21/10/2022 - Page 2 of 5 - Indole Building Blocks

Kim, Taegwan’s team published research in Molecules in 2022 | 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.Application of 120-72-9

Application of 120-72-9In 2022 ,《Recent Advances in Divergent Synthetic Strategies for Indole-Based Natural Product Libraries》 appeared in Molecules. The author of the article were Kim, Taegwan; Ha, Min Woo; Kim, Jonghoon. The article conveys some information:

A review. Considering the potential bioactivities of natural product and natural product-like compounds with highly complex and diverse structures, the screening of collections and small-mol. libraries for high-throughput screening (HTS) and high-content screening (HCS) has emerged as a powerful tool in the development of novel therapeutic agents. Herein, we review the recent advances in divergent synthetic approaches such as complexity-to-diversity (Ctd) and biomimetic strategies for the generation of structurally complex and diverse indole-based natural product and natural product-like small-mol. libraries. The results came from multiple reactions, including the reaction of 1H-Indole(cas: 120-72-9Application of 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

Kumar, Alok’s team published research in ACS Sensors in 2020 | CAS: 120-72-9

《Ultrafast detection and discrimination of methanol gas using a polyindole-embedded substrate integrated waveguide microwave sensor》 was written by Kumar, Alok; Wang, Cong; Meng, Fan-Yi; Jiang, Cheng-Peng; Yan, Guo-Feng; Zhao, Meng; Jing, Chang-Qiang; Wang, Lei. COA of Formula: C8H7N And the article was included in ACS Sensors in 2020. The article conveys some information:

The fast and sensitive detection of methanol gas using cost-effective sensors in the industry is a significant issue to be addressed. Herein, a polyindole (PIn)-deposited substrate integrated waveguide (SIW) has been introduced to perform quant. and qual. methanol gas sensing with quick response and recovery time at room temperature First, PIn is synthesized and deposited in the microwell etched at the intensified elec. field region of the microwave-based cavity resonator, which gives a sensing response through variation of PIn’s high-frequency conductivity and dielec. property caused by the adsorption and desorption of methanol gas. Second, an enhanced filling factor and high Q factor have been attained using the proposed microwell etched SIW structure, which exhibits high sensitivity in terms of frequency shift (3.33 kHz/ppm), amplitude shift (0.005 dB/ppm), bandwidth broadening (3.66 kHz/ppm), and loaded Q factor (10.60 Q value/ppm). Third, the gas measurement results reveal excellent long-term stability with a relative standard deviation (RSD) of 0.02% for 7 days, excellent repeatability with an RSD of 0.004%, and desired response and recovery time of 95 and 120 s, resp. The results indicate that the proposed microwave sensor has great potential to achieve high sensitivity and fast response toward methanol gas mols. at room temperature In the experiment, the researchers used many compounds, for example, 1H-Indole(cas: 120-72-9COA of Formula: C8H7N)

Zhao, Fei’s team published research in ACS Catalysis 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

Recommanded Product: 5-Fluoro-1H-indoleIn 2021 ,《Chemo-, Regio-, and Stereoselective Assembly of Polysubstituted Furan-2(5H)-ones Enabled by Rh(III)-Catalyzed Domino C-H Alkenylation/Directing Group Migration/Lactonization: A Combined Experimental and Computational Study》 appeared in ACS Catalysis. The author of the article were Zhao, Fei; Zhou, Zhi; Lu, Yangbin; Qiao, Jin; Zhang, Xiaoning; Gong, Xin; Liu, Siyu; Lin, Shuang; Wu, Xiaowei; Yi, Wei. The article conveys some information:

Exploring multistep cascade reactions triggered by C-H activation are recognized as appealing, yet challenging. Herein, author disclose a Rh(III)-catalyzed domino C-H coupling of N-carbamoyl indoles and 4-hydroxy-2-alkynoates for the streamlined assembly of highly functionalized furan-2(5H)-ones in which the carbamoyl-directing group (DG) is given a dual role of an auxiliary group and a migrating acylating reagent via the cleavage of stable C-N bonds at room temperature More importantly, the obtained furan-2(5H)-one skeleton could be further functionalized under air in situ via C5-H hydroxylation by simply switching the solvent or additive, providing fully substituted furan-2(5H)-ones with the installation of an alc.-based C5 quaternary carbon center. Detailed exptl. studies and d. functional theory calculations reveal that a Rh(III)-mediated tandem C-H activation/alkyne insertion/DG migration/lactonization accounts for the developed transformation to achieve high functionalities with the observed exclusive selectivity. The potential biol. application of the obtained furan-2(5H)-ones as a class of potent PPARγ ligands further highlights the synthetic utility of the developed methodol. This protocol is endowed with several salient features including efficient multistep cascade triggered by C-H activation, excellent chemo-, regio-, and stereoselectivity, high bond-forming efficiency (e.g., two C-C and two C-O bonds), solvent- or additive-controlled product selectivity. In the part of experimental materials, we found many familiar compounds, such as 5-Fluoro-1H-indole(cas: 399-52-0Recommanded Product: 5-Fluoro-1H-indole)

Zou, Bin’s team published research in Tetrahedron in 2014 | CAS: 885518-25-2

6-Fluoro-1H-indol-4-amine(cas: 885518-25-2) belongs to anime. Nitrous acid converts secondary amines (aliphatic or aromatic) to N-nitroso compounds (nitrosamines): R2NH + HNO2 → R2N―NO. Some nitrosamines are potent cancer-inducing substances, and their possible formation is a serious consideration when nitrites, which are salts of nitrous acid, are present in foods or pharmaceutical preparations. Tertiary amines give rise to nitrosamines more slowly; an alkyl group is eliminated as an aldehyde or ketone, along with nitrous oxide, N2O.Electric Literature of C8H7FN2

Zou, Bin; Chen, Chun; Leong, Seh Yong; Ding, Mei; Smith, Paul W. published an article on January 21 ,2014. The article was titled 《An efficient synthesis of 4,6-dihydrospiro[azepino[4,3,2-cd]indole-3,3′-indoline]-2′,5(1H)-diones via multi-component reaction》, and you may find the article in Tetrahedron.Electric Literature of C8H7FN2 The information in the text is summarized as follows:

A facile and efficient one-pot three-component synthesis of spiroazepinoindolones has been developed. Using DMF as solvent without any addnl. acid or metal catalysts, the three-component reaction of readily available isatins, indolamines, and Meldrum’s acid affords a new class of spiroheterocycles in moderate yield. In the experimental materials used by the author, we found 6-Fluoro-1H-indol-4-amine(cas: 885518-25-2Electric Literature of C8H7FN2)

Somboonna, Naraporn’s team published research in mBio in 2019 | CAS: 120-72-9

In 2019,mBio included an article by Somboonna, Naraporn; Ziklo, Noa; Ferrin, Thomas E.; Suh, Jung Hyuk; Dean, Deborah. Application In Synthesis of 1H-Indole. The article was titled 《Clinical persistence of Chlamydia trachomatis sexually transmitted strains involves novel mutations in the functional αββα tetramer of the tryptophan synthase operon》. The information in the text is summarized as follows:

We examined serial urogenital samples from a woman who had recurrent Ct infections over 4 years despite antibiotic treatment. The Ct isolates from each infection episode were genome sequenced and analyzed for phenotypic, structural, and functional characteristics. Each isolate displayed an altered αββα structure, could not synthesize tryptophan from indole, and had significantly lower trpBA expression but higher intracellular tryptophan levels compared with those of reference Ct strain F/IC-Cal3. Our data indicate that emergent mutations in the tryptophan operon, which were previously thought to be restricted only to ocular Ct strains, likely resulted in in vivo persistence in the described patient and represents a novel host-pathogen adaptive strategy for survival. IMPORTANCE:Chlamydia trachomatis (Ct) is the most common sexually transmitted bacterium with more than 131 million cases occurring annually worldwide. Here, we discovered that the genomes of serial isolates from a woman with recurrent, treated Ct STIs over many years were identical with a novel synthase mutation. Our findings indicate an emerging adaptive host-pathogen evolutionary strategy for survival in the urogenital tract that will prompt the field to further explore chlamydial persistence, evaluate the genetics of mutant Ct strains and fitness within the host, and their implications for disease pathogenesis. In the experiment, the researchers used 1H-Indole(cas: 120-72-9Application In Synthesis of 1H-Indole)

Yu, Zong-Yi’s team published research in RSC Advances 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.Electric Literature of C8H6FN

《Rose bengal as photocatalyst: visible light-mediated Friedel-Crafts alkylation of indoles with nitroalkenes in water》 was written by Yu, Zong-Yi; Zhao, Jing-Nan; Yang, Fan; Tang, Xiao-Fei; Wu, Yu-Feng; Ma, Cun-Fei; Song, Bo; Yun, Lei; Meng, Qing-Wei. Electric Literature of C8H6FN And the article was included in RSC Advances in 2020. The article conveys some information:

A novel and facile visible-light-mediated alkylation of indoles and nitroalkenes has been developed. In this protocol, rose bengal acts as a photosensitizer, and environmentally benign water was used as the green and efficient reaction medium. Indoles reacted smoothly with nitroalkenes under the irradiation of visible-light and generated corresponding 3-(2-nitroalkyl)indoles I (R1 = H, 5-F, 6-Me, etc.; R2 = C6H5, 4-FC6H4, 2-thienyl, etc.) in moderate to good yields (up to 87%). In the experiment, the researchers used 5-Fluoro-1H-indole(cas: 399-52-0Electric Literature of C8H6FN)

Lee, C. I.’s team published research in HortScience in 1977 | 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.SDS of cas: 60096-23-3

《Promotion of rooting in stem cuttings of several ornamental plants by pretreatment with acid or base》 was published in HortScience in 1977. These research results belong to Lee, C. I.; Paul, J. L.; Hackett, W. P.. SDS of cas: 60096-23-3 The article mentions the following:

Rooting of stem cuttings of Bougainvillea cv. San Diego Red, Ceratonia siliqua, Chrysanthemum morifolium cvs. Golden Anne and Mandalay, Euonymus japonica, cv. Yellow Edge, Euphorbia pulcherrima cv. Eckspoint C-1 Red, Hedera helix, Trachelospermum jasminoides, Juglans hindsii, Pistacia chinensis, and Salix laevigata was greatly promoted by basal dipping in 2N H2SO4 prior to applying 3000 ppm IBA K salt (I K salt) [60096-23-3]. Pretreatment with NaOH (pH 10.5) resulted in considerable increase of rooting of cuttings of Rhododendron cv. Sweetheart Supreme, Bougainvillea, Liquidambar styraciflua, Osmanthus heterophyllus cv. Ilicifolius, and Pinus radiataa. In the experiment, the researchers used Potassium 4-(1H-indol-3-yl)butanoate(cas: 60096-23-3SDS of cas: 60096-23-3)

Minuth, Tobias’s team published research in Synlett in 2008 | 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.Related Products 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.

Related Products of 99409-32-2On June 13, 2008, Minuth, Tobias; Boysen, Mike M. K. published an article in Synlett. The article was 《A general and efficient route to 3-O-modified carbohydrate bis(oxazoline) ligands》. The article mentions the following:

An efficient route to derivatives of carbohydrate-based bis(oxazoline) ligands with 3-O substituents of varying steric demand is described. The synthesis of the new ligands proceeds via a thioglucoside key intermediate. The double cyclization to the desired bis(oxazolines) is initiated with N-iodosuccinimide under mild conditions. Employing this strategy, four new 3-O-modified bis(oxazoline) ligands were obtained in good yields. 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: 99409-32-2Related Products of 99409-32-2) was used in this study.

Tang, Zhi’s team published research in Organic Letters in 2019 | CAS: 399-52-0

In 2019,Organic Letters included an article by Tang, Zhi; Liu, Zhili; Tong, Zhou; Xu, Zhihui; Au, Chak-Tong; Qiu, Renhua; Kambe, Nobuaki. Product Details of 399-52-0. The article was titled 《Cu-Catalyzed Cross-Dehydrogenative Coupling of Heteroaryl C(sp2)-H and Tertiary C(sp3)-H Bonds for the Construction of All-Carbon Triaryl Quaternary Centers》. The information in the text is summarized as follows:

A Cu-catalyzed protocol for cross-dehydrogenative coupling of benzofuranones with quinolines, indoles, carbazoles, and thiophene, which furnishes highly functionalized 3,3-diaryl benzofuranones bearing a three aryl quaternary carbon center at the C3 position in good yields, has been developed. A radical mechanism is proposed. In the part of experimental materials, we found many familiar compounds, such as 5-Fluoro-1H-indole(cas: 399-52-0Product Details of 399-52-0)

Mohr, Yorck’s team published research in ACS Catalysis in 2020 | CAS: 399-52-0

《Regiospecificity in Ligand-Free Pd-Catalyzed C-H Arylation of Indoles: LiHMDS as Base and Transient Directing Group》 was written by Mohr, Yorck; Renom-Carrasco, Marc; Demarcy, Clement; Quadrelli, Elsje Alessandra; Camp, Clement; Wisser, Florian M.; Clot, Eric; Thieuleux, Chloe; Canivet, Jerome. COA of Formula: C8H6FN And the article was included in ACS Catalysis in 2020. The article conveys some information:

A highly efficient catalyst-base pair for the C-H arylation of free (NH)-indoles in the C-3 position was reported. Ligand-free palladium acetate coupled with lithium hexamethyldisilazide (LiHMDS) catalyzed the regiospecific, i.e. 100% regioselective, C-3 arylation of indoles with high turnover numbers This catalytic system was successfully applied to a wide range of substrates including various functional aryl halides and indolic cores. The unique role of LiHMDS as both a base and unexpected transient directing group was revealed exptl. and elucidated computationally, in line with a Heck-type insertion-elimination mechanism. In the experimental materials used by the author, we found 5-Fluoro-1H-indole(cas: 399-52-0COA of Formula: C8H6FN)