02/02/2023 - Page 5 of 11 - Indole Building Blocks

Song, Jiahui et al. published their research in Asian Journal of Organic Chemistry in 2013 | CAS: 1256359-99-5

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. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Computed Properties of C20H28BNO5

Copper-Catalyzed N-Alkynylation of N-tert-Butoxycarbonyl (BOC)-Protected Indoles was written by Song, Jiahui;Wang, Qingbo;Fu, Haixing;Fu, Songlin;Li, Shaobin;Shi, Feng;Wu, Chunrui. And the article was included in Asian Journal of Organic Chemistry in 2013.Computed Properties of C20H28BNO5 This article mentions the following:

N-BOC-indole derivatives undergo a copper-catalyzed N-alkynylation with alkynyl bromides after in situ deprotection. Potassium tert-butoxide was used for the deprotection of substrates and as a base during the cross-coupling stage. For substrates that contain a 2-pyridine group or similar group, a phenanthroline ligand was not needed. This serves as an alternative protocol for N-alkynylation of indoles with a broader scope of substrates. The title compounds thus formed included an (ethynyl)indole derivative (I) and related substances. The synthesis of the target compounds was achieved using 3-(2-pyridinyl)-1H-indole-1-carboxylic acid 1,1-dimethylethyl ester, 5-(2-pyridinyl)-1H-indole-1-carboxylic acid 1,1-dimethylethyl ester, 1H-Indole-1,2-dicarboxylic acid 1,2-bis(1,1-dimethylethyl) ester, 4-cyano-1H-indole-1-carboxylic acid 1,1-dimethylethyl ester, etc., as starting materials in a reaction with bromoalkyne derivatives A similar reaction of 1H-benzimidazole-1-carboxylic acid 1,1-dimethylethyl ester gave 1-(2-phenylethynyl)-1H-benzimidazole. A reaction of 1H-pyrrole-1-carboxylic acid 1,1-dimethylethyl ester derivatives gave 1-(2-phenylethynyl)-1H-pyrrole derivatives 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: 1256359-99-5Computed Properties of C20H28BNO5).

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

Pratihar, Sanjay et al. published their research in Organic & Biomolecular Chemistry in 2014 | 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Quality Control of 5-Chloroindole-3-carboxaldehyde

Electrophilicity and nucleophilicity of commonly used aldehydes was written by Pratihar, Sanjay. And the article was included in Organic & Biomolecular Chemistry in 2014.Quality Control of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

The present approach for determining the electrophilicity (E) and nucleophilicity (N) of aldehydes includes a kinetic study of KMNO₄ oxidation and NaBH₄ reduction of aldehydes. A transition state anal. of the KMNO₄ promoted aldehyde oxidation reaction has been performed, which shows a very good correlation with exptl. results. The validity of the exptl. method has been tested using the exptl. activation parameters of the two reactions. The utility of the present approach is further demonstrated by the theor. vs. exptl. relationship, which provides easy access to E and N values for various aldehydes and offers an at-a-glance assessment of the chem. reactivity of aldehydes in various reactions. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Quality Control of 5-Chloroindole-3-carboxaldehyde).

Li, Xiang et al. published their research in ACS Catalysis in 2014 | 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). Application of 170489-16-4

Aerobic Transition-Metal-Free Visible-Light Photoredox Indole C-3 Formylation Reaction was written by Li, Xiang;Gu, Xiangyong;Li, Yongjuan;Li, Pixu. And the article was included in ACS Catalysis in 2014.Application of 170489-16-4 This article mentions the following:

An aerobic visible-light-promoted indole C-3 formylation reaction catalyzed by Rose Bengal has been developed. This transition-metal-free process employs mol. oxygen as the terminal oxidant and uses TMEDA as the one-carbon source through C-N bond cleavage. The reaction is compatible with a variety of functional groups. In the experiment, the researchers used many compounds, for example, 1,4-Dimethyl-1H-indole-3-carbaldehyde (cas: 170489-16-4Application of 170489-16-4).

Sharma, K. et al. published their research in Russian Journal of Coordination Chemistry in 2009 | 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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Application In Synthesis of 7-Nitroindoline-2,3-dione

Coordination chemistry of palladium(II) and platinum(II) complexes with bioactive Schiff bases: Synthetic, spectral, and biocidal aspects was written by Sharma, K.;Biyala, M. K.;Swami, M.;Fahmi, N.;Singh, R. V.. And the article was included in Russian Journal of Coordination Chemistry in 2009.Application In Synthesis of 7-Nitroindoline-2,3-dione This article mentions the following:

The Schiff bases, 5-nitro-indol-2,3-dionehydrazinecarboxamide (HSCZ¹) and 7-nitro-indol-2,3-dionehydrazinecarboxamide (HSCZ²), were synthesized by the condensation of 5-nitro-indol-2,3-dione and 7-nitro-1H-indol-2,3-dione with semicarbazide hydrochloride, resp. The palladium(II) and platinum(II) complexes were prepared by mixing palladium chloride and platinum chloride in 1:2 molar ratios with monobasic bidentate Schiff bases. The ligands and complexes of palladium and platinum were characterized by elemental analyses, m.p. determinations, conductance measurements, mol. weight determinations, and IR, ¹H NMR, and UV spectral studies. The ligands coordinate to the metal atoms in a monobasic bidentate mode, coordinating through oxygen and nitrogen donor systems. Thus, a tetracoordinated environment around the metal atom is proposed. Both the ligands and their complexes were screened for their biol. activity on several pathogenic fungi and bacteria and possess appreciable fungicidal and bactericidal properties. Plant growth regulating activity of one of the ligands and its complexes also was recorded on gram plant, and results are discussed. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Application In Synthesis of 7-Nitroindoline-2,3-dione).

Guan, Xu-Kai et al. published their research in Organic Letters in 2019 | 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. 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). Safety of 5-Chloroindole-3-carboxaldehyde

Chiral Imidodiphosphoric Acid-Catalyzed Highly Diastereo- and Enantioselective Synthesis of Poly-Substituted 3,4-Dihydro-2H-pyrans: [4 + 2] Cycloadditions of β,γ-Unsaturated α-Ketoesters and 3-Vinylindoles was written by Guan, Xu-Kai;Liu, Guo-Feng;An, Dong;Zhang, Heng;Zhang, Suo-Qin. And the article was included in Organic Letters in 2019.Safety of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

Imidodiphosphoric acids were employed to catalyze inverse-electron-demand hetero-Diels-Alder reaction of β,γ-unsaturated α-ketoesters and 3-vinylindoles. A series of optically active 3,4-dihydro-2H-pyran derivatives with three contiguous stereogenic centers was synthesized in excellent yields (70-99%), diastereoselectivities (>20:1), and enantioselectivities (73-99%). The resulting indole containing 3,4-dihydro-2H-pyran could be converted to tetrahydropyran derivatives, which appear in several biol. active compounds by simple hydrogenation reduction In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Safety of 5-Chloroindole-3-carboxaldehyde).

Siebeneicher, Holger et al. published their research in ChemMedChem in 2016 | CAS: 774-47-0

5,6-Difluoroindoline-2,3-dione (cas: 774-47-0) 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Product Details of 774-47-0

Identification and Optimization of the First Highly Selective GLUT1 Inhibitor BAY-876 was written by Siebeneicher, Holger;Cleve, Arwed;Rehwinkel, Hartmut;Neuhaus, Roland;Heisler, Iring;Mueller, Thomas;Bauser, Marcus;Buchmann, Bernd. And the article was included in ChemMedChem in 2016.Product Details of 774-47-0 This article mentions the following:

Despite the long-known fact that the facilitative glucose transporter GLUT1 is one of the key players safeguarding the increase in glucose consumption of many tumor entities even under conditions of normal oxygen supply (known as the Warburg effect), only few endeavors have been undertaken to find a GLUT1-selective small-mol. inhibitor. Because other transporters of the GLUT1 family are involved in crucial processes, these transporters should not be addressed by such an inhibitor. A high-throughput screen against a library of â? million compounds was performed to find a small mol. with this challenging potency and selectivity profile. The N-(1H-pyrazol-4-yl)quinoline-4-carboxamides were identified as an excellent starting point for further compound optimization. After extensive structure-activity relationship explorations, single-digit nanomolar inhibitors with a selectivity factor of >100 against GLUT2, GLUT3, and GLUT4 were obtained. The most promising compound, BAY-876 [N⁴-[1-(4-cyanobenzyl)-5-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]-7-fluoroquinoline-2,4-dicarboxamide], showed good metabolic stability in vitro and high oral bioavailability in vivo. In the experiment, the researchers used many compounds, for example, 5,6-Difluoroindoline-2,3-dione (cas: 774-47-0Product Details of 774-47-0).

Jia, Xue-Gong et al. published their research in Chemical Science in 2018 | CAS: 210345-56-5

Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5) 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Application In Synthesis of Methyl 5-bromo-1H-indole-2-carboxylate

Dual nickel and Lewis acid catalysis for cross-electrophile coupling: the allylation of aryl halides with allylic alcohols was written by Jia, Xue-Gong;Guo, Peng;Duan, Jicheng;Shu, Xing-Zhong. And the article was included in Chemical Science in 2018.Application In Synthesis of Methyl 5-bromo-1H-indole-2-carboxylate This article mentions the following:

A general and practical strategy to address the reaction between reactive and unreactive electrophiles by a combination of nickel and Lewis acid catalysis is reported. This strategy is used for the coupling of aryl bromides R¹Br (R¹ = 4-MeO₂CC₆H₄, benzofuran-5-yl, indol-4-yl, etc.) with allylic alcs. R²CH:CHCR³R⁴OH (R² = H, Me, Ph, etc.; R³ = R⁴ = H, Me; R³ = Me, Et, Ph, R⁴ = H) to form linear allylarenes R¹CR³R⁴CH:CHR². The reaction tolerates a wide range of functional groups (e.g. silanes, boronates, anilines, esters, alcs., and various heterocycles) and works with various allylic alcs. Complementary to most current routes for the C3 allylation of an unprotected indole, this method provides access to C2 and C4-C7 allylated indoles. Preliminary mechanistic experiments revealed that the reaction might start with an aryl nickel intermediate, which then reacts with Lewis acid activated allylic alcs. in the presence of Mn. In the experiment, the researchers used many compounds, for example, Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5Application In Synthesis of Methyl 5-bromo-1H-indole-2-carboxylate).

Dassonville, Alexandra et al. published their research in Journal of Enzyme Inhibition and Medicinal Chemistry in 2008 | CAS: 6639-06-1

3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1) 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.Reference of 6639-06-1

N-Pyridinyl(methyl)-indole-1- or 3-propanamides and propenamides acting as topical and systemic inflammation inhibitors was written by Dassonville, Alexandra;Lardic, Morgane;Breteche, Anne;Nourrisson, Marie Renee;Le Baut, Guillaume;Grimaud, Nicole;Petit, Jean-Yves;Duflos, Muriel. And the article was included in Journal of Enzyme Inhibition and Medicinal Chemistry in 2008.Reference of 6639-06-1 This article mentions the following:

In this study, the synthetic way to new N-pyridinyl(methyl)indolylpropanamides acting as non acidic NSAIDs has been described. Pharmacomodulation was carried out at N1 and C5 of the indole ring and at the level of the propanamide chain. N3-pyridinylmethyl-[1(4-chlorobenzyl-5-chloroindol-3-yl)propanamide represents one of the most potent compounds in the TPA-induced mouse ear swelling assay, with a level of activity higher than that of ibuprofen and comparable to that of dexamethasone. In the experiment, the researchers used many compounds, for example, 3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1Reference of 6639-06-1).

Zhu, Zhiqiang et al. published their research in European Journal of Organic Chemistry in 2014 | CAS: 167631-84-7

Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7) 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Recommanded Product: Methyl 5-fluoro-1H-indole-2-carboxylate

Ligand-Free Copper-Catalyzed One-Pot Synthesis of Indole-2-carboxylic Esters was written by Zhu, Zhiqiang;Yuan, Jiangjun;Zhou, Yirong;Qin, Yang;Xu, Jingshi;Peng, Yiyuan. And the article was included in European Journal of Organic Chemistry in 2014.Recommanded Product: Methyl 5-fluoro-1H-indole-2-carboxylate This article mentions the following:

A simple, efficient, and facile synthetic route for the preparation of indole-2-carboxylic esters was described. The cascade reactions of 2-bromobenzaldehyde and glycine ester hydrochloride were promoted by Cu₂O and a base to provide the corresponding products in good yields. Com. available, inexpensive substrates and reagents were employed under mild reaction conditions in this one-pot operation, which is complementary to existing methods for access to 2-substituted indoles. In the experiment, the researchers used many compounds, for example, Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7Recommanded Product: Methyl 5-fluoro-1H-indole-2-carboxylate).

Zhang, Dongxin et al. published their research in Organic Letters in 2020 | CAS: 774-47-0

5,6-Difluoroindoline-2,3-dione (cas: 774-47-0) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. 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). Category: indole-building-block

Direct Catalytic Asymmetric Synthesis of Oxindole-Derived δ-Hydroxy-β-ketoesters by Aldol Reactions was written by Zhang, Dongxin;Chen, Yan;Cai, Hu;Yin, Lei;Zhong, Junchao;Man, Jingjing;Zhang, Qian-Feng;Bethi, Venkati;Tanaka, Fujie. And the article was included in Organic Letters in 2020.Category: indole-building-block This article mentions the following:

Direct asym. synthesis of δ-hydroxy-β-ketoesters was accomplished via regio- and enantioselective aldol reactions of β-ketoesters with isatins catalyzed by cinchona alkaloid thiourea derivatives The C-C bond formation of the reactions occurred only at the γ-position of the β-ketoesters. Reaction progress monitoring and product stability analyses under the conditions that included the catalyst indicated that the γ-position reaction products were formed kinetically. Various δ-hydroxy-β-ketoesters bearing 3-alkyl-3-hydroxyoxindole cores relevant to the development of bioactive mols. were synthesized. In the experiment, the researchers used many compounds, for example, 5,6-Difluoroindoline-2,3-dione (cas: 774-47-0Category: indole-building-block).