October 2022 - Page 16 of 72 - Indole Building Blocks

Hong, Bor-Cherng et al. published their research in Journal of Organic Chemistry in 2008 |CAS: 79815-20-6

The Article related to erratum cyclohexadienecarboxaldehyde stereoselective enantioselective preparation, palitantin stereoselective enantioselective preparation erratum, organo catalytic stereoselective enantioselective robinson annulation unsaturated aldehyde erratum, amine catalyst stereoselective enantioselective robinson annulation unsaturated aldehyde erratum and other aspects.Synthetic Route of 79815-20-6

On March 21, 2008, Hong, Bor-Cherng; Wu, Ming-Fun; Tseng, Hsing-Chang; Huang, Guo-Fong; Su, Cheng-Feng; Liao, Ju-Hsiou published an article.Synthetic Route of 79815-20-6 The title of the article was Organo-catalytic asymmetric Robinson annulation of α,β-unsaturated aldehydes: applications to the total synthesis of (+)-palitantin. [Erratum to document cited in CA148:033412]. And the article contained the following:

The absolute configurations for 3g, 3h, 9 and 10 were incorrect in the Abstract, Table 3 and Schemes 3 and 4. The correct configurations are given. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).Synthetic Route of 79815-20-6

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

Ruiz, Nerea et al. published their research in Chemistry – A European Journal in 2008 |CAS: 79815-20-6

The Article related to beta nitroacrolein dimethyl acetal aldehyde chiral organocatalyst conjugate addition, aldehyde nitro derivative stereoselective preparation reduction intramol reductive amination, nitroaldehyde derivative stereoselective preparation olefination reduction intramol aza michael, pyrrolidine polysubstituted derivative chemoselective stereoselective preparation and other aspects.Reference of H-Idc-OH

Ruiz, Nerea; Reyes, Efraim; Vicario, Jose L.; Badia, Dolores; Carrillo, Luisa; Uria, Uxue published an article in 2008, the title of the article was Organocatalytic enantioselective synthesis of highly functionalized polysubstituted pyrrolidines.Reference of H-Idc-OH And the article contains the following content:

The organocatalytic conjugate addition of different aldehydes to β-nitroacrolein di-Me acetal, generating the corresponding highly functionalized nitroaldehydes in high yields and with high stereoselectivities, has been studied in detail. These transformations have been achieved by using both readily available starting materials in a 1:1 ratio as well as com. available catalysts at a 10 mol% catalyst loading. Furthermore, a very short and efficient protocol has been devised for the preparation of highly enantioenriched pyrrolidines containing two or three contiguous stereocenters starting from the obtained Michael adducts. 3,4-Disubstituted pyrrolidines have been obtained in a single step by Zn-mediated chemoselective reduction of the nitro group followed by intramol. reductive amination, and trisubstituted homoproline derivatives have been prepared by means of an olefination reaction and a cascade process involving chemoselective reduction of the nitro group followed by a fully diastereoselective intramol. aza-Michael reaction. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).Reference of H-Idc-OH

Takahashi, Fumie et al. published their patent in 2010 |CAS: 879562-21-7

The Article related to allergy, allergy inhibitors, antiasthmatics, antirheumatic agents, antitumor agents, asthma, atopic dermatitis, autoimmune disease, b cell, crohn disease, homo sapiens, human, interleukin 2 role: bsu (biological study, unclassified), biol (biological study) (production inhibitors), leukemia, neoplasm (hematol.), psoriasis, rheumatoid arthritis, systemic lupus erythematosus, transplant rejection (inhibitors), ulcerative colitis and other aspects.Recommanded Product: 1-(Cyclopropanecarbonyl)indoline-5-sulfonyl chloride

On August 19, 2010, Takahashi, Fumie; Imada, Sunao; Shiwaku, Masahiko; Kato, Koji; Fukahori, Hidehiko published a patent.Recommanded Product: 1-(Cyclopropanecarbonyl)indoline-5-sulfonyl chloride The title of the patent was Preparation of 2-(difluoromethyl)-1-(morpholinoheterocyclyl)benzimidazole derivatives as selective phosphatidyl inositol-3-kinase (PI3Kδ) inhibitors. And the patent contained the following:

The title compounds [I; R1 = A1, A2, A3 = CH or N, provided that at least 2 of A1-A3 are N; W = NH, O; R1 = Q, Q1; R2 = H, lower alkyl, hydroxy-lower alkyl; R3 = H, halo; B1, B2 = bond, C1-4 alkylene; B3 = O, S, NR0; B4 = (un)substituted CH, N; R0 = H, lower alkyl; R10 = H, (un)substituted lower alkenyl, lower alkynyl, optionally alkoxy-substituted phenyl-lower alkyl, phenyl-lower alkoxy-lower alkyl; R11 = H, R100, C(O)R101, C(O)O R102, (un)substituted CONH2, SO2R105; or NR10R11 = (un)substituted 3- to 8-membered monocyclic heterocyclyl containing 1-4 heteroatoms selected from O, S, and N; R100 = (un)substituted lower alkyl, lower alkynyl, each ring-(un)substituted cycloalkyl, cycloalkylalkyl, heterocyclyl, or heterocyclylalkyl, (un)substituted NH2; R101 = each (un)substituted lower alkyl, CONH2, or piperadinylcarbonyl, cyano, HO, lower alkoxy, etc.; R102 = lower alkyl; R105 = (un)substituted lower alkyl, lower alkenyl, etc.] or salts thereof were prepared It is found that these tri-substituted triazine derivative or tri-substituted pyrimidine derivatives have a selective inhibitory activity on PI3Kδ over PI3Kα and/or an inhibitory activity on the production of IL-2 and/or an inhibitory activity on the proliferation of B cells (including an inhibitory activity on the activation of B cells) and can be used as prophylactic or therapeutic agents for rejections in various types of organ transplantation, allergic diseases (e.g., asthma, atopic dermatitis), autoimmune diseases (e.g., rheumatoid arthritis, psoriasis, ulcerative colitis, Crohn diseases, systemic lupus erythematosus), hematol. tumors (e.g., leukemia) and others. Thus, a solution of 2.27 g 2-(difluoromethyl)-1-[2-(methylsulfonyl)-6-(morpholin-4-yl)pyrimidin-4-yl]-1H-benzimidazole in 57 mL N,N-dimethylacetamide was treated with 5.45 g trans-cyclohexane-1,4-diamine and 1.15 g K2CO3 and stirred at 100° for 1 h to give, after workup and silica gel chromatog., 2.21 g trans-N-[4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(morpholin-4-yl)pyrimidin-2-yl]cyclohexane-1,4-diamine (II). A mixture of 100 mg II, 0.04 mL pyridine, and 1 mL CH2Cl2 was treated with 0.04 mL 3-chloropropane-1-sulfonyl chloride under ice-cooling, stirred at room temperature overnight, and concentrated to give, after silica gel chromatog., the precursor. Th precursor was dissolved in 1 mL N,N-dimethylformamide, treated with 27 mg 60% NaH, stirred at 0° for 1 h and at room temperature for 2 h to give, after workup and silica gel chromatog., 6-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-[trans-4-(1,1-dioxoisothiazolidin-2-yl)cyclohexyl]-2-(morpholin-4-yl)pyrimidin-4-amine (III). III and urea derivative (IV) showed IC50 of 5.0 and 0.85 nM, resp., against human PI3Kδ and IC50 of 2,900 and 460 nM, resp., against human PI3Kα, resp. The experimental process involved the reaction of 1-(Cyclopropanecarbonyl)indoline-5-sulfonyl chloride(cas: 879562-21-7).Recommanded Product: 1-(Cyclopropanecarbonyl)indoline-5-sulfonyl chloride

Kumar, Aman’s team published research in mBio 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.Recommanded Product: 120-72-9

The author of 《Indole signaling at the host-microbiota-pathogen interface》 were Kumar, Aman; Sperandio, Vanessa. And the article was published in mBio in 2019. Recommanded Product: 120-72-9 The author mentioned the following in the article:

Microbial establishment within the gastrointestinal (GI) tract requires surveillance of the gut biogeog. The gut microbiota coordinates behaviors by sensing host- or microbiota-derived signals. Here we show for the first time that microbiota-derived indole is highly prevalent in the lumen compared to the intestinal tissue. This difference in indole concentration plays a key role in modulating virulence gene expression of the enteric pathogens enterohemorrhagic Escherichia coli (EHEC) and Citrobacter rodentium. Indole decreases expression of genes within the locus of enterocyte effacement (LEE) pathogenicity island, which is essential for these pathogens to form attaching and effacing (AE) lesions on enterocytes. We synthetically altered the concentration of indole in the GI tracts of mice by employing mice treated with antibiotics to deplete the microbiota and reconstituted with indole-producing commensal Bacteroides thetaiotaomicron (B. theta) or a B. theta ΔtnaA mutant (does not produce indole) or by engineering an indole-producing C. rodentium strain. This allowed us to assess the role of self-produced vs. microbiota-produced indole, and the results show that decreased indole concentrations promote bacterial pathogenesis, while increased levels of indole decrease bacterial virulence gene expression. Moreover, we identified the bacterial membrane-bound histidine sensor kinase (HK) CpxA as an indole sensor. In the part of experimental materials, we found many familiar compounds, such as 1H-Indole(cas: 120-72-9Recommanded Product: 120-72-9)

Yan, Xue’s team published research in Molecules in 2020 | 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

《Oxidative dearomative cross-dehydrogenative coupling of indoles with diverse C-H nucleophiles: efficient approach to 2,2-disubstituted indolin-3-ones》 was written by Yan, Xue; Tang, Ying-De; Jiang, Cheng-Shi; Liu, Xigong; Zhang, Hua. SDS of cas: 399-52-0 And the article was included in Molecules in 2020. The article conveys some information:

The oxidative, dearomative cross-dehydrogenative coupling of indoles with various C-H nucleophiles was developed. This process features a broad substrate scope with respect to both indoles and nucleophiles, affording structurally diverse 2,2-disubstituted indolin-3-ones in high yields (up to 99%). The oxidative dimerization and trimerization of indoles were demonstrated under the same conditions. In the experimental materials used by the author, we found 5-Fluoro-1H-indole(cas: 399-52-0SDS of cas: 399-52-0)

Jiang, Xingmao’s team published research in Fuel in 2019 | CAS: 120-72-9

The author of 《Extractive removal of both basic and non-basic nitrogens from fuel oil by dicarboxyl-modified polyethylene glycol: Performance and mechanism》 were Jiang, Xingmao; Zhu, Shuang; Gao, Jiajun; Yu, Yaqian; Xiong, Chunyan; Li, Chunxi; Yang, Weimin. And the article was published in Fuel in 2019. Recommanded Product: 1H-Indole The author mentioned the following in the article:

Polyethylene glycol [PEG, H(OCH2CH2)nOH] like PEG-600, a green extractant for organic N-compounds in fuel oil, was very active for non-basic nitrogens but not effective for basic ones. Modification of PEG that replaced -OH group with -OCH2COOH group can produce HOOCCH2(OCH2CH2)nOCH2COOH (dcPEG). For denitrogenation, dcPEG-600 was highly effective for both basic and non-basic nitrogens. N-distribution coefficient [DN, (μgN·g-1dcPEG)/(μgN·g-1oil)] of dcPEG-600 to n-octane can reach as high as 200 for indole, 92.6 for pyrrole, 42.0 for quinoline, and 81.5 for pyridine, resp. Besides, denitrogenation selectivity of dcPEG-600 to toluene (DN/Dtoluene) can amount to 462 for indole, 230 for pyrrole, 146 for quinoline, and 366 for pyridine, resp. The high performance was ascribed to contribution of active O atom on ether group and active H atom on -COOH group. The active O atom (Lewis basic site) formed H-bond with the non-basic nitrogen (Bronsted acid). The active H atom (Bronsted acidic site) not only interacted with the basic one (Lewis base) but also brought in the good selectivity. Moreover, dcPEG-600 was still effective for real oil and could be recycled for several times without the denitrogenation performance significantly decreasing.1H-Indole(cas: 120-72-9Recommanded Product: 1H-Indole) was used in this study.

Rivaroli, D.’s team published research in Animal in 2019 | CAS: 120-72-9

The author of 《Tannin-rich sainfoin pellet supplementation reduces fat volatile indoles content and delays digestive parasitism in lambs grazing alfalfa》 were Rivaroli, D.; Prunier, A.; Meteau, K.; do Prado, I. N.; Prache, S.. And the article was published in Animal in 2019. SDS of cas: 120-72-9 The author mentioned the following in the article:

Lambs grazing alfalfa or white clover are prone to flavor taint which can be an impediment to consumer acceptance. Here we investigated whether condensed tannin (CT)-rich sainfoin pellet supplementation of lambs grazing alfalfa influences meat sensory quality. Using three groups of 18 male Romane weaned lambs, we compared three feeding regimes: alfalfa grazing (AF), alfalfa grazing + daily supplementation with CT-rich sainfoin pellets (15 g dry matter (DM)/kg live weight, AS) and stall feeding with concentrate and grass hay indoors (SI). We also investigated the potential interest of sainfoin pellet supplementation for controlling digestive parasitism. The sainfoin pellets contained 42 g of CT/kg of DM and they represented on average 36% of the diet in AS lambs. Skatole and indole were detected in most of the AF and AS lambs, whereas in very few SI lambs. Skatole and indole concentrations in perirenal and dorsal fat were lower in the AS lambs than the AF lambs (P < 0.025 to P < 0.001), but the intensity of 'animal' odor and 'animal' flavor of the chops did not differ between both forage-grazing groups. Longissimus thoracis et lumborum muscle lightness was lower in the AF and AS lambs than the SI lambs (P < 0.001) with the other muscle color coordinates being unaffected by the treatment and between-treatment group differences in muscle color coordinates remaining constant throughout the 9-day display period. S.c. fat color coordinates were not influenced by the treatment. The number of individual anthelmintic drenches necessary to keep nematode faecal egg count below a threshold of 550 eggs/g of faeces was lower in the AS than the AF lambs (0.94 per lamb v. 1.63 per lamb; P < 0.001). Faecal oocyst count was lower in the AS than the AF lambs for the first measurement made 56 days after the beginning of the experiment (P < 0.001) and was not significantly different between both forage-grazing groups thereafter. The use of CT-rich sainfoin pellets to supplement lambs that are concurrently grazing alfalfa reduced fat volatile skatole and indole concentrations and delayed the onset of both helminth and coccidian infections. In the experimental materials used by the author, we found 1H-Indole(cas: 120-72-9SDS of cas: 120-72-9)

Ye, Meng’s team published research in Plant Cell in 2019 | CAS: 120-72-9

The author of 《Molecular dissection of early defense signaling underlying volatile-mediated defense regulation and herbivore resistance in rice》 were Ye, Meng; Glauser, Gaetan; Lou, Yonggen; Erb, Matthias; Hu, Lingfei. And the article was published in Plant Cell in 2019. Application In Synthesis of 1H-Indole The author mentioned the following in the article:

Herbivore-induced plant volatiles prime plant defenses and resistance, but how they are integrated into early defense signaling and whether a causal relationship exists between volatile defense priming and herbivore resistance is unclear. The impact of indole, a common herbivore-induced plant volatile and modulator of many physiol. processes in plants, bacteria, and animals, on early defense signaling and herbivore resistance in rice (Oryza sativa). Rice plants infested by fall armyworm (Spodoptera frugiperda) caterpillars release indole at a rate of up to 25 ng*h-1. Exposure to equal doses of exogenous indole enhances rice resistance to S. frugiperda. Screening of early signaling components revealed that indole pre-exposure directly enhances the expression of the leucine-rich repeat-receptor-like kinase OsLRR-RLK1. Pre-exposure to indole followed by simulated herbivory increases (i.e. primes) the transcription, accumulation, and activation of the mitogen-activated protein kinase OsMPK3 and the expression of the downstream WRKY transcription factor gene OsWRKY70 as well as several jasmonate biosynthesis genes, resulting in higher jasmonic acid (JA) accumulation. Anal. of transgenic plants defective in early signaling showed that OsMPK3 is required and that OsMPK6 and OsWRKY70 contribute to indole-mediated defense priming of JA-dependent herbivore resistance. Therefore, herbivore-induced plant volatiles increase plant resistance to herbivores by pos. regulating early defense signaling components. The results came from multiple reactions, including the reaction of 1H-Indole(cas: 120-72-9Application In Synthesis of 1H-Indole)

Hibbard, J.’s team published research in Anaerobe in 2019 | CAS: 120-72-9

In 2019,Anaerobe included an article by Hibbard, J.; Jiang, Z.-D.; DuPont, H. L.. Name: 1H-Indole. The article was titled 《Fecal calprotectin and fecal indole predict outcome of fecal microbiota transplantation in subjects with recurrent Clostridium difficile infection》. The information in the text is summarized as follows:

Fecal calprotectin and indole were studied in 134 subjects with recurrent CDI before and after FMT. Reduced fecal calprotectin (p = 0.0353, 95% CI 0.1305-0.1439) and rising levels of indole (p < 0.0001, 95% CI < 0.0001-0.0003) predicted successful treatment. A ratio of recal calprotectin/indole may provide prognostic value for FMT (p = 0.0004, 95% CI 0.22-0.87). In the experiment, the researchers used 1H-Indole(cas: 120-72-9Name: 1H-Indole)

Wood, Thomas K.’s team published research in mBio in 2019 | CAS: 120-72-9

Quality Control of 1H-IndoleIn 2019 ,《Precedence for the role of indole with pathogens》 appeared in mBio. The author of the article were Wood, Thomas K.; Lee, Jintae. The article conveys some information:

A review. Kumar and Sperandio recently reported that indole represses the expression of virulence genes of the gastrointestinal tract pathogens enterohemorrhagic Escherichia coli (EHEC) and Citrobacter rodentium. Indole has been shown previously to act as a true signal for E. coli and it has been argued by us that indole is likely hydroxylated by oxygenases to become an even more potent signal in the gastrointestinal tract. Indole has been shown to increase the competitiveness of commensal E. coli with P. aeruginosa by inhibiting its quorum sensing. The experimental process involved the reaction of 1H-Indole(cas: 120-72-9Quality Control of 1H-Indole)