18/10/2022 - Page 8 of 11 - Indole Building Blocks

Pillaiyar, Thanigaimalai’s team published research in Advanced Synthesis & Catalysis 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.Application In Synthesis of 5-Fluoro-1H-indole

In 2019,Advanced Synthesis & Catalysis included an article by Pillaiyar, Thanigaimalai; Uzair, Muhammad; Ullah, Saif; Schnakenburg, Gregor; Mueller, Christa E.. Application In Synthesis of 5-Fluoro-1H-indole. The article was titled 《Decarboxylative Coupling Reaction of 2-(1H-indol-3-yl)acetic Acids with Indole, Azaindole, Benzimidazole and Indazole Derivatives》. The information in the text is summarized as follows:

A new, mild and efficient copper(II)-promoted decarboxylative coupling reaction of 2-(1H-indol-3-yl)acetic acid derivatives I (R = H, 4-Cl, 5-OCH3, 6-F, 5-Cl, 6-Cl; R1 = H, CH3) with a variety of (substituted) indoles II (R2 = H, Ph, CO2Et; R3 = H, CH3; R4 = H, Me, F, Br, MeO, CHO; R5 = H, MeO, CHO, F; R6 = H, Cl, Br, MeO, Et, CN; R7 = H, Br; R6R7 = CH=CH-CH=CH) yielding (un)sym. substituted 3,3′-diindolylmethanes (DIMs) III have been reported. Reaction of 2-(1H-indol-3-yl)acetic acid I (R = R1 = H) with 7-azaindole led to 3-((1H-indol-3-yl)methyl)-1H-pyrrolo[2,3-b]pyridine, while 4-, 5-, and 6-azaindoles and benzimidazole reacted at the N1-nitrogen atom. Reaction of I (R = R1 = H) with 1H-indazole led to a mixture of 1-((1H-indol-3-yl)methyl)-1H-indazole and 2-((1H-indol-3-yl)methyl)-2H-indazole. The new method allows large-scale synthesis of biol. active DIMs. After reading the article, we found that the author used 5-Fluoro-1H-indole(cas: 399-52-0Application In Synthesis of 5-Fluoro-1H-indole)

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

Meng, Tingting’s team published research in Archiv der Pharmazie (Weinheim, Germany) in 2021 | 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.Safety of 1H-Indole

Safety of 1H-IndoleIn 2021 ,《Recent advances in indole dimers and hybrids with antibacterial activity against methicillin-resistant Staphylococcus aureus》 appeared in Archiv der Pharmazie (Weinheim, Germany). The author of the article were Meng, Tingting; Hou, Yani; Shang, Congshan; Zhang, Jing; Zhang, Bo. The article conveys some information:

A review. Methicillin-resistant Staphylococcus aureus (MRSA), one of the major and most dangerous pathogens in humans, is a causative agent of severe pandemic of mainly skin and soft tissue and occasionally fatal infections. Therefore, it is imperative to develop potent and novel anti-MRSA agents. Indole derivatives could act against diverse enzymes and receptors in bacteria, occupying a salient place in the development of novel antibacterial agents. Dimerization and hybridization are common strategies to discover new drugs, and a number of indole dimers and hybrids possess potential antibacterial activity against a panel of clin. important pathogens including MRSA. Accordingly, indole dimers and hybrids are privileged scaffolds for the discovery of novel anti-MRSA agents. This outlines the recent development of indole dimers and hybrids with a potential activity against MRSA, covering articles published between 2010 and 2020. The structure-activity relationship and the mechanism of action are also discussed to facilitate further rational design of more effective candidates. In the experiment, the researchers used 1H-Indole(cas: 120-72-9Safety of 1H-Indole)

Starbuck, C. J.’s team published research in Journal of Environmental Horticulture in 1987 | 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.Application In Synthesis of Potassium 4-(1H-indol-3-yl)butanoate

Application In Synthesis of Potassium 4-(1H-indol-3-yl)butanoateOn September 30, 1987 ,《Increasing production of new roots by potted roses with root applied IBA》 was published in Journal of Environmental Horticulture. The article was written by Starbuck, C. J.. The article contains the following contents:

Dormant bare root rose (Rosa × hybrida ‘Las Vegas’) plants with roots dipped in a 500 ppm solution of indole-3-butyric acid (IBA) produced 50% more new roots than untreated plants. However, plants treated with 100 and 500 ppm IBA had fewer open flower buds 8 wks after potting and shorter average shoot length after 18 wks than did controls. Treatment with the potassium salt of IBA (KIBA) at 100 and 500 ppm also stimulated new root production and retarded flower bud development but did not reduce shoot length. Addition of starch-polyacrylate gel to treatment solutions counteracted the root promoting effect of IBA but not of KIBA. Gel itself also caused a reduction in average shoot length. In the experimental materials used by the author, we found Potassium 4-(1H-indol-3-yl)butanoate(cas: 60096-23-3Application In Synthesis of Potassium 4-(1H-indol-3-yl)butanoate)

Misra, A. K.’s team published research in Bioorganic & Medicinal Chemistry Letters in 2001 | 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.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.

Electric Literature of C22H25NO9SOn October 22, 2001 ,《Efficient synthesis of lactosaminylated core-2 O-glycans》 was published in Bioorganic & Medicinal Chemistry Letters. The article was written by Misra, A. K.; Fukuda, M.; Hindsgaul, O.. The article contains the following contents:

A series of lactosaminylated oligosaccharides found in mucin type O-glycans was synthesized using a generalized block strategy. The synthesis involved the addition of a protected lactosamine donor to a partially protected T-disaccharide derivative The nonreducing galactose residues of the deblocked oligosaccharide products could be removed by β-galactosidase from jack bean to produce the corresponding GlcNAc terminated compounds A series of tri- to hexasaccharides was thus efficiently produced. 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: 99409-32-2Electric Literature of C22H25NO9S) was used in this study.

Chery, Florence’s team published research in European Journal of Organic Chemistry in 2002 | 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.

Chery, Florence; Cassel, Stephanie; Wessel, Hans Peter; Rollin, Patrick published an article on January 31 ,2002. The article was titled 《Synthesis of anomeric sulfimides and their use as a new family of glycosyl donors》, and you may find the article in European Journal of Organic Chemistry.Recommanded Product: Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside The information in the text is summarized as follows:

We introduce a convenient synthesis of anomeric sulfimides, the ability of which to act as glycosyl donors has been tested with various thiophilic reagents and acceptors. The experimental process involved the reaction 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.

Peters, J. L.’s team published research in NATO ASI Series, Series H: Cell Biology 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.Product Details of 99409-32-2They 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.

In 1991,NATO ASI Series, Series H: Cell Biology included an article by Peters, J. L.; Wesselius, J. C.; Georghiou, K. C.; Kendrick, R. E.; Van Tuinen, A.; Koornneef, M.. Product Details of 99409-32-2. The article was titled 《The physiology of photomorphogenetic tomato mutants》. The information in the text is summarized as follows:

A review with 37 references Photomorphogenesis of higher plants is a complex process resulting from the co-action of at least 3 different photoreceptors: phytochrome, a blue light (B)/UV-A photoreceptor (cryptochrome) and a UV-B photoreceptor. The existence of multiple photoreceptor types, e.g. type I (PI) or light-labile phytochrome and type II (PII) or light-stable phytochrome, adds to the complexity. The assignment of specific functions to the distinct mol. species of the photoreceptor is therefore being studied with the aid of photomorphogenetic mutants in which certain parts of the morphogenetic pathway are eliminated or altered. The relevance of the changed part in the mutant is directly indicated by its difference in response compared to its isogenic wild type. Mutants can be found (isolated) from natural populations or varieties (cultivars) or more efficiently after mutagenic treatment: using e.g. chems., irradiation; somaclonal variation; transposon insertion; transformation; introduction of antisense RNA. Photomorphogenetic mutants can be divided into three groups: photoreceptor mutants, lacking the photoreceptor or containing a modified photoreceptor which is non-functional; transduction chain mutants and response mutants. The first two will be pleiotropic for all responses regulated by the photoreceptor, while the latter are modified with respect to particular responses. Tomato (Lycospersicon esculentum) has several features which make it suitable for genetic anal. It is widely studied since it is a crop species of economic importance and many mutants are available. In addition it has a relatively small genome, is diploid with 12 chromosomes, is self pollinating, individual plants producing a large number (≈2000) of relatively large seeds which result in seedlings suitable for physiol. anal. and it is amenable for Agrobacterium-mediated transformation. Mutants of tomato which are important for the study of photomorphogenesis are discussed. In the experiment, the researchers used Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2Product Details of 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.Product Details of 99409-32-2They 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.

Struve, Daniel K.’s team published research in Canadian Journal of Forest Research in 1986 | CAS: 60096-23-3

Struve, Daniel K.; Arnold, Michael A. published an article in Canadian Journal of Forest Research. The title of the article was 《Aryl esters of indolebutyric acid increase root regeneration in 3-0 red oak seedlings》.COA of Formula: C12H12KNO2 The author mentioned the following in the article:

Dormant 3-0 red oak seedlings (Quercus rubra) were given a 3-s basal dip in 20 mM solutions of indole-3-butyric acid (IBA) [133-32-4], the K salt of IBA (K-IBA) [60096-23-3], N-phenyl indolyl-3-butyramide (NP-IBA) [104055-89-2], phenyl indole-3-thiolobutyrate (P-ITB) [85977-73-7], or phenyl indolyl-3-butyrate (P-IBA) [72218-92-9]. Seedlings dipped in water or 95% EtOH served as controls. Fifty-six days after treatment, seedlings treated with NP-IBA and P-ITB regenerated ≥3-fold more roots (48.7 and 40.0 roots, resp.) than did EtOH-treated control seedlings, which regenerated 14.3 roots. Seedlings treated with P-IBA regenerated 26 roots per seedling. Seedlings treated with NP-IBA and P-ITB had smaller leaves than IBA- and K-IBA treated seedlings. NP-IBA treated seedlings had more leaves than IBA- or K-IBA treated seedlings (155.3 vs. 59 and 53.3, resp.), but had similar leaf surface area. P-ITB-treated seedlings had similar numbers of leaves as IBA- and K-IBA-treated seedlings, but leaves were smaller in size, resulting in less total leaf area. P-IBA-treated seedlings had the greatest total leaf surface area, 1509 cm2; water- and EtOH-treated seedlings had total leaf surface areas of 1271 and 866 cm2, resp. In the experiment, the researchers used many compounds, for example, Potassium 4-(1H-indol-3-yl)butanoate(cas: 60096-23-3COA of Formula: C12H12KNO2)

Ma, Qiao’s team published research in International Biodeterioration & Biodegradation in 2019 | CAS: 120-72-9

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)

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

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)