13/10/2022 - Page 5 of 6 - Indole Building Blocks

Ledvina, Miroslav’s team published research in Collection of Czechoslovak Chemical Communications in 1998 | CAS: 99409-32-2

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.Reference 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.

《New effective synthesis of (N-acetyl- and N-stearoyl-2-amino-2-deoxy-β-D-glucopyranosyl)-(1→4)-N-acetylnormuramoyl-L-2-aminobutanoyl-D-isoglutamine, analogs of GMDP with immunopotentiating activity》 was written by Ledvina, Miroslav; Zyka, Daniel; Jezek, Jan; Trnka, Tomas; Saman, David. Reference of Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside And the article was included in Collection of Czechoslovak Chemical Communications on April 30 ,1998. The article conveys some information:

Et 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (5), prepared by benzylation of Et 2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside, was transformed by reaction with bromine into 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide (6). Thioglycoside 5 in the presence of Me triflate and glycosyl bromide 6 in the presence of silver triflate were used as glycosyl donors for condensation with benzyl 2-acetamido-3-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside, to give benzyl 2-acetamido-3-O-allyl-6-O-benzyl-4-O-(3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-2-deoxy-α-D-glucopyranoside (8). Its reductive dephthaloylation with NaBH4/AcOH afforded benzyl 2-acetamido-3-O-allyl-4-O-(2-amino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-6-O-benzyl-2-deoxy-α-D-glucopyranoside (11). Compound 11 was N-acylated to give benzyl 2-acetamido-4-O-(2-acylamino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranosides. These compounds were converted into corresponding benzyl 2-acetamido-4-O-(2-acylamino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-6-O-benzyl-3-O-carboxymethyl-2-deoxy-α-D-glucopyranosides which, by condensation with H-L-Abu-D-isoGln(OBzl) followed by hydrogenolysis of protective benzyl groups, furnished the title glycopeptides. Intramol. O→N migration of the allyl protecting group followed by its reduction to the Pr residue by reaction of compound 8 with hydrazine or hydrazinium acetate, to give benzyl 2-acetamido-4-O-(3,4,6-tri-O-benzyl-2-deoxy-2-propylamino-β-D-glucopyranosyl)-6-O-benzyl-2-deoxy-α-D-glucopyranoside, is also described. 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: 99409-32-2Reference of Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside)

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

Lee, C. I.’s team published research in Journal of the American Society for Horticultural Science in 1976 | CAS: 60096-23-3

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.Category: indole-building-block

In 1976,Journal of the American Society for Horticultural Science included an article by Lee, C. I.; Hackett, W. P.. Category: indole-building-block. The article was titled 《Root regeneration of transplanted Pistacia chinensis Bunge seedlings at different growth stages》. The information in the text is summarized as follows:

The root-regenerating potential (RRP) of 1-year-old P. chinensis seedlings at different growth states, was determined by recording the number of newly initiated roots during 4 weeks after bareroot transplanting into a bottom misting chamber. RRP of intact pistacias was greatest when leaves were fully expanded and the terminal bud was forming (stage III), and lowest when seedlings were dormant (stages V and VI). However, seedlings disbudded before transplanting and root cuttings showed 2 peaks in RRP; 1 at spring bud break (stage I) and the other at stage III. Removal of buds resulted in decreased RRP at stage I, but had little effect when plants were dormant. Thiourea [62-56-6] sprays of growing seedlings and chilling of dormant seedlings enhanced bud break and RRP. K indolebutyrate [60096-23-3] applied to the root system promoted RRP but did not eliminate the seasonal variation of RRP. K indolebutyrate could replace the influence of buds only when seedlings were not dormant. Sucrose [57-50-1] feeding via the stem increased RRP at spring bud break. Dormant condition of buds and the availability of carbohydrates are the factors controlling the RRP of bareroot transplanted pistacias. In the experiment, the researchers used many compounds, for example, Potassium 4-(1H-indol-3-yl)butanoate(cas: 60096-23-3Category: indole-building-block)

Cobo, Maria Mercedes’s team published research in In Vitro Cellular & Developmental Biology: Plant in 2018 | CAS: 60096-23-3

Cobo, Maria Mercedes; Gutierrez, Bernardo; Torres, Maria de Lourdes published an article on February 28 ,2018. The article was titled 《Regeneration of mortinõ (Vaccinium floribundum Kunth) plants through axillary bud culture》, and you may find the article in In Vitro Cellular & Developmental Biology: Plant.Recommanded Product: 60096-23-3 The information in the text is summarized as follows:

The use of conventional propagation strategies for Vaccinium floribundum Kunth has proven difficult, which has resulted in this species’ escape from formal cultivation, despite its importance as a gastronomic and nutraceutical fruit. The current report presents an efficient propagation methodol. for V. floribundum using axillary bud growth. Axillary buds were cultured on modified Woody Plant medium (mWPM) supplemented with 3.0 mg L-1 N6-isopentenyladenine (2iP) or with 5.0 mg L-1 2iP plus 0.1 mg L-1 1-naphthaleneacetic acid (NAA). The best results for plant propagation were obtained on mWPM with 2iP and NAA, where significantly higher numbers of shoots per bud were observed In vitro-rooted plants were successfully acclimatized to a peat and vermiculite substrate, while unrooted plants could be efficiently grown after an ex vitro rooting treatment by submersion in an 0.5 g L-1 indole-3-butyric acid (IBA) or potassium IBA (KIBA) solution This is the first report of an efficient propagation methodol. for V. floribundum using plant tissue culture protocols, and provides a tool for the implementation of conservation strategies for this species. In the experiment, the researchers used Potassium 4-(1H-indol-3-yl)butanoate(cas: 60096-23-3Recommanded Product: 60096-23-3)

Krezdorn, A. H.’s team published research in Proceedings of the Florida State Horticultural Society in 1977 | CAS: 60096-23-3

Category: indole-building-blockOn May 1, 1977 ,《Advances in rooting avocados》 appeared in Proceedings of the Florida State Horticultural Society. The author of the article were Krezdorn, A. H.; Marte, D.; Marte, R. J.. The article conveys some information:

Avocado (Persea americana) cuttings were rooted by applying bottom heat, combined with K indolebutyrate [60096-23-3] treatment. Other treatments were ineffective. Cuttings placed under intermittnet mist showed foliar Na, K, and K leaching. In the experiment, the researchers used Potassium 4-(1H-indol-3-yl)butanoate(cas: 60096-23-3Category: indole-building-block)

Khan, Nazmul Abedin’s team published research in Chemical Engineering Journal (Amsterdam, Netherlands) in 2020 | CAS: 120-72-9

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.Formula: C8H7N

《Cu2O-incorporated MAF-6-derived highly porous carbons for the adsorptive denitrogenation of liquid fuel》 was published in Chemical Engineering Journal (Amsterdam, Netherlands) in 2020. These research results belong to Khan, Nazmul Abedin; Shin, Subin; Hwa Jhung, Sung. Formula: C8H7N The article mentions the following:

Metal-organic framework (MOF)-derived carbons (MDCs) with remarkable porosity were synthesized through pyrolysis of a MOF (metal-azolate framework-6 or MAF-6) in the presence of KOH activating agent. Further, Cu2O particles were synthesized under a mild condition within the MDCs. The Cu2O/MDCs showed very efficient adsorptions of both quinoline (454 mg/g) and indole (435 mg/g) from liquid fuel. Or, the Cu2O/MDC resulted in increase of quinoline and indole adsorption, by around 213% and 243%, resp., compared with simple MDC, prepared without KOH. Addnl., the new adsorbent showed around 5-6 times efficiency in removal of such adsorbates to that of conventional activated carbon. The maximum adsorption capacities (Qm) of the studied adsorbent for quinoline and indole also stand at the first and second positions, resp., among the carbon-based adsorbents reported so far. Moreover, compared with other studied adsorbents, the Cu2O-incorporated MDCs had a good selectivity towards both adsorbates, especially during the adsorptions in the presence of toluene as a co-solvent. The remarkable adsorptions with Cu2O/MDC were explained by the π-complexation and huge porosity. In addition, the adsorbents could be regenerated for several cycles via a simple solvent wash. In the experiment, the researchers used 1H-Indole(cas: 120-72-9Formula: C8H7N)

Thanikachalam, Punniyakoti Veeraveedu’s team published research in European Journal of Medicinal Chemistry in 2019 | CAS: 120-72-9

Quality Control of 1H-IndoleIn 2019 ,《An insight into the medicinal perspective of synthetic analogs of indole: A review》 appeared in European Journal of Medicinal Chemistry. The author of the article were Thanikachalam, Punniyakoti Veeraveedu; Maurya, Rahul Kumar; Garg, Vishali; Monga, Vikramdeep. The article conveys some information:

A review. Heterocycles occupy a salient place in chem. due to their wide range of activity in the fields of drug design, photochem., agrochems., dyes, and so on. Amongst all, indole scaffold is considered as one of the most promising heterocycles found in natural and synthetic sources and has been shown to possess various biol. activity, including anti-inflammatory, anti-HIV, antitubercular, antimalarial, anticonvulsant, antidiabetic, antihypertensive, analgesics, antidepressant, anticancer, antioxidant, antifungal, and antimicrobial, etc. All the reported indole mols. bind to multiple receptors with high affinity, thus expedite the research on the development of novel biol. active compounds through the various approach. In this review, we aimed to highlight synthetic and medicinal perspective on the development of indole-based analogs. In addition, structural activity relationship (SAR) study to correlate for their biol. activity also discussed. In the experiment, the researchers used many compounds, for example, 1H-Indole(cas: 120-72-9Quality Control of 1H-Indole)

Struve, Daniel K.’s team published research in Journal of the American Society for Horticultural Science in 1984 | CAS: 60096-23-3

Struve, Daniel K.; Moser, Bruno C. published an article on January 31 ,1984. The article was titled 《Auxin effects on root regeneration of scarlet oak seedlings》, and you may find the article in Journal of the American Society for Horticultural Science.Quality Control of Potassium 4-(1H-indol-3-yl)butanoate The information in the text is summarized as follows:

Dipping root systems of scarlet oak seedlings (Quercus coccinea) in indol-3-butyric acid K salt (K-IBA) [60096-23-3], 2,4-D [94-75-7], 2,4,5-T [93-76-5], 2,4,5-trichloropropanoic acid [93-72-1], β-naphthoxyacetic acid [120-23-0], and NAA [86-87-3], induced a 6-fold increase in adventitious root regeneration, as compared to control seedlings. Time to first root initiation was increased and root elongation rate was decreased for auxin-treated seedlings relative to untreated controls. Under field conditions, 1-yr-old seedlings treated with NAA, at 3000 mg/L, or K-IBA, at 1000 or 3000 mg/L, regenerated more roots and developed greater root length than did control plants. Toothpicks impregnated with a 1000 mg/L K-IBA solution and inserted into tap roots stimulated an 18-fold increase in root length, as compared to control seedlings. In the part of experimental materials, we found many familiar compounds, such as Potassium 4-(1H-indol-3-yl)butanoate(cas: 60096-23-3Quality Control of Potassium 4-(1H-indol-3-yl)butanoate)

Yildiz, Halit’s team published research in Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy in 2021 | CAS: 120-72-9

Yildiz, Halit; Tokalioglu, Serife; Soykan, Cengiz published an article in 2021. The article was titled 《Preparation of polyacrylonitrile/polyindole conducting polymer composite and its use for solid phase extraction of copper in a certified reference material》, and you may find the article in Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy.Application In Synthesis of 1H-Indole The information in the text is summarized as follows:

A polyacrylonitrile/polyindole (PAN/PIN) [50, 50] conducting polymer composite was chem. synthesized using FeCl3 as an oxidizing agent in chloroform solution and nitrogen atm. at 10°C. The formation of the composite was supported by Fourier transform IR spectroscopy. The morphol. properties of the composite were investigated by at. force microscopy and SEM. The thermal properties of the composite were examined by using thermogravimetric analyses. It was found that the composite had good thermal stability. The conducting polymer composite was used for the first time as an adsorbent for solid phase extraction of Cu (II). The optimum pH was found to be 7. The adsorption and elution shaking times were 5 and 15 min, resp. The elution was done with 5 mL of 2 mol L-1 HNO3. The accuracy of the developed method was confirmed by analyzing certified reference material (TMDA-70.2 Lake Water). In the experiment, the researchers used 1H-Indole(cas: 120-72-9Application In Synthesis of 1H-Indole)

Sekhar, Abinitha S.’s team published research in International Journal of Pharmaceutical Sciences Review and Research in 2016 | CAS: 162100-42-7

6-Chloro-5-methyl-1H-indole(cas: 162100-42-7) 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 of 162100-42-7

In 2016,International Journal of Pharmaceutical Sciences Review and Research included an article by Sekhar, Abinitha S.; Saranya, T. S.; Baskar, Vaishnav; Manakadan, Asha Ashokan. Application of 162100-42-7. The article was titled 《In silico approach of apoptosis induing ability of different indole derivatives by interaction with caspase9》. The information in the text is summarized as follows:

Indole compounds are well known for their wide variety of pharmacol. activities. It is the combination of benzene with pyrrole ring. Compounds having indole group are biol. important. They are used as antimicrobial, antiviral, antitubercular, antiinflammatory, anticancer, ant-diabetic and anticonvulsant agents. Because of the wide variety of biol. application, several substituted indole derivatives are studied for their mol. structure, mol. docking and bioavailability. The purpose of the study is to carry out the docking studies of indole derivatives containing electrophilic substitution and nucleophilic substitution with the anticancer target casp9. Fifty compounds were designed and by using Argus lab version 4.0.1. Their docking score was calculated and compared with the standard drug casodex. The drug likeness of compounds was performed using Lipinski rule of five. Result showed that 1,1′-(1H-indole-5,6-diyl)diethanone and 5-(trichloromethyl)-1H-indole and the phytoconstituent curcumin showed better docking score than that of the standard drug casodex. It is concluded that certain indole derivatives show greater affinity with casp9 protein. These compounds may be helpful in studying anticancer targets for casp9 protein. In the part of experimental materials, we found many familiar compounds, such as 6-Chloro-5-methyl-1H-indole(cas: 162100-42-7Application of 162100-42-7)

Yang, Jingyun’s team published research in Proceedings of the National Academy of Sciences of the United States of America in 2020 | CAS: 120-72-9

《Biphasic chemotaxis of Escherichia coli to the microbiota metabolite indole》 was written by Yang, Jingyun; Chawla, Ravi; Rhee, Kathy Y.; Gupta, Rachit; Manson, Michael D.; Jayaraman, Arul; Lele, Pushkar P.. Application of 120-72-9 And the article was included in Proceedings of the National Academy of Sciences of the United States of America in 2020. The article conveys some information:

Bacterial chemotaxis to prominent microbiota metabolites such as indole is important in the formation of microbial communities in the gastrointestinal (GI) tract. However, the basis of chemotaxis to indole is poorly understood. Here, we exposed Escherichia coli to a range of indole concentrations and measured the dynamic responses of individual flagellar motors to determine the chemotaxis response. Below 1 mM indole, a repellent-only response was observed At 1 mM indole and higher, a time-dependent inversion from a repellent to an attractant response was observed The repellent and attractant responses were mediated by the Tsr and Tar chemoreceptors, resp. Also, the flagellar motor itself mediated a repellent response independent of the receptors. Chemotaxis assays revealed that receptor-mediated adaptation to indole caused a bipartite response-wild-type cells were attracted to regions of high indole concentration if they had previously adapted to indole but were otherwise repelled. We propose that indole spatially segregates cells based on their state of adaptation to repel invaders while recruiting beneficial resident bacteria to growing microbial communities within the GI tract. The results came from multiple reactions, including the reaction of 1H-Indole(cas: 120-72-9Application of 120-72-9)