02/02/2023 - Page 7 of 11 - Indole Building Blocks

Goodfellow, Val S. et al. published their research in Journal of Medicinal Chemistry in 2013 | CAS: 754214-56-7

7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7) 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.Recommanded Product: 7-Azaindole-5-boronic Acid Pinacol Ester

Discovery, Synthesis, and Characterization of an Orally Bioavailable, Brain Penetrant Inhibitor of Mixed Lineage Kinase 3 was written by Goodfellow, Val S.;Loweth, Colin J.;Ravula, Satheesh B.;Wiemann, Torsten;Nguyen, Thong;Xu, Yang;Todd, Daniel E.;Sheppard, David;Pollack, Scott;Polesskaya, Oksana;Marker, Daniel F.;Dewhurst, Stephen;Gelbard, Harris A.. And the article was included in Journal of Medicinal Chemistry in 2013.Recommanded Product: 7-Azaindole-5-boronic Acid Pinacol Ester This article mentions the following:

Inhibition of mixed lineage kinase 3 (MLK3) is a potential strategy for treatment of Parkinson’s disease and HIV-1 associated neurocognitive disorders (HAND), requiring an inhibitor that can achieve significant brain concentration levels. We report here URMC-099 (1) an orally bioavailable (F = 41%), potent (IC₅₀ = 14 nM) MLK3 inhibitor with excellent brain exposure in mouse PK models and minimal interference with key human CYP450 enzymes or hERG channels. The compound inhibits LPS-induced TNFα release in microglial cells, HIV-1 Tat-induced release of cytokines in human monocytes and up-regulation of phospho-JNK in Tat-injected brains of mice. Compound 1 likely functions in HAND preclin. models by inhibiting multiple kinase pathways, including MLK3 and LRRK2 (IC₅₀ = 11 nM). We compare the kinase specificity and BBB penetration of 1 with CEP-1347 (2). Compound 1 is well tolerated, with excellent in vivo activity in HAND models, and is under investigation for further development. In the experiment, the researchers used many compounds, for example, 7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7Recommanded Product: 7-Azaindole-5-boronic Acid Pinacol Ester).

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

Fu, Liqiang et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2012 | CAS: 110568-64-4

6-Nitroisoindolin-1-one (cas: 110568-64-4) 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.Recommanded Product: 6-Nitroisoindolin-1-one

Design, synthesis, and structure-activity relationship studies of conformationally restricted mutilin 14-carbamates was written by Fu, Liqiang;Liu, Xin;Ling, Chenyu;Cheng, Jianjun;Guo, Xingsheng;He, Huili;Ding, Shi;Yang, Yushe. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2012.Recommanded Product: 6-Nitroisoindolin-1-one This article mentions the following:

We report herein the design, synthesis, and structure-activity relationship studies of conformationally restricted mutilin 14-carbamates based on the structure of SB-222734. For example, reacting benzoates I (R¹ = H, MeO, NO₂, R² = H, F, NO₂, R⁹ = H) with N-bromosuccinimide gave the brominated compounds I (R⁹ = Br), which cyclized to give isoindolinones II. II were then coupled with 4-epi-mutilin 14-chloroformate III and treated with a saturated solution of ZnCl₂ in concentrated HCl resulting in a reverse 1,5-hydride shift to afford desired products IV. The antibacterial activities of these newly synthesized compounds were also evaluated and compared with linezolid and retapamulin. Results showed that most of the target compounds exhibit good potency in inhibiting the growth of Gram-pos. bacteria including Methicillin-susceptible Staphylococcus aureus MSSA (MIC: 0.0625-2 μg/mL), Methicillin-resistant S. aureus MRSA (MIC: 0.0625-2 μg/mL), Methicillin-susceptible Staphylococcus epidermidis MSSE (MIC: 0.0625-2 μg/mL), Methicillin-resistant S. epidermidis MRSE (MIC: 0.0625-2 μg/mL), and Streptococcus pneumonia (MIC: 0.0625-4 μg/mL). In particular, three remarkable compounds of this series IV (R¹ = NH₂, R² = H; R¹ = H, R² = NH₂) and isoquinolinyl derivative V exhibited comparable in vitro antibacterial profiles to that of retapamulin. In the experiment, the researchers used many compounds, for example, 6-Nitroisoindolin-1-one (cas: 110568-64-4Recommanded Product: 6-Nitroisoindolin-1-one).

Li, Jianxiao et al. published their research in Journal of Organic Chemistry in 2016 | CAS: 4769-96-4

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

Palladium-catalyzed oxidative sulfenylation of indoles and related electron-rich heteroarenes with aryl boronic acids and elemental sulfur was written by Li, Jianxiao;Li, Chunsheng;Yang, Shaorong;An, Yanni;Wu, Wanqing;Jiang, Huanfeng. And the article was included in Journal of Organic Chemistry in 2016.Name: 6-Nitro-1H-indole This article mentions the following:

An efficient and convenient palladium-catalyzed C-H bond oxidative sulfenylation of 1-R²-2-R⁴-R³-indoles and 2-R⁴-6-R³-imidazo[1,2-a]pyridines with aryl boronic acids and elemental sulfur for the synthesis of 3-sulfenylindole derivatives I and II, resp. (R¹ = H, alkyl, MeO, halo, CN; R² = H, Me, PhCH₂; R³ = H, halo, alkyl, MeO, NO₂; R⁴ = H, Me, CO₂Et, Ph) is disclosed. This procedure provides a useful and direct approach for the assembly of a wide range of structurally diverse 3-sulfenylheteroarenes with moderate to excellent yields from simple and readily available starting materials. Moreover, this synthetic protocol is suitable for N-protected and unprotected indoles. Notably, the construction of two C-S bonds in one step was also achieved in this transformation. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Name: 6-Nitro-1H-indole).

Ittiamornkul, Kuljira et al. published their research in Chemical Science in 2015 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Related Products of 827-01-0

Promiscuous indolyl vinyl isonitrile synthases in the biogenesis and diversification of hapalindole-type alkaloids was written by Ittiamornkul, Kuljira;Zhu, Qin;Gkotsi, Danai S.;Smith, Duncan R. M.;Hillwig, Matthew L.;Nightingale, Nicole;Goss, Rebecca J. M.;Liu, Xinyu. And the article was included in Chemical Science in 2015.Related Products of 827-01-0 This article mentions the following:

The hapalindole-type alkaloids naturally show striking late stage diversification of what was believed to be a conserved intermediate, cis-indolyl vinyl isonitrile I. Here we demonstrate enzymically, as well as through applying a synthetic biol. approach, that the pathway generating I (itself, a potent natural broad-spectrum antibiotic) is also dramatically flexible. We harness this to enable early stage diversification of the natural product and generation of a wide range of halo-analogs of I. This approach allows the preparatively useful generation of a series of antibiotics with increased lipophilicity over that of the parent antibiotic. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Related Products of 827-01-0).

Song, Bo et al. published their research in Gaodeng Xuexiao Huaxue Xuebao in 2008 | CAS: 146368-07-2

1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2) 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Reference of 146368-07-2

Synthesis and spectral properties of new water-soluble fluorescent label squarylium indocyanine dyes was written by Song, Bo;Zhang, Qian;Peng, Xiao-Jun;Ma, Wen-Hui;Wang, Bing-Shuai;Fu, Xin-Mei. And the article was included in Gaodeng Xuexiao Huaxue Xuebao in 2008.Reference of 146368-07-2 This article mentions the following:

Six water-soluble squarylium indocyanine dyes were synthesized and their structures were confirmed by ¹H NMR and MS spectroscopy. The absorption and emission spectra of these dyes in water, methanol, ethanol, DMF, DMSO were studied. The spectra of these dyes exhibit a neg. solvatochromism. The photo stability of these dyes in water was investigated as well. It is demonstrated that the electron-withdrawing group on N-position of cyanine dyes improves the photo stability as compared with the dyes with electron-donating group which decreases the photo stability obviously. In the experiment, the researchers used many compounds, for example, 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2Reference of 146368-07-2).

Li, Xiaomeng et al. published their research in Journal of Organic Chemistry in 2018 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Formula: C14H9NO2S

Hydrochloric Acid-Promoted Intermolecular 1,2-Thiofunctionalization of Aromatic Alkenes was written by Li, Xiaomeng;Guo, Yunlong;Shen, Zengming. And the article was included in Journal of Organic Chemistry in 2018.Formula: C14H9NO2S This article mentions the following:

An efficient method for making 1,2-thiofunctionalized products via the difunctionalization of aromatic alkenes was developed. In this method, cheap and readily available hydrochloric acid was used to promote 1,2-thiofunctionalization of aryl alkenes with N-arylsulfenylphthalimide and different types of nucleophiles. Importantly, extension of nucleophiles can reach aryl ethers, indoles, and carboxylic acids with good reactivity. This practical and convenient method has broad substrate scope and high yields under metal-free and mild conditions. Furthermore, we achieved conversion and application for making sulfoxide and sulfone by oxidation In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Formula: C14H9NO2S).

Zhao, Yin et al. published their research in Synlett in 2022 | CAS: 170489-16-4

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

Visible-Light-Promoted Indole C-3 Formylation Using Eosin Y as a Photoredox Catalyst was written by Zhao, Yin;Li, Hongfang;Yin, Shan;Wu, Yandan;Ni, Guanghui. And the article was included in Synlett in 2022.Name: 1,4-Dimethyl-1H-indole-3-carbaldehyde This article mentions the following:

A visible-light-mediated C-3 formylation of indole catalyzed by eosin Y has been developed using tetramethylethylenediamine as a carbon source and air as an oxidant. This protocol shows high tolerance to a large quantity of functional groups under mild conditions and provides 3-formylated indoles with good yields. This method is a highly attractive alternative to the approach of traditional formylation. In the experiment, the researchers used many compounds, for example, 1,4-Dimethyl-1H-indole-3-carbaldehyde (cas: 170489-16-4Name: 1,4-Dimethyl-1H-indole-3-carbaldehyde).

Lu, Xieqin et al. published their research in Hebei Yiyao in 2012 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Quality Control of 2-(Phenylthio)isoindoline-1,3-dione

Sulfuration reaction of glycine tert-butyl ester derivatives by phase transfer catalysis was written by Lu, Xieqin;Dong, Xiaoyang;Dai, Zhenya;You, Qidong. And the article was included in Hebei Yiyao in 2012.Quality Control of 2-(Phenylthio)isoindoline-1,3-dione This article mentions the following:

Sulfuration of glycine tert-Bu ester derivatives by phase transfer catalysis was tried to provide. The best condition was using TEBA as catalyst, 50% KOH as alk. and THF as solvent. α-Sulfuration reaction by phase transfer catalysis was successfully made, and ee in asymmetry could up to 70%. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Quality Control of 2-(Phenylthio)isoindoline-1,3-dione).

Padma, Bairy et al. published their research in International Journal of Research in Pharmacy and Chemistry in 2020 | CAS: 112656-95-8

7-Nitroindoline-2,3-dione (cas: 112656-95-8) 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.Reference of 112656-95-8

Synthesis and antioxidant activity of 3-[4-(2,5-dimethylamino-1H-pyrrol-1-yl-phenyl)][1,3,4]-oxadiazino[6,5-b]substituted indole was written by Padma, Bairy;Gadea, Sammaiah. And the article was included in International Journal of Research in Pharmacy and Chemistry in 2020.Reference of 112656-95-8 This article mentions the following:

Fifteen new 3-[4-(2,5-di-Me amino-1H pyrrol-1-yl-phenyl)][1,3,4]-oxadiazino [6,5-b] substituted indoles I (R = 6-Cl, 8-Br, 6-F, etc.) have been synthesized. The chem. structures of the products I were confirmed by ¹HNMR, IR and mass spectral data. The compounds I were screened for antioxidant activity by standard DPPH assay method. IC₅₀ values of these compounds I were determined Compounds I (R = 8-F, 8-C(O)₂H, 8-C(O)₂Et) potent antioxidant and remaining compounds showed significant antioxidant activity. Ascorbic acid was taken as standard drug. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Reference of 112656-95-8).

Shershov, V. E. et al. published their research in Journal of Fluorescence in 2017 | CAS: 146368-07-2

1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.COA of Formula: C13H17NO3S

Comparative Study of Novel Fluorescent Cyanine Nucleotides: Hybridization Analysis of Labeled PCR Products Using a Biochip was written by Shershov, V. E.;Lapa, S. A.;Kuznetsova, V. E.;Spitsyn, M. A.;Guseinov, T. O.;Polyakov, S. A.;Stomahin, A. A.;Zasedatelev, A. S.;Chudinov, A. V.. And the article was included in Journal of Fluorescence in 2017.COA of Formula: C13H17NO3S This article mentions the following:

This study investigated the synthesis and substrate properties of Cy5-labeled dUTP derivatives with different substituents, linkers between the dye unit and pyrimidine heterocycle and fluorophore charges. Fluorescently labeled nucleoside triphosphates were studied as substrates using multiplex PCR with Taq and Vent (exo-) DNA polymerases, the typical representatives of the A and B polymerase families. The efficiency of nucleotide incorporation during PCR was assessed with a multi-parameter hybridization anal. using a diagnostic DNA microarray. The hybridization anal. indirectly estimates the incorporation efficiency of dye-labeled nucleotides in multiplex PCR. Our results demonstrated higher efficiencies of substrates with elec. neutral dyes than electropos. and electroneg. Cy5 residues. In the experiment, the researchers used many compounds, for example, 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2COA of Formula: C13H17NO3S).