved organic matter (DOM) using excitation emission matrix fluorescence spectroscopy, gas chromatog.-mass spectrometry, and Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR MS). Results showed that protein-like components and benzene were ubiquitous in all these wastewaters. Oxygen-containing volatile organic compounds had higher contents in crude distillation and stripping wastewater than those in elec. desalting wastewater. Among the three refinery processes, mol. composition of DOM in the stripping wastewater had the highest complexity. The Ox and O_xS_y class species assigned from the neg.-ion electrospray ionization FT-ICR MS were dominant in all wastewaters. The O_xS₂ class species which were effectively removed during stripping treatment had highest relative abundance in stripping influent. These results are instructive to guide the development of ”divide and conquer” and would improve the treatment and management of refinery wastewater streams. In the experiment, the researchers used many compounds, for example, 4-Methyl-1H-indole (cas: 16096-32-5HPLC of Formula: 16096-32-5).

Wang, Zhen et al. published their research in Journal of Medicinal Chemistry in 2019 | CAS: 16732-75-5

6-Chloroindole-2-carboxylic acid (cas: 16732-75-5) 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. 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.COA of Formula: C9H6ClNO2

Optimization of Peptidomimetics as Selective Inhibitors for the 尾-Catenin/T-Cell Factor Protein-Protein Interaction was written by Wang, Zhen;Zhang, Min;Wang, Jin;Ji, Haitao. And the article was included in Journal of Medicinal Chemistry in 2019.COA of Formula: C9H6ClNO2 This article mentions the following:

The 尾-catenin/T-cell factor (Tcf) protein-protein interaction (PPI) plays a critical role in the 尾-catenin signaling pathway which is hyperactivated in many cancers and fibroses. Based on compound 1, which was designed to target the Tcf4 G¹³ANDE¹⁷ binding site of 尾-catenin, extensive structure-activity relationship studies have been conducted. As a result, compounds 53 and 57 were found to disrupt the 尾-catenin/Tcf PPI with the K_i values of 0.64 and 0.44 渭M, resp., and exhibit good selectivity for 尾-catenin/Tcf over 尾-catenin/E-cadherin and 尾-catenin/adenomatous polyposis coli (APC) PPIs. The 3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl)-2H-tetrazolium (MTS) cell viability assays revealed that 56, the Et ester of 53, was more potent than 53 in inhibiting viability of most of the Wnt/尾-catenin hyperactive cancer cells. Further cell-based studies indicated that 56 disrupted the 尾-catenin/Tcf PPI without affecting the 尾-catenin/E-cadherin and 尾-catenin/APC PPIs, suppressed transactivation of Wnt/尾-catenin signaling in dose-dependent manners, and inhibited migration and invasiveness of Wnt/尾-catenin-dependent cancer cells. In the experiment, the researchers used many compounds, for example, 6-Chloroindole-2-carboxylic acid (cas: 16732-75-5COA of Formula: C9H6ClNO2).

Zhang, Jiang et al. published their research in Environmental and Experimental Botany in 2022 | CAS: 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

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).

Xiong, Cheng et al. published their research in Journal of Organic Chemistry in 2020 | CAS: 20780-72-7

4-Bromoindoline-2,3-dione (cas: 20780-72-7) 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Application of 20780-72-7

Iodine-Catalyzed Aerobic Oxidation of Spirovinylcyclopropyl Oxindoles to Form Spiro-1,2-dioxolanes Diastereoselectively was written by Xiong, Cheng;Cheng, Kunpeng;Wang, Jiahua;Yang, Fulai;Lu, Jinrong;Zhou, Qingfa. And the article was included in Journal of Organic Chemistry in 2020.Application of 20780-72-7 This article mentions the following:

A novel method of iodine-catalyzed aerobic oxidation with spirovinylcyclopropyl oxindoles under mild conditions has been described. A series of spiro-1,2-dioxolanes were prepared in good to excellent yields and considerable diastereoselectivities. The new approach is operationally simple, scalable, and tolerant of various functional groups. In the experiment, the researchers used many compounds, for example, 4-Bromoindoline-2,3-dione (cas: 20780-72-7Application of 20780-72-7).

Jahn, Linda et al. published their research in International Journal of Molecular Sciences in 2021 | CAS: 879-37-8

Indole-3-acetamide (cas: 879-37-8) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. 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

Indole-3-acetic acid is synthesized by the endophyte Cyanodermella asteris via a tryptophan-dependent and -independent way and mediates the interaction with a non-host plant was written by Jahn, Linda;Hofmann, Uta;Ludwig-mueller, Jutta. And the article was included in International Journal of Molecular Sciences in 2021.Category: indole-building-block This article mentions the following:

The plant hormone indole-3-acetic acid (IAA) is one of the main signals playing a role in the communication between host and endophytes. Endophytes can synthesize IAA de novo to influence the IAA homeostasis in plants. Although much is known about IAA biosynthesis in microorganisms, there is still less known about the pathway by which IAA is synthesized in fungal endophytes. The aim of this study is to examine a possible IAA biosynthesis pathway in Cyanodermella asteris. In vitro cultures of C. asteris were incubated with the IAA precursors tryptophan (Trp) and indole, as well as possible intermediates, and they were addnl. treated with IAA biosynthesis inhibitors (2-mercaptobenzimidazole and yucasin DF) to elucidate possible IAA biosynthesis pathways. It was shown that (a) C. asteris synthesized IAA without adding precursors; (b) indole-3-acetonitrile (IAN), indole-3-acetamide (IAM), and indole-3-acetaldehyde (IAD) increased IAA biosynthesis; and (c) C. asteris synthesized IAA also by a Trp-independent pathway. Together with the genome information of C. asteris, the possible IAA biosynthesis pathways found can improve the understanding of IAA biosynthesis in fungal endophytes. The uptake of fungal IAA into Arabidopsis thaliana is necessary for the induction of lateral roots and other fungus-related growth phenotypes, since the application of the influx inhibitor 2-naphthoxyacetic acid (NOA) but not the efflux inhibitor N-1-naphtylphthalamic acid (NPA) were altering these parameters. In addition, the root phenotype of the mutation in an influx carrier, aux1, was partially rescued by C. asteris. In the experiment, the researchers used many compounds, for example, Indole-3-acetamide (cas: 879-37-8Category: indole-building-block).