January 2023 - Page 7 of 26 - Indole Building Blocks

Hucher, Nicolas et al. published their research in European Journal of Organic Chemistry in 2005 | CAS: 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Category: indole-building-block

Exocyclic-endocyclic N-acyliminium ion equilibration via an intramolecular α-thioamidoalkylation in the synthesis of fused N,S-heterocyclic systems: Some new parameters was written by Hucher, Nicolas;Pesquet, Anthony;Netchitailo, Pierre;Daich, Adam. And the article was included in European Journal of Organic Chemistry in 2005.Category: indole-building-block This article mentions the following:

The reactivity of N-[aryl(or alkyl)thio(or seleno)]alkylamidals bearing the N-(CH₂)_n-X-(CH₂)_m-Ar functionality towards neat TFA has been examined These substrates give both the products of the “expected” π-cyclization process and “unexpected” products resulting from a new tandem heteroamidoalkylation/isomerization/π-cyclization. E.g., TFA catalyzed the reactions of α-hydroxy lactam I to give a mixture of II and III (92% yield, ratio 5.5:4.5). The composition of the final isomeric mixture depends on the temperature of the reaction, with a high selectivity in favor of the “expected” π-cyclization product as a thermodn. isomer. Furthermore, the results demonstrate again the relevance of TFA catalysis and support two reaction pathways involving the formation of an aza-sulfonium cation as a valuable intermediate which undergoes the π-cyclization process alone or in tandem with the thiocyclization/isomerization to give the cyclized products cited above. For the latter tandem reaction, we have established clearly that the n value should be equal to 1, the process can be performed independently for both the succinimide and phthalimide series, the reaction depends on the nucleophilicity of the heteroatom, and can be generalized to other heterocycles. Only the role of the benzene substitution has still to be totally elucidated. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Category: indole-building-block).

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

Ley, Steven V. et al. published their research in Journal of the Chemical Society, Chemical Communications in 1982 | CAS: 85696-95-3

1-Methyl-1H-indol-4-amine (cas: 85696-95-3) 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Computed Properties of C9H10N2

An unexpected rearrangement of 4-alkylaminoindoles was written by Ley, Steven V.;Porter, Roderick A.. And the article was included in Journal of the Chemical Society, Chemical Communications in 1982.Computed Properties of C9H10N2 This article mentions the following:

The aminoindoles I (R = Me, CH₂Ph, CH₂CO₂Et, R¹ = H) rearranged on refluxing in PhMe containing 4-MeC₆H₄SO₃H for 23, 21, and 44 h, resp., to give the indoles I (R = H, R¹ = Me, CH₂Ph, CH₂CO₂Et) in 75, 90, and 77% yield, resp. The mechanism involves initial ring opening to give a diamino aldehyde intermediates which recyclizes to give the thermodynamically preferred 1-alkyl-4-aminoindoles. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-indol-4-amine (cas: 85696-95-3Computed Properties of C9H10N2).

Yamamoto, Iwao et al. published their research in Journal of Organic Chemistry in 1974 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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.HPLC of Formula: 5388-42-1

Synthesis of phthalimidines from aromatic dicarbonyl compounds was written by Yamamoto, Iwao;Yanagi, Shoichi;Mamba, Akio;Gotoh, Haruo. And the article was included in Journal of Organic Chemistry in 1974.HPLC of Formula: 5388-42-1 This article mentions the following:

Addnl. data considered in abstracting and indexing are available from a source cited in the original document. The reaction between o-benzoylbenzaldehyde (I) and aromatic isocyanates RNCO (R = Ph, m-tolyl, α- and β-naphthyl) afforded 2,3-disubstituted phthalimidines II in good yield, which would be formed via o-benzoylbenzylideneaniline intermediate followed by migration of Ph group. The same product II (R = Ph) was obtained by the reaction using I and aniline. On the other hand, no reaction was observed between o-carbethoxybenzaldehyde (III) and PhNCO, but the reaction of III with aniline gave o-carbethoxybenzylideneaniline and 3-anilino-2-phenylphthalimidine in 83% and 7% yields, resp. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1HPLC of Formula: 5388-42-1).

Jiang, B. et al. published their research in Bioorganic & Medicinal Chemistry in 2000 | CAS: 90271-86-6

5-Bromo-3-cyanoindole (cas: 90271-86-6) 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.HPLC of Formula: 90271-86-6

Syntheses and cytotoxicity evaluation of bis(indolyl)thiazole, bis(indolyl)pyrazinone and bis(indolyl)pyrazine: analogues of cytotoxic marine bis(indole) alkaloid was written by Jiang, B.;Gu, X.-H.. And the article was included in Bioorganic & Medicinal Chemistry in 2000.HPLC of Formula: 90271-86-6 This article mentions the following:

2,4-Bis(3′-indolyl)thiazoles, 3,5-bis(3′-indolyl)-2(1H)pyrazinone and 3,6-bis(3′-indolyl)pyrazine were synthesized and evaluated for cytotoxic activity against diverse human cancer cell lines by the National Cancer Institute. These compounds demonstrated significant inhibitory effects in the growth of a range of cancer cell lines. 2,4-Bis(3′-indolyl)thiazole displayed selective cytotoxicity against certain leukemia cell lines with GI₅₀ values in the low micromolar range while the substituted derivatives showed a broad spectrum of cytotoxic activity. 3,5-Bis(3′-indolyl)-2(1H)pyrazinone and 3,6-bis[3′-(N-methyl-indolyl)]pyrazine possessed strong inhibitory activity against a wide range of human tumor cell lines. The mechanism of action remained unknown. The results suggested that 2,4-bis(3′-indolyl)thiazoles, 3,5-bis(3′-indolyl)-2(1H)pyrazinone and 3,6-bis[3′-(N-methyl-indolyl)] pyrazine offer potential as lead compounds for the discovery of anticancer agents. In the experiment, the researchers used many compounds, for example, 5-Bromo-3-cyanoindole (cas: 90271-86-6HPLC of Formula: 90271-86-6).

Wu, Chunlei et al. published their research in Bulletin of the Korean Chemical Society in 2013 | CAS: 112656-95-8

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

An efficient method for multicomponent synthesis of spiro[4H-pyran-oxindole] derivatives catalyzed by magnesium perchlorate was written by Wu, Chunlei;Shen, Runpu;Chen, Jianhui;Hu, Chunqi. And the article was included in Bulletin of the Korean Chemical Society in 2013.Synthetic Route of C8H4N2O4 This article mentions the following:

A simple and efficient method for the synthesis of spiro[4H-pyran-oxindole] derivatives by means of three-component reaction between isatins, malononitrile or Et cyanoacetate, and 1,3-dicarbonyl compounds in the presence of catalytic amount of magnesium perchlorate in 50% aqueous ethanol medium has been described. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Synthetic Route of C8H4N2O4).

Xu, Chang-Jiang et al. published their research in Synthesis in 2020 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) 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.Quality Control of 5-Chloroindole-3-carboxaldehyde

Lewis Basic Amine Catalyzed Aza-Michael Reaction of Indole- and Pyrrole-3-carbaldehydes was written by Xu, Chang-Jiang;Du, Wei;Albrecht, Lukasz;Chen, Ying-Chun. And the article was included in Synthesis in 2020.Quality Control of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

3-Formyl substituted indoles or pyrroles can form HOMO-raised dearomative aza-dienamine-type intermediates with secondary amines, which can undergo direct aza-Michael addition to β-trifluoromethyl enones to afford N-alkylated products efficiently, albeit with low to fair enantioselectivity. In addition, similar asym. aza-Michael additions of these heteroarenes and crotonaldehyde are realized under dual catalysis of chiral amines, and the adducts are obtained with moderate to good enantioselectivity. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Quality Control of 5-Chloroindole-3-carboxaldehyde).

Bursavich, Matthew G. et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2010 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) 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.Safety of 5-Chloroindole-3-carboxaldehyde

Novel benzofuran-3-one indole inhibitors of PI3 kinase-α and the mammalian target of rapamycin: hit to lead studies was written by Bursavich, Matthew G.;Brooijmans, Natasja;Feldberg, Lawrence;Hollander, Irwin;Kim, Stephen;Lombardi, Sabrina;Park, Kaapjoo;Mallon, Robert;Gilbert, Adam M.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2010.Safety of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

A series of benzofuran-3-one indole phosphatidylinositol-3-kinases (PI3K) inhibitors identified via HTS has been prepared The optimized inhibitors possess single digit nanomolar activity against p110α (PI3K-α), good pharmaceutical properties, selectivity vs. p110γ (PI3K-γ), and tunable selectivity vs. the mammalian target of rapamycin (mTOR). Modeling of compounds I (R = H; CH₂CH₂CH₂NMe₂) in homol. models of PI3K-α and mTOR supports the proposed rationale for selectivity. Compounds show activity in multiple cellular proliferation assays with signaling through the PI3K pathway confirmed via phospho-Akt inhibition in PC-3 cells. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Safety of 5-Chloroindole-3-carboxaldehyde).

Audubert, Clement et al. published their research in Angewandte Chemie, International Edition in 2017 | CAS: 167631-84-7

Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7) 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.COA of Formula: C10H8FNO2

Batch and Continuous-Flow One-Pot Processes using Amine Diazotization to Produce Silylated Diazo Reagents was written by Audubert, Clement;Gamboa Marin, Oscar Javier;Lebel, Helene. And the article was included in Angewandte Chemie, International Edition in 2017.COA of Formula: C10H8FNO2 This article mentions the following:

A novel synthesis of trimethylsilyldiazomethane (TMSCHN₂) by diazotization of trimethylsilylmethylamine (TMSCH₂NH₂) is reported using batch and continuous flow syntheses. The latter affords a daily production of 275 g (2.4 mol) of TMSCHN₂. Other silylated methylamines were also successfully reacted under the developed reaction conditions to furnish various silicon-bearing diazomethane reagents. The applicability of the process is highlighted by disclosure of batch and continuous flow one-pot esterification and 1,3-dipolar cycloaddition processes. Furthermore, the high-yielding esterification of carboxylic acids with silylated and substituted methylamines in continuous flow is disclosed. Finally, work-up and purification procedures are reported for the preparation of a 2-MeTHF solution of TMSCHN₂, which can be used in rhodium-catalyzed methylenation and homologation reactions. In the experiment, the researchers used many compounds, for example, Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7COA of Formula: C10H8FNO2).

Ramachandran, Sreekanth A. et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2017 | CAS: 754214-56-7

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

Discovery of pyrazolopyrimidine derivatives as novel inhibitors of ataxia telangiectasia and rad3 related protein (ATR) was written by Ramachandran, Sreekanth A.;Jadhavar, Pradeep S.;Singh, Manvendra P.;Sharma, Ankesh;Bagle, Gaurav N.;Quinn, Kevin P.;Wong, Po-yin;Protter, Andrew A.;Rai, Roopa;Pham, Son M.;Lindquist, Jeffrey N.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2017.Recommanded Product: 7-Azaindole-5-boronic Acid Pinacol Ester This article mentions the following:

The ATR pathway is a critical mediator of the replication stress response in cells. In aberrantly proliferating cancer cells, this pathway can help maintain sufficient genomic integrity for cancer cell progression. Herein the authors describe the discovery of 1-(4-(methylsulfonyl)phenyl)-3-(1H-pyrrolo[2,3-b]pyridin-5-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine, a pyrazolopyrimidine-containing inhibitor of ATR via a strategic repurposing of compounds targeting PI3K. 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).

Forbes, Ian T. et al. published their research in Journal of Medicinal Chemistry in 1993 | CAS: 85696-95-3

1-Methyl-1H-indol-4-amine (cas: 85696-95-3) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Related Products of 85696-95-3

N-(1-Methyl-5-indolyl)-N’-(3-pyridyl)urea hydrochloride: the first selective 5-HT_1C receptor antagonist was written by Forbes, Ian T.;Kennett, Guy A.;Gadre, Angela;Ham, Peter;Hayward, Clare J.;Martin, Roger T.;Thompson, Mervyn;Wood, Martyn D.;Baxter, Gordon S.. And the article was included in Journal of Medicinal Chemistry in 1993.Related Products of 85696-95-3 This article mentions the following:

Development of specific 5-HT_1C receptor antagonists has been impeded by the marked similarity between this site and the 5-HT₂ receptor. A series of pyridyl indolyl ureas I (4-, 5-, 6-, 7-NHCOCNHR¹; R¹ = 3-pyridyl) were synthesized and shown to have affinity for the 5-HT_1C receptor. One of these, I (R = 5-NHCONHR¹, R¹ = 3-pyridyl)(II) shows ≥48 fold selectivity in ligand binding studies for the 5-HT_1C (pK_I = 6.86) over the 5-HT₂, 5-HT_1A, 5-HT_1D, 5-HT₃, adrenergic α₁, α_2A, α_2B, β₁, β₂, dopaminergic D₁, and D₂ receptors. II is a silent, competitive antagonist of 5-HT-stimulated phosphoinositide hydrolysis in the pig choroid plexus (pK_B = 7.03), a model of 5-HT_1C receptor functional activity and was also a surmountable antagonist of the 5-HT_1C-like receptor in the rat stomach fundus (pA₂ = 7.52). Thus, II represents the first reported selective 5-HT_1C receptor antagonist. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-indol-4-amine (cas: 85696-95-3Related Products of 85696-95-3).