100-200 | - Page 19 of 93 - Indole Building Blocks

Chang, Yu-Hsuan et al. published their research in Chemical Communications (Cambridge, United Kingdom) 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. 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

Palladium-catalyzed α-arylation of indolin-3-ones was written by Chang, Yu-Hsuan;Peng, Wan-Ling;Chen, I-Chia;Hsu, Hsin-Yun;Wu, Yen-Ku. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2020.Safety of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

A method for the catalytic α-arylation of indolin-3-ones was developed. The catalytic system comprising Pd(dba)₂ and PAd₃ was found to be optimal for the transformation. The protocol features broad functional group compatibility in that a range of arylated indoxyl derivatives bearing a fully substituted carbon center was synthesized with high efficiency. A preliminary bioassay study revealed that the selected indole-substituted indolin-3-ones exhibit favorable cytotoxic activities against HCT-116 cancer cell line. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Safety of 5-Chloroindole-3-carboxaldehyde).

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

Wilk, Wolfram et al. published their research in Chemistry – A European Journal in 2009 | 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.Formula: C9H6ClNO

Biology-Oriented Combined Solid- and Solution-Phase Synthesis of a Macroline-Like Compound Collection was written by Wilk, Wolfram;Noeren-Mueller, Andrea;Kaiser, Markus;Waldmann, Herbert. And the article was included in Chemistry – A European Journal in 2009.Formula: C9H6ClNO This article mentions the following:

Macrolines constitute a class of natural products that has more than 100 members and displays diverse biol. activities. These compounds feature a cycloocta[b]indole scaffold that represents an interesting target structure for biol.-oriented synthesis (BIOS). We have presented a solid-phase synthesis of isomerically pure cycloocta[b]indoles (e.g. I) by employing the Pictet-Spengler reaction and the Dieckmann cyclization as key steps. The scope of this reaction sequence was investigated in more detail by using various addnl. diversification procedures, such as Pd-catalyzed Sonogashira or Suzuki couplings on a solid phase, thus allowing, for example, the generation of 10-substituted cycloocta[b]indole derivatives Finally, solution-phase decoration of the cycloocta[b]indole skeleton by reduction and saponification was evaluated, thereby further extending the scope of the solid-phase synthesis. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Formula: C9H6ClNO).

Rogness, Donald C. et al. published their research in Tetrahedron Letters in 2009 | CAS: 167631-84-7

Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. 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 Methyl 5-fluoro-1H-indole-2-carboxylate

Rapid synthesis of the indole-indolone scaffold via [3+2] annulation of arynes by methyl indole-2-carboxylates was written by Rogness, Donald C.;Larock, Richard C.. And the article was included in Tetrahedron Letters in 2009.Quality Control of Methyl 5-fluoro-1H-indole-2-carboxylate This article mentions the following:

The reaction of Me indole-2-carboxylates, e.g., I, and arynes afforded a very efficient, high yielding synthesis of a novel indole-indolone ring system, e.g., II, which tolerated considerable functionality, was broad in scope, and proceeded under mild reaction conditions. In the experiment, the researchers used many compounds, for example, Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7Quality Control of Methyl 5-fluoro-1H-indole-2-carboxylate).

Mei, Haibo et al. published their research in Organic Letters in 2022 | CAS: 827-01-0

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

Visible-Light-Irradiated Cascade Reaction of Indole-Tethered Alkenes to Access Tetracyclic Tetrahydro-γ-carbolines was written by Mei, Haibo;Liu, Aiyao;He, Jingrui;Yu, Yingjie;Han, Jianlin. And the article was included in Organic Letters in 2022.Quality Control of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

A series of indole-derived alkenes I (R = H, Cl, Br; R¹ = Me, OMe, F, etc.; R² = H, Me, F, etc.; R³ = R⁴ = H, Me; Ar = Ph, 4-methylphenyl, 4-bromophenyl, 4-methyoxphenyl) have been designed and applied in a photocatalytic cascade reaction with bromodifluoroacetate esters BrCF₂C(O)OR⁵ (R⁵ = Me, Bn, cyclopentyl, etc.), affording an unknown type of tetracyclic tetrahydro-γ-carboline derivative II in up to 90% yields. Mechanistic studies suggest that the reaction proceeds with tetrahydro-γ-carboline III (Ar = 4-methylphenyl, R⁵ = Et;) as a key intermediate. The reaction tolerates a diverse pool of substrates, which provides an efficient method for the construction of tetracyclic tetrahydro-γ-carboline II compounds In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Quality Control of 5-Chloroindole-3-carboxaldehyde).

Kuett, Agnes et al. published their research in European Journal of Organic Chemistry in 2021 | 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Reference of 4769-96-4

Strengths of Acids in Acetonitrile was written by Kuett, Agnes;Tshepelevitsh, Sofja;Saame, Jaan;Lokov, Maert;Kaljurand, Ivari;Selberg, Sigrid;Leito, Ivo. And the article was included in European Journal of Organic Chemistry in 2021.Reference of 4769-96-4 This article mentions the following:

The equilibrium acidity scale (pK_a scale) in acetonitrile has been supplemented by numerous new compounds and new ΔpK_a measurements. It now contains altogether 231 acids – over twice more than published previously – linked by 569 ΔpK_a measurements and spans between the pK_a values of hydrogen iodide (2.8) and indole (32.57), covering close to 30 orders of magnitude. Measurement results acquired over the last 15 years were added to the scale and new least-squares treatment was carried out. The treatment yielded revised pK_a values for the compounds published previously, with the root mean square difference between revised and previous values 0.04, demonstrating very good stability of the scale. Correlation equations were developed for estimating pK_a values for the studied types of compounds in water, DMSO, DMF, and 1,2-dichloroethane on the basis of pK_a values in acetonitrile. These equations enable predicting pK_a values with an average error around or less than 1 pK_a unit, which is a sufficient accuracy for many applications. The scale is expected to be a useful tool for the widest possible research areas in organic chem., electrochem. power sources, catalysis, etc. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Reference of 4769-96-4).

Kosuge, Yasuhiro et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2017 | CAS: 150560-58-0

5-Isopropylindoline-2,3-dione (cas: 150560-58-0) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Formula: C11H11NO2

Indirubin derivatives protect against endoplasmic reticulum stress-induced cytotoxicity and down-regulate CHOP levels in HT22 cells was written by Kosuge, Yasuhiro;Saito, Hiroaki;Haraguchi, Tatsuki;Ichimaru, Yoshimi;Ohashi, Sachiyo;Miyagishi, Hiroko;Kobayashi, Shunsuke;Ishige, Kumiko;Miyairi, Shinichi;Ito, Yoshihisa. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2017.Formula: C11H11NO2 This article mentions the following:

Indirubin and its derivatives have been reported to exhibit anticancer and anti-inflammatory activities. Recently, some of its derived analogs have been shown to have neuroprotective potential. Endoplasmic reticulum (ER) stress has been demonstrated to contribute to the pathogenesis of various neurodegenerative diseases, whereas the effects of indirubin derivatives on ER stress-induced cell death have not been addressed. In the present study, a series of 44 derivatives of indirubin was prepared to search for a novel class of neuroprotective agents against ER stress-induced neuronal death. The MTT reduction assay indicated that tunicamycin (TM), an inducer of ER stress, significantly decreased the viability of hippocampal neuronal HT22 cells. Among the compounds tested, eight showed significant inhibitory activity against TM-induced cell death. Western blot anal. showed that application of these analogs to the cells simultaneously with TM reduced the TM-induced expression of CHOP, an established mediator of ER stress. The results suggest that the preventive effect of these indirubin derivatives against ER stress-induced neuronal death may be due, at least in part, to attenuation of the CHOP-dependent signaling system. In the experiment, the researchers used many compounds, for example, 5-Isopropylindoline-2,3-dione (cas: 150560-58-0Formula: C11H11NO2).

Trinh, Trieu N. et al. published their research in Organic & Biomolecular Chemistry in 2016 | 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Safety of 5-Chloroindole-3-carboxaldehyde

Quinolone-1-(2H)-ones as hedgehog signalling pathway inhibitors was written by Trinh, Trieu N.;McLaughlin, Eileen A.;Abdel-Hamid, Mohammed K.;Gordon, Christopher P.;Bernstein, Ilana R.;Pye, Victoria;Cossar, Peter;Sakoff, Jennette A.;McCluskey, Adam. And the article was included in Organic & Biomolecular Chemistry in 2016.Safety of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

A series of quinolone-2-(1H)-ones derived from the Ugi-Knoevenagel three- and four-component reaction were prepared exhibiting low micromolar cytotoxicity against a panel of eight human cancer cell lines known to possess the hedgehog signalling pathway (HSP) components, as well as the seminoma TCAM-2 cell line. A focused SAR study was conducted and revealed core characteristics of the quinolone-2-(1H)-ones required for cytotoxicity. These requirements included a C3-tethered indole moiety, an indole C5-Me moiety, an aliphatic tail or an ester, as well as an addnl. aromatic moiety. Further investigation in the SAG-activated Shh-LIGHT2 cell line with the most active analogs such as 2-(3-cyano-2-oxo-4-phenylquinolin-1(2H)-yl)-2-(1-methyl-1H-indol-3-yl)-N-(pentan-2-yl)acetamide, 2-(3-cyano-2-oxo-4-phenylquinolin-1(2H)-yl)-2-(5-methyl-1H-indol-3-yl)-N-(pentan-2-yl)acetamide and Et (2-(3-cyano-2-oxo-4-phenylquinolin-1(2H)-yl)-2-(5-methyl-1H-indol-3-yl)acetyl)glycinate demonstrated a down regulation of the HSP via a reduction in Gli expression and in the mRNA levels of Ptch₁ and Gli₂ and these compounds returned in cell inhibition values of 11.6, 2.9 and 3.1 μM, resp. making this new HSP-inhibitor pharmacophore amongst the most potent non-Smo inhibitors thus far reported. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Safety of 5-Chloroindole-3-carboxaldehyde).

Liu, Xiao-Dong et al. published their research in Tetrahedron 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. 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.Name: 6-Nitro-1H-indole

Cs₂CO₃-catalyzed alkylation of indoles with trifluoromethyl ketones was written by Liu, Xiao-Dong;Wang, Yi;Ma, Hai-Yan;Xing, Chun-Hui;Yuan, Yu;Lu, Long. And the article was included in Tetrahedron in 2017.Name: 6-Nitro-1H-indole This article mentions the following:

A Cs₂CO₃-catalyzed alkylation reaction of indoles with trifluoromethyl ketones was presented. Both alicyclic and aromatic trifluoromethyl ketones as well as various substituted indoles are compatible with the methodol. Good to excellent yields of the corresponding trifluoromethyl substituted tertiary alcs. 2,2,2-tritrifluoro-1-(1H-indol-3-yl)-ethan-1-ols were acquired as the sole products. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Name: 6-Nitro-1H-indole).

Bento, Ian et al. published their research in Synthetic Communications in 2020 | 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 was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Formula: C8H6N2O2

Ultrasound-assisted rapid reduction of nitroaromatics to anilines using gallium metal was written by Bento, Ian;Bernaldez, Mabel;Noguchi, Ryden;Kawakami, Joel. And the article was included in Synthetic Communications in 2020.Formula: C8H6N2O2 This article mentions the following:

The reduction of nitroarom. compounds to anilines is widely used throughout organic synthesis. Typical methods of performing this transformation utilize hydrogenation over a pyrophoric catalyst or a finely divided reducing metal, which often affords heterogeneous mixtures that are difficult to purify. Herein, for the first time gallium metal is used as a reducing agent in organic synthesis. The reaction proceeds under aerobic conditions and affords homogeneous mixtures for a convenient workup. Using this method, twelve anilines were obtained in 33% to quant. yields with short reaction times of 10-60 min. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Formula: C8H6N2O2).

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 was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Formula: C8H6N2O2

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).