Indole Building Blocks

Synthetic Route of C8H7NIn 2020 ,《Low temperature synergistically promotes woundinginduced indole accumulation by INDUCER OF CBF EXPRESSION-mediated alterations of jasmonic acid signaling in Camellia sinensis》 was published in Journal of Experimental Botany. The article was written by Zhou, Ying; Zeng, Lanting; Hou, Xingliang; Liao, Yinyin; Yang, Ziyin. The article contains the following contents:

Plants have to cope with various environmental stress factors which signifiantly impact plant physiol. and secondary metabolism Individual stresses, such as low temperature, are known to activate plant volatile compounds as a defense. However, less is known about the effect of multiple stresses on plant volatile formation. Here, the effect of dual stresses (wounding and low temperature) on volatile compounds in tea (Camellia sinensis) plants and the underlying signalling mechanisms were investigated. Indole, an insect resistance volatile, was maintained at a higher content and for a longer time under dual stresses compared with wounding alone. CsMYC2a, a jasmonate (JA)- responsive transcription factor, was the major regulator of CsTSB2, a gene encoding a tryptophan synthase β-subunit essential for indole synthesis. During the recovery phase after tea wounding, low temperature helped to maintain a higher JA level. Further study showed that CsICE2 interacted directly with CsJAZ2 to relieve inhibition of CsMYC2a, thereby promoting JA biosynthesis and downstream expression of the responsive gene CsTSB2 ultimately enhancing indole biosynthesis. These fidings shed light on the role of low temperature in promoting plant damage responses and advance knowledge of the mol. mechanisms by which multiple stresses coordinately regulate plant responses to the biotic and abiotic environment. The experimental part of the paper was very detailed, including the reaction process of 1H-Indole(cas: 120-72-9Synthetic Route of C8H7N)

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.Synthetic Route of C8H7N

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

《Asymmetric Synthesis of 1,1,1-Triarylethanes by Chiral Imidodiphosphoric Acid Catalyzed Nucleophilic Addition of Pyrrole and Indoles to 3-Vinylindoles》 was written by Guan, Xu-Kai; Zhang, Heng; Gao, Ji-Gang; Sun, Dong-Yang; Qin, Xiang-Shuo; Jiang, Guo-Feng; Zhang, Guang-Liang; Zhang, Suoqin. Related Products of 399-52-0This research focused ontriarylethane asym preparation imidodiphosphorate catalyst nucleophilic pyrrole indole vinylindole. The article conveys some information:

Chiral imidodiphosphoric acids were employed as efficient catalysts in the enantioselective addition reaction of pyrrole and indoles to 3-vinylindoles. A series of optically active 1,1,1-triarylethanes bearing quaternary stereocenters were synthesized in excellent yields (up to 99% yield) and enantioselectivities (up to 98% ee). Gram-scale reactions demonstrated the synthetic utility of this methodol. Control experiments showed that the formation of a double H-bond between the catalyst and substrates is necessary for an excellent outcome. In the experimental materials used by the author, we found 5-Fluoro-1H-indole(cas: 399-52-0Related Products of 399-52-0)

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).Related Products of 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

《Determination of 4-chloroindole-3-acetic acid methyl ester in Lathyrus, Vicia and Pisum by gas chromatography-mass spectrometry》 was written by Engvild, Kjeld C.; Egsgaard, Helge; Larsen, Elfinn. Name: Methyl 2-(5-chloro-1H-indol-3-yl)acetate And the article was included in Physiologia Plantarum on April 15 ,1980. The article conveys some information:

4-Chloroindole-3-acetic acid Me ester was identified unequivocally in L. latifolius, V. fava, and P. sativum by thin-layer chromatog., gas chromatog., and mass spectrometry. The gas chromatog. system was able to sep. underivatized chloroindole-3-acetic acid Me ester isomers. The quant. determination of 4-chloroindole-3-acetic acid Me ester in immature seeds of these 3 species was performed by gas chromatog.-mass spectrometry using deuterated 4-chloro-indole-3-acetic acid Me ester as an internal standard P. sativum Contained ∼25, V. fava 1-2, and L. latifolius 2 mg/kg dry weight In addition to this study using Methyl 2-(5-chloro-1H-indol-3-yl)acetate, there are many other studies that have used Methyl 2-(5-chloro-1H-indol-3-yl)acetate(cas: 74339-45-0Name: Methyl 2-(5-chloro-1H-indol-3-yl)acetate) was used in this study.

Methyl 2-(5-chloro-1H-indol-3-yl)acetate(cas: 74339-45-0) 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.Name: Methyl 2-(5-chloro-1H-indol-3-yl)acetate

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

Name: Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranosideOn March 15, 2004, Misra, Anup Kumar; Agnihotri, Geetanjali published an article in Carbohydrate Research. The article was 《Chloramine-T-mediated chemoselective hydrolysis of thioglycosides into glycosyl hemiacetals under neutral conditions》. The article mentions the following:

A metal-free, mild, efficient and chemoselective hydrolysis of several thioalkylglycosides into their corresponding 1-hydroxy sugars using sodium N-chloro-p-toluenesulfonamide trihydrate (chloramine-T) without affecting other functional groups is reported. The results came from multiple reactions, including the reaction of Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2Name: 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.Name: 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.

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

Quality Control of Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranosideOn October 10, 2003 ,《A mild and convenient indium(III) chloride-catalyzed synthesis of thioglycosides》 was published in Carbohydrate Research. The article was written by Das, Saibal Kumar; Roy, Joyita; Reddy, Kalusani Anantha; Abbineni, Chandrasekhar. The article contains the following contents:

The efficiency of glycosidation reactions generally involves a high chem. yield, as well as high/complete stereo- and regioselectivity. All these depend on the compatibility of the reactivity of glycosyl donors and acceptors. Among glycosyl donors, thioglycosides are widely used because of their high degree of stability in many organic reactions. Although there are number of methods available for the preparation of thioglycosides, all of them have one or more disadvantages, especially concerning the time factor and cumbersome workup procedures. Here we report a convenient and high-yielding method for the preparation of thioglycosides. In addition to this study using Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside, there are many other studies that have used Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2Quality Control of Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside) was used in this study.

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.Quality Control 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

Das, Saibal Kumar; Roy, Nirmolendu published their research in Carbohydrate Research on December 24 ,1996. The article was titled 《An improved method for the preparation of some ethyl 1-thioglycosides》.Electric Literature of C22H25NO9S The article contains the following contents:

Et 1-thioglycosides were prepared in almost quant. yield from sugar peracetates in 3:2 chloroform-ether, with boron trifluoride di-Et etherate as catalyst. D-Galactose, D-glucose, and 2-deoxy-2-phthalimido-D-glucose yielded almost exclusively β anomers, whereas L-rhamnose and D-mannose resulted predominantly in the α anomers. The experimental part of the paper was very detailed, including the reaction process of Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2Electric Literature of C22H25NO9S)

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.Electric Literature of C22H25NO9SThey are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.

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 《Plant Growth Regulators Enhance Saline-Alkali Tolerance by Upregulating the Levels of Antioxidants and Osmolytes in Soybean Seedlings》 were Yu, Minglong; Wu, Qiong; Zheng, Dianfeng; Feng, Naijie; Liang, Xilong; Liu, Meiling; Li, Yao; Mou, Baomin. And the article was published in Journal of Plant Growth Regulation in . Synthetic Route of C12H12KNO2 The author mentioned the following in the article:

Soil salinization has become a global problem and seriously endangers crop growth and yield improvement. In the present study, soybean (Hefeng 50) seedlings were used as test materials to study the mitigation effect of foliar spraying of different plant growth regulators (PGRs) [50 mg L-1 indole-3-butyric acid potassium salt (IBAK), 50 mg L-1 chitosan oligosaccharide (COS), 2 mg L-1 abscisic acid (ABA), 30 mg L-1 5-aminolevulinic acid (ALA), and 1.2 mg L-1 brassinolide (BR)] on oxidative stress caused by the mixed Saline-Alkali concentration of 110 mmol L-1. The results showed that the application of PGRs promoted the growth of Saline-Alkali stressed plants, where the maximum increase in shoot FW was treated with COS, and in root FW, root length, root surface area, and root volume were obtained with the IBAK treatment. Treatments ABA, ALA, and BR had higher net photosynthetic rates, and the chlorophyll content was considerably increased under COS and BR treatments compared with Saline-Alkali treatment. Moreover, PGRs markedly enhanced the activities of antioxidant enzymes, the concentration of ascorbate (AsA), glutathione (GSH), proline, soluble protein, soluble sugar, sucrose, and starch, and the ratios of AsA/DHA and GSH/GSSG, but reduced the concentration of malondialdehyde (MDA), electrolyte leakage (EL), hydrogen peroxide (H2O2), and superoxide radical (O2·-) in soybean seedlings compared with Saline-Alkali treatment. The principal component anal. revealed that the ranking of PGRs enhancing Saline-Alkali tolerance of soybean seedlings was BR > IBAK > ABA > COS > ALA, and the most effective treatment was BR, which may be assigned to more vigorous antioxidant defense and osmotic adjustment. The experimental part of the paper was very detailed, including the reaction process of Potassium 4-(1H-indol-3-yl)butanoate(cas: 60096-23-3Synthetic Route of C12H12KNO2)

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.Synthetic Route of C12H12KNO2

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 2019,Infection and Immunity included an article by Howard, Mondraya F.; Bina, X. Renee; Bina, James E.. COA of Formula: C8H7N. The article was titled 《Indole inhibits ToxR regulon expression in Vibrio cholerae》. The information in the text is summarized as follows:

Indole is a degradation product of tryptophan that functions as a signaling mol. in many bacteria. This includes Vibrio cholerae, where indole was shown to regulate biofilm and type VI secretion in nontoxigenic environmental isolates. Indole is also produced by toxigenic V. cholerae strains in the human intestine, but its significance in the host is unknown. We investigated the effects of indole on toxigenic V. cholerae O1 El Tor during growth under virulence inducing conditions. The indole transcriptome was defined by RNA sequencing and showed widespread changes in the expression of genes involved in metabolism, biofilm production, and virulence factor production In contrast, genes involved in type VI secretion were not affected by indole. We subsequently found that indole repressed genes involved in V. cholerae pathogenesis, including the ToxR virulence regulon. Consistent with this, indole inhibited cholera toxin and toxin-coregulated pilus production in a dosedependent manner. The effects of indole on virulence factor production and biofilm were linked to ToxR and the ToxR-dependent regulator LeuO. The expression of Y was increased by exogenous indole and linked to repression of the ToxR virulence regulon. This process was dependent on the ToxR periplasmic domain, suggesting that indole was a ToxR agonist. This conclusion was further supported by results showing that the ToxR periplasmic domain contributed to indole-mediated increased biofilm production Collectively, our results suggest that indole may be a niche-specific cue that can function as a ToxR agonist to modulate virulence gene expression and biofilm production in V. cholerae. In the experimental materials used by the author, we found 1H-Indole(cas: 120-72-9COA of Formula: C8H7N)

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.COA of Formula: C8H7N

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

Sun, Minghe; Liu, Min; Li, Changkun published an article in 2021. The article was titled 《Rhodium-Catalyzed Chemodivergent Regio- and Enantioselective Allylic Alkylation of Indoles》, and you may find the article in Chemistry – A European Journal.Computed Properties of C8H6FN The information in the text is summarized as follows:

The control of C3/N1 chemoselectivity in indole alkylation with the same electrophiles is still challenging. An Rh/bisoxazolinephosphane-catalyzed chemodivergent regio- and enantioselective allylic alkylation of indoles was developed. Chiral C3- and N1-allylindoles was selectively obtained with high branched/linear ratio and up to 99% ee by changing the counteranion of Rh, the allylic carbonate, the reaction temperature, and the ligand. In addition to this study using 5-Fluoro-1H-indole, there are many other studies that have used 5-Fluoro-1H-indole(cas: 399-52-0Computed Properties of C8H6FN) was used in this study.

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.Computed Properties of 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

Computed Properties of C8H6FNIn 2019 ,《Redox-Neutral Cascade Dearomatization of Indoles via Hydride Transfer: Divergent Synthesis of Tetrahydroquinoline-Fused Spiroindolenines》 was published in Journal of Organic Chemistry. The article was written by Shen, Yao-Bin; Li, Long-Fei; Xiao, Ming-Yan; Yang, Jian-Ming; Liu, Qing; Xiao, Jian. The article contains the following contents:

The redox-neutral cascade dearomatization of indoles with o-aminobenzaldehydes was realized via the hydride transfer strategy, achieving the condition- and substrate-controlled divergent synthesis of tetrahydroquinoline-fused spiroindolenines. The integration of hydride transfer-involved C(sp3)-H functionalization with dearomatization provides a promising platform for the construction of structurally diverse mols.5-Fluoro-1H-indole(cas: 399-52-0Computed Properties of C8H6FN) was used in this study.

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).Computed Properties of 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