18/10/2022 - Page 3 of 11 - Indole Building Blocks

Shukla, Nalin’s team published research in Trends in Carbohydrate Research in 2011 | 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.

In 2011,Trends in Carbohydrate Research included an article by Shukla, Nalin; Srivastava, Sanjay; Khare, Naveen K.; Mukhopadhay, Balaram; Khare, Anakshi. Safety of Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside. The article was titled 《Concise synthesis of a di- and a trisaccharide related to the pentasaccharide repeating unit of the O-antigen from E. coli O141》. The information in the text is summarized as follows:

Synthesis of a di- and a trisaccharide related to the pentasaccharide repeating unit of the O-antigen from E. coli O141 have been accomplished using com. available D-mannose, L-rhamnose and D-glucose. These di and trisaccharides have been synthesized as their p-methoxyphenyl and allyl glycosides, resp., which can be cleaved selectively for further conjugation with suitable aglycon. 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)

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

Tois, Jan’s team published research in Journal of Combinatorial Chemistry in 2001 | CAS: 380448-07-7

5-Chloro-3-formyl-1H-indole-2-carboxylic acid(cas: 380448-07-7) is a member of organic chlorides. Organic chlorides are compounds containing a carbon-chlorine bond, which are widely used in the oil field as a wax dissolver. They are generally not present in crude oils and are typically the result of additives, cleaning solutions or chemicals used for oil recovery.Application In Synthesis of 5-Chloro-3-formyl-1H-indole-2-carboxylic acid

Tois, Jan; Franzen, Robert; Aitio, Olli; Laakso, Into; Kylaenlahti, Irene published their research in Journal of Combinatorial Chemistry on December 31 ,2001. The article was titled 《Vilsmeier formylation of 2-carboxyindoles and preparation of O-benzylhydroxyureas on solid phase》.Application In Synthesis of 5-Chloro-3-formyl-1H-indole-2-carboxylic acid The article contains the following contents:

The Vilsmeier formylation has been introduced for the solid-phase functionalization of five different 2-carboxyindoles, e.g. 2-carboxyindole. The aldehyde functionality has been utilized in the preparation of O-benzylhydroxyureas, e.g. I. In the experimental materials used by the author, we found 5-Chloro-3-formyl-1H-indole-2-carboxylic acid(cas: 380448-07-7Application In Synthesis of 5-Chloro-3-formyl-1H-indole-2-carboxylic acid)

Feng, Tao’s team published research in Applied and Environmental Microbiology 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.Reference of 1H-Indole

The author of 《Interspecies and intraspecies signals synergistically regulate Lysobacter enzymogenes twitching motility》 were Feng, Tao; Han, Yong; Li, Bingqing; Li, Zhiqiang; Yu, Yameng; Sun, Qingyang; Li, Xiaoyu; Du, Liangcheng; Zhang, Xiao-Hua; Wang, Yan. And the article was published in Applied and Environmental Microbiology in 2019. Reference of 1H-Indole The author mentioned the following in the article:

The twitching motility of bacteria is closely related to environmental adaptability and pathogenic behaviors. Lysobacter is a good genus in which to study twitching motility because of the complex social activities and distinct movement patterns of its members. Regardless, the mechanism that induces twitching motility is largely unknown. In this study, we found that the interspecies signal indole caused Lysobacter to have irregular, random twitching motility with significantly enhanced speed. Deletion of qseC or qseB from the two-component system for indole signaling perception resulted in the disappearance of rapid, random movements and significantly decreased twitching activity. Indole-induced, rapid, random twitching was achieved through upregulation of expression of gene cluster pilE1-pilY11-pilX1-pilW1-pilV1-fimT1. In addition, under conditions of extremely low bacterial d., individual Lysobacter cells grew and divided in a stable manner in situ without any movement. The intraspecies quorum-sensing signaling factor 13-methyltetradecanoic acid, designated L. enzymogenes diffusible signaling factor (LeDSF), was essential for Lysobacter to produce twitching motility through indirect regulation of gene clusters pilM-pilN-pilO-pilP-pilQ and pilS1-pilR-pilA-pilB-pilC. These results demonstrate that the motility of Lysobacter is induced and regulated by indole and LeDSF, which reveals a novel theory for future studies of the mechanisms of bacterial twitching activities. The results came from multiple reactions, including the reaction of 1H-Indole(cas: 120-72-9Reference of 1H-Indole)

Cera, Gianpiero’s team published research in Organic & Biomolecular Chemistry in 2020 | 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).Quality Control of 5-Fluoro-1H-indole

《Trisulfonamide calix[6]arene-catalysed Michael addition to nitroalkenes》 was written by Cera, Gianpiero; Balestri, Davide; Bazzoni, Margherita; Marchio, Luciano; Secchi, Andrea; Arduini, Arturo. Quality Control of 5-Fluoro-1H-indole And the article was included in Organic & Biomolecular Chemistry in 2020. The article conveys some information:

The application of a novel family of trisulfonamide (TSA) calix[6]arenes I in general acid catalysis was described. Hydrogen-bonding interactions between acidic TSA and methanol boosted the reactivity of the Michael addition of indoles II (R = H, Me; R1 = H, F, Br, OH, OMe) to nitroalkene derivatives 3-R2-4-R3-C6H3CH=CHNO2 (R2 = H, OMe; R3 = H, Me, Br, Cl, OMe). The transformation occurs at a low catalyst loading of 5 mol%, allowing for the synthesis of nitroalkanes III with good yields and functional group tolerance. The experimental process involved the reaction of 5-Fluoro-1H-indole(cas: 399-52-0Quality Control of 5-Fluoro-1H-indole)

Ye, Yaqing’s team published research in European Journal of Organic Chemistry in 2021 | 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.COA of Formula: C8H6FN

Ye, Yaqing; Yue, Yuanyuan; Guo, Xiaohui; Chao, Junli; Yang, Yan; Sun, Chunying; Lv, Qingzhang; Liu, Jianming published an article in 2021. The article was titled 《Copper-Catalyzed Aerobic Oxidation of N-Pyridylindole Leading to Fused Quinazolinones》, and you may find the article in European Journal of Organic Chemistry.COA of Formula: C8H6FN The information in the text is summarized as follows:

Copper catalyzed aerobic oxidation enables the tandem selective and efficient transformation of N-pyridylindole for the construction of 11H-pyrido[2,1-b]quinazolin-11-ones. The reaction shows good efficiency to accomplish the aerobic oxidation Mechanistic investigation indicated the facile oxidation of N-pyridylindole underwent the single-electron-transfer oxidation, the capture of mol. oxygen and the extrusion of carbon monoxide to deliver the desired 11H-pyrido[2,1-b]quinazolin-11-ones. In the part of experimental materials, we found many familiar compounds, such as 5-Fluoro-1H-indole(cas: 399-52-0COA of Formula: C8H6FN)

Bozilovic, Jelena’s team published research in Collection Symposium Series in 2005 | CAS: 113162-36-0

Methyl 4-fluoro-1H-indole-2-carboxylate(cas: 113162-36-0) 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).Category: indole-building-block

《Synthesis and crystal structures of fluorinated indoles as RNA analogues》 was published in Collection Symposium Series in 2005. These research results belong to Bozilovic, Jelena; Bats, Jan W.; Engels, Joachim W.. Category: indole-building-block The article mentions the following:

Fluorinated indole nucleosides I (R1 = H, R2 = F; R1 = R2 = F; R1 = H, R2 = H) have been synthesized as RNA nucleosides. We crystallized two of the synthesized nucleosides. The sugar ring of I (R1 = H, R2 = F) has between a C3′-endo envelope and C2′-exo,C3′-endo half-chair conformation. The sugar ring of I (R1 = R2 = F) has a C3′-endo envelope conformation. Both fluoroindole groups are essentially planar. Neighboring layers of both crystals are connected by C-H···F-C interactions with bond distances of 2,39 and 2.40Å with C-H-F angles of 155°. All the synthesized nucleosides are going to be incorporated in RNA oligonucleotides and UV-melting profiles and CD-spectra are going to be determined The experimental process involved the reaction of Methyl 4-fluoro-1H-indole-2-carboxylate(cas: 113162-36-0Category: indole-building-block)

Bobbitt, James M.’s team published research in Journal of Organic Chemistry in 1980 | CAS: 59132-30-8

2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole-1,3-dicarboxylic acid(cas: 59132-30-8) 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.SDS of cas: 59132-30-8They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.

SDS of cas: 59132-30-8On May 9, 1980 ,《Electrochemistry of natural products. 7. Oxidative decarboxylation of some tetrahydro-β-carbolinecarboxylic acids》 appeared in Journal of Organic Chemistry. The author of the article were Bobbitt, James M.; Willis, John P.. The article conveys some information:

A series of 1,2,3,4-tetrahydro-β-carboline-1- and -3-carboxylic acids containing various substituents in positions 1, 2, and 3 were oxidized electrochem. In general, the acids were decarboxylated, and unsaturation was introduced into the C ring. The oxidation appears to take place through the indole ring, N, and possible mechanisms of the reactions are given. Parallels between the observed reactions and early steps in indole alkaloid biosynthesis are discussed. The oxidative dimerization of tetrahydrocarbazole is reported. The experimental process involved the reaction of 2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole-1,3-dicarboxylic acid(cas: 59132-30-8SDS of cas: 59132-30-8)

Cao, Suoding’s team published research in Journal of Carbohydrate Chemistry in 1998 | 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.SDS of cas: 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.

Cao, Suoding; Hernandez-Mateo, Fernando; Roy, Rene published an article in Journal of Carbohydrate Chemistry. The title of the article was 《Scope and applications of “”active and latent”” thioglycosyl donors. Part 4》.SDS of cas: 99409-32-2 The author mentioned the following in the article:

The relative reactivity of various thioglycosyl donors having Et, Ph, or para-substituted Ph groups with electron donating (N-Ac) or electron withdrawing (NO2) substituents were compared using 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose as standard glycosyl acceptor. The reactivity order was found to decrease from Et > Ph > p-acetamidophenyl > p-nitrophenyl. In the latter situation, when the thioglycosyl donor was also equipped with “”disarming”” ester protecting groups, they were found to be inert or inactive toward common thiophilic promoters. Alternatively, it was possible to selectively activate the “”armed”” perbenzylated p-nitrophenyl 1-thio-β-D-galactopyranoside in the presence of the corresponding “”disarmed”” perbenzoylated p-nitrophenyl 2,3,4-tri-O-benzoyl-1-thio-β-D-galactopyranoside which served as the glycosyl acceptor. When both “”armed”” perbenzylated thioglycosides were used as thioglycosyl donor and thioglycosyl acceptor, resp., the milder thiophilic promoter Me triflate was required for chemoselective activation. These results further demonstrate the potential of “”armed and disarmed”” “”active and latent”” thioglycosides in blockwise oligosaccharide syntheses. In the experimental materials used by the author, we found Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2SDS of 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.SDS of cas: 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.

Das, Banibrata’s team published research in Journal of Medicinal Chemistry in 2015 | CAS: 883500-73-0

5-Bromo-7-fluoro-1H-indole(cas: 883500-73-0) 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).Name: 5-Bromo-7-fluoro-1H-indole

Das, Banibrata; Vedachalam, Seenuvasan; Luo, Dan; Antonio, Tamara; Reith, Maarten E. A.; Dutta, Aloke K. published their research in Journal of Medicinal Chemistry on December 10 ,2015. The article was titled 《Development of a Highly Potent D2/D3 Agonist and a Partial Agonist from Structure-Activity Relationship Study of N6-(2-(4-(1H-Indol-5-yl)piperazin-1-yl)ethyl)-N6-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine Analogues: Implication in the Treatment of Parkinson’s Disease》.Name: 5-Bromo-7-fluoro-1H-indole The article contains the following contents:

The structure-activity relationship studies with N6-(2-(4-(1H-indol-5-yl)piperazin-1-yl)ethyl)-N6-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine derivatives led to development of a lead compound I which exhibited very high affinity (Ki, D2 = 16.4 nM, D3 = 1.15 nM) and full agonist activity (EC50 (GTPγS); D2 = 3.23 and D3 = 1.41 nM) at both D2 and D3 receptors. A partial agonist mol. II (EC50 (GTPγS); D2 = 21.6 (Emax = 27%) and D3 = 10.9 nM) was also identified. In a Parkinson’s disease (PD) animal model, I was highly efficacious in reversing hypolocomotion in reserpinized rats with a long duration of action, indicating its potential as an anti-PD drug. Compound II was also able to elevate locomotor activity in the above PD animal model significantly, implying its potential application in PD therapy. Furthermore, I was shown to be neuroprotective in protecting neuronal PC12 from toxicity of 6-OHDA. This report, therefore, underpins the notion that a multifunctional drug like I might have the potential not only to ameliorate motor dysfunction in PD patients but also to modify disease progression by protecting DA neurons from progressive degeneration. In the experiment, the researchers used many compounds, for example, 5-Bromo-7-fluoro-1H-indole(cas: 883500-73-0Name: 5-Bromo-7-fluoro-1H-indole)

Ma, Chun’s team published research in Angewandte Chemie, International Edition in 2019 | CAS: 120-72-9

In 2019,Angewandte Chemie, International Edition included an article by Ma, Chun; Jiang, Fei; Sheng, Feng-Tao; Jiao, Yinchun; Mei, Guang-Jian; Shi, Feng. Application of 120-72-9. The article was titled 《Design and Catalytic Asymmetric Construction of Axially Chiral 3,3′-Bisindole Skeletons》. The information in the text is summarized as follows:

The first catalytic asym. construction of 3,3′-bisindole skeletons bearing both axial and central chirality has been established by organocatalytic asym. addition reactions of 2-substituted 3,3′-bisindoles with 3-indolylmethanols (up to 98 % yield, all >95:5 d.r., >99 % ee). This reaction also represents the first highly enantioselective construction of axially chiral 3,3′-bisindole skeletons, and utilizes the strategy of introducing a bulky group to the ortho-position of prochiral 3,3′-bisindoles. This reaction not only provides a good example for simultaneously controlling axial and central chirality in one operation, but also serves as a new strategy for catalytic enantioselective construction of axially chiral 3,3′-bisindole backbones from prochiral substrates. After reading the article, we found that the author used 1H-Indole(cas: 120-72-9Application of 120-72-9)