20/02/2023 - Page 8 of 14 - Indole Building Blocks

Avramenko, V. G. et al. published their research in Khimiya Geterotsiklicheskikh Soedinenii in 1974 | CAS: 1912-45-4

2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4) 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.Formula: C10H8ClNO2

Indole derivatives. XCIX. Reaction of indoles with chloroacetic acids was written by Avramenko, V. G.;Nazina, V. D.;Levinova, N. N.;Plutitskii, D. N.;Suvorov, N. N.. And the article was included in Khimiya Geterotsiklicheskikh Soedinenii in 1974.Formula: C10H8ClNO2 This article mentions the following:

The indoles I (R = H, Me, Ph; R1 = H, Cl, MeO, HO) were condensed with ClCH2CO2H in aqueous KOH at 240-50闂?and 5 atm to give the indoleacetates II. Similarly, Cl2CHCO2H and HOCH2CO2Et reacted with 1H-indole (III) to give II (R = R1 = H) in 91.5% and 46.3% yield, resp. Condensation of III with PhCH2Cl gave 21% 3-benzyl-1H-indole. In the experiment, the researchers used many compounds, for example, 2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4Formula: C10H8ClNO2).

Referemce:
Indole alkaloid derivatives as building blocks of natural products from闂佽壈浜崹淇沜illus thuringiensis闂佽壈浜粋鍧闂佽壈浜崹淇沜illus velezensis闂佽壈浜粋鍧 their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Lavrenov, Sergey N. et al. published their research in Pharmaceuticals in 2020 | CAS: 6639-06-1

3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1) 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.Reference of 6639-06-1

N-(Hydroxyalkyl) derivatives of tris(1H-indol-3-yl)methylium salts as promising antibacterial agents: synthesis and biological evaluation was written by Lavrenov, Sergey N.;Isakova, Elena B.;Panov, Alexey A.;Simonov, Alexander Y.;Tatarskiy, Viktor V.;Trenin, Alexey S.. And the article was included in Pharmaceuticals in 2020.Reference of 6639-06-1 This article mentions the following:

The main objective of the study was to prepare and elucidate the effect of substitutions in tris(1H-indol-3-yl)methylium derivatives I [n = 1,2,3,4,5] on their antibacterial activity and toxicity to human cells. Antibacterial activity of compounds I was performed in vitro on 12 bacterial strains, including drug resistant strains, that were clin. isolates or collection strains. The cytotoxic effect of the compounds was determined using an test with HPF-hTERT (human postnatal fibroblasts, immortalized with hTERT) cells. The min. inhibitory concentration (MIC) of the most active compound I [n = 5] on Gram-pos. bacteria, including MRSA, was 0.5濠电偞鎸鹃幐?mL. Compounds I [n = 4,5] also revealed high activity against Staphylococcus epidermidis (1.0 and 0.5濠电偞鎸鹃幐?mL, resp.) and moderate activity against Gram-neg. bacteria Escherichia coli (8濠电偞鎸鹃幐?mL) and Klebsiella pneumonia (2 and 8濠电偞鎸鹃幐?mL, resp.). However, they had no activity against Salmonella cholerasuis and Pseudomonas aeruginosa. The most active compounds I [n = 4,5] revealed higher antibacterial activity on MRSA than the reference drug levofloxacin, and their ratio between antibacterial and cytotoxic activity exceeded 10 times. In the experiment, the researchers used many compounds, for example, 3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1Reference of 6639-06-1).

Karadayi, Fikriye Zengin et al. published their research in New Journal of Chemistry in 2021 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) 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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Name: 5-Chloroindole-3-carboxaldehyde

Design, synthesis, anticancer activity, molecular docking and ADME studies of novel methylsulfonyl indole-benzimidazoles in comparison with ethylsulfonyl counterparts was written by Karadayi, Fikriye Zengin;Yaman, Murat;Kisla, Mehmet Murat;Konu, Ozlen;Ates-Alagoz, Zeynep. And the article was included in New Journal of Chemistry in 2021.Name: 5-Chloroindole-3-carboxaldehyde This article mentions the following:

In this study, novel methylsulfonyl indole-benzimidazole derivatives I (R¹ = Me, cyclohexyl, (3,4-dichlorophenyl)methyl, etc.; R² = H, OMe, Cl, Br) have been synthesized upon substitution of resp. first (R¹) and fifth (R²) positions of benzimidazole and indole groups. Structure and activity relationships were then studied via ¹H NMR, ¹³C NMR, mass spectral and in silico docking analyses, as well as cell viability measurements. The compounds I that exhibited substantial affinity levels towards ER alpha (ER婵? were found. In addition, the correlation anal. of cytotoxicity profiles between ethyl- and methyl-sulfonyl indole-benzimidazoles revealed a collection of effective and consistent R¹ and R² substitutions. However, for some candidate derivatives, I distinctive cytotoxicity levels and varying viability vs. ER婵?affinity correlations were observable across the studies, suggesting that the sulfonyl side chain modifications themselves can also influence the ER婵?binding levels. These results demonstrated that novel methylsulfonyl indole-benzimidazole derivatives, I similar to their ethylsulfonyl counterparts, exhibit anticancer effects with potential estrogen receptor modulatory actions. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Name: 5-Chloroindole-3-carboxaldehyde).

Ma, Liang et al. published their research in Applied Microbiology and Biotechnology in 2017 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) 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 was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Recommanded Product: 5-Chloroindole-3-carboxaldehyde

Identification and characterization of a biosynthetic gene cluster for tryptophan dimers in deep sea-derived Streptomyces sp. SCSIO 03032 was written by Ma, Liang;Zhang, Wenjun;Zhu, Yiguang;Zhang, Guangtao;Zhang, Haibo;Zhang, Qingbo;Zhang, Liping;Yuan, Chengshan;Zhang, Changsheng. And the article was included in Applied Microbiology and Biotechnology in 2017.Recommanded Product: 5-Chloroindole-3-carboxaldehyde This article mentions the following:

Tryptophan dimers (TDs) are an important class of natural products with diverse bioactivities and share conserved biosynthetic pathways. We report the identification of a partial gene cluster (spm) responsible for the biosynthesis of a class of unusual TDs with non-planar skeletons including spiroindimicins (SPMs), indimicins (IDMs), and lynamicins (LNMs) from the deep-sea derived Streptomyces sp.SCSIO 03032. Bioinformatics anal., targeted gene disruptions, and heterologous expression studies confirmed the involvement of the spm gene cluster in the biosynthesis of SPM/IDM/LNMs, and revealed the indispensable roles for the halogenase/reductase pair SpmHF, the amino acid oxidase SpmO, and the chromopyrrolic acid (CPA) synthase SpmD, as well as the pos. regulator SpmR and the putative transporter SpmA. However, the spm gene cluster was unable to confer a heterologous host the ability to produce SPM/IDM/LNMs. In addition, the P 450 enzyme SpmP and the monooxygenase SpmX2 were found to be non-relevant to the biosynthesis of SPM/IDM/LNMs. Sequence alignment and structure modeling suggested the lack of key conserved amino acid residues in the substrate-binding pocket of SpmP. Furthermore, feeding experiments in the non-producing 闂佸墽绮锕憁O mutant revealed several biosynthetic precursors en route to SPMs, indicating that key enzymes responsible for the biosynthesis of SPMs should be encoded by genes outside of the identified spm gene cluster. Finally, the biosynthetic pathways of SPM/IDM/LNMs are proposed to lay a basis for further insights into their intriguing biosynthetic machinery. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Recommanded Product: 5-Chloroindole-3-carboxaldehyde).

Prey, V. et al. published their research in Monatshefte fuer Chemie in 1960 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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. 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.SDS of cas: 5388-42-1

The rearrangement of 1-thiophthalide was written by Prey, V.;Kerres, B.;Berbalk, H.. And the article was included in Monatshefte fuer Chemie in 1960.SDS of cas: 5388-42-1 This article mentions the following:

The rearrangement of the title compound (I) in the presence of primary, secondary, and tertiary bases, with or without pressure, was studied and a reaction scheme was proposed, and through conductivity, heat of combustion, and infrared measurement, the important intermediate stages for tertiary bases were identified. Thus, 2 g. I and 5 g. PhNH₂ was heated in a sealed tube 3 hrs. at 190闂? and then about 0.1N HCl was added and a brown oil separated; this was crystallized from EtOH and then from H₂O to give 1.65 g. 2-thiophthalide (II), m. 59-60闂? Some similar representative experiments with I were (reagent, molar ratio of reagent to I, temperature, time, product, m. p., % yield given): PhNH₂, 1:5, 180闂? 1 hr., II, 60闂? quant.; PhNH₂, 1:25, 190闂? 2 hrs., N-phenylphthalimide (III), 168闂? 92; PhNH₂, 1:4 (sealed), room, 1 month, I, 116-17闂? 95; PhNH₂, 1:4 (open), room, 1 week, III, 168闂? -; MePhNH, 1:1, 190闂? 3 hrs., I, -, 100; Et₂PhN, 1:5, 190闂? 3 hrs., I, -, 100; o-ClC₆H₄NH₂, 1:5, 190闂? 3 hrs., N-(o-chlorophenyl)phthalimide, 206闂? 86; p-ClC₆H₄NH₂, 1:5, 190闂? 3 hrs., N-(p-chlorophenyl)phthalimide, 182-3闂? 96; o-toluidine, 1:5,190闂? 3 hrs., I,-, 100; BuNH₂, 1:4, 190闂? 3 hrs., o,o’-bis(butylaminomethyl)benzoyl sulfide (IV), 181-2闂? about 5; aqueous NH₃, -, 190闂? 3 hrs., diphthalyldiimide (V), 300闂? -; aqueous NH₃, -, 240闂? 3 hrs., II, -, 40; aqueous NH₃, -, reflux, 3 hrs., phthalide, 68-70闂? 50; pyridine, 1:5, about 100闂? 3 hrs., II,-, 100; quinoline, 1:5, 190闂? 3 hrs., II,-, 100; Et₃N, 1:1, 190闂? 4 hrs., II,-, 97. IV when heated with H₂O gave H₂S, and the filtrate from IV when treated with concentrated HCl gave II. A solution of 2.4 g. NaHS and 5 g. phthalide was heated 3 hrs. at 200闂?and treated with concentrated HCl to give 3.5 g. dibenzyl sulfide-o,o’ dicarboxylic acid, m. 230-3闂? dibutylamide m. 244-6闂? The EtOH filtrate from V was concentrated and the residue was purified with tetrahydrofuran and C to give 21.7% II, m. 54-9闂? In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1SDS of cas: 5388-42-1).

Liu, Ruixing et al. published their research in Organic Letters in 2019 | CAS: 4769-96-4

6-Nitro-1H-indole (cas: 4769-96-4) 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-Nitro-1H-indole

Activation Relay on Rhodium-Catalyzed C-H Aminomethylation in Cooperation with Photoredox Catalysis was written by Liu, Ruixing;Liu, Jiaxin;Wei, Yin;Shi, Min. And the article was included in Organic Letters in 2019.Name: 6-Nitro-1H-indole This article mentions the following:

A site selective C-H aminomethylation at indole’s C3 position was achieved by merging rhodium(III)-catalyzed C-H activation and photoredox catalysis in a one-pot manner. A study of the mechanistic insights rationalized the essence of the activation relay and the combination mode. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Name: 6-Nitro-1H-indole).

Wang, Tianlong et al. published their research in Tetrahedron in 2020 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Application In Synthesis of 2-Phenylisoindolin-1-one

Investigation towards the reductive amination of levulinic acid by B(C₆F₅)₃/hydrosilane system was written by Wang, Tianlong;Xu, Hai;He, Jianghua;Zhang, Yuetao. And the article was included in Tetrahedron in 2020.Application In Synthesis of 2-Phenylisoindolin-1-one This article mentions the following:

The selective transformation of the renewable biomass resources into the highly value-added platform chems. is essentially important for sustainable chem. Here the authors report a simple and highly efficient strategy for the synthesis of N-heterocyclic compounds from the reductive amination of the bio-derived levulinic acid and a wide range of anilines by metal-free B(C₆F₅)₃/hydrosilane catalyst system. Through adjusting the amounts of hydrosilane, the authors can synthesize a series of pyrrolidones or pyrrolidines, resp. Isotope-labeled NMR experiments were conducted to investigate the possible reaction pathway. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Application In Synthesis of 2-Phenylisoindolin-1-one).

Delacroix, Thomas et al. published their research in Journal of Organic Chemistry in 2000 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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.Formula: C14H11NO

Preparation of Functionalized Arylmagnesium Reagents Bearing an o-Chloromethyl Group was written by Delacroix, Thomas;Berillon, Laurent;Cahiez, Gerard;Knochel, Paul. And the article was included in Journal of Organic Chemistry in 2000.Formula: C14H11NO This article mentions the following:

The selective iodine-magnesium exchange of 2-chloromethyl-1-iodobenzenes such as 3,2-I(ClCH₂)C₆H₃R (R = H CO₂Me) are reported. The resulting organomagnesium reagents 3,2-(BrMg)(ClCH₂)C₆H₃R (R = same as above) are synthetic equivalent of a zwitterionic synthon and prove to be well suited for participation in cyclization reactions. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Formula: C14H11NO).

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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.Formula: C14H11NO

Carbone, Daniela et al. published their research in European Journal of Medicinal Chemistry in 2022 | CAS: 90271-86-6

5-Bromo-3-cyanoindole (cas: 90271-86-6) 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.Product Details of 90271-86-6

Metabolomics-assisted discovery of a new anticancer GLS-1 inhibitor chemotype from a nortopsentin-inspired library: From phenotype screening to target identification was written by Carbone, Daniela;Vestuto, Vincenzo;Ferraro, Maria Rosalia;Ciaglia, Tania;Pecoraro, Camilla;Sommella, Eduardo;Cascioferro, Stella;Salviati, Emanuela;Novi, Sara;Tecce, Mario Felice;Amodio, Giuseppina;Iraci, Nunzio;Cirrincione, Girolamo;Campiglia, Pietro;Diana, Patrizia;Bertamino, Alessia;Parrino, Barbara;Ostacolo, Carmine. And the article was included in European Journal of Medicinal Chemistry in 2022.Product Details of 90271-86-6 This article mentions the following:

The enzyme glutaminase-1 (GLS-1) has shown a clear and coherent implication in the progression and exacerbation of different aggressive tumors such as glioblastoma, hepatocarcinoma, pancreas, bone, and triple-neg. breast cancer. Few chemotypes are currently available as selective GLS-1 inhibitors, and still, fewer of them are at the clin. stage. In the present paper, starting from a naturally-inspired antitumor compound library, metabolomics has been used to putatively identify the mol. mechanism underlying biol. activity. GLS-1 was identified as a potential target. Biochem. anal. confirmed the hypothesis leading to the identification of a new hit compound acting as a GLS-1 selective inhibitor (IC₅₀ = 3.96 闂?1.05 濠电偞鎸鹃幏?, compared to the GLS-2 isoform (IC₅₀ = 12.90 闂?0.87 濠电偞鎸鹃幏?, with remarkable antitumor potency over different aggressive tumor cell lines. Mol. modeling studies revealed new insight into the drug-target interaction providing robust SAR clues for the rational hit-to-lead development. The approach undertaken underlines the wide potential of metabolomics applied to drug discovery, particularly in target identification and hit discovery following phenotype screening. In the experiment, the researchers used many compounds, for example, 5-Bromo-3-cyanoindole (cas: 90271-86-6Product Details of 90271-86-6).

Khadim, Mohammad A. et al. published their research in Magnetic Resonance in Chemistry in 1985 | CAS: 5388-42-1

Carbon-13 delta shifts and steric interactions in N-Aryl-1-isoindolinones and -isoindoline-1,3-diones was written by Khadim, Mohammad A.;Colebrook, L. D.. And the article was included in Magnetic Resonance in Chemistry in 1985.Quality Control of 2-Phenylisoindolin-1-one This article mentions the following:

Consistently deshielding ¹³C 闂?shifts resulting from the presence of aryl ortho substituents are determined for the 3-methylene C atoms of N-aryl-1-isoindolinones (0.12-3.25 ppm) and for the C:O group C atoms of these compounds and corresponding N-arylisoindoline-1,3-diones (0.04-1.47 ppm). Low-temperature (-75 and -150 闂? ¹H NMR studies indicate that steric barriers to internal rotation about the aryl C-N bonds in the N-aryl-1-isoindolinones are low. The compounds with the bulkiest aryl ortho substituents tend to show the largest 闂?shifts (particularly for the 3-methylene C atoms). No consistent correlation with the size of aryl ortho-substituents or their expected electronic properties is evident. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Quality Control of 2-Phenylisoindolin-1-one).