04/01/2023 - Page 7 of 11 - Indole Building Blocks

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).

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

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).

Huang, Hong-Ming et al. published their research in Organic Chemistry Frontiers in 2020 | CAS: 827-01-0

Cu(II)-Catalyzed formal [4+2] cycloaddition between quinone methides (QMs) and electron-poor 3-vinylindoles was written by Huang, Hong-Ming;Wu, Xu-Yan;Leng, Bo-Rong;Zhu, Yi-Long;Meng, Xin-Chao;Hong, Yu;Jiang, Bo;Wang, De-Cai. And the article was included in Organic Chemistry Frontiers in 2020.COA of Formula: C9H6ClNO This article mentions the following:

A new Cu(II)-catalyzed formal [4+2] cycloaddition between o-hydroxybenzyl alcs./quinone methides (QMs) including para-quinone methides (p-QMs) and ortho-quinone methides (o-QMs) and electron-poor 3-vinylindoles was established. A wide range of richly decorated indole-containing chromane derivatives, e.g., I, was synthesized in acceptable yields and diastereoselectivity. Based on several control experiments, a possible mechanism was also proposed to elucidate the catalytic cycle pathway. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0COA of Formula: C9H6ClNO).

Sakurai, Buhei et al. published their research in Bulletin of the Chemical Society of Japan in 1930 | 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Electric Literature of C14H11NO

The electrolytic reduction of phthalimides. I was written by Sakurai, Buhei. And the article was included in Bulletin of the Chemical Society of Japan in 1930.Electric Literature of C14H11NO This article mentions the following:

An alc. HCl solution of phthalimide (I) was electrolyzed between Pb electrodes, at 20 amp./sq. dm. and at 20-30°, yielding hydroxyphthalimidinc, m. 105°, needles. Reisert’s hydroxyphalimidine, m. 171° (cf. C. A. 7,2578), was found to be a polymer containing 2 mols. It was also prepd from alc. H₂SO₄ solution Cu electrodes, being used. With stronger acid, at 60 amp./sq. dm. and at 30-40°, Phthalimidine, m. 149°, needles, was obtained. Phthalimide could not be reduced in 2 N NaOH, but hydrolyzed to phthalamic acid and phthalic acid. Methylphthalimide (II) yielded methylphthalimidine, m. 45°, plates, with Pb cathode; with Cu cathode it yielded methylhydroxyphthalimidine, m. 129°, prisms. In alk. solution II hydrolyzed to phthalic acid and MeNH₂. Ethylphthalimide (III) yielded ethylphthalimidine, colorless oil, with Pb electrodes; with Cu or Ni cathode ethylhydroxyphthalimidine was obtained instead. In alk. solution III hydrolyzed to ethylphthalamic acid, m. 136°, needles, also phthalic acid and EtNH₂. Phenylphthalimide (IV) yielded phenylphthalimidine, scaly crystals. Hydroxyphenylphthalimide could not be obtained. In alk. solution IV hydrolyzed completely into phthalic acid and PhNH₂. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Electric Literature of C14H11NO).

Wen, Kangmei et al. published their research in ACS Omega in 2022 | CAS: 89245-41-0

4-Bromoindole-3-acetic Acid (cas: 89245-41-0) 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Application In Synthesis of 4-Bromoindole-3-acetic Acid

Copper-Mediated Decarboxylative Coupling of 3-Indoleacetic Acids with Pyrazolones was written by Wen, Kangmei;Wu, Yinrong;Chen, Jiewen;Shi, Jie;Zheng, Mulin;Yao, Xingang;Tang, Xiaodong. And the article was included in ACS Omega in 2022.Application In Synthesis of 4-Bromoindole-3-acetic Acid This article mentions the following:

A copper-mediated decarboxylative coupling reaction of 3-indoleacetic acids with pyrazolones was described. This protocol realized new functionalization of pyrazolones under simple reaction conditions and exhibited high functional group compatibility and broad substrate scope. Notably, the products displayed antiproliferative activity against cancer cells. In the experiment, the researchers used many compounds, for example, 4-Bromoindole-3-acetic Acid (cas: 89245-41-0Application In Synthesis of 4-Bromoindole-3-acetic Acid).

Ordonez, Mario et al. published their research in Synthesis in 2012 | CAS: 5388-42-1

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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Recommanded Product: 5388-42-1

An easy approach for the synthesis of N-substituted isoindolin-1-ones was written by Ordonez, Mario;Tibhe, Gaurao D.;Zamudio-Medina, Angel;Viveros-Ceballos, Jose Luis. And the article was included in Synthesis in 2012.Recommanded Product: 5388-42-1 This article mentions the following:

A practical and efficient two-step synthesis of N-substituted isoindolin-1-ones was developed. The one-pot reaction of 2-formylbenzoic acid with amines and di-Me phosphite proceeds in short time either with conventional heating or microwave irradiation under catalyst-free conditions to afford the corresponding N-substituted di-Me 3-oxoisoindolin-1-ylphosphonates in good yield which, by means of a dephosphonylation reaction with lithium aluminum hydride, give the target N-substituted isoindolin-1-ones in moderate to good yield. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Recommanded Product: 5388-42-1).

Audubert, Clement et al. published their research in Organic Letters in 2017 | CAS: 167631-84-7

Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7) 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.Category: indole-building-block

Mild Esterification of Carboxylic Acids via Continuous Flow Diazotization of Amines was written by Audubert, Clement;Lebel, Helene. And the article was included in Organic Letters in 2017.Category: indole-building-block This article mentions the following:

A new continuous flow protocol for the diazotization of methylamine with 1,3-propanedinitrite in THF is reported. The synthesis of Me esters was achieved in high yields from a variety of carboxylic acids in 20 min at 90 °C. Addnl., this protocol was extended to other aryl and alkyl amines, namely secondary amines, to produce various substituted esters in high yield using 2-MeTHF as a solvent. The reaction conditions were compatible with many functional groups, namely nitrogen-containing heterocycles, alkynes, alkenes, alcs., and phenols. Mechanistic investigations reveal that the reaction appears to proceed through a transient diazonium species rather than a diazo intermediate. In the experiment, the researchers used many compounds, for example, Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7Category: indole-building-block).

Li, Chang-Feng et al. published their research in Organic Letters in 2007 | CAS: 210345-56-5

Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Recommanded Product: 210345-56-5

Enantioselective Organocatalytic Intramolecular Ring-Closing Friedel-Crafts-Type Alkylation of Indoles was written by Li, Chang-Feng;Liu, Hiu;Liao, Jie;Cao, Yi-Ju;Liu, Xiao-Peng;Xiao, Wen-Jing. And the article was included in Organic Letters in 2007.Recommanded Product: 210345-56-5 This article mentions the following:

An enantioselective organocatalytic intramol. ring-closing Friedel-Crafts-type alkylation of indolyl α,β-unsaturated aldehydes has been developed. This powerful new strategy allows enantioselective access to THPIs (tetrahydropyrano[3,4-b]indoles), e.g., I, and THBCs (tetrahydro-β-carbolines), e.g., II, in a straightforward and atom-economical manner. In the experiment, the researchers used many compounds, for example, Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5Recommanded Product: 210345-56-5).

Singh, R. et al. published their research in Phosphorus, Sulfur and Silicon and the Related Elements in 2006 | CAS: 112656-95-8

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

Structural Studies with Antimicrobial and Antifertility Activity of a Monofunctional Bidentate Ligand with its Boron(III), Palladium(II), and Platinum(II) Complexes was written by Singh, R.;Biyala, M.. And the article was included in Phosphorus, Sulfur and Silicon and the Related Elements in 2006.Reference of 112656-95-8 This article mentions the following:

The reaction of the sulfur donor Schiff base ligand, (7-nitro-2-oxoindolin-3-ylidene)hydrazinecarbothioamide (HL, I), with phenyldihydroxyboron in benzene, and palladium(II)chloride and platinum(II) chloride in ethanol, gave the mononuclear tetracoordinated [PhB(OH)L], [PhB(L)₂], [M(HL)₂]Cl₂ and [M(L)₂] complexes. The Schiff base ligand coordinated to the boron atom in 1:1 and 1:2 molar ratios and to the palladium and platinum metals in only 1:2 molar ratios in the presence of an acidic or basic medium. Tentative structural conclusions are drawn for reaction products based upon elemental anal., elec. conductance, and spectral (electronic, IR, ¹H NMR, ¹³C NMR, and ¹¹B NMR) data. The antifertility activity of the ligand and its nonmetal/metal complexes are discussed with a comparative study in an effective manner. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Reference of 112656-95-8).