January 2023 - Page 21 of 26 - Indole Building Blocks

Pradhan, Suman et al. published their research in Chemical Communications (Cambridge, United Kingdom) in 2020 | CAS: 4769-96-4

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

Nitrosoarene-catalyzed regioselective aromatic C-H sulfinylation with thiols under aerobic conditions was written by Pradhan, Suman;Patel, Sandeep;Chatterjee, Indranil. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2020.Related Products of 4769-96-4 This article mentions the following:

Aromatic amines, e.g. PhX (X = Me₂N, Et₂N, PhNH, morpholin-4-yl, etc.), and (hetero)arenes, such as indoles and pyrroles, were regioselectively sulfinylated using aryl thiols RSH (R = Ph, 4-MeC₆H₄, 4-ClC₆H₄, 2-thienyl, 2-pyridyl, etc.) under mild aerobic conditions using nitrosoarenes as a redox-catalyst to give (arylsulfinyl)amines p-XC₆H₄S(O)R, 3-(arylsulfinyl)indoles and 2-(arylsulfinyl)pyrroles. The nitrosoarene is involved in the electron transfer process with arenes to generate a crucial arene radical cation intermediate for C-H sulfinylation. The present methodol. requires no directing group, could be scaled up easily and is applicable for the late-stage functionalization of drug mols. and natural products with high regioselectivity. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Related Products of 4769-96-4).

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

Tripathy, Rabindranath et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2007 | CAS: 170489-16-4

1,4-Dimethyl-1H-indole-3-carbaldehyde (cas: 170489-16-4) 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Safety of 1,4-Dimethyl-1H-indole-3-carbaldehyde

1,2,3-Thiadiazole substituted pyrazolones as potent KDR/VEGFR-2 kinase inhibitors was written by Tripathy, Rabindranath;Ghose, Arup;Singh, Jasbir;Bacon, Edward R.;Angeles, Thelma S.;Yang, Shi X.;Albom, Mark S.;Aimone, Lisa D.;Herman, Joseph L.;Mallamo, John P.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2007.Safety of 1,4-Dimethyl-1H-indole-3-carbaldehyde This article mentions the following:

KDR kinase inhibition is considered to play an important role in regulating angiogenesis, which is vital for the survival and proliferation of tumor cells. Recently we disclosed a structure-based kinase inhibitor design strategy which led to the identification of a new class of VEGFR-2/KDR kinase inhibitors bearing heterocyclic substituted pyrazolones as the core template. Instability in a rat S9 preparation and poor iv PK profiles for most of these inhibitors necessitated exploration of new pyrazolones to identify new analogs with improved metabolic stability. Optimization of the heterocyclic moiety led to the identification of the thiadiazole series of pyrazolones (D) as potent VEGFR-2/KDR kinase inhibitors. SAR modifications, kinase selectivity profiling, and structural elements for improved PK properties were explored. Oral bioavailability up to 29% was achieved in the rat. Modeling results based on the Glide XP docking approach supported our postulation regarding the interaction of the lactam segment of the pyrazolones with the hinge region of the KDR kinase. In the experiment, the researchers used many compounds, for example, 1,4-Dimethyl-1H-indole-3-carbaldehyde (cas: 170489-16-4Safety of 1,4-Dimethyl-1H-indole-3-carbaldehyde).

Yan, Junlei et al. published their research in Science China: Chemistry in 2015 | 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 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). Quality Control of 6-Nitro-1H-indole

Metal-organic framework MIL-53(Al): synthesis, catalytic performance for the Friedel-Crafts acylation, and reaction mechanism was written by Yan, Junlei;Jiang, Sai;Ji, Shengfu;Shi, Da;Cheng, Hefei. And the article was included in Science China: Chemistry in 2015.Quality Control of 6-Nitro-1H-indole This article mentions the following:

Metal-organic framework MIL-53(Al) was synthesized by a solvothermal method using aluminum nitrate as the aluminum source and 1,4-benzenedicarboxylic acid (H2BDC) as the organic ligand. The structure of samples was characterized by X-ray diffraction (XRD) and Fourier transform IR spectroscopy (FT-IR). The catalytic activity and recyclability of MIL-53(Al) catalyst for the Friedel-Crafts acylation reaction of indole with benzoyl chloride were evaluated. The reaction conditions were optimized and a reaction mechanism was suggested. The results showed that the MIL-53(Al) catalyst exhibited good catalytic activity and recyclability for the Friedel-Crafts acylation reaction. When the molar ratio of indole and MIL-53(Al) catalyst was 1:0.06 (n₁:n _catalyst), the molar ratio of indole and benzoyl chloride was 1:3, and the solvent was dichloromethane, the conversion of indole could reach 97.1% and the selectivity of 3-acylindole could reach 81.1% at 25 °C after 8 h. The catalyst can be reused without significant degradation in catalytic activity. After the catalyst was reused five times, the conversion of indole was 87.6% and the selectivity of 3-acylindole was 79.5%. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Quality Control of 6-Nitro-1H-indole).

Xie, Guilin et al. published their research in Organic Letters in 2021 | CAS: 4769-96-4

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

Palladium-Catalyzed Direct and Specific C-7 Acylation of Indolines with 1,2-Diketones was written by Xie, Guilin;Zhao, Yuhan;Cai, Changqun;Deng, Guo-Jun;Gong, Hang. And the article was included in Organic Letters in 2021.HPLC of Formula: 4769-96-4 This article mentions the following:

Herein, a palladium-catalyzed direct and specific C-7 acylation of indolines in the presence of an easily removed directing group was developed. This strategy usually considered as a practical strategy for the preparation of acylated indoles because indoline can be easily converted to indole under oxidation conditions. In particular, these strategy greatly improved the alkacylation yield of indolines for which only an unsatisfactory yield could be achieved in the previous studies. Furthermore, the reaction can be scaled up to gram level in the standard reaction conditions with a much lower palladium loading (1 mol %). In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4HPLC of Formula: 4769-96-4).

Zhang, Jingyu et al. published their research in Advanced Synthesis & Catalysis in 2017 | CAS: 4769-96-4

6-Nitro-1H-indole (cas: 4769-96-4) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. 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). HPLC of Formula: 4769-96-4

Dehydrogenation of Nitrogen Heterocycles Using Graphene Oxide as a Versatile Metal-Free Catalyst under Air was written by Zhang, Jingyu;Chen, Shiya;Chen, Fangfang;Xu, Wensheng;Deng, Guo-Jun;Gong, Hang. And the article was included in Advanced Synthesis & Catalysis in 2017.HPLC of Formula: 4769-96-4 This article mentions the following:

Graphene oxide (GO) has been developed as an inexpensive, environmental friendly, metal-free carbocatalyst for the dehydrogenation of nitrogen heterocycles. Valuable compounds, such as quinoline, 3,4-dihydroisoquinoline, quinazoline, and indole derivatives, have been successfully used as substrates. The investigation of various oxygen-containing mols. with different conjugated systems indicated that both the oxygen-containing groups and large π-conjugated system in GO sheets are essential for this reaction. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4HPLC of Formula: 4769-96-4).

Padma, Bairy et al. published their research in Pharma Innovation in 2020 | CAS: 112656-95-8

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

Synthesis, characterization and evaluation of antioxidant activity of N-([1,3,4]oxadiazino[6,5-b] substituted indol-3-ylmethyl)aniline was written by Padma, Bairy;Gadea, Sammaiah. And the article was included in Pharma Innovation in 2020.Computed Properties of C8H4N2O4 This article mentions the following:

A novel series of N-([1,3,4]oxadiazino[6,5-b] substituted indol-3-ylmethyl)anilines I [R = H, 5-Me, 7-Br, etc.] were synthesized in good yields and characterized by IR, NMR and mass spectral analyses. Synthesized compounds I were evaluated for their antioxidant activity by standard DPPH assay method. By taking ascorbic acid as standard drug, among the series the compounds I [R = 7-Cl, 5-COOEt, 7-OH] were potent antioxidant and remaining compounds showed significant antioxidant activity. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Computed Properties of C8H4N2O4).

Huttunen, Kristiina M. et al. published their research in Journal of Medicinal Chemistry in 2009 | CAS: 14204-27-4

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

The First Bioreversible Prodrug of Metformin with Improved Lipophilicity and Enhanced Intestinal Absorption was written by Huttunen, Kristiina M.;Mannila, Anne;Laine, Krista;Kemppainen, Eeva;Leppanen, Jukka;Vepsalainen, Jouko;Jarvinen, Tomi;Rautio, Jarkko. And the article was included in Journal of Medicinal Chemistry in 2009.Recommanded Product: 14204-27-4 This article mentions the following:

Metformin is a potent antidiabetic agent and currently used as a first-line treatment for patients with type 2 diabetes. Unfortunately, the moderate absorption and uncomfortable gastrointestinal adverse effects associated with metformin therapy impair its use. In this study, two novel prodrugs of a biguanidine functionality containing antidiabetic agent, metformin, were designed, synthesized, and evaluated in vitro and in vivo to accomplish improved lipophilicity and, consequently, enhanced oral absorption of this highly water-soluble drug. These results represent that the more lipophilic prodrug 2a biotransformed quant. to metformin mainly after absorption. The enhanced oral absorption consequently promoted the bioavailability of metformin from 43% to 65% in rats. Thus, this novel prodrug may offer a solution to reduce the required daily doses of metformin, which may decrease the uncomfortable adverse effects associated with metformin therapy. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Recommanded Product: 14204-27-4).

Weiwer, Michel et al. published their research in ACS Medicinal Chemistry Letters in 2012 | CAS: 150560-58-0

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

A Potent and Selective Quinoxalinone-Based STK33 Inhibitor Does Not Show Synthetic Lethality in KRAS-Dependent Cells was written by Weiwer, Michel;Spoonamore, James;Wei, Jingqiang;Guichard, Boris;Ross, Nathan T.;Masson, Kristina;Silkworth, Whitney;Dandapani, Sivaraman;Palmer, Michelle;Scherer, Christina A.;Stern, Andrew M.;Schreiber, Stuart L.;Munoz, Benito. And the article was included in ACS Medicinal Chemistry Letters in 2012.Quality Control of 5-Isopropylindoline-2,3-dione This article mentions the following:

The KRAS oncogene is found in up to 30% of all human tumors. In 2009, RNAi experiments revealed that lowering mRNA levels of a transcript encoding the serine/threonine kinase STK33 was selectively toxic to KRAS-dependent cancer cell lines, suggesting that small-mol. inhibitors of STK33 might selectively target KRAS-dependent cancers. To test this hypothesis, we initiated a high-throughput screen using compounds in the Mol. Libraries Small Mol. Repository (MLSMR). Several hits were identified, and one of these, a quinoxalinone derivative, was optimized. Extensive SAR studies were performed and led to the chem. probe ML281 that showed low nanomolar inhibition of purified recombinant STK33 and a distinct selectivity profile as compared to other STK33 inhibitors that were reported in the course of these studies. Even at the highest concentration tested (10 μM), ML281 had no effect on the viability of KRAS-dependent cancer cells. These results are consistent with other recent reports using small-mol. STK33 inhibitors. Small mols. having different chem. structures and kinase-selectivity profiles are needed to fully understand the role of STK33 in KRAS-dependent cancers. In this regard, ML281 is a valuable addition to small-mol. probes of STK33. In the experiment, the researchers used many compounds, for example, 5-Isopropylindoline-2,3-dione (cas: 150560-58-0Quality Control of 5-Isopropylindoline-2,3-dione).

Moraes, Ana Daura Travassos de Oliveira et al. published their research in Bioorganic & Medicinal Chemistry in 2018 | CAS: 827-01-0

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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Safety of 5-Chloroindole-3-carboxaldehyde

Synthesis, in vitro and in vivo biological evaluation, COX-1/2 inhibition and molecular docking study of indole-N-acylhydrazone derivatives was written by Moraes, Ana Daura Travassos de Oliveira;Miranda, Mirelly Dianne Santos de;Jacob, Iris Trindade Tenorio;Amorim, Cezar Augusto da Cruz;Moura, Ricardo Olimpio de;Silva, Simone Angela Soares da;Soares, Milena Botelho Pereira;Almeida, Sinara Monica Vitalino de;Souza, Tulio Ricardo Couto de Lima;Oliveira, Jamerson Ferreira de;Silva, Teresinha Goncalves da;Melo, Cristiane Moutinho Lagos de;Moreira, Diogo Rodrigo Magalhaes;Lima, Maria do Carmo Alves de. And the article was included in Bioorganic & Medicinal Chemistry in 2018.Safety of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

The objective of this work was to obtain and evaluate anti-inflammatory in vitro, in vivo and in silico potential of novel indole-N-acylhydrazone derivatives In total, 10 new compounds (3a-j) were synthesized in satisfactory yields, through a condensation reaction in a single synthesis step. In the lymphoproliferation assay, using mice splenocytes, 3a and 3b showed inhibition of lymphocyte proliferation of 62.7% (±3.5) and 50.7% (±2), resp., while dexamethasone presented an inhibition of 74.6% (±2.4). Moreover, compound 3b induced higher Th2 cytokines production in mice splenocytes cultures. The results for COX inhibition assays showed that compound 3b is a selective COX-2 inhibitor, but with less potency when compared to celecoxib, and compound 3a not presented selectivity towards COX-2. The mol. docking results suggest compounds 3a and 3b interact with the active site of COX-2 in similar conformations, but not with the active site of COX-1, and this may be the main reason to the COX-2 selectivity of compound 3b. In vivo carrageenan-induced paw edema assays were adopted for the confirmation of the anti-inflammatory activity. Compound 3b showed better results in suppressing edema at all tested concentrations and was able to induce an edema inhibition of 100% after 5 h of carrageenan injection at the 30 mg kg^-1 dosage, corroborating with the COX inhibition and lymphoproliferation results. I addition to our exptl. results, in silico anal. suggest that compounds 3a and 3b present a well-balanced profile between pharmacodynamics and pharmacokinetics. Thus, our preliminary results revealed the potentiality of a new COX-2 selective derivative in the modulation of the inflammatory process. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Safety of 5-Chloroindole-3-carboxaldehyde).

McNeil, Nicole M. R. et al. published their research in Molecules in 2015 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Electric Literature of C14H9NO2S

Oxidation of disulfides to thiolsulfinates with hydrogen peroxide and a cyclic seleninate ester catalyst was written by McNeil, Nicole M. R.;McDonnell, Ciara;Hambrook, Miranda;Back, Thomas G.. And the article was included in Molecules in 2015.Electric Literature of C14H9NO2S This article mentions the following:

A variety of aryl and alkyl disulfides underwent facile oxidation with hydrogen peroxide in the presence of catalytic benzo-1,2-oxaselenolane Se-oxide affording the corresponding thiolsulfinates as the principal products. Unsym. disulfides typically afforded mixtures of regioisomers. Lipoic acid and N,N’-dibenzoylcystine di-Me ester were oxidized readily under similar conditions. Although isolated yields of the product thiolsulfinates were generally modest, these experiments demonstrate that the method nevertheless has preparative value because of its mild conditions. The results also confirm the possibility that cyclic seleninate esters could catalyze the further undesired oxidation of disulfides in vivo. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Electric Literature of C14H9NO2S).