175.18 | - Indole Building Blocks

Lan, Linfeng et al. published their research in Advanced Materials (Weinheim, Germany) in 2022 | CAS: 10601-19-1

5-Methoxy-1H-indole-3-carbaldehyde (cas: 10601-19-1) 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Name: 5-Methoxy-1H-indole-3-carbaldehyde

Organic Single-Crystal Actuators and Waveguides that Operate at Low Temperatures was written by Lan, Linfeng;Li, Liang;Di, Qi;Yang, Xuesong;Liu, Xiaokong;Naumov, Pance;Zhang, Hongyu. And the article was included in Advanced Materials (Weinheim, Germany) in 2022.Name: 5-Methoxy-1H-indole-3-carbaldehyde This article mentions the following:

Applications in extreme conditions, such as those encountered in space exploration, require lightweight materials that can retain their elasticity in extremely cold environments. However, cryogenic treatment of most soft polymeric and elastomeric materials results in complete loss of their ability for elastic flow, whereby such materials that are normally ductile become stiff, brittle, and prone to cracking. Here, a facile method for preparation of hybrid organic crystalline materials that are not only cryogenically robust but are also capable of large, recoverable, and reversible deformation at low temperatures is reported. To that end, flexible organic crystals are first mech. reinforced by a polymer coating and combined with a thermally responsive polymer. The resulting hybrid materials respond linearly and reversibly to temperatures from -15 to -120掳 C without fatigue in air as well as in cold vacuum. The approach proposed here not only circumvents one of the main drawbacks that are inherent to the amorphous nature and has thus far limited the applications of polymeric materials at low temperatures, but it also provides a cost-effective access to a myriad of lightweight sensing, electronic, optical or actuating devices that can operate in low-temperature environmental settings. In the experiment, the researchers used many compounds, for example, 5-Methoxy-1H-indole-3-carbaldehyde (cas: 10601-19-1Name: 5-Methoxy-1H-indole-3-carbaldehyde).

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

Chien, Chun Sheng et al. published their research in Chemical & Pharmaceutical Bulletin in 1984 | CAS: 16800-68-3

1-Acetylindolin-3-one (cas: 16800-68-3) 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 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: 1-Acetylindolin-3-one

Oxidation of 1-acylindoles with oxodiperoxomolybdenum (VI), peroxomolybdenum.HMPA. Preparation of 2,3-dihydroxyindoline and indoxyl derivatives was written by Chien, Chun Sheng;Suzuki, Takako;Kawasaki, Tomomi;Sakamoto, Masanori. And the article was included in Chemical & Pharmaceutical Bulletin in 1984.Recommanded Product: 1-Acetylindolin-3-one This article mentions the following:

The oxidation of 1-acylindoles with MoO₅.HMPA, in dry methanol gives a variety of products depending on the indole substituents; trans (I)- and cis (II)-1-acyl-3-hydroxy-2-methoxyindolines are obtained from 2,3-unsubstituted 1-acylindoles, 1-acetyl-2-hydroxy-3-methoxy-3-methylindoline (III) from 1-acetyl-3-methylindole, 1-acetyl-2,3-dihydroxy-2,3-dimethylindoline from 1-acetyl-2,3-dimethylindole, and 1-acetyl-2-hydroxy-2-methylindoxyl from 1-acetyl-2-methylindole. Reaction of I and II with acids gives 1-acylindoxyl while reaction of III with the acid gives 3-methyloxindole. Treatment of 3-acetoxy-1-acetyl-2-methoxyindoline with SnCl₄ gives 1-acetylindoxyl and 1-acetyl-3-chloroindole. In the experiment, the researchers used many compounds, for example, 1-Acetylindolin-3-one (cas: 16800-68-3Recommanded Product: 1-Acetylindolin-3-one).

Gao, Qinghe et al. published their research in Organic & Biomolecular Chemistry in 2018 | CAS: 10601-19-1

5-Methoxy-1H-indole-3-carbaldehyde (cas: 10601-19-1) 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.Computed Properties of C10H9NO2

I₂-Triggered N-O cleavage of ketoxime acetates for the synthesis of 3-(4-pyridyl)indoles was written by Gao, Qinghe;Wang, Yakun;Wang, Qianqian;Zhu, Yanping;Liu, Zhaomin;Zhang, Jixia. And the article was included in Organic & Biomolecular Chemistry in 2018.Computed Properties of C10H9NO2 This article mentions the following:

Synthesis of 3-(4-pyridyl)indole derivatives I (R = H, 5-OCH₂C₆H₅, 6-F, 7-NO₂, etc.; R¹ = H, CH₃; Ar = C₆H₅, 2H-1,3-benzodioxol-5-yl, naphthalen-2-yl, etc.) and II from a facile and complementary [3+2+1] annulation of aryl ketoxime acetates Ar(CH₃)C=NOC(O)CH₃ and 1,2,3,4-tetrahydronaphthalen-1-ylideneamino acetate and 3-formylindoles III is reported. The condensation reaction demonstrated that I₂ was capable of triggering N-O bond cleavage of ketoxime acetates to generate iminyl radicals via a single electron transfer pathway. This direct and operationally simple protocol provides a fundamental platform to synthesize 3-(4-pyridyl)indole derivatives I and II with high functional group compatibility and high regioselectivity. In the experiment, the researchers used many compounds, for example, 5-Methoxy-1H-indole-3-carbaldehyde (cas: 10601-19-1Computed Properties of C10H9NO2).

Campanico, Andre et al. published their research in ChemMedChem in 2019 | CAS: 16800-68-3

1-Acetylindolin-3-one (cas: 16800-68-3) 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.Recommanded Product: 16800-68-3

Azaaurones as potent antimycobacterial agents active against MDR- and XDR-TB was written by Campanico, Andre;Carrasco, Marta P.;Njoroge, Mathew;Seldon, Ronnett;Chibale, Kelly;Perdigao, Joao;Portugal, Isabel;Warner, Digby F.;Moreira, Rui;Lopes, Francisca. And the article was included in ChemMedChem in 2019.Recommanded Product: 16800-68-3 This article mentions the following:

Herein we report the screening of a small library of aurones and their isosteric counterparts, azaaurones and N-acetylazaaurones, against Mycobacterium tuberculosis. Aurones were found to be inactive at 20 渭M, whereas azaaurones and N-acetylazaaurones emerged as the most potent compounds, with nine derivatives displaying MIC₉₉ values ranging from 0.4 to 2.0 渭M. In addition, several N-acetylazaaurones were found to be active against multidrug-resistant (MDR) and extensively drug-resistant (XDR) clin. M. tuberculosis isolates. The antimycobacterial mechanism of action of these compounds remains to be determined; however, a preliminary mechanistic study confirmed that they do not inhibit the mycobacterial cytochrome bc1 complex. Addnl., microsomal metabolic stability and metabolite identification studies revealed that N-acetylazaaurones are deacetylated to their azaaurone counterparts. Overall, these results demonstrate that azaaurones and their N-acetyl counterparts represent a new entry in the toolbox of chemotypes capable of inhibiting M. tuberculosis growth. In the experiment, the researchers used many compounds, for example, 1-Acetylindolin-3-one (cas: 16800-68-3Recommanded Product: 16800-68-3).

Wen, Zhonghang et al. published their research in European Journal of Medicinal Chemistry in 2017 | CAS: 10601-19-1

5-Methoxy-1H-indole-3-carbaldehyde (cas: 10601-19-1) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Quality Control of 5-Methoxy-1H-indole-3-carbaldehyde

Novel 3′,5′-diprenylated chalcones inhibited the proliferation of cancer cells in vitro by inducing cell apoptosis and arresting cell cycle phase was written by Wen, Zhonghang;Zhang, Yongqiang;Wang, Xinghui;Zeng, Xiaoping;Hu, Zhanxing;Liu, Yi;Xie, Yuxin;Liang, Guangyi;Zhu, Jianguo;Luo, Heng;Xu, Bixue. And the article was included in European Journal of Medicinal Chemistry in 2017.Quality Control of 5-Methoxy-1H-indole-3-carbaldehyde This article mentions the following:

A double Claisen rearrangements synthetic strategy was established for the total synthesis of 4,4′-dimethyl medicagenin (I, compound 6c). A series of its analogs also were prepared, including two novel 3′,5′-diprenylated chalcones, in which ring B was replaced by azaheterocycle. The structures of the twenty-two newly synthesized compounds were confirmed by ¹H NMR, ¹³C NMR and ESI-MS. In vitro, the cytotoxicity of the target compounds was evaluated using cancer cells. Noticeably, compound 10 (II) exhibited broad-spectrum cytotoxicity on PC3 prostate cancer cells, MDA-MB-231 breast cancer cells (MDA), HEL and K562 erythroleukemia cells with IC₅₀ values of 2.92, 3.14, 1.85 and 2.64 渭M, resp. Further studies indicated that compound 10 induced apoptosis and arrested the cell cycle phase of the above mentioned four cancer cell lines. By contrast, compound 6g (III) selectively displayed potent inhibitory activity against the proliferation of HEL cells with an IC₅₀ value of 4.35 渭M. Compound 6g slightly induced apoptosis and arrested cell cycle phase of HEL cells. Preliminary structure-activity relationship studies indicated that, in all cancer cell lines evaluated, the 3-pyridinyl group was essential for cytotoxicity. In the experiment, the researchers used many compounds, for example, 5-Methoxy-1H-indole-3-carbaldehyde (cas: 10601-19-1Quality Control of 5-Methoxy-1H-indole-3-carbaldehyde).

5-Methoxy-1H-indole-3-carbaldehyde (cas: 10601-19-1) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Quality Control of 5-Methoxy-1H-indole-3-carbaldehyde

Merour, Jean Yves et al. published their research in Tetrahedron Letters in 1992 | CAS: 16800-68-3

1-Acetylindolin-3-one (cas: 16800-68-3) 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.Electric Literature of C10H9NO2

Arylation of 3-oxo-2,3-dihydroindoles with aryllead triacetates was written by Merour, Jean Yves;Chichereau, Lucien;Finet, Jean Pierre. And the article was included in Tetrahedron Letters in 1992.Electric Literature of C10H9NO2 This article mentions the following:

Arylation of 2-alkoxycarbonyl-3-oxo-2,3-dihydroindoles I (R = H, Me, COMe; R¹ = CO₂Me, CO₂Et; R² = H) with aryllead (IV) triacetates II (R³ = H, OMe) leads selectively to 2-alkoxycarbonyl-2-aryl-3-oxo-2,3-dihydroindoles III. Direct selective C-arylation of 1-substituted-3-oxo-2,3-dihydroindoles I (R = COMe, SO₂Ph; R¹ = H, Me, Ph; R² = H, Me, OMe) with II (R³ = OMe) affords the corresponding 1-substituted-2-aryl-3-oxo-2,3-dihydroindoles III. In the experiment, the researchers used many compounds, for example, 1-Acetylindolin-3-one (cas: 16800-68-3Electric Literature of C10H9NO2).

1-Acetylindolin-3-one (cas: 16800-68-3) 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.Electric Literature of C10H9NO2

Guo, Jing et al. published their research in Organic Chemistry Frontiers in 2017 | CAS: 16800-68-3

1-Acetylindolin-3-one (cas: 16800-68-3) 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Name: 1-Acetylindolin-3-one

Asymmetric amination of 2-substituted indolin-3-ones catalyzed by natural cinchona alkaloids was written by Guo, Jing;Lin, Zi-Hui;Chen, Kai-Bin;Xie, Ying;Chan, Albert S. C.;Weng, Jiang;Lu, Gui. And the article was included in Organic Chemistry Frontiers in 2017.Name: 1-Acetylindolin-3-one This article mentions the following:

The natural quinine-catalyzed enantioselective amination of 2-substituted indolin-3-ones with azodicarboxylates was developed. These reactions provided a broad spectrum of 2,2-disubstituted indolin-3-ones containing a nitrogen-attached quaternary stereocenter at the C2-position in extremely high yields and with excellent enantioselectivities. The readily available catalyst, broad substrate scope, and mild reaction conditions highlighted the practical utility of this process. In the experiment, the researchers used many compounds, for example, 1-Acetylindolin-3-one (cas: 16800-68-3Name: 1-Acetylindolin-3-one).

Chen, Rongxiang et al. published their research in Organic & Biomolecular Chemistry in 2021 | CAS: 16800-68-3

1-Acetylindolin-3-one (cas: 16800-68-3) 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). Product Details of 16800-68-3

A copper iodide-catalyzed coupling reaction of benzofuran-3(2H)-ones with amines: an approach to 伪-ketoamides was written by Chen, Rongxiang;Jia, Ruo-Ling;Li, Wenbo;Zhao, Wei;Wang, Kai-Kai;Wang, Zhan-Yong;Ma, Xueji;Dai, Wei;Sun, Aili. And the article was included in Organic & Biomolecular Chemistry in 2021.Product Details of 16800-68-3 This article mentions the following:

A CuI-catalyzed coupling reaction of benzofuran-3(2H)-ones with amines has been well established for the direct synthesis of 伪-ketoamides. This process involves C-O bond cleavage and C=O/C-N bond formation. Mechanism studies indicated that this 伪-ketoamide formation reaction may involve a free radical process. In the experiment, the researchers used many compounds, for example, 1-Acetylindolin-3-one (cas: 16800-68-3Product Details of 16800-68-3).

Purgatorio, Rosa et al. published their research in Molecules in 2020 | CAS: 10601-19-1

5-Methoxy-1H-indole-3-carbaldehyde (cas: 10601-19-1) 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.Formula: C10H9NO2

Pharmacophore modeling and 3D-QSAR study of indole and isatin derivatives as antiamyloidogenic agents targeting Alzheimer’s disease was written by Purgatorio, Rosa;Gambacorta, Nicola;Catto, Marco;de Candia, Modesto;Pisani, Leonardo;Espargaro, Alba;Sabate, Raimon;Cellamare, Saverio;Nicolotti, Orazio;Altomare, Cosimo D.. And the article was included in Molecules in 2020.Formula: C10H9NO2 This article mentions the following:

Thirty-six novel indole-containing compounds, mainly 3-(2-phenylhydrazono) isatins and structurally related 1H-indole-3-carbaldehyde derivatives, were synthesized and assayed as inhibitors of beta amyloid (A尾) aggregation, a hallmark of pathophysiol. of Alzheimer’s disease. The newly synthesized mols. spanned their IC₅₀ values from sub- to two-digit micromolar range, bearing further information into structure-activity relationships. Some of the new compounds showed interesting multitarget activity, by inhibiting monoamine oxidases A and B. A cell-based assay in tau overexpressing bacterial cells disclosed a promising addnl. activity. The accumulated data of either about ninety published and thirty-six newly synthesized mols. were used to generate a pharmacophore hypothesis of antiamyloidogenic activity exerted in a wide range of potencies, satisfactorily discriminating the ‘active’ compounds from the ‘inactive’ (poorly active) ones. An atom-based 3D-QSAR model was also derived for about 80% of ‘active’ compounds, i.e., those achieving finite IC₅₀ values lower than 100渭M. The 3D-QSAR model (encompassing 4 PLS factors), featuring acceptable predictive statistics either in the training set (n = 45, q² = 0.596) and in the external test set (n = 14, r²ext = 0.695), usefully complemented the pharmacophore model by identifying the physicochem. features mainly correlated with the A尾 anti-aggregating potency of the indole and isatin derivatives studied herein. In the experiment, the researchers used many compounds, for example, 5-Methoxy-1H-indole-3-carbaldehyde (cas: 10601-19-1Formula: C10H9NO2).

Purgatorio, Rosa et al. published their research in Molecules in 2018 | CAS: 10601-19-1

5-Methoxy-1H-indole-3-carbaldehyde (cas: 10601-19-1) 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 C10H9NO2

Insights into structure-activity relationships of 3-arylhydrazonoindolin-2-one derivatives for their multitarget activity on 尾-amyloid aggregation and neurotoxicity was written by Purgatorio, Rosa;de Candia, Modesto;De Palma, Annalisa;De Santis, Francesco;Pisani, Leonardo;Campagna, Francesco;Cellamare, Saverio;Altomare, Cosimo Damiano;Catto, Marco. And the article was included in Molecules in 2018.Computed Properties of C10H9NO2 This article mentions the following:

A series of new 3-(2-arylhydrazono)indolin-2-one derivatives I [R = H, n-Bu, 5-MeO; R¹ = H; R² = H, Br; R³ = H, Me, cyclopropyl, Bn, (CH₂)₂C₆H₅, (CH₂)₃C₆H₅; R⁴ = H, Me; RR¹ = OCH₂O; Ar = 4-iPrC₆H₄, 4-NCC₆H₄, 1-naphthyl, etc.]was synthesized and assayed, investigating the effects of substitutions on both the indole core and arylhydrazone moiety. Compared with the reference we disclosed equipotent derivatives bearing alkyl substituents at the indole nitrogen and fairly tolerated bioisosteric replacements at the arylhydrazone moiety. For most of the investigated compounds, the inhibition of A尾40 aggregation (expressed as pIC₅₀) was found to be correlated with lipophilicity, as assessed by a reversed-phase HPLC method, through a bilinear relationship. The compound I [R = MeO, R¹ = R² = H, R³ = cyclopropyl, R⁴ = H Ar = 4-iPrC₆H₄] was tested in cell-based assays of A尾42 oligomer toxicity and oxidative stress induced by hydrogen peroxide, showing significant cytoprotective effects. This study confirmed the versatility of isatin in preparing multitarget small mols. affecting different biochem. pathways involved in Alzheimer’s disease. In the experiment, the researchers used many compounds, for example, 5-Methoxy-1H-indole-3-carbaldehyde (cas: 10601-19-1Computed Properties of C10H9NO2).

5-Methoxy-1H-indole-3-carbaldehyde (cas: 10601-19-1) 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 C10H9NO2