22/02/2023 - Page 2 of 66 - Indole Building Blocks

Parasuraman, Perumalsamy et al. published their research in RSC Advances in 2020 | CAS: 20780-72-7

4-Bromoindoline-2,3-dione (cas: 20780-72-7) 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Computed Properties of C8H4BrNO2

Simple organocatalyst component system for asymmetric hetero Diels-Alder reaction of isatins with enones was written by Parasuraman, Perumalsamy;Begum, Zubeda;Chennapuram, Madhu;Seki, Chigusa;Okuyama, Yuko;Kwon, Eunsang;Uwai, Koji;Tokiwa, Michio;Tokiwa, Suguru;Takeshita, Mitsuhiro;Nakano, Hiroto. And the article was included in RSC Advances in 2020.Computed Properties of C8H4BrNO2 This article mentions the following:

A simple two catalyst component system consisting of primary 尾-amino alcs. as a catalyst and amino acids as a co-catalyst put together worked as an efficient organocatalyst system in hetero Diels-Alder reaction of isatins with enones to afford chiral spirooxindole-tetrahydropyranones I [R¹ = H, Cl, Br; R² = H, Me, Br; R³ = H, Cl; R⁴ = allyl, Pr, iso-Pr, hexyl] in good chem. yields and stereoselectivities (up to 86%, up to 85 : 15 dr., up to 95% ee). In the experiment, the researchers used many compounds, for example, 4-Bromoindoline-2,3-dione (cas: 20780-72-7Computed Properties of C8H4BrNO2).

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

Somashekar, P. L. et al. published their research in Chemical Science Transactions in 2013 | CAS: 15362-40-0

1-(2,6-Dichlorophenyl)-2-indolinone (cas: 15362-40-0) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. 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.Computed Properties of C14H9Cl2NO

Synthesis and characterization of specified impurities of aceclofenac was written by Somashekar, P. L.;Pai, P. N. Sanjay;Rao, Gopalkrishna. And the article was included in Chemical Science Transactions in 2013.Computed Properties of C14H9Cl2NO This article mentions the following:

The present study aimed at synthesizing the process related potential impurities of aceclofenac. Aceclofenac is an orally administered benzeneacetic acid derivative with effects on a variety of inflammatory mediators. Process-related impurities of aceclofenac listed in the British Pharmacopoeia have been synthesized by modified methods and characterized by FT IR, MS and ¹H NMR data. Impurity A [i.e., [2-[(2,6-dichlorophenyl)amino]phenyl]acetic acid (diclofenac)] was synthesized by acid hydrolysis of diclofenac sodium. Impurity B [i.e., Me [2-[(2,6-dichlorophenyl)amino]phenyl]acetate (Me ester of diclofenac)], impurity C [i.e., Et [2-[(2,6-dichlorophenyl)amino]phenyl]acetate (Et ester of diclofenac)], impurity D [i.e., Me [[[2-[(2,6-dichlorophenyl)amino]phenyl]acetyl]oxy]acetate (Me ester of aceclofenac)], impurity E [i.e., Et [[[2-[(2,6-dichlorophenyl)amino]phenyl]acetyl]oxy]acetate (Et ester of aceclofenac)] were synthesized by simple and convenient direct methylation and ethylation of diclofenac and aceclofenac resp. instead of a tedious esterification process. Impurity F [i.e., benzyl [[[2-[(2,6-dichlorophenyl)amino]phenyl]acetyl]oxy]acetate (benzyl ester of aceclofenac)] was synthesized by a condensation reaction of diclofenac sodium with benzyl bromoacetate. Impurity I [i.e., 1-(2,6-dichlorophenyl)-1,3-dihydro-2H-indol-2-one] was synthesized by an acid mediated cyclization of diclofenac. The present study has provided an efficient method for synthesis of process related aceclofenac impurities. The synthesis of the target compounds was achieved using 2-[(2,6-dichlorophenyl)amino]benzeneacetic acid carboxymethyl ester (Aceclofenac) also as a starting material. In the experiment, the researchers used many compounds, for example, 1-(2,6-Dichlorophenyl)-2-indolinone (cas: 15362-40-0Computed Properties of C14H9Cl2NO).

Dodani, Sheel C. et al. published their research in ChemBioChem in 2014 | CAS: 17332-70-6

2-Amino-3-(7-methyl-1H-indol-3-yl)propanoic acid (cas: 17332-70-6) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Electric Literature of C12H14N2O2

Structural, Functional, and Spectroscopic Characterization of the Substrate Scope of the Novel Nitrating Cytochrome P450 TxtE was written by Dodani, Sheel C.;Cahn, Jackson K. B.;Heinisch, Tillmann;Brinkmann-Chen, Sabine;McIntosh, John A.;Arnold, Frances H.. And the article was included in ChemBioChem in 2014.Electric Literature of C12H14N2O2 This article mentions the following:

A novel cytochrome P 450 enzyme, TxtE, was recently shown to catalyze the direct aromatic nitration of L-tryptophan. This unique chem. inspired us to ask whether TxtE could serve as a platform for engineering new nitration biocatalysts to replace current harsh synthetic methods. As a first step toward this goal, and to better understand the wild-type enzyme, we obtained high-resolution structures of TxtE in its substrate-free and substrate-bound forms. We also screened a library of substrate analogs for spectroscopic indicators of binding and for production of nitrated products. From these results, we found that the wild-type enzyme accepts moderate decoration of the indole ring, but the amino acid moiety is crucial for binding and correct positioning of the substrate and therefore less amenable to modification. A nitrogen atom is essential for catalysis, and a carbonyl must be present to recruit the 伪B’₁ helix of the protein to seal the binding pocket. In the experiment, the researchers used many compounds, for example, 2-Amino-3-(7-methyl-1H-indol-3-yl)propanoic acid (cas: 17332-70-6Electric Literature of C12H14N2O2).

Mansour, Ritam et al. published their research in Physical Chemistry Chemical Physics in 2022 | CAS: 271-29-4

1H-Pyrrolo[2,3-c]pyridine (cas: 271-29-4) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. 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 of 271-29-4

Pre-Dewar structure modulates protonated azaindole photodynamics was written by Mansour, Ritam;Mukherjee, Saikat;Pinheiro, Max Jr.;Noble, Jennifer A.;Jouvet, Christophe;Barbatti, Mario. And the article was included in Physical Chemistry Chemical Physics in 2022.Application of 271-29-4 This article mentions the following:

Recent exptl. work revealed that the lifetime of the S₃ state of protonated 7-azaindole is about ten times longer than that of protonated 6-azaindole. We simulated the nonradiative decay pathways of these mols. using trajectory surface hopping dynamics after photoexcitation into S₃ to elucidate the reason for this difference. Both isomers mainly follow a common 蟺蟺* relaxation pathway involving multiple state crossings while coming down from S₃ to S₁ in the subpicosecond time scale. However, the simulations reveal that the excited-state topogs. are such that while the 6-isomer can easily access the region of nonadiabatic transitions, the internal conversion of the 7-isomer is delayed by a pre-Dewar bond formation with a boat conformation. In the experiment, the researchers used many compounds, for example, 1H-Pyrrolo[2,3-c]pyridine (cas: 271-29-4Application of 271-29-4).

Chen, Guan-yuan et al. published their research in Analytica Chimica Acta in 2018 | CAS: 879-37-8

Indole-3-acetamide (cas: 879-37-8) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Safety of Indole-3-acetamide

Simultaneous determination of tryptophan and its 31 catabolites in mouse tissues by polarity switching UHPLC-SRM-MS was written by Chen, Guan-yuan;Zhong, Wei;Zhou, Zhanxiang;Zhang, Qibin. And the article was included in Analytica Chimica Acta in 2018.Safety of Indole-3-acetamide This article mentions the following:

Tryptophan (TRP) and its catabolites have attracted a lot of attention because of their clin. significance to human health. Recently, microbiome-gut-brain axis has links to many diseases based on the imbalance of TRP catabolism. By using ultra-HPLC coupled to electrospray ionization triple quadrupole mass spectrometry, the authors present a rapid, robust and comprehensive method to determine 31 TRP catabolites covering three major pathways – kynurenic, serotonergic and bacterial degradation – within 5 min. Polarity switching was employed to analyze catabolites in both ionization modes simultaneously for greatly improved anal. throughput. The intra-day and inter-day precision were 0.5-15.8% and 1.5-16.7%, resp. Accuracy was 75.8-126.9%. The developed method was applied to study the tissue level of TRP catabolites in the liver, ileum, ileal contents, brain and plasma samples from 8 mice, and clear differences in the distribution of TRP catabolites were observed in different tissues. Ratios of key catabolites to TRP were used to evaluate the activities of specific enzyme and pathway in resp. tissues. This method has potential in high throughput anal. of TRP catabolites in biol. matrixes, which can facilitate understanding the influence of TRP catabolites on microbiome-gut-brain axis and on human health. In the experiment, the researchers used many compounds, for example, Indole-3-acetamide (cas: 879-37-8Safety of Indole-3-acetamide).

Sato, Yota et al. published their research in Frontiers in Immunology in 2020 | CAS: 172922-91-7

5,11-Dihydroindolo[3,2-b]carbazole-6-carbaldehyde (cas: 172922-91-7) 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 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). Product Details of 172922-91-7

Possible roles of proinflammatory signaling in keratinocytes through aryl hydrocarbon receptor ligands for the development of squamous cell carcinoma was written by Sato, Yota;Fujimura, Taku;Hidaka, Takanori;Lyu, Chunbing;Tanita, Kayo;Matsushita, Shigeto;Yamamoto, Masayuki;Aiba, Setsuya. And the article was included in Frontiers in Immunology in 2020.Product Details of 172922-91-7 This article mentions the following:

Aryl hydrocarbon receptor (AhR) provides a deeper insight into the pathogenesis of cutaneous squamous cell carcinoma (cSCC). AhR ligands, such as 6-formylindolo[3,2-b] carbazole (FICZ), and 7,12-Dimethylbenz[a]anthracene (DMBA), constitute major substrates for the cytochrome P 450 (CYP) family, and influence the expression of various cytokine genes, including IL-17 and IL-23-related genes via the AhR. On the other hand, proinflammatory cytokines could drive tumor progression through the TRAF-ERK5 signaling pathway in cSCC. From the above findings, we hypothesized that AhR ligands might enhance the mRNA expression of proinflammatory cytokines via the AhR, leading to the development of cSCC. The purpose of this study was to investigate (1) the immunomodulatory effects of FICZ and DMBA on normal human keratinocytes (NHKCs), focusing on IL-17, and related cytokines/chemokines (IL-23, IL-36 gamma, and CCL20), (2) the expression of these factors in AhR-dependent pathways using a two-stage chem. induced skin carcinogenesis mouse model, and (3) the expression of these factors in lesion-affected skin in cSCC. Both FICZ and DMBA augmented the expression of CYP1A1, p19, CCL20, and IL-36 gamma mRNA in NHKCs in vitro. Moreover, the mRNA expression of these proinflammatory factors, as well as IL-17, in mouse cSCC is significantly decreased in the AhR-(fl/fl) Krt5-(Cre) mice compared to wild type mice, leading to a decrease in the number of developed cSCC lesions. Furthermore, CCL20, IL-23, as well as IL-17, are detected in the lesion-affected skin of cSCC patients. Our study demonstrates a possible mechanism for the development of cSCC involving AhR-mediated signaling by epidermal keratinocytes and recruitment of Th17 cells. In the experiment, the researchers used many compounds, for example, 5,11-Dihydroindolo[3,2-b]carbazole-6-carbaldehyde (cas: 172922-91-7Product Details of 172922-91-7).

Yoshida, Ayaka et al. published their research in Experimental Dermatology in 2021 | 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.Safety of 3-(2,4-Dichlorophenyl)-4-(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione

Sunitinib decreases the expression of KRT6A and SERPINB1 in 3D human epidermal models was written by Yoshida, Ayaka;Yamamoto, Kazuhiro;Ishida, Takahiro;Omura, Tomohiro;Itoh, Tomoo;Nishigori, Chikako;Sakane, Toshiyasu;Yano, Ikuko. And the article was included in Experimental Dermatology in 2021.Safety of 3-(2,4-Dichlorophenyl)-4-(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione This article mentions the following:

Hand-foot skin reaction (HFSR) is a common side effect caused by several tyrosine kinase inhibitors, including sunitinib. However, the nature of the cornifying factors related to the mol. biol. mechanisms underlying HFSR remains poorly understood. We used human keratinocyte models to investigate the key cornifying factors for dermatol. and biol. abnormalities induced by sunitinib. On the basis of the results of microarray anal. using the three-dimensional (3D) human epidermal model, keratin (KRT)6A, serine protease inhibitor (SERPIN)B1, KRT5, and SERPIN Kazal-type 6 were selected as candidate genes related to HFSR. Sunitinib treatment significantly decreased the expression of SERPINB1 and KRT6A in the immunohistochem. staining of the 3D epidermal model. In PSVK1 cells, but not in normal human epidermal keratinocyte cells, both of which are human normal keratinocyte cell lines, sunitinib decreased the expression of KRT6A with a concomitant decrease in levels of phosphorylated extracellular signal-regulated kinases (ERK)1/2 and phosphorylated p38 mitogen-activated protein kinase (MAPK). Inhibitors of the ERK and p38 MAPK signal pathways also significantly decreased KRT6A expression. Sunitinib-induced decrease in KRT6A expression was suppressed by the inhibition of glycogen synthase kinase-3尾 by enhancing ERK1/2 and p38 MAPK phosphorylation. Thus, sunitinib reduces the expression of KRT6A and SERPINB1 by inhibiting the ERK1/2 and p38 MAPK signalling pathways in the skin model. These changes in expression contribute to the pathol. of HFSR. 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: 280744-09-4Safety of 3-(2,4-Dichlorophenyl)-4-(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione).

Wang, Qiang et al. published their research in Food Science & Nutrition (Hoboken, NJ, United States) in 2021 | CAS: 244-63-3

9H-Pyrido[3,4-b]indole (cas: 244-63-3) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Application of 244-63-3

Effects of turmeric on reducing heterocyclic aromatic amines in Chinese tradition braised meat products and the underlying mechanism was written by Wang, Qiang;Li, Jin;Li, Kaikai;Li, Chunmei. And the article was included in Food Science & Nutrition (Hoboken, NJ, United States) in 2021.Application of 244-63-3 This article mentions the following:

Braised meat products are kinds of popular traditional meat food in China. However, current data on the formation of Amino-carboline congeners Heterocyclic aromatic amines (HAAs) and the inhibitory methods in braised meat products are limited. In the present study, the inhibition effect of turmeric and curcumin on the formation of 尾-carboline heterocyclic aromatic amines in braised meat were investigated. And the preliminary mechanism of curcumin inhibiting the formation of 尾-carboline heterocyclic amines was also explored in the chem. model. The results indicated that 5% of turmeric could significantly inhibit the formation of harman (94.8%) and norharman (49.56%) in braised meat, and curcumin was one of the key active compound accounting for this effect. In the tryptophan model, 0.05 mmol of curcumin significantly inhibited the formation of norharman and harman by over 70% (p < .05). Further investigation indicated that curcumin inhibited the formation of 尾-carboline heterocyclic amines mainly by inhibiting the formation of carbonyl compounds and 1,2,3,4-Tetrahydro-尾-carboline-3-carboxylic acid and scavenging 尾-carboline HAAs. These results could provide a natural spice-based method for reducing heterocyclic aromatic amines in Chinese tradition braised meat products. In the experiment, the researchers used many compounds, for example, 9H-Pyrido[3,4-b]indole (cas: 244-63-3Application of 244-63-3).

Kilic, H. et al. published their research in New Journal of Chemistry in 2017 | CAS: 387-44-0

7-Fluoroindole (cas: 387-44-0) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Formula: C8H6FN

Bismuth nitrate-promoted disproportionative condensation of indoles with cyclohexanone: a new-type azafulvenium reactivity of indole was written by Kilic, H.;Bayindir, S.;Erdogan, E.;Agopcan Cinar, S.;Konuklar, F. A. S.;Bali, S. K.;Saracoglu, N.;Aviyente, V.. And the article was included in New Journal of Chemistry in 2017.Formula: C8H6FN This article mentions the following:

The bismuth nitrate-promoted disproportionative condensation of indoles such as 1H-indole, 2-methyl-1H-indole, 5-methoxy-1H-indole, 7-fluoro-1H-indole, etc. with cyclohexanone in one pot, to yield C3-cyclohexyl substituted indoles I (R¹ = R² = R⁵ = R⁷ = H; R¹ = R² = CH₃, R⁵ = R⁷ = H; R¹ = R² = R⁷ = H, R⁵ = OCH₃, etc.) and 1,3-di(1H-indol-3-yl)benzene derivatives II is reported for the first time. Using 3-methylindole with cyclopentanone, cyclohexanone, and cycloheptanone results in new and different synthetic pathways. The plausible reaction mechanisms are presented and supported with DFT (M06-2X/6-31+G(d,p)) calculations In the experiment, the researchers used many compounds, for example, 7-Fluoroindole (cas: 387-44-0Formula: C8H6FN).

Cheval, Nicolas P. et al. published their research in Tetrahedron in 2018 | CAS: 14396-90-8

2-(But-3-yn-1-yl)isoindoline-1,3-dione (cas: 14396-90-8) 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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Reference of 14396-90-8

Vinyl nosylates as partner in copper and silver co-catalyzed Sonogashira cross-coupling reactions was written by Cheval, Nicolas P.;Hoffmann, Barbara;Dikova, Anna;Sirindil, Fatih;Bertus, Philippe;Blanc, Aurelien;Weibel, Jean-Marc;Pale, Patrick. And the article was included in Tetrahedron in 2018.Reference of 14396-90-8 This article mentions the following:

Vinyl nosylates, readily obtained from 尾-dicarbonyl derivatives, could be efficiently engaged in Sonogashira cross-coupling reactions, co-catalyzed by either copper or silver salts. The para-nitrobenzenesulfonate (nosylate) group allows this coupling to be performed under very mild conditions (room temperature). This new leaving group and mild conditions could be applied to the synthesis of acetylenic coumarinyl derivatives and to the total synthesis of an acetylenic monoterpene natural product, cleviolide. In the experiment, the researchers used many compounds, for example, 2-(But-3-yn-1-yl)isoindoline-1,3-dione (cas: 14396-90-8Reference of 14396-90-8).