Month: February 2023

Peptoid-based reprogrammable template for cell-permeable inhibitors of protein-protein interactions was written by Fukuda, Yasuhiro;Yokomine, Marin;Kuroda, Daisuke;Tsumoto, Kouhei;Morimoto, Jumpei;Sando, Shinsuke. And the article was included in Chemical Science in 2021.Category: indole-building-block This article mentions the following:

The development of inhibitors of intracellular protein-protein interactions (PPIs) is of great significance for drug discovery, but the generation of a cell-permeable mol. with high affinity to protein is challenging. Oligo(N-substituted glycines) (oligo-NSGs), referred to as peptoids, are attractive as potential intracellular PPI inhibitors owing to their high membrane permeability. However, their intrinsically flexible backbones make the rational design of inhibitors difficult. Here, we propose a peptoid-based rational approach to develop cell-permeable PPI inhibitors using oligo(N-substituted alanines) (oligo-NSAs). The rigid structures of oligo-NSAs enable independent optimization of each N-substituent to improve binding affinity and membrane permeability, while preserving the backbone shape. A mol. with optimized N-substituents inhibited a target PPI in cells, which demonstrated the utility of oligo-NSA as a reprogrammable template to develop intracellular PPI inhibitors. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Category: indole-building-block).

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) 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. 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.Category: indole-building-block

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

Electrosynthesis of (hetero)aryl nitriles from 伪-imino-oxy acids via oxidative decarboxylation/N-O cleavage was written by Lin, Hui-Shan;Chen, Shu-Jun;Huang, Jing-Mei. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2022.SDS of cas: 170489-16-4 This article mentions the following:

A new method for the synthesis of (hetero)aryl nitriles via iminyl radicals was developed through the electrochem. oxidative decarboxylation of 伪-imino-oxy acids. This protocol provides an efficient approach to nitriles with a broad range of functional-group tolerance under ambient conditions and can be applied for one-pot gram-scale synthesis. In the experiment, the researchers used many compounds, for example, 1,4-Dimethyl-1H-indole-3-carbaldehyde (cas: 170489-16-4SDS of cas: 170489-16-4).

1,4-Dimethyl-1H-indole-3-carbaldehyde (cas: 170489-16-4) 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.SDS of cas: 170489-16-4

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

Studies on the syntheses of heterocyclic compounds. Part 742. Studies on the syntheses of analgesics. Part 50. Synthesis of optically active 2-[4-(1-oxo-2-isoindolinyl)phenyl]propanoic acid was written by Kametani, Tetsuji;Kigasawa, Kazuo;Hiiragi, Mineharu;Ishimaru, Haruhide;Haga, Seiji;Shirayama, Keiko. And the article was included in Journal of Heterocyclic Chemistry in 1978.Name: 2-Phenylisoindolin-1-one This article mentions the following:

Analgesic and antiinflammatory I (R = CHMeCO₂H), prepared from I (R = COMe) (II) via oxidation of I (R = CHMeCOCO₂H) (III) or hydrolysis of I (R = Q, R¹ = H, R² = CH), was resolved via diastereoisomeric salts with cinchonidine. III was obtained from II in 5 steps via I [R = CMe:C(CN)CO₂Et; Q, where R¹ = CO₂NH₂, R² = CO₂Et and R¹ = CONH₂, R² = CO₂Na; R = COCONH₂] or by Darzens reaction of II with ClCH₂CO₂Et and treatment of the resulting I (R = Q, R¹ = H, R² = CO₂Et) with concentrated HCl and HOAc. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Name: 2-Phenylisoindolin-1-one).

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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: 2-Phenylisoindolin-1-one

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

Synthesis of scalaridine A was written by Kim, Se Hun;Sperry, Jonathan. And the article was included in Tetrahedron Letters in 2015.Recommanded Product: tert-Butyl 5-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate This article mentions the following:

A synthesis of the pyridine-linked bisindole alkaloid scalaridine A is described. An iridium catalyzed, directed C-H borylation of N-Boc-5-methoxyindole gave the corresponding 3-borylindole, which underwent a one-pot, double Suzuki-Miyaura cross-coupling reaction with 3,5-dibromopyridine to install the entire heteroaromatic framework of the natural product. Removal of the protecting groups gave a synthetic sample of scalaridine A, which was spectroscopically identical to that described in the isolation report. In the experiment, the researchers used many compounds, for example, tert-Butyl 5-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate (cas: 1256359-99-5Recommanded Product: tert-Butyl 5-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate).

tert-Butyl 5-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate (cas: 1256359-99-5) 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 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). Recommanded Product: tert-Butyl 5-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate

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

Discovery of the cancer cell selective dual acting anti-cancer agent (Z)-2-(1H-indol-3-yl)-3-(isoquinolin-5-yl)acrylonitrile (A131) was written by See, Cheng Shang;Kitagawa, Mayumi;Liao, Pei-Ju;Lee, Kyung Hee;Wong, Jasmine;Lee, Sang Hyun;Dymock, Brian W.. And the article was included in European Journal of Medicinal Chemistry in 2018.Electric Literature of C9H6ClNO This article mentions the following:

Selective targeting of cancer cells over normal cells is a key objective of targeted therapy. However few approaches achieve true mechanistic selectivity resulting in debilitating side effects and dose limitation. In this work we describe the discovery of A131 (4a), a new agent with an unprecedented dual mechanism of action targeting both mitosis and autophagy. Compound 4a was first identified in a phenotypic screen in which HeLa cells treated with 4a manifested mitotic arrest along with formation of multiple vesicles. Further investigations showed that 4a causes an increase in mitotic marker pH3 and autophagy marker LC3. Importantly 4a induces cell death in cancer cells while sparing normal cells which regrow after 4a is removed. Dual activities against pH3 and LC3 markers are required for cancer cell selectivity. An extensive SAR investigation confirmed 4a as the optimal dual inhibitor with potency against a panel of 30 cancer cell lines (average antiproliferative GI₅₀ 1.5渭M). In a mouse model of paclitaxel-resistant colon cancer, 4a showed 74% tumor growth inhibition when administered at a dose of 20mg/kg IP twice a day. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Electric Literature of C9H6ClNO).

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) 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.Electric Literature of C9H6ClNO

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

H-尾 zeolite, an efficient reusable catalyst for one-pot synthesis of isatins from anilines was written by Raj, I. Victor Paul;Shaikh, Tanveer Mahamadali;Sudalai, Arumugam. And the article was included in Acta Chimica Slovenica in 2010.Recommanded Product: 150560-58-0 This article mentions the following:

The authors described a simple and highly efficient procedure for the single-step preparation of isatins from the com. available anilines using H-尾 zeolite as a truly heterogeneous catalyst. H-尾 zeolite is readily separated from the reaction mixture by simple filtration and was reused several times without considerable loss of activity. In the experiment, the researchers used many compounds, for example, 5-Isopropylindoline-2,3-dione (cas: 150560-58-0Recommanded Product: 150560-58-0).

5-Isopropylindoline-2,3-dione (cas: 150560-58-0) 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.Recommanded Product: 150560-58-0

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

Discovery of Aminopiperidine Indoles That Activate the Guanine Nucleotide Exchange Factor SOS1 and Modulate RAS Signaling was written by Abbott, Jason R.;Hodges, Timothy R.;Daniels, R. Nathan;Patel, Pratiq A.;Kennedy, J. Phillip;Howes, Jennifer E.;Akan, Denis T.;Burns, Michael C.;Sai, Jiqing;Sobolik, Tammy;Beesetty, Yugandhar;Lee, Taekyu;Rossanese, Olivia W.;Phan, Jason;Waterson, Alex G.;Fesik, Stephen W.. And the article was included in Journal of Medicinal Chemistry in 2018.Safety of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

Indole-substituted tryptophan amides such as I were prepared through optimization of aminopiperidine-substituted indoles as activators of the guanine nucleotide exchange factor (GEF) son of sevenless homolog 1 (SOS1) for use in modulating RAS signaling and thus as potential antitumor agents. Substitution patterns on the indole nucleus, the pendant amino acid moiety, and the linker unit connecting these two fragments were modified to determine structure-activity relations for the SOS1-mediated activation of nucleotide exchange. Effective compounds such as I activated the nucleotide exchange process at sub-micromolar concentrations in vitro (IC₅₀ for I = 0.8 卤 0.36 渭M), increased levels of active RAS-GTP in HeLa cells, and elicited signaling changes in the mitogen-activated protein kinase/extracellular regulated kinase (MAPK/ERK) pathway, resulting in a decrease in pERK1/2^T202/Y204 protein levels at higher compound concentrations The structures of selected compounds bound to the ternary complex of RAS, SOS1, and RAS were determined by X-ray crystallog. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Safety of 5-Chloroindole-3-carboxaldehyde).

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Safety of 5-Chloroindole-3-carboxaldehyde

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

Photoredox Imino Functionalizations of Olefins was written by Davies, Jacob;Sheikh, Nadeem S.;Leonori, Daniele. And the article was included in Angewandte Chemie, International Edition in 2017.HPLC of Formula: 14204-27-4 This article mentions the following:

Shown herein is that polyfunctionalized nitrogen heterocycles can be easily prepared by a visible-light-mediated radical cascade process. This divergent strategy features the oxidative generation of iminyl radicals and subsequent cyclization/radical trapping, which allows the effective construction of highly functionalized heterocycles. The reactions proceed efficiently at room temperature, utilize an organic photocatalyst, use simple and readily available materials, and generate, in a single step, valuable building blocks that would be difficult to prepare by other methods. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4HPLC of Formula: 14204-27-4).

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) 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. 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.HPLC of Formula: 14204-27-4

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

Synthesis and screening of 3-[N-substituted phenylamino-2-phenyl-4-thiazolidinon-5-ylidene]-1,3-dihydro-indol-2-ones for in vivo anti-inflammatory activity was written by Devi, N. Saritha;Srinivas, B.;Sarangapani, Manda. And the article was included in Journal of Pharmaceutical Sciences and Research in 2019.Formula: C8H4N2O4 This article mentions the following:

A novel 3-[N-substituted phenylamino-2-phenyl-4-thiazolidinon-5-ylidene]-1,3-dihydro-indol-2-ones I (R = H, 5-F, 7-Me) was synthesized by condensation of isatins II with 2-phenyl-3-(phenylamino)-1,3-thiazolidin-4-one. The compounds I (5-Cl, 7-Cl, 5-F, 5-Br, 5,6-Cl₂, 5-OH) evaluated for in vivo anti-inflammatory activity. The compound I (R = 5,6-Cl₂) showed more in vivo anti-inflammatory activity with 72.5% of inhibition among test compounds The compounds I (R = 5-F, 5Cl, 5-Br, 7-Cl,5-OH) were next in the order of exhibiting in vivo anti-inflammatory activity with 65.75, 63.0, 61.25, 52.5 and 51.25% resp., when compared to standard drug Indomethacin with 73.7% of inhibition. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Formula: C8H4N2O4).

7-Nitroindoline-2,3-dione (cas: 112656-95-8) 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.Formula: C8H4N2O4

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