22/02/2023 - Page 9 of 66 - Indole Building Blocks

Huang, Guiting et al. published their research in International Journal of Pharmaceutics (Amsterdam, Netherlands) in 2021 | CAS: 442-51-3

7-Methoxy-1-methyl-9H-pyrido[3,4-b]indole (cas: 442-51-3) belongs to indole derivatives. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Recommanded Product: 442-51-3

Nose-to-brain delivery of drug nanocrystals by using Ca²⁺ responsive deacetylated gellan gum based in situ-nanogel was written by Huang, Guiting;Xie, Jin;Shuai, Shuyuan;Wei, Shaofeng;Chen, Yingchong;Guan, Zhiyu;Zheng, Qin;Yue, Pengfei;Wang, Changhong. And the article was included in International Journal of Pharmaceutics (Amsterdam, Netherlands) in 2021.Recommanded Product: 442-51-3 This article mentions the following:

The objective of this study is to use a carbohydrate polymer deacetylated gellan gum (DGG) as matrix to design nanocrystals based intranasal in situ gel (IG) for nose-to -brain delivery of drug. The harmine nanocrystals (HAR-NC) as model drug were prepared by coupling homogenization and spray-drying technol. The HAR-NC was redispersed in the (DGG) solutions and formed the ionic-triggered harmine nanocrystals based in situ gel (HAR-NC-IG). The crystal state of HAR remained unchanged during the homogenization and spray-drying. And the HAR-NC-IG with 0.5% DGG exhibited excellent in situ-gelation ability, water retention property and in vitro release behavior. The bioavailability in brain of intranasal HAR-NC-IG were 25-fold higher than that of oral HAR-NC, which could be attributed to nanosizing effect of HAR-NC and bioadhesive property of DGG triggered by nasal fluid. And the HAR-NC-IG could significantly inhibit the expression of acetylcholinesterase (AchE) and increase the content of acetylcholin (ACh) in brain compared with those of reference formulations (p < 0.01). The DGG based nanocrystals-in situ gel was a promising carrier for nose-to-brain delivery of poorly soluble drug, which could prolong the residence time and improve the bioavailability of poorly soluble drugs in brain. In the experiment, the researchers used many compounds, for example, 7-Methoxy-1-methyl-9H-pyrido[3,4-b]indole (cas: 442-51-3Recommanded Product: 442-51-3).

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Yuan, Jifang et al. published their research in Biomaterials Science in 2020 | CAS: 280744-09-4

3-(2,4-Dichlorophenyl)-4-(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione (cas: 280744-09-4) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.HPLC of Formula: 280744-09-4

Sustained release of inhibitor from bionic scaffolds for wound healing and functional regeneration was written by Yuan, Jifang;Hou, Qian;Zhong, Lingzhi;Dai, Xin;Lu, Qiang;Li, Meirong;Fu, Xiaobing. And the article was included in Biomaterials Science in 2020.HPLC of Formula: 280744-09-4 This article mentions the following:

Small mols. play remarkable roles in promoting tissue regeneration, but are limited by their burst release. Various bioactive mols. are required to create a suitable niche for better skin regeneration by controlling their release behaviors. Herein, a small mol. SB216763, a GSK-3 inhibitor, was loaded on silk fibroin nanofibers (SNF), and then mixed with chitosan (CS) to prepare the small mol.-loaded composite bionic scaffolds (CSNF-SB). Given the interaction of SNF and SB216763, the sustained release of SB216763 for more than 21 days was achieved for SNF and CSNF-SB composite scaffolds. Compared to drug-free CSNF scaffolds, CSNF-SB showed better cell adhesion and proliferation capacity, suggesting bioactivity. The upregulated expression of 尾-catenin in fibroblasts in vitro revealed that the released small mols. maintained their function in composite scaffolds. Quicker and better wound healing was realized with the drug-loaded scaffolds, which was significantly superior to that treated with drug-free scaffolds. Unlike the DFO-loaded silk hydrogel system, hair follicle neogenesis was also found in the drug-loaded-scaffold treatment wounds, demonstrating functional recovery. Therefore, silk nanofibers as versatile carriers for different small bioactive mols. could be used to fabricate scaffolds with optimized niches and then achieve functional recovery of tissues. The small mol.-loaded bionic scaffolds have a promising future in skin tissue regeneration. In the experiment, the researchers used many compounds, for example, 3-(2,4-Dichlorophenyl)-4-(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione (cas: 280744-09-4HPLC of Formula: 280744-09-4).

Takaishi, Kazuto et al. published their research in Chemical Communications (Cambridge, United Kingdom) in 2021 | CAS: 2521-13-3

5-Methoxy-1-methyl-1H-indole (cas: 2521-13-3) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Category: indole-building-block

C-Methylenation of anilines and indoles with CO₂ and hydrosilane using a pentanuclear zinc complex catalyst was written by Takaishi, Kazuto;Kosugi, Hiroyasu;Nishimura, Ritsuki;Yamada, Yuya;Ema, Tadashi. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2021.Category: indole-building-block This article mentions the following:

The one-step C-methylenation of anilines and indoles with CO₂ and phenylsilane was catalyzed by a pentanuclear Zn^II complex to give diarylmethanes via geminal C-H and C-C bond formation. It was proposed that the zinc-hydride complex generated in-situ was a catalytically active species and that bis(silyl)acetal was a key intermediate. When aniline was used as a substrate, both the C-methylenation and N-methylation proceeded. In the experiment, the researchers used many compounds, for example, 5-Methoxy-1-methyl-1H-indole (cas: 2521-13-3Category: indole-building-block).

Cameron, Kimberly O. et al. published their research in Journal of Medicinal Chemistry in 2016 | CAS: 1467057-23-3

6-Chloro-5-(4-(1-hydroxycyclobutyl)phenyl)-1H-indole-3-carboxylic acid (cas: 1467057-23-3) belongs to indole derivatives. Indole, first isolated in 1866, and it is commonly synthesized from phenylhydrazine and pyruvic acid, although several other procedures have been discovered.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Application In Synthesis of 6-Chloro-5-(4-(1-hydroxycyclobutyl)phenyl)-1H-indole-3-carboxylic acid

Discovery and Preclinical Characterization of 6-Chloro-5-[4-(1-hydroxycyclobutyl)phenyl]-1H-indole-3-carboxylic Acid (PF-06409577), a Direct Activator of Adenosine Monophosphate-activated Protein Kinase (AMPK), for the Potential Treatment of Diabetic Nephropathy was written by Cameron, Kimberly O.;Kung, Daniel W.;Kalgutkar, Amit S.;Kurumbail, Ravi G.;Miller, Russell;Salatto, Christopher T.;Ward, Jessica;Withka, Jane M.;Bhattacharya, Samit K.;Boehm, Markus;Borzilleri, Kris A.;Brown, Janice A.;Calabrese, Matthew;Caspers, Nicole L.;Cokorinos, Emily;Conn, Edward L.;Dowling, Matthew S.;Edmonds, David J.;Eng, Heather;Fernando, Dilinie P.;Frisbie, Richard;Hepworth, David;Landro, James;Mao, Yuxia;Rajamohan, Francis;Reyes, Allan R.;Rose, Colin R.;Ryder, Tim;Shavnya, Andre;Smith, Aaron C.;Tu, Meihua;Wolford, Angela C.;Xiao, Jun. And the article was included in Journal of Medicinal Chemistry in 2016.Application In Synthesis of 6-Chloro-5-(4-(1-hydroxycyclobutyl)phenyl)-1H-indole-3-carboxylic acid This article mentions the following:

Adenosine monophosphate-activated protein kinase (AMPK) is a protein kinase involved in maintaining energy homeostasis within cells. On the basis of human genetic association data, AMPK activators were pursued for the treatment of diabetic nephropathy. Identification of an indazole amide high throughput screening (HTS) hit followed by truncation to its minimal pharmacophore provided an indazole acid lead compound Optimization of the core and aryl appendage improved oral absorption and culminated in the identification of indole acid, PF-06409577 (7). Compound 7 was advanced to first-in-human trials for the treatment of diabetic nephropathy. In the experiment, the researchers used many compounds, for example, 6-Chloro-5-(4-(1-hydroxycyclobutyl)phenyl)-1H-indole-3-carboxylic acid (cas: 1467057-23-3Application In Synthesis of 6-Chloro-5-(4-(1-hydroxycyclobutyl)phenyl)-1H-indole-3-carboxylic acid).

Azizi, Mohamed Salah et al. published their research in European Journal of Organic Chemistry in 2016 | CAS: 5428-09-1

2-Allylisoindoline-1,3-dione (cas: 5428-09-1) belongs to indole derivatives. 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. Indole plays a fundamental role for QS in E. coli, being one of the signal molecules responsible for the transcription of a variety of genes (gabT, and tnaB ASTD). Reference of 5428-09-1

Nickel(0)-Catalyzed N-Allylation of Amides and p-Toluenesulfonamide with Allylic Alcohols under Neat and Neutral Conditions was written by Azizi, Mohamed Salah;Edder, Youssef;Karim, Abdallah;Sauthier, Mathieu. And the article was included in European Journal of Organic Chemistry in 2016.Reference of 5428-09-1 This article mentions the following:

Nickel(0)-catalyzed direct N-allylation of amides and p-toluenesulfonamide with allylic alcs. took place in the presence of Ni⁰-diphosphine complexes. The corresponding N-allylated (and/or N,N-diallylated) products were obtained in moderate to high yields under neutral conditions. In the experiment, the researchers used many compounds, for example, 2-Allylisoindoline-1,3-dione (cas: 5428-09-1Reference of 5428-09-1).

Tang, Qing-Gang et al. published their research in Organic Letters in 2020 | CAS: 20780-72-7

4-Bromoindoline-2,3-dione (cas: 20780-72-7) belongs to indole derivatives. 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.Quality Control of 4-Bromoindoline-2,3-dione

Organocatalytic Aza-Michael/Michael Cyclization Cascade Reaction: Enantioselective Synthesis of Spiro-oxindole Piperidin-2-one Derivatives was written by Tang, Qing-Gang;Cai, Sen-Lin;Wang, Chuan-Chuan;Lin, Guo-Qiang;Sun, Xing-Wen. And the article was included in Organic Letters in 2020.Quality Control of 4-Bromoindoline-2,3-dione This article mentions the following:

A simple, direct and highly enantioselective synthesis of spiro-oxindole piperidin-2-one derivatives was achieved through an aza-Michael/Michael cyclization cascade sequence using a squaramide catalyst. The desired products were obtained in excellent yields (up to 99%) and good to high stereoselectivities (up to >20:1 dr and up to 99% ee) under mild conditions. In the experiment, the researchers used many compounds, for example, 4-Bromoindoline-2,3-dione (cas: 20780-72-7Quality Control of 4-Bromoindoline-2,3-dione).

Wang, Qimeng et al. published their research in International Journal of Molecular Medicine in 2018 | CAS: 172922-91-7

5,11-Dihydroindolo[3,2-b]carbazole-6-carbaldehyde (cas: 172922-91-7) belongs to indole derivatives. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Category: indole-building-block

Aryl hydrocarbon receptor inhibits inflammation in DSS-induced colitis via the MK2/p-MK2/TTP pathway was written by Wang, Qimeng;Yang, Kunqiu;Han, Bin;Sheng, Baifa;Yin, Jiuheng;Pu, Aimin;Li, Liangzi;Sun, Lihua;Yu, Min;Qiu, Yuan;Xiao, Weidong;Yang, Hua. And the article was included in International Journal of Molecular Medicine in 2018.Category: indole-building-block This article mentions the following:

The pathogenesis of inflammatory bowel disease (IBD) is believed to be associated with the abnormal expression of inflammatory factors. The aryl hydrocarbon receptor (AhR) is a ligand-dependent transcription factor, which can suppress the inflammatory response and attenuate exptl. colitis. However, the detailed mechanism underlying the effects of AhR remains unclear. The present study investigated the role of AhR in the pathogenesis of IBD. Colitis was induced in mice by administration of 3% dextran sulfate sodium (DSS) for 7 days. The mice were also administered injections of the AhR agonist, 6-formylindolo(3,2-b)carbazole (FICZ), starting 2 days after the first administration of DSS. Furthermore, LoVo cells were treated with lipopolysaccharide (LPS) in the presence or absence of FICZ for 8 h. The protein expression levels of AhR, cytochrome P 450 1A1 (CYP1A1) and tristetraprolin (TTP) were assessed by western blotting and immunofluorescence, whereas mRNA expression levels were assessed by reverse transcription-quant. polymerase chain reaction. The results indicated that injection of mice with FICZ significantly attenuated DSS-induced colitis; in addition, the expression levels of inflammatory cytokines were markedly downregulated. Conversely, the expression levels of AhR and TTP were upregulated. In addition, mice in the AhR-knockout + DSS group exhibited elevated inflammatory cytokine production and developed more severe colitis. In LoVo cells, incubation with FICZ decreased the expression levels of inflammatory cytokines, whereas AhR and TTP expression was increased. In addition, the levels of phosphorylated-mitogen-activated protein kinase-activated protein kinase 2 (p-MK2) were decreased. These results suggested that AhR deficiency resulted in increased susceptibility to colitis, whereas activation of AhR by FICZ could ameliorate DSS-induced colitis via the MK2/p-MK2/TTP pathway. In the experiment, the researchers used many compounds, for example, 5,11-Dihydroindolo[3,2-b]carbazole-6-carbaldehyde (cas: 172922-91-7Category: indole-building-block).

Pis Diez, Cristian M. et al. published their research in Natural Product Research in 2022 | CAS: 17422-33-2

6-Chloro-1H-indole (cas: 17422-33-2) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Name: 6-Chloro-1H-indole

Synthesis and cytotoxicity evaluation of olivacine-indole hybrids tethered by alkyl linkers was written by Pis Diez, Cristian M.;Cespedes, Mariela;Di Venosa, Gabriela M.;Calvo, Gustavo;Avigliano, Esteban;Casas, Adriana G.;Palermo, Jorge A.. And the article was included in Natural Product Research in 2022.Name: 6-Chloro-1H-indole This article mentions the following:

In this work, eleven new derivatives were prepared of the alkaloid olivacine (1), which was isolated from the bark of Aspidosperma australe. These compounds are hybrids of olivacine and indoles or carbazole, tethered by alkyl chains of variable lengths (C-4, C-5 or C-6). Compounds showed increased cytotoxicity towards a panel of four cell lines. The subcellular localization of olivacine and of the synthetic derivatives was studied by fluorescence microscopy. The cycles of K562 cells exposed to olivacine or compounds were analyzed by flow cytometry, and showed, for some of the new derivatives, a different profile of cell distribution among the phases of the cycle when compared to olivacine, which is indicative of lysosomal apoptosis. In the experiment, the researchers used many compounds, for example, 6-Chloro-1H-indole (cas: 17422-33-2Name: 6-Chloro-1H-indole).

Luan, Xinjun et al. published their research in Organic Letters in 2010 | CAS: 1912-48-7

1-Methyl-3-indoleacetic acid (cas: 1912-48-7) belongs to indole derivatives. The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Application In Synthesis of 1-Methyl-3-indoleacetic acid

Highly Chemo- and Enantioselective Synthesis of 3-Allyl-3-aryl Oxindoles via the Direct Palladium-Catalyzed 伪-Arylation of Amides was written by Luan, Xinjun;Wu, Linglin;Drinkel, Emma;Mariz, Ronaldo;Gatti, Michele;Dorta, Reto. And the article was included in Organic Letters in 2010.Application In Synthesis of 1-Methyl-3-indoleacetic acid This article mentions the following:

Nonracemic cinnamyl imidazolidinylenepalladium complexes such as I (R = Et₂CH) are prepared as catalysts for the chemoselective and enantioselective arylation of N-(2-bromophenyl) allyl-substituted acetamides such as II (R¹ = Ph, 1-naphthyl, 2-naphthyl, 2-MeC₆H₄, 2-FC₆H₄, 2-MeOC₆H₄, 4-MeC₆H₄, 4-FC₆H₄, 4-F₃CC₆H₄, 4-PhC₆H₄, 3-MeC₆H₄, 3-FC₆H₄, 3-MeOC₆H₄, 3,5-Me₂C₆H₃, 1-Me-3-indolyl, Me; R² = H, Me; R³ = H, MeO) to give nonracemic (aryl)(allyl)oxindoles such as III (R¹ = Ph, 1-naphthyl, 2-naphthyl, 2-MeC₆H₄, 2-FC₆H₄, 2-MeOC₆H₄, 4-MeC₆H₄, 4-FC₆H₄, 4-F₃CC₆H₄, 4-PhC₆H₄, 3-MeC₆H₄, 3-FC₆H₄, 3-MeOC₆H₄, 3,5-Me₂C₆H₃, 1-Me-3-indolyl, Me; R² = H, Me; R³ = H, MeO) in 40-98% yields and in 4-91% ee (with all but three of the 21 examples in 69-91% ee) with none of the isomeric benzazepinone products formed in most cases. In the experiment, the researchers used many compounds, for example, 1-Methyl-3-indoleacetic acid (cas: 1912-48-7Application In Synthesis of 1-Methyl-3-indoleacetic acid).

Serra, A. et al. published their research in Tetrahedron in 1985 | CAS: 3130-75-4

4-(1,3-Dioxoisoindolin-2-yl)butanoic acid (cas: 3130-75-4) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. They 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: 3130-75-4

New glycidyl ester compounds containing a preformed imide ring – I was written by Serra, A.;Cadiz, V.;Mantecon, A.;Martinez, P. A.. And the article was included in Tetrahedron in 1985.SDS of cas: 3130-75-4 This article mentions the following:

Glycidyl esters I and II [R = glycidyl; X = CH₂, (CH₂)₃, (CH₂)₅, 1,3-phenylene, 1,4-phenylene] were prepared by condensation of I and II (R = H) with a large excess of epichlorohydrin. The structure of glycidyl esters was determined by elementary anal., IR and ¹H and ¹³C NMR spectra. The phys. properties were also defined. In the experiment, the researchers used many compounds, for example, 4-(1,3-Dioxoisoindolin-2-yl)butanoic acid (cas: 3130-75-4SDS of cas: 3130-75-4).