Indole Building Blocks

Ma, Qiao’s team published research in International Biodeterioration & Biodegradation 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.Category: indole-building-block

Category: indole-building-blockIn 2019 ,《Identification and functional study of an iif2 gene cluster for indole degradation in Burkholderia sp. IDO3》 was published in International Biodeterioration & Biodegradation. The article was written by Ma, Qiao; Yang, Bingyu; Qu, Hui; Gao, Zhen; Qu, Yuanyuan; Sun, Yeqing. The article contains the following contents:

Burkholderia sp. IDO3 is an indole-degrading bacterium isolated from activated sludge. A previous genomic clone library assay identified an iif1 gene cluster for indole metabolism in strain IDO3. To further explore the underlying indole degradation mechanisms, the complete genome of strain IDO3 was sequenced (8,003,806 bp). The genome contained three circular chromosomes and one plasmid, and 7550 genes were predicted. Interestingly, in addition to iif1 on chromosome 3, bioinformatic analyses identified a second indole oxygenase gene cluster, iif2, on chromosome 1. Both iif clusters were up-regulated in response to indole. Heterologous expression of iifC1D1 and iifC2D2 in Escherichia coli BL21(DE3) demonstrated that these genes were capable of oxidizing indole to indigo. Gene knockout assays provided addnl. evidence that iifC2 played crucial roles in indole metabolism In addition, we identified a novel gene (iifF) in the iif2 cluster. This gene was shown to encode an isatin hydrolase. IifF was expressed in E. coli, and a purified his-tagged enzyme preparation was obtained. IifF converted isatin to isatinate with Km of 4.4 ± 0.7μM and kcat of 95.5 ± 4 s-1. This is the first study to show that indole can be degraded by two iif gene clusters, and that isatin hydrolase is involved in indole metabolism, improving our understanding of indole metabolic processes. The results came from multiple reactions, including the reaction of 1H-Indole(cas: 120-72-9Category: indole-building-block)

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

Owa, Takashi’s team published research in Bioorganic & Medicinal Chemistry Letters in 2000 | CAS: 292636-12-5

4-Chloro-1H-indol-7-amine(cas: 292636-12-5) belongs to anime. Large quantities of aliphatic amines are made synthetically. The most widely used industrial method is the reaction of alcohols with ammonia at a high temperature, catalyzed by metals or metal oxide catalysts (e.g., nickel or copper). Mixtures of primary, secondary, and tertiary amines are thereby produced.Name: 4-Chloro-1H-indol-7-amine

Name: 4-Chloro-1H-indol-7-amineOn June 5, 2000, Owa, Takashi; Okauchi, Tatsuo; Yoshimatsu, Kentaro; Sugi, Naoko Hata; Ozawa, Yoichi; Nagasu, Takeshi; Koyanagi, Nozomu; Okabe, Tadashi; Kitoh, Kyosuke; Yoshino, Hiroshi published an article in Bioorganic & Medicinal Chemistry Letters. The article was 《A focused compound library of novel N-(7-indolyl)benzenesulfonamides for the discovery of potent cell cycle inhibitors》. The article mentions the following:

A series of compounds containing an N-(7-indolyl)benzenesulfonamide pharmacophore, e.g. I, was synthesized and evaluated as a potential antitumor agent. Cell cycle anal. with P388 murine leukemia cells revealed that there were two different classes of potent cell cycle inhibitors; one disrupted mitosis and the other caused G1 accumulation. The structure-activity relationships of the substituent patterns on this pharmacophore template are described. In the experimental materials used by the author, we found 4-Chloro-1H-indol-7-amine(cas: 292636-12-5Name: 4-Chloro-1H-indol-7-amine)

Dirr, Michael A.’s team published research in Journal of Environmental Horticulture in 1989 | 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.HPLC of Formula: 60096-23-3

Dirr, Michael A. published their research in Journal of Environmental Horticulture on December 31 ,1989. The article was titled 《Rooting response of Photinia × fraseri dress ‘Birmingham’ to 25 carrier and carrier plus IBA formulations》.HPLC of Formula: 60096-23-3 The article contains the following contents:

Twenty-five carriers (solvents) either sep. or in combination with IBA were tested for effectiveness in promoting rooting of Photinia × fraseri Birmingham, Fraser photinia. Maximum rooting percentages, root numbers and lengths resulted from carrier plus IBA solutions, although 85% ethanol produced 87% rooting. IBA plus 95 and 50% ethanol, 20 and 10% polyethylene glycol (PEG), 20 and 1% DMSO (DMSO) produced the highest rooting percentages, root numbers and lengths. K-IBA and water was largely ineffective, suggesting that carriers enhanced the effect of the K-IBA. Twenty percent formulations of PEG, DMSO, and N,N-dimethylformamide (DMF) without IBA improved rooting response compared to 10 and 1% concentrations The lack of effectiveness of K-IBA and water, and the relative effectiveness of higher rates of PEG, DMSO, and DMF without IBA suggest that carriers may have a significant effect of rooting with or without IBA. The experimental process involved the reaction of Potassium 4-(1H-indol-3-yl)butanoate(cas: 60096-23-3HPLC of Formula: 60096-23-3)

Liu, Xiao Gao’s team published research in Bioorganic & Medicinal Chemistry Letters in 1994 | 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.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.

Liu, Xiao Gao; Jain, Rakesh K.; Saha, Raj; Matta, Khushi L. published an article in Bioorganic & Medicinal Chemistry Letters. The title of the article was 《Synthesis of Gal-β-(1→4)-6-O-SO3Na-GlcNAc-β-(1→6)-Man-α-OR as a part of glycoprotein (gp) 120》.Safety of Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside The author mentioned the following in the article:

The synthesis of Gal-β-(1→4)-6-O-SO2Na-GlcNAc-β-(1→6)-Man-α-OR (as a part of gp 120) containing an anomeric p-nitrophenyl group was accomplished via stereoselective glycosidation of Et 3,4,6-tri-O-chloroacetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside. Title oligosaccharide can act as acceptor of α-2,3-sialyltransferase to give NeuAcα-(2→3)-Gal-β-(1→4)-6-O-SO2Na-GlcNAc-β-(1→6)-Man-α-OR which occurs as a part of gp 120. 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)

Silwanis, Basim Azmy’s team published research in Journal of Carbohydrate Chemistry in 1991 | 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.Recommanded Product: 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.

Silwanis, Basim Azmy; El-Sokkary, Ramadan I.; Nashed, Mina A.; Paulsen, Hans published their research in Journal of Carbohydrate Chemistry on December 31 ,1991. The article was titled 《A comparison in the efficiency of six standard 2-amino-2-deoxyglucosyl donors for the synthesis of (2-deoxy-2-phthalimido-β-D-glucopyranosyl) (1→4)-β-D-glucopyranosides》.Recommanded Product: Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside The article contains the following contents:

A systematic study is presented for the most common methods used for the preparation of the disaccharide benzyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1→4)-3,6-di-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranoside from standard 2-amino-2-deoxyglucopyranosyl donors, e.g. I (R = Br, Cl, F, OAc, OC(NH)CCl3, SEt, R1 = phthalimido), and benzyl 3,6-di-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranoside as an acceptor. It was found that the highest yield was obtained when the trichloroacetimidate derivative I was coupled to the 4 position of acceptor 7. After reading the article, we found that the author used Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2Recommanded Product: 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.Recommanded Product: 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.

Nagorny, Pavel’s team published research in Journal of the American Chemical Society in 2009 | 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.Recommanded Product: 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.

《Toward Fully Synthetic Homogeneous β-Human Follicle-Stimulating Hormone (β-hFSH) with a Biantennary N-Linked Dodecasaccharide. Synthesis of β-hFSH with Chitobiose Units at the Natural Linkage Sites》 was written by Nagorny, Pavel; Fasching, Bernhard; Li, Xuechen; Chen, Gong; Aussedat, Baptiste; Danishefsky, Samuel J.. Recommanded Product: Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside And the article was included in Journal of the American Chemical Society on April 29 ,2009. The article conveys some information:

A highly convergent synthesis of the sialic acid-rich biantennary N-linked glycan found in human glycoprotein hormones and its use in the synthesis of a fragment derived from the β-domain of human FSH (hFSH) are described. The synthesis highlights the use of the Sinay radical glycosidation protocol for the simultaneous installation of both biantennary side-chains of the dodecasaccharide as well as the use of glycal chem. to construct the tetrasaccharide core in an efficient manner. The synthetic glycan was used to prepare the glycosylated 20-27aa domain of the β-subunit of hFSH under a Lansbury aspartylation protocol. The proposed strategy for incorporating the prepared N-linked dodecasaccharide-containing 20-27aa domain into β-hFSH subunit was validated in the context of a model system, providing protected β-hFSH subunit functionalized with chitobiose at positions 7 and 24. 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: 99409-32-2Recommanded Product: 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.Recommanded Product: 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.

Griffin, Jason J.’s team published research in Journal of Environmental Horticulture in 2008 | CAS: 60096-23-3

Reference of Potassium 4-(1H-indol-3-yl)butanoateOn March 31, 2008, Griffin, Jason J. published an article in Journal of Environmental Horticulture. The article was 《IBA formulation, concentration, and stock plant growth stage affect rooting of stem cuttings of Viburnum rufidulum》. The article mentions the following:

Viburnum rufidulum Raf. (southern or rusty blackhaw) has potential to be a popular landscape plant as it is an attractive large shrub tolerant of many common landscape stresses. However, propagation difficulties have thus far limited wide scale use. Therefore, the influence of IBA formulation and concentration on adventitious rooting of stem cuttings of southern blackhaw taken at different stock plant growth stages throughout the year were investigated. Liquid formulations of the potassium salt (K-salt) of indolebutyric acid (K-IBA) at 0, 3000, 6000, or 9000 ppm (0, 0.3, 0.6, or 0.9%) as well as talc formulations of IBA at 1000, 3000, or 8000 ppm (0.1, 0.3 or 0.8%) were utilized. Talc formulations failed to stimulate rooting regardless of concentration or growth stage. A quick-dip of K-IBA increased rooting percentage at all growth stages. Softwood and hardwood cuttings had the highest rooting percentages. Hardwood cuttings treated with 6000 ppm (0.6%) or 9000 ppm (0.9%) rooted 90 and 100%, resp. Softwood cuttings treated with 6000 ppm (0.6%) rooted 87%. K-IBA improved root number per rooted cutting for softwood cuttings, whereas root length was unaffected by K-IBA at any growth stage. In the experiment, the researchers used Potassium 4-(1H-indol-3-yl)butanoate(cas: 60096-23-3Reference of Potassium 4-(1H-indol-3-yl)butanoate)

Kalir, Asher’s team published research in Israel Journal of Chemistry in 1968 | 23077-43-2

Israel Journal of Chemistry published new progress about 23077-43-2. 23077-43-2 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Product Details of C9H6FNO2.

Kalir, Asher; Balderman, D. published the artcile< Improved synthesis of some fluoroindoles>, Product Details of C9H6FNO2, the main research area is fluoroindoles; indoles fluoro.

2,5-F2-C6-H3NO2 (109 g.) was treated with 155 g. NCCH2CO2Et and 31.6 g. Na in 1000 ml. EtOH for 2 hrs. to give 26% 4-fluoroanthro-xanonitrile, m. 70-1°. 2,4-(O2N)FC6H3Me (155 g.) was refluxed 14 hrs. with 196 g. N-bromosuccinimide in 600 ml. CCl4 and 2 g. benzoyl peroxide and treated directly with pyridine to give 198 g. I (X = 4-F), m. 201-2°, and 37 g. 2,4-(O2N)FC6H3-CHBr2, m. 63-4°. I (X = 5-F and 6-F), m. 189-90°, and 202-4°, resp., were similarly obtained in 64 and 71% yield. I (X = 4-F) was treated with 150 g. p-ONC6H4NMe2.HCl in 1 l. EtOH and 720 ml. 2.5N NaOH at <5° for 1 hr., and then treated with 1.5 l. 6N H2SO4 to give 86 g. 2-O2N X C6H3CHO (II) (where X = 4-F), m. 32-3°, via III (X = 4-F), m. 165-6°. The following compounds were similarly prepared (X, % yield II, m.p. II, % yield III, and m.p. III given): 5-F, 86, 94-5°, 92, 155-6°; 6-F, 95, 62-3°, 96, 151-2°. II (X = 6-F) was treated with MeNO2 to give 76% 2,4-F(O2N)C6H3CH:CHNO2, m. 84°, which was catalytically reduced to 34-63% 4-fluoroindole, m. 29-30°, accompanied by IV, m. 200° (decomposition). The method of K. and S. Szara (1963) was used to prepare V (R, % yield, and m.p. given): CHO, 73, 190-1°; CH:CMeNO2, 81, 191-2°; CH2CHMeNH2, 64, 103-5° (HCl salt m. 240-1°, picrate m. 222-3°). 6-Fluoro-3-(2-nitrovinyl)indole, m. 190-2°, and 6-fluorotryptamine m. 83-4°, were similarly prepared in 68 and 51% yield, resp. V (R = CHO) (3.5 g.) was treated with 6 g. KMnO4 in 120 ml. Me2CO at <40° to give 47% V (R = CO2H), m. 273° (decomposition). 5-Fluoro-3-indolecarboxylic acid, m. 234-6° (decomposition), and 6-fluoro-3-indolecarboxylic acid, m. 242-4° (decomposition), were similarly prepared in 54 and 48% yield, resp. V (R = CH2CHMeNH2) was less active than the 5-fluoro derivative, but more active than the 6-fluoro derivative in the activity cage test on mice. Israel Journal of Chemistry published new progress about 23077-43-2. 23077-43-2 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Product Details of C9H6FNO2.

Ding, Lu’s team published research in Chemistry – A European Journal in 2019 | 399-76-8

Chemistry – A European Journal published new progress about Acid chlorides Role: RCT (Reactant), RACT (Reactant or Reagent). 399-76-8 belongs to class indole-building-block, and the molecular formula is C9H6FNO2, Safety of 5-Fluoroindole-2-carboxylic acid.

Ding, Lu; Gao, Run-Duo; You, Shu-Li published the artcile< Palladium(0)-Catalyzed Intermolecular Asymmetric Cascade Dearomatization Reaction of Indoles with Propargyl Carbonate>, Safety of 5-Fluoroindole-2-carboxylic acid, the main research area is alkylindolyl methyl malonate preparation propargyl carbonate palladium tandem dearomatization; alkyl methylene dihydrocarbazole dicarboxylate chemoselective regioselective enantioselective preparation; allylic compounds; asymmetric catalysis; cascade reactions; dearomatization; palladium.

An intermol. asym. cascade dearomatization reaction of indole derivatives with propargyl carbonate was developed. The challenges associated with both the chemoselectivity between the carbon and nitrogen nucleophile and the enantioselective control during the formation of an all-carbon quaternary stereogenic center were well addressed by a Pd catalytic system derived from the Feringa ligand. A series of enantioenriched multiply substituted fused indolenines were provided in good yields (71-86%) with excellent enantioselectivity (91-96% ee) and chemoselectivity (3/4>19:1 in most cases).

Cadelis, Melissa M’s team published research in European Journal of Medicinal Chemistry in 2019-12-01 | 93247-78-0

European Journal of Medicinal Chemistry published new progress about Amines Role: ADV (Adverse Effect, Including Toxicity), PAC (Pharmacological Activity), RCT (Reactant), SPN (Synthetic Preparation), THU (Therapeutic Use), BIOL (Biological Study), RACT (Reactant or Reagent), PREP (Preparation), USES (Uses). 93247-78-0 belongs to class indole-building-block, and the molecular formula is C10H9NO2, Quality Control of 93247-78-0.

Cadelis, Melissa M.; Pike, Elliot I. W.; Kang, Weirong; Wu, Zimei; Bourguet-Kondracki, Marie-Lise; Blanchet, Marine; Vidal, Nicolas; Brunel, Jean Michel; Copp, Brent R. published the artcile< Exploration of the antibiotic potentiating activity of indolglyoxylpolyamines>, Quality Control of 93247-78-0, the main research area is bis indolyloxoacetamidopropyl butane diaminium trifluoroacetate preparation; antibacterial antifungal activity cytotoxicity SAR; Antimicrobial; Indole; Indolglyoxylamide; Polyamine; Potentiation.

A series of substituted di-indolglyoxylamido-spermine analogs I [R1 = 7-Me, 5-F, 5,6-di-Br, etc.] were prepared and evaluated for intrinsic antimicrobial properties and the ability to enhance antibiotic action. As a compound class, intrinsic activity was typically observed towards Gram-pos. bacteria and the fungus Cryptococcus neoformans, with notable exceptions being the compounds I [R1 = 5-Br, 5-Cl] analogs which also exhibited modest activity (MIC 34-50 μM) towards the Gram-neg. bacteria Escherichia coli and Klebsiella pneumoniae. Several analogs enhanced the activity of doxycycline towards the Gram-neg. bacteria Pseudomonas aeruginosa, E. coli, K. pneumoniae and Acinetobacter baumannii. Of particular note was the identification of five antibiotic enhancing analogs I [R1 = 5-Br, 7-F, 7-Me] which also exhibited low to no cytotoxicity and red blood cell haemolytic properties. The mechanisms of action of the I [R1 = 5-Br, 7-F] analogs were attributed to the ability to disrupt the integrity and depolarize, bacterial membranes.