22/02/2023 - Indole Building Blocks

Molleti, Nagaraju et al. published their research in Organic & Biomolecular Chemistry in 2016 | 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Product Details of 20780-72-7

Catalyst-free synthesis of 伪¹-oxindole-伪-hydroxyphosphonates via phospha-aldol reaction of isatins employing N-heterocyclic phosphine (NHP)-thiourea was written by Molleti, Nagaraju;Yong Kang, Jun. And the article was included in Organic & Biomolecular Chemistry in 2016.Product Details of 20780-72-7 This article mentions the following:

A highly efficient phospha-aldol reaction for the synthesis of 伪¹-oxindole-伪-hydroxyphosphonates is developed using N-heterocyclic phosphine (NHP)-thiourea as a phosphonylation reagent under catalyst, additive free conditions. This methodol. encompasses a variety of isatin derivatives to provide 伪¹-oxindole- 伪-hydroxyphosphonates up to 99% yield. In the experiment, the researchers used many compounds, for example, 4-Bromoindoline-2,3-dione (cas: 20780-72-7Product Details of 20780-72-7).

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

Hiremath, Shivayogi P. et al. published their research in Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry in 1982 | CAS: 83515-06-4

5-Bromo-2-phenyl-1H-indole (cas: 83515-06-4) 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Related Products of 83515-06-4

Synthesis and reactions of 2-phenylindol-3-ones was written by Hiremath, Shivayogi P.;Biradar, Jaiprakash S.;Mruthyunjayaswamy, B. H. M.. And the article was included in Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry in 1982.Related Products of 83515-06-4 This article mentions the following:

2-Phenyl-3-aminoindoles were synthesized and converted into the corresponding 2-phenylindol-3-ones (I), which on reaction with o-phenylenediamines and nitrostyrene gave 9-substituted 5H-5a,6-dihydro-5a-phenylindolo[2,3-b]quinoxalines and 9-substituted 6,6a,7,12a-tetrahydro-6-nitro-6a-phenylindolo[1,2-a]quinolin-7-ones resp. Semicarbazones and thiosemicarbazones were also prepared from I. The antimicrobial activity of some of the compounds has also been studied. In the experiment, the researchers used many compounds, for example, 5-Bromo-2-phenyl-1H-indole (cas: 83515-06-4Related Products of 83515-06-4).

Takayama, Ken-ichi et al. published their research in Cancer Research in 2021 | CAS: 1914-02-9

3,3-Dimethylindoline (cas: 1914-02-9) 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.Electric Literature of C10H13N

Targeting epigenetic and posttranscriptional gene regulation by PSF impairs hormone therapy-refractory cancer growth was written by Takayama, Ken-ichi;Honma, Teruki;Suzuki, Takashi;Kondoh, Yasumitsu;Osada, Hiroyuki;Suzuki, Yutaka;Yoshida, Minoru;Inoue, Satoshi. And the article was included in Cancer Research in 2021.Electric Literature of C10H13N This article mentions the following:

RNA-binding protein PSF functions as an epigenetic modifier by interacting with long noncoding RNAs and the corepressor complex. PSF also promotes RNA splicing events to enhance oncogenic signals. In this study, we conducted an in vitro chem. array screen and identified multiple small mols. that interact with PSF. Several mols. inhibited RNA binding by PSF and decreased prostate cancer cell viability. Among these mols. and its derivatives was a promising mol., Number 10-3 [7,8-dihydroxy-4-(4-methoxyphenyl)chromen-2-one], that was the most effective at blocking PSF RNA-binding ability and suppressing treatment-resistant prostate and breast cancer cell proliferation. Exposure to Number 10-3 inhibited PSF target gene expression at the mRNA level. Treatment with Number 10-3 reversed epigenetically repressed PSF downstream targets, such as cell-cycle inhibitors, at the transcriptional level. Chromatin immunoprecipitation sequencing in prostate cancer cells revealed that Number 10-3 enhances histone acetylation to induce expression of apoptosis as well as cell-cycle inhibitors. Furthermore, Number 10-3 exhibited antitumor efficacy in a hormone therapy-resistant prostate cancer xenograft mouse model, suppressing treatment-resistant tumor growth. Taken together, this study highlights the feasibility of targeting PSF-mediated epigenetic and RNA-splicing activities for the treatment of aggressive cancers. In the experiment, the researchers used many compounds, for example, 3,3-Dimethylindoline (cas: 1914-02-9Electric Literature of C10H13N).

Mondejar-Parreno, Gema et al. published their research in Journal of Physiology (Oxford, United Kingdom) in 2019 | CAS: 194413-58-6

(Z)-3-((3,5-Dimethyl-1H-pyrrol-2-yl)methylene)indolin-2-one (cas: 194413-58-6) 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.Product Details of 194413-58-6

miR-1 is increased in pulmonary hypertension and downregulates Kv1.5 channels in rat pulmonary arteries was written by Mondejar-Parreno, Gema;Callejo, Maria;Barreira, Bianca;Morales-Cano, Daniel;Esquivel-Ruiz, Sergio;Moreno, Laura;Cogolludo, Angel;Perez-Vizcaino, Francisco. And the article was included in Journal of Physiology (Oxford, United Kingdom) in 2019.Product Details of 194413-58-6 This article mentions the following:

Key points : The expression of miR-1 is increased in lungs from the Hyp/Su5416 PAH rat model. Pulmonary artery smooth muscle cells from this animal model are more depolarized and show decreased expression and activity of voltage-dependent potassium channel (Kv)1.5. miR-1 directly targets Kv1.5 channels, reduces Kv1.5 activity and induces membrane depolarization. Antagomir-1 prevents Kv1.5 channel downregulation and the depolarization induced by hypoxia/Su5416 exposition. Impairment of the voltage-dependent potassium channel (Kv) plays a central role in the development of cardiovascular diseases, including pulmonary arterial hypertension (PAH). MicroRNAs are non-coding RNAs that regulate gene expression by binding to the 3′-untranslated region region of specific mRNAs. The present study aimed to analyze the effects of miR-1 on Kv channel function in pulmonary arteries (PA). Kv channel activity was studied in PA from healthy animals transfected with miR-1 or scrambled-miR. Kv currents were studied using the whole-cell configuration of the patch clamp technique. The characterization of the Kv1.5 currents was performed with the selective inhibitor DPO-1. MiR-1 expression was increased and Kv1.5 channels were decreased in lungs from a rat model of PAH induced by hypoxia and Su5416. MiR-1 transfection increased cell capacitance, reduced Kv1.5 currents and induced membrane depolarization in isolated pulmonary artery smooth muscle cells. A luciferase reporter assay indicated that KCNA5, which encodes Kv1.5 channels, is a direct target gene of miR-1. Incubation of PA with Su5416 and hypoxia (3% O₂) increased miR-1 and induced a decline in Kv1.5 currents, which was prevented by antagomiR-1. In conclusion, these data indicate that miR-1 induces pulmonary artery smooth muscle cell hypertrophy and reduces the activity and expression of Kv channels, suggesting a pathophysiol. role in PAH. In the experiment, the researchers used many compounds, for example, (Z)-3-((3,5-Dimethyl-1H-pyrrol-2-yl)methylene)indolin-2-one (cas: 194413-58-6Product Details of 194413-58-6).

Calderon, Felix et al. published their research in ACS Medicinal Chemistry Letters in 2012 | CAS: 2343-22-8

5-Fluoroindoline (cas: 2343-22-8) 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.Application In Synthesis of 5-Fluoroindoline

A Divergent SAR Study Allows Optimization of a Potent 5-HT_2c Inhibitor to a Promising Antimalarial Scaffold was written by Calderon, Felix;Vidal-Mas, Jaume;Burrows, Jeremy;de la Rosa, Juan Carlos;Jimenez-Diaz, Maria Belen;Mulet, Teresa;Prats, Sara;Solana, Jorge;Witty, Michael;Gamo, Francisco Javier;Fernandez, Esther. And the article was included in ACS Medicinal Chemistry Letters in 2012.Application In Synthesis of 5-Fluoroindoline This article mentions the following:

From the 13 533 chem. structures published by GlaxoSmithKline in 2010, we identified 47 quality starting points for lead optimization. One of the most promising hits was the TCMDC-139046, a mol. presenting an indoline core, which is well-known for its anxiolytic properties by interacting with serotonin antagonist receptors 5-HT₂. The inhibition of this target will complicate the clin. development of these compounds as antimalarials. Herein, we present the antimalarial profile of this series and our efforts to avoid interaction with this receptor, while maintaining a good antiparasitic potency. By using a double-divergent structure-activity relationship anal., we have obtained a novel lead compound harboring an indoline core. In the experiment, the researchers used many compounds, for example, 5-Fluoroindoline (cas: 2343-22-8Application In Synthesis of 5-Fluoroindoline).

Shan, Xiang-Huan et al. published their research in Nature Communications in 2019 | CAS: 83515-06-4

5-Bromo-2-phenyl-1H-indole (cas: 83515-06-4) 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.Reference of 83515-06-4

Copper-catalyzed oxidative benzylic C-H cyclization via iminyl radical from intermolecular anion-radical redox relay was written by Shan, Xiang-Huan;Zheng, Hong-Xing;Yang, Bo;Tie, Lin;Fu, Jia-Le;Qu, Jian-Ping;Kang, Yan-Biao. And the article was included in Nature Communications in 2019.Reference of 83515-06-4 This article mentions the following:

The combination of base-promoted benzylic C-H cleavage and copper-catalyzed carbanion-radical redox relay was reported. Catalytic amount of naturally abundant and inexpensive copper salt, such as copper(II) sulfate, was used for anion-radical redox relay without any external oxidant. By avoiding using N-O/N-N homolysis or radical initiators to generate iminyl radicals, this strategy realized modular synthesis of N-H indoles and analogs from abundant feedstocks, such as toluene and nitrile derivatives, and also enabled rapid synthesis of large scale pharmaceuticals. In the experiment, the researchers used many compounds, for example, 5-Bromo-2-phenyl-1H-indole (cas: 83515-06-4Reference of 83515-06-4).

Niu, Ben et al. published their research in Chemical Communications (Cambridge, United Kingdom) in 2021 | CAS: 723-89-7

1-Phenylindoline-2,3-dione (cas: 723-89-7) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Formula: C14H9NO2

Palladium catalyzed divergent cycloadditions of vinylidenecyclopropane-diesters with methyleneindolinones enabled by zwitterionic 蟺-propargyl palladium species was written by Niu, Ben;Wei, Yin;Shi, Min. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2021.Formula: C14H9NO2 This article mentions the following:

A palladium-catalyzed divergent synthesis of spirooxindoles fused with a five- or a six-membered ring by a cycloaddition reaction of vinylidenecyclopropane-diesters with methyleneindolinones was disclosed. This protocol features an in situ generated unprecedented zwitterionic 蟺-propargyl palladium species in cycloaddition reactions and a switchable process between (3+2) and (4+2) cycloadditions by changing the phosphine ligand. In the experiment, the researchers used many compounds, for example, 1-Phenylindoline-2,3-dione (cas: 723-89-7Formula: C14H9NO2).

Zhang, Qian et al. published their research in Journal of Separation Science in 2020 | CAS: 153-94-6

H-D-Trp-OH (cas: 153-94-6) 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.Safety of H-D-Trp-OH

Differentiating Westlake Longjing tea from the first- and second-grade producing regions using ultra high performance liquid chromatography with quadrupole time-of-flight mass spectrometry-based untargeted metabolomics in combination with chemometrics was written by Zhang, Qian;Zhang, Yu-Ying;Liu, Zhi;Zhang, Yue-Ming;Lu, Ning;Hai, Guo-Qing;Shao, Sheng-Zhi;Zheng, Qing-Xia;Zhang, Xia;Fu, Hai-Yan;Bai, Chang-Cai;Yu, Yong-Jie;She, Yuanbin. And the article was included in Journal of Separation Science in 2020.Safety of H-D-Trp-OH This article mentions the following:

There are numerous articles published for geog. discrimination of tea. However, few research works focused on the authentication and traceability of Westlake Longjing green tea from the first- and second-grade producing regions because the tea trees are planted in a limited growing zone with identical cultivate condition. In this work, a comprehensive anal. strategy was proposed by ultrahigh performance liquid chromatog.-quadrupole time-of-flight mass spectrometry-based untargeted metabolomics coupled with chemometrics. The automatic untargeted data anal. strategy was introduced to screen metabolites that expressed significantly among different regions. Chromatog. features of metabolites can be automatically and efficiently extracted and registered. Meanwhile, those that were valuable for geog. origin discrimination were screened based on statistical anal. and contents in samples. Metabolite identification was performed based on high-resolution mass values and tandem mass spectra of screened peaks. Twenty metabolites were identified, based on which the two-way encoding partial least squares discrimination anal. was built for geog. origin prediction. Monte Caro simulation results indicated that prediction accuracy was up to 99%. Our strategy can be applicable for practical applications in the quality control of Westlake Longjing green tea. In the experiment, the researchers used many compounds, for example, H-D-Trp-OH (cas: 153-94-6Safety of H-D-Trp-OH).

Schwarthoff, Sigrid et al. published their research in Bioorganic & Medicinal Chemistry in 2021 | CAS: 5094-12-2

2-Methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (cas: 5094-12-2) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. 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.Recommanded Product: 5094-12-2

Evaluation of 纬-carboline-phenothiazine conjugates as simultaneous NMDA receptor blockers and cholinesterase inhibitors was written by Schwarthoff, Sigrid;Tischer, Nicolas;Sager, Henrike;Schaetz, Bianca;Rohrbach, Marius M.;Raztsou, Ihar;Robaa, Dina;Gaube, Friedemann;Arndt, Hans-Dieter;Winckler, Thomas. And the article was included in Bioorganic & Medicinal Chemistry in 2021.Recommanded Product: 5094-12-2 This article mentions the following:

Alzheimer’s disease (AD) is the most common form of dementia. It is associated with the impairment of memory and other cognitive functions that are mainly caused by progressive defects in cholinergic and glutamatergic signaling in the central nervous system. Inhibitors of acetylcholinesterase (AChE) and ionotropic glutamate receptors of the N-methyl-D-aspartate (NMDA) receptor family are currently approved as AD therapeutics. We previously showed using a cell-based assay of NMDA receptor-mediated glutamate-induced excitotoxicity that bis-纬-carbolinium conjugates are useful NMDA receptor blockers. However, these compounds also act as subnanomolar AChE inhibitors, which may cause serious anticholinergic side effects when applied in vivo. Here, we evaluated new structures containing 纬-carbolines linked to phenothiazine via a propionyl spacer. These compounds were superior to the previously characterized bis-纬-carbolinium conjugates because they blocked NMDA receptors without requiring a quaternary pyridine N-atom and inhibited AChE with moderate IC50 values of 0.54-5.3渭M. In addition, these new compounds displayed considerable selectivity for the inhibition of butyrylcholinesterase (BChE; IC₅₀ = 0.008-0.041渭M), which may be favorable for AD treatment. Inhibitory activities towards the NMDA receptors and AChE were in the same micromolar range, which may be beneficial for equal dosing against multiple targets in AD patients. In the experiment, the researchers used many compounds, for example, 2-Methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (cas: 5094-12-2Recommanded Product: 5094-12-2).

Yuan, Si-Wen et al. published their research in Angewandte Chemie, International Edition in 2019 | CAS: 387-44-0

7-Fluoroindole (cas: 387-44-0) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Recommanded Product: 7-Fluoroindole

Intermolecular C-H Amidation of (Hetero)arenes to Produce Amides through Rhodium-Catalyzed Carbonylation of Nitrene Intermediates was written by Yuan, Si-Wen;Han, Hui;Li, Yan-Lin;Wu, Xueli;Bao, Xiaoguang;Gu, Zheng-Yang;Xia, Ji-Bao. And the article was included in Angewandte Chemie, International Edition in 2019.Recommanded Product: 7-Fluoroindole This article mentions the following:

Amide bond formation is one of the most important reactions in organic chem. because of the widespread presence of amides in pharmaceuticals and biol. active compounds Existing methods for amides synthesis are reaching their inherent limits. Described herein is a novel rhodium-catalyzed three-component reaction to synthesize amides from organic azides, carbon monoxide, and (hetero)arenes via nitrene-intermediates and direct C-H functionalization. Notably, the reaction proceeds in an intermol. fashion with N₂ as the only byproduct, and neither directing groups nor additives are required. The computational and mechanistic studies show that the amides are formed via a key Rh-nitrene intermediate. Thus, e.g., 1-methylindole + CO + TsN₃ 鈫?1-methyl-N-tosylindole-3-carboxamide (92%, 88% isolated) in presence of [Rh(cod)Cl]₂ in MeCN. In the experiment, the researchers used many compounds, for example, 7-Fluoroindole (cas: 387-44-0Recommanded Product: 7-Fluoroindole).