20/10/2022 - Page 3 of 8 - Indole Building Blocks

Zhong, Qiaoshi’s team published research in Scientific Reports in 2019 | 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.SDS of cas: 120-72-9

The author of 《Profiles of volatile indole emitted by Escherichia coli based on CDI-MS》 were Zhong, Qiaoshi; Cheng, Feng; Liang, Juchao; Wang, Xiaozhong; Chen, Yanhui; Fang, Xueyao; Hu, Longhua; Hang, Yaping. And the article was published in Scientific Reports in 2019. SDS of cas: 120-72-9 The author mentioned the following in the article:

Escherichia coli is an important pathogen of nosocomial infection in clin. research, Thus, exploring new methods for the rapid detection of this pathogen is urgent. We reported the early release of mol. volatile indole vapor of E. coli cultures and blood cultures analyzed by direct atm. corona discharge ionization mass spectrometry (CDI-MS). The concentration of indole in E. coli cultures remarkably increases during the early log and lag phases of bacterial growth, thereby enabling early detection. Tech. replicates were cultivated for 3 days for reference diagnosis using current conventional bacteremia detection. A reference MS screen of common microbes from other genera confirmed that the peaks at m/z 116 signal corresponded to indole were specifically present in E. coli. Our results indicated that volatile indole based on CDI-MS without the need for any sample pretreatment is highly suitable for the reliable and cost-efficient differentiation of E. coli, especially for bacteremia in humans. The experimental process involved the reaction of 1H-Indole(cas: 120-72-9SDS of cas: 120-72-9)

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

Zarkan, Ashraf’s team published research in Scientific Reports in 2019 | CAS: 120-72-9

The author of 《Indole Pulse Signalling Regulates the Cytoplasmic pH of E. coli in a Memory-Like Manner》 were Zarkan, Ashraf; Cano-Muniz, Santiago; Zhu, Jinbo; Al Nahas, Kareem; Cama, Jehangir; Keyser, Ulrich F.; Summers, David K.. And the article was published in Scientific Reports in 2019. Computed Properties of C8H7N The author mentioned the following in the article:

Bacterial cells are critically dependent upon pH regulation. Here we demonstrate that indole plays a critical role in the regulation of the cytoplasmic pH of Escherichia coli. Indole is an aromatic mol. with diverse signalling roles. Two modes of indole signalling have been described: persistent and pulse signalling. The latter is illustrated by the brief but intense elevation of intracellular indole during stationary phase entry. We show that under conditions permitting indole production, cells maintain their cytoplasmic pH at 7.2. In contrast, under conditions where no indole is produced, the cytoplasmic pH is near 7.8. We demonstrate that pH regulation results from pulse, rather than persistent, indole signalling. Furthermore, we illustrate that the relevant property of indole in this context is its ability to conduct protons across the cytoplasmic membrane. Addnl., we show that the effect of the indole pulse that occurs normally during stationary phase entry in rich medium remains as a “”memory”” to maintain the cytoplasmic pH until entry into the next stationary phase. The indole-mediated reduction in cytoplasmic pH may explain why indole provides E. coli with a degree of protection against stresses, including some bactericidal antibiotics. The experimental process involved the reaction of 1H-Indole(cas: 120-72-9Computed Properties of C8H7N)

Shin, Jonghoon’s team published research in Scientific Reports in 2019 | 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.HPLC of Formula: 399-52-0

The author of 《Design, synthesis, and discovery of novel oxindoles bearing 3-heterocycles as species-specific and combinatorial agents in eradicating Staphylococcus species》 were Shin, Jonghoon; Magar, Krishna Bahadur Somai; Lee, Jungwoon; Kim, Kwang-sun; Lee, Yong Rok. And the article was published in Scientific Reports in 2019. HPLC of Formula: 399-52-0 The author mentioned the following in the article:

A series of new functionalized 3-indolylindolin-2-ones I [R1 = H, 5-MeO, 5-Cl, etc.; R2 = H, Ome, F], 3-(1-methylpyrrol-2-yl)indolin-2-ones, and 3-(thiophen-2-yl)indolin-2-ones II [R3 = H, 5-MeO, 4-Cl, etc.; X = S, NMe] were synthesized by using novel indium (III)-catalyzed reaction of various 3-diazoindolin-2-ones with indoles, 1-methylpyrrole, or thiophene via one-pot procedure. The newly synthesized compounds were characterized and screened for their in vitro antibacterial activity against various Staphylococcus species, including methicillin-resistant Staphylococcus aureus. results revealed that five compounds II [R3 = 4-Cl, 4-Br, 5-Br; X = NMe] and [R3 = 5-Cl, 5-Br; X = S] exhibited potent and specific antibacterial activity against Staphylococcus species albeit inactive against Gram-neg. bacteria. Especially, compounds exhibited superior antibacterial potency against Staphylococcus epidermidis compared to the reference drug streptomycin. The most potential compound II [R3 = 4-Br; X = S] also increased the susceptibility of Staphylococcus aureus to ciprofloxacin, gentamicin, kanamycin, and streptomycin. Among them, II [R3 = 4-Br; X = S] was found to be a synergistic compound with gentamicin and kanamycin. Furthermore, the cellular level of autolysin protein was increased from the II [R3 = 4-Br; X = S]-treated Staphylococcus aureus cells. Finally, in vitro CCK-8 assays showed that II [R3 = 4-Br; X = S] exhibited no cytotoxicity at the min. inhibitory concentrations used for killing Staphylococcus species. From all our results, novel oxindole compounds directly have lethal action or boost existing antibiotic power with the reduction of doses and toxicity in the treatment of multidrug-resistant Staphylococcus species. In addition to this study using 5-Fluoro-1H-indole, there are many other studies that have used 5-Fluoro-1H-indole(cas: 399-52-0HPLC of Formula: 399-52-0) was used in this study.

Hu, Miao’s team published research in New Journal of Chemistry in 2021 | CAS: 399-52-0

Hu, Miao; Jiang, Yong; Sun, Nan; Hu, Baoxiang; Shen, Zhenlu; Hu, Xinquan; Jin, Liqun published their research in New Journal of Chemistry in 2021. The article was titled 《Nickel-catalyzed C3-alkylation of indoles with alcohols via a borrowing hydrogen strategy》.Quality Control of 5-Fluoro-1H-indole The article contains the following contents:

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 experimental materials used by the author, we found 5-Fluoro-1H-indole(cas: 399-52-0Quality Control of 5-Fluoro-1H-indole)

Liu, Cuixia’s team published research in Bioresource Technology in 2019 | CAS: 120-72-9

In 2019,Bioresource Technology included an article by Liu, Cuixia; Duan, Xuejun; Chen, Qishi; Chao, Cong; Lu, Zhenghao; Lai, Qingji; Megharaj, Mallavarapu. HPLC of Formula: 120-72-9. The article was titled 《Investigations on pyrolysis of microalgae Diplosphaera sp. MM1 by TG-FTIR and Py-GC/MS: Products and kinetics》. The information in the text is summarized as follows:

In this work, pyrolysis characteristics and kinetics of microalgae Diplosphaera sp. MM1 cultivated in different mediums were investigated by TG-FTIR and Py-GC/MS. Harvested MM1s biomass varied with the changing in proximate and ultimate analyses presented different weight loss behaviors. The weight loss of MM1s cultivated in dairy and winery wastewater in main pyrolysis region was ∼48.4 wt% and ∼52.9 wt%, resp., and both showed secondary weight loss after 570°C. However, MM1 harvested from BG-11 medium exhibited maximum weight loss of ∼63.5 wt% and no secondary weight loss. Further, the activation energies of MM1s harvested from dairy and winery wastewater (176.3 kJ/mol and 130.4 kJ/mol, resp.) were lower than that of BG-11medium (189.4 kJ/mol). The best mechanism function for MM1s pyrolysis was third-order f(α) = (1-α)3. Py-GC/MS results of MM1 cultivated in winery wastewater showed highest contents of C4-C10 and C11-C21 that characterized the carbon level of gasoline and diesel, resp., which are the major components of bio-oils. In the part of experimental materials, we found many familiar compounds, such as 1H-Indole(cas: 120-72-9HPLC of Formula: 120-72-9)

Wang, Wangyang’s team published research in Tetrahedron Letters in 2019 | CAS: 399-52-0

The author of 《I2O5 promoted iodosulfenylation of indoles under metal-free conditions》 were Wang, Wangyang; Zhu, Fuyuan; Yan, Zhaohua; He, Mingchuang; Lin, Sen. And the article was published in Tetrahedron Letters in 2019. Related Products of 399-52-0 The author mentioned the following in the article:

A mild, efficient, and metal-free strategy to construct 2-iodo-3-arylthioindoles I (R = Cl, Me, Br, F, OMe; R1 = H, 4-Me, 5-OMe, 6-Br, etc.; R2 = H, Me) was developed via I2O5-promoted iodosulfenylation of indoles II utilizing simple, cheap and easily available thiophenols 4-RC6H4SH as sulfur sources. It is the first time that the iodothiolation difunctionalization of indoles II at C-2 and C-3 positions was accomplished with the formation of 2-iodo-3-arylthioindoles I in moderate to good yields. In the experiment, the researchers used 5-Fluoro-1H-indole(cas: 399-52-0Related Products of 399-52-0)

Zhang, Shanshan’s team published research in Scientific Reports in 2022 | CAS: 120-72-9

Zhang, Shanshan; Yang, Qian; Fu, Songzhe; Janssen, Colin R.; Eggermont, Mieke; Defoirdt, Tom published an article in 2022. The article was titled 《Indole decreases the virulence of the bivalve model pathogens Vibrio tasmaniensis LGP32 and Vibrio crassostreae J2-9》, and you may find the article in Scientific Reports.COA of Formula: C8H7N The information in the text is summarized as follows:

Abstract: Indole signaling plays an important role in bacterial pathogenesis. In this study, the impact of indole on biofilm formation, swimming and swarming motility were explored in Vibrio tasmaniensis LGP32 and Vibrio crassostreae J2-9, two model pathogens of bivalves. The results showed that indole decreased swimming and swarming motility in both strains, and decreased biofilm formation in V. crassostreae J2-9. Furthermore, indole affected a large number of genes at RNA level, including genes related to metabolism, ABC transporters, flagellar assembly, chemotaxis, and response regulators. Finally, the bacterial virulence towards mussel larvae was decreased by pretreatment with indole in both V. tasmaniensis LGP32 and V. crassostreae J2-9. After 5 days, the survival rate of mussel larvae increased 2.4-fold and 2.8-fold in mussel larvae challenged with V. tasmaniensis LGP32 pretreated with 200 μM and 500 μM indole, resp. The survival rate of mussel larvae increased 1.5-fold and 1.9-fold in mussel larvae challenged with V. crassostreae J2-9 pretreated with 200 μM and 500 μM indole, resp. These data indicate that indole has a significant impact on the virulence of V. tasmaniensis LGP32 and V. crassostreae J2-9, and indole signaling could be a promising target for antivirulence therapy. The experimental process involved the reaction of 1H-Indole(cas: 120-72-9COA of Formula: C8H7N)

Nunewar, Saiprasad’s team published research in Organic Letters in 2021 | CAS: 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).Recommanded Product: 5-Fluoro-1H-indole

《Rh(III)-Catalyzed Chemodivergent Annulations between Indoles and Iodonium Carbenes: A Rapid Access to Tricyclic and Tetracyclic N-Heterocylces》 was written by Nunewar, Saiprasad; Kumar, Sanjeev; Pandhare, Harishchandra; Nanduri, Srinivas; Kanchupalli, Vinaykumar. Recommanded Product: 5-Fluoro-1H-indoleThis research focused ontricyclic tetracyclic nitrogen heterocycle preparation; indole iodonium carbene chemodivergent annulation rhodium catalyst. The article conveys some information:

Herein, an acid-controlled highly tunable selectivity of Rh(III)-catalyzed [4 + 2] and [3 + 3] annulations of N-carboxamide indoles with iodonium ylides lead to form synthetically important tricyclic and tetracyclic N-heterocycles is reported. Here, iodonium ylide serves as a carbene precursor. The protocol proceeds under operationally simple conditions and provides novel tricyclic and tetracyclic scaffolds such as 3,4-dihydroindolo[1,2-c]quinazoline-1,6(2H,5H)-dione and 1H-[1,3]oxazino[3,4-a]indol-1-one derivatives with a broad range of functional group tolerance and moderate to excellent yields. Furthermore, the protocol synthetic utility was extended for various chem. transformations and was easily scaled up to a large-scale level. In the experiment, the researchers used 5-Fluoro-1H-indole(cas: 399-52-0Recommanded Product: 5-Fluoro-1H-indole)

Lonn, Hans’s team published research in Carbohydrate Research in 1985 | 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.Formula: C22H25NO9SThey are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.

Lonn, Hans published an article in Carbohydrate Research. The title of the article was 《Synthesis of a tri- and a heptasaccharide which contain α-L-fucopyranosyl groups and are part of the complex type of carbohydrate moiety of glycoproteins》.Formula: C22H25NO9S The author mentioned the following in the article:

Me triflate-promoted condensation of Et 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside with benzyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside and with benzyl 2,4-di-O-benzyl-3,6-di-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranoside gave a trisaccharide and a heptasaccharide derivative, resp. The trisaccharide α-L-Fucp-(1→3)-β-D-GlcpNAc-(1→2)-D-Man and the heptasaccharide I, which are parts of the complex type of glycoproteins, were obtained by removal of the protecting groups and N-acetylation. 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: 99409-32-2Formula: C22H25NO9S)

Kim, Woo H.’s team published research in Frontiers in Immunology in 2019 | CAS: 120-72-9

In 2019,Frontiers in Immunology included an article by Kim, Woo H.; Lillehoj, Hyun S.; Min, Wongi. Application In Synthesis of 1H-Indole. The article was titled 《Indole treatment alleviates intestinal tissue damage induced by chicken coccidiosis through activation of the aryl hydrocarbon receptor》. The information in the text is summarized as follows:

In the present study, we examined the effects of dietary indoles, 3,3′-diindolylmethane (DIM) and indole-3-carbinol (I3C), on CD4+T cell population and functions in chickens. Furthermore, the effects of dietary DIM treatment on chicken coccidiosis caused by an apicomplexan parasite were investigated. Dietary treatment of healthy chickens with DIM and I3C induced increased CD4+CD25+ (Treg) cells and the mRNA expression of IL-10, while decreasing number of CD4+IL-17A+ (Th17) cells and Th17-related cytokines transcripts expression in the intestine. In addition, we explored the role of AhR in indole-treated splenic lymphocytes by using AhR antagonist and our results suggested that DIM is a ligand for chicken AhR. In chicken coccidiosis, treatment of DIM increased the ratio of Treg/Th17 cells and significantly reduced intestinal lesion although no significant changes in body weight and fecal oocyst production were noted compared to non-treated control group. These results indicate that DIM is likely to affect the ratios of Treg/Th17 reducing the level of local inflammatory response induced by Eimeria or facilitate repairing process of inflamed gut following Eimeria infection. The results described herein are thus consistent with the concept that AhR ligand modulates the T cell immunity through the alteration of Treg/Th17 cells with Treg dominance. To our knowledge, present study is the first scientific report showing the effects of dietary indole on T cell immunity in poultry species. In the part of experimental materials, we found many familiar compounds, such as 1H-Indole(cas: 120-72-9Application In Synthesis of 1H-Indole)