Indole Building Blocks

In 2022,Zhang, Shang-Shi; Liu, Yan-Zhi; Zheng, Yi-Chuan; Xie, Hui; Chen, Shao-Yong; Song, Jia-Lin; Shu, Bing published an article in Advanced Synthesis & Catalysis. The title of the article was 《Rhodium(III)-Catalyzed Regioselective C-H Allylation and Prenylation of Indoles at C4-Position》.SDS of cas: 399-52-0 The author mentioned the following in the article:

Herein, Rh(III)-catalyzed C4-selective C-H allylation and prenylation of indoles, e.g., I (R = H), by using a weak carbonyl coordination directing group have been reported. By employing 5-methylene-1,3-dioxan-2-ones, 4-vinyl-1,3-dioxolan-2-ones and 2-methyl-2,3-butadiene as scalable cross-coupling partners, these divergent synthesis protocols proceed smoothly under redox-neutral reaction conditions, delivering various allylated and prenylated indoles, e.g., I [R = CH2C(=CH2)CH2OH, CH2CH=CHCH2OH], in moderate to satisfactory yields. This transformation exhibits high functional-groups compatibility and broad substrate scope. A scale-up experiment and mechanistic studies were also accomplished. In the experimental materials used by the author, we found 5-Fluoro-1H-indole(cas: 399-52-0SDS of cas: 399-52-0)

5-Fluoro-1H-indole(cas: 399-52-0) is a member of aromaticfluorinated building blocks. Fluorine-containing aromatics have been incorporated into crop-protection chemicals (herbicides, insecticides, fungicides). Liquid crystals, positron emission tomography, and imaging systems represent new areas where fluoroaromatics and fluoroheterocyclics have gained attention.SDS of cas: 399-52-0

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

Application In Synthesis of 1H-IndoleIn 2020 ,《The importance of indole and azaindole scaffold in the development of antitumor agents》 appeared in European Journal of Medicinal Chemistry. The author of the article were Han, Yu; Dong, Wei; Guo, Qunqun; Li, Xiufen; Huang, Longjiang. The article conveys some information:

A review. With some indoles and azaindoles being successfully developed as anticancer drugs, the design and synthesis of indole and azaindole derivatives with remarkable antitumor activity has received increasing attention and significant progress has been made. This paper reviews the recent progress in the study of tumorigenesis, mechanism of actions and structure activity relationships about anticancer indole and azindole derivatives Combining structure activity relationships and mol. targets-related knowledge, this review will help researchers design more effective, safe and cost-effective anticancer indoles and azindoles agents. In the experimental materials used by the author, we found 1H-Indole(cas: 120-72-9Application In Synthesis of 1H-Indole)

1H-Indole(cas: 120-72-9) belongs to indole. 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.Application In Synthesis of 1H-Indole

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

《Identification of β carbolines isolated from fluorescent human lens proteins》 was published in Nature (London, United Kingdom) in 1976. These research results belong to Dillon, James; Spector, Abraham; Nakanishi, Koji. Application of 59132-30-8 The article mentions the following:

The fluorescent 43,000 mol. weight protein (C1) obtained on alk. degradation of the insoluble or high mol. weight protein fraction of human lens gave 2 fully aromatic β-carbolines (I and II) on decomposition or oxidation These β-carbolines were also obtained on decomposition or oxidation of 3,4-dihydro-β-carboline 3-carboxylic acids (III and IV) showing that C1 is a mit. of III and IV. Protein hydrolysates from 45- and 77-year-old but not young human lens contained I and II, suggesting that there is an age-dependent formation of the β-carboline skeleton in human lens. Preliminary experiments suggested 1,2,3,4-tetrahydro-β-carboline 1,3-dicarboxylic acid (V) and its 1-Me derivative (VI) are the in vivo precursors of IV and III, resp. The experimental part of the paper was very detailed, including the reaction process of 2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole-1,3-dicarboxylic acid(cas: 59132-30-8Application of 59132-30-8)

2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole-1,3-dicarboxylic acid(cas: 59132-30-8) belongs to indole.The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades.Application of 59132-30-8They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.

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

《Oxidative trimerization of indoles via water-assisted visible-light photoredox catalysis and the study of their anti-cancer activities》 was written by Cheng, Li-Ting; Luo, Sheng-Qi; Hong, Bor-Cherng; Chen, Chia-Ling; Li, Wen-Shan; Lee, Gene-Hsiang. Formula: C8H6FNThis research focused ontrisindolone preparation antitumor crystal structure mol; indole oxidative trimerization photocatalyst water assisted. The article conveys some information:

A series of trisindolones I [R = H, 5-Me, 6-Br, etc.] was synthesized via water assisted visible-light photocatalyzed oxidative trimerization of indoles under mild and scalable reaction conditions. Compounds I were evaluated against three human cancer cell lines (MDA-MB-231, A549 and HeLa). Compound I [R = 5-I] represented a potent, micromolar to submicromolar range anticancer agent against MDA-MB-231, A549 and HeLa cells. The successful example of the catalyst-free CFL irradiation of 5-iodo-1H-indole provided a green, natural, and convenient synthetic process of compound I [R = 5-I]. The experimental process involved the reaction of 5-Fluoro-1H-indole(cas: 399-52-0Formula: C8H6FN)

5-Fluoro-1H-indole(cas: 399-52-0) is a member of aromaticfluorinated building blocks. Depending on which substituents are present, fluoroaromatic intermediates can be converted into fluorinated or fluorine-free commercial end products.Fluorine-containing aromatics have been incorporated into drugs (hypnotics, tranquilizers, antiinflammatory agents, analgesics, antibacterials).Formula: C8H6FN

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

Electric Literature of C10H8FNO2On May 31, 1988, Fagan, Gay P.; Chapleo, Christopher B.; Lane, Anthony C.; Myers, Malcolm; Roach, Alan G.; Smith, Colin F. C.; Stillings, Michael R.; Welbourn, Anthony P. published an article in Journal of Medicinal Chemistry. The article was 《Indoline analogs of idazoxan: potent α2-antagonists and α1-agonists》. The article mentions the following:

The synthesis and α-adrenergic activity of a series of substituted 2-imidazolinylindolines are described. Substitution in the indoline ring generated compounds with a spectrum of adrenoreceptor antagonist/agonist profiles that proved sensitive to both the nature and position of the substituent. Many of the derivatives possess greater presynaptic antagonist potency than the corresponding benzodioxan, dihydrobenzofuran, and indan analogs; however, this α2-antagonism is often accompanied by α1-agonist activity. It was not possible to sep. α2-antagonist from α1-agonist properties in this series. Compounds of most interest proved to be the N-Et, 5-chloro-N-Me, and 5-chloro-N-Et derivatives, all being potent α2-antagonists and α1-agonists. Substitution at the 4- and 7-position of the indoline ring generally gave compounds with nonselective agonist properties. In the part of experimental materials, we found many familiar compounds, such as Methyl 4-fluoro-1H-indole-2-carboxylate(cas: 113162-36-0Electric Literature of C10H8FNO2)

Methyl 4-fluoro-1H-indole-2-carboxylate(cas: 113162-36-0) is a member of aromaticfluorinated building blocks. Depending on which substituents are present, fluoroaromatic intermediates can be converted into fluorinated or fluorine-free commercial end products.Fluorine-containing aromatics have been incorporated into drugs (hypnotics, tranquilizers, antiinflammatory agents, analgesics, antibacterials).Electric Literature of C10H8FNO2

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

Application In Synthesis of Potassium 4-(1H-indol-3-yl)butanoateOn November 30, 2004 ,《Peroxidases during adventitious rooting in cuttings of Arbutus unedo and Taxus baccata as affected by plant genotype and growth regulator treatment》 appeared in Plant Growth Regulation. The author of the article were Metaxas, Demetrios J.; Syros, Thomas D.; Yupsanis, Traianos; Economou, Athanasios S.. The article conveys some information:

Cuttings of Arbutus unedo (strawberry tree) and Taxus baccata (yew) were treated with 8.0 and 10.0 g l-1, resp., of KIBA, IBA, IAA, NAA and Paclobutrazol. No rooting occurred without growth regulator treatment. The effect of growth regulators on percentage of rooting followed the order KIBA > IBA > IAA = NAA = Paclobutrazol = 0% (for A. unedo) and KIBA > IBA > IAA > NAA > Paclobutrazol = 0% (for T. baccata). Genotypes of the above plant species had significant effects on the number and length of roots, percentage of rooting and peroxidase specific activity (PA) on KIBA-treated cuttings. High PA seems to be related with low percentage of rooting in the case of A. unedo cuttings while no similar results were noticed in the case of T. baccata. Electrophoretic anal. revealed the appearance of two to three anionic and one cationic peroxidase isoforms in A. unedo cuttings, while six to nine anionic and no cationic peroxidases isoforms appeared in the case of T. baccata genotypes. During adventitious rooting, the PA showed the three interdependent phases (induction, initiation, expression) in both K-IBA treated cuttings of A. unedo and T. baccata, but in a different time course. In addition to this study using Potassium 4-(1H-indol-3-yl)butanoate, there are many other studies that have used Potassium 4-(1H-indol-3-yl)butanoate(cas: 60096-23-3Application In Synthesis of Potassium 4-(1H-indol-3-yl)butanoate) was used in this study.

Potassium 4-(1H-indol-3-yl)butanoate(cas: 60096-23-3) is auxin-family plant hormone, and is thought to be a precursor of indole-3-acetic acid (IAA) the most abundant and the basic auxin natively occurring and functioning in plants. IAA generates the majority of auxin effects in intact plants, and is the most potent native auxin.Application In Synthesis of Potassium 4-(1H-indol-3-yl)butanoate

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

In 2011,Trends in Carbohydrate Research included an article by Shukla, Nalin; Srivastava, Sanjay; Khare, Naveen K.; Mukhopadhay, Balaram; Khare, Anakshi. Safety of Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside. The article was titled 《Concise synthesis of a di- and a trisaccharide related to the pentasaccharide repeating unit of the O-antigen from E. coli O141》. The information in the text is summarized as follows:

Synthesis of a di- and a trisaccharide related to the pentasaccharide repeating unit of the O-antigen from E. coli O141 have been accomplished using com. available D-mannose, L-rhamnose and D-glucose. These di and trisaccharides have been synthesized as their p-methoxyphenyl and allyl glycosides, resp., which can be cleaved selectively for further conjugation with suitable aglycon. In the part of experimental materials, we found many familiar compounds, such as Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2Safety of Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside)

Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2) belongs to indole.The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades.Safety of Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranosideThey are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.

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

Tois, Jan; Franzen, Robert; Aitio, Olli; Laakso, Into; Kylaenlahti, Irene published their research in Journal of Combinatorial Chemistry on December 31 ,2001. The article was titled 《Vilsmeier formylation of 2-carboxyindoles and preparation of O-benzylhydroxyureas on solid phase》.Application In Synthesis of 5-Chloro-3-formyl-1H-indole-2-carboxylic acid The article contains the following contents:

The Vilsmeier formylation has been introduced for the solid-phase functionalization of five different 2-carboxyindoles, e.g. 2-carboxyindole. The aldehyde functionality has been utilized in the preparation of O-benzylhydroxyureas, e.g. I. In the experimental materials used by the author, we found 5-Chloro-3-formyl-1H-indole-2-carboxylic acid(cas: 380448-07-7Application In Synthesis of 5-Chloro-3-formyl-1H-indole-2-carboxylic acid)

5-Chloro-3-formyl-1H-indole-2-carboxylic acid(cas: 380448-07-7) is a member of organic chlorides. Organic chlorides are compounds containing a carbon-chlorine bond, which are widely used in the oil field as a wax dissolver. They are generally not present in crude oils and are typically the result of additives, cleaning solutions or chemicals used for oil recovery.Application In Synthesis of 5-Chloro-3-formyl-1H-indole-2-carboxylic 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

The author of 《Interspecies and intraspecies signals synergistically regulate Lysobacter enzymogenes twitching motility》 were Feng, Tao; Han, Yong; Li, Bingqing; Li, Zhiqiang; Yu, Yameng; Sun, Qingyang; Li, Xiaoyu; Du, Liangcheng; Zhang, Xiao-Hua; Wang, Yan. And the article was published in Applied and Environmental Microbiology in 2019. Reference of 1H-Indole The author mentioned the following in the article:

The twitching motility of bacteria is closely related to environmental adaptability and pathogenic behaviors. Lysobacter is a good genus in which to study twitching motility because of the complex social activities and distinct movement patterns of its members. Regardless, the mechanism that induces twitching motility is largely unknown. In this study, we found that the interspecies signal indole caused Lysobacter to have irregular, random twitching motility with significantly enhanced speed. Deletion of qseC or qseB from the two-component system for indole signaling perception resulted in the disappearance of rapid, random movements and significantly decreased twitching activity. Indole-induced, rapid, random twitching was achieved through upregulation of expression of gene cluster pilE1-pilY11-pilX1-pilW1-pilV1-fimT1. In addition, under conditions of extremely low bacterial d., individual Lysobacter cells grew and divided in a stable manner in situ without any movement. The intraspecies quorum-sensing signaling factor 13-methyltetradecanoic acid, designated L. enzymogenes diffusible signaling factor (LeDSF), was essential for Lysobacter to produce twitching motility through indirect regulation of gene clusters pilM-pilN-pilO-pilP-pilQ and pilS1-pilR-pilA-pilB-pilC. These results demonstrate that the motility of Lysobacter is induced and regulated by indole and LeDSF, which reveals a novel theory for future studies of the mechanisms of bacterial twitching activities. The results came from multiple reactions, including the reaction of 1H-Indole(cas: 120-72-9Reference of 1H-Indole)

1H-Indole(cas: 120-72-9) belongs to indole. 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.Reference of 1H-Indole

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

《Trisulfonamide calix[6]arene-catalysed Michael addition to nitroalkenes》 was written by Cera, Gianpiero; Balestri, Davide; Bazzoni, Margherita; Marchio, Luciano; Secchi, Andrea; Arduini, Arturo. Quality Control of 5-Fluoro-1H-indole And the article was included in Organic & Biomolecular Chemistry in 2020. The article conveys some information:

The application of a novel family of trisulfonamide (TSA) calix[6]arenes I in general acid catalysis was described. Hydrogen-bonding interactions between acidic TSA and methanol boosted the reactivity of the Michael addition of indoles II (R = H, Me; R1 = H, F, Br, OH, OMe) to nitroalkene derivatives 3-R2-4-R3-C6H3CH=CHNO2 (R2 = H, OMe; R3 = H, Me, Br, Cl, OMe). The transformation occurs at a low catalyst loading of 5 mol%, allowing for the synthesis of nitroalkanes III with good yields and functional group tolerance. The experimental process involved the reaction of 5-Fluoro-1H-indole(cas: 399-52-0Quality Control of 5-Fluoro-1H-indole)

5-Fluoro-1H-indole(cas: 399-52-0) is a member of aromaticfluorinated building blocks. Depending on which substituents are present, fluoroaromatic intermediates can be converted into fluorinated or fluorine-free commercial end products.Fluorine-containing aromatics have been incorporated into drugs (hypnotics, tranquilizers, antiinflammatory agents, analgesics, antibacterials).Quality Control of 5-Fluoro-1H-indole

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