05/01/2023 - Page 10 of 11 - Indole Building Blocks

Li, Guangzhe et al. published their research in Asian Journal of Organic Chemistry in 2013 | 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. 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 2-(Phenylthio)isoindoline-1,3-dione

Rhodium-Catalyzed Synthesis and Reactions of N-Acylphthalimides was written by Li, Guangzhe;Arisawa, Mieko;Yamaguchi, Masahiko. And the article was included in Asian Journal of Organic Chemistry in 2013.Safety of 2-(Phenylthio)isoindoline-1,3-dione This article mentions the following:

Synthesis of N-acylphthalimides using rhodium catalysts for the imidation of thioesters or acid fluorides with N-(organothio)phthalimides and its reaction with non protic organic compounds is discussed. Thioesters and N-(phosphinoyl)phthalimides were obtained from reactions with phosphinothioates, acid fluorides and N-(tetrafluoroaryl)phthalimides were obtained from reactions with substituted pentafluorobenzenes. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Safety of 2-(Phenylthio)isoindoline-1,3-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

Zasedateleva, Olga A. et al. published their research in Nucleic Acids Research in 2018 | CAS: 146368-07-2

1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2) 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.Electric Literature of C13H17NO3S

dUTPs conjugated with zwitterionic Cy3 or Cy5 fluorophore analogues are effective substrates for DNA amplification and labelling by Taq polymerase was written by Zasedateleva, Olga A.;Vasiliskov, Vadim A.;Surzhikov, Sergey A.;Kuznetsova, Viktoriya E.;Shershov, Valeriy E.;Guseinov, Timur O.;Smirnov, Igor P.;Yurasov, Roman A.;Spitsyn, Maksim A.;Chudinov, Alexander V.. And the article was included in Nucleic Acids Research in 2018.Electric Literature of C13H17NO3S This article mentions the following:

To develop structural modifications of dNTPs that are compatible with Taq DNA polymerase activity, we synthesized eight dUTP derivatives conjugated with Cy3 or Cy5 dye analogs that differed in charge and charge distribution throughout the fluorophore. These dUTP derivatives and com. Cy3-and Cy5-dUTP were studied in Taq polymerase dependent polymerase chain reactions (PCRs) and in primer extension reactions using model templates containing one, two and three adjacent adenine nucleotides. The relative amounts of amplified DNA and the kinetic parameters Km and Vmax characterizing the incorporation of labeled dUMPs have been estimated using fluorescence measurements and analyzed. The dUTPs labeled with electroneutral zwitterionic analogs of Cy3 or Cy5 fluorophores were used by Taq polymerase approx. one order of magnitude more effectively than the dUTPs labeled with neg. charged analogs of Cy3 or Cy5. The nucleotidyl transferase activity of Taq polymerase was also observed and resulted in the addition of dUMPs labeled with electroneutral or pos. charged fluorophores to the 3 ends of DNA. The introduction of mutually compensating charges into fluorophores or other functional groups conjugated to dNTPs can be considered a basis for the creation of PCR-compatible modified nucleoside triphosphates. In the experiment, the researchers used many compounds, for example, 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2Electric Literature of C13H17NO3S).

Rajini Priya, V. et al. published their research in Journal of Pharma Research in 2013 | CAS: 112656-95-8

7-Nitroindoline-2,3-dione (cas: 112656-95-8) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Recommanded Product: 7-Nitroindoline-2,3-dione

Synthesis and screening method of new isatin derivatives was written by Rajini Priya, V.;Aruna Devi, M.;Raghunandan, N.;Venkateshwar Rao, J.. And the article was included in Journal of Pharma Research in 2013.Recommanded Product: 7-Nitroindoline-2,3-dione This article mentions the following:

The compound isatin derivatives I (R = H, 7-CH₃, 5-Cl, etc.) were prepared by the treatment of 2-chloro-N1-[2-oxo-1,2-dihydro-3H-indol-3-ylidene] acetohydrazides with 1H-benzimidazole-2-ylmethanethiol in good yields. All the compounds were screened for their anti-inflammatory activities. The compound I (R = 5-CH₃, 7-CH₃) exhibited maximum activity with percentage of inhibition of 68.56 and 61.41. All the synthesized compounds showed mild to moderate anti-inflammatory activity. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Recommanded Product: 7-Nitroindoline-2,3-dione).

Du, Yanlong et al. published their research in Chemical Communications (Cambridge, United Kingdom) in 2017 | CAS: 774-47-0

5,6-Difluoroindoline-2,3-dione (cas: 774-47-0) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.HPLC of Formula: 774-47-0

Direct N-H/α,α,β,β-C(sp³)-H functionalization of piperidine via an azomethine ylide route: synthesis of spirooxindoles bearing 3-substituted oxindoles was written by Du, Yanlong;Yu, Aimin;Jia, Jiru;Zhang, Youquan;Meng, Xiangtai. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2017.HPLC of Formula: 774-47-0 This article mentions the following:

A protocol for the direct functionalization of N-H/α,α,β,β-C(sp³)-H of piperidine without any metal or external oxidants was reported. This reaction was promoted by 4-(trifluoromethyl)benzoic acid via an azomethine ylide intermediate. This was a simple method for the synthesis of spirooxindoles bearing 3-substituted oxindole moieties. In the experiment, the researchers used many compounds, for example, 5,6-Difluoroindoline-2,3-dione (cas: 774-47-0HPLC of Formula: 774-47-0).

Markova, Larysa I. et al. published their research in Dyes and Pigments in 2013 | CAS: 146368-07-2

1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2) 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.Category: indole-building-block

Comparison of a series of hydrophilic squaraine and cyanine dyes for use as biological labels was written by Markova, Larysa I.;Terpetschnig, Ewald A.;Patsenker, Leonid D.. And the article was included in Dyes and Pigments in 2013.Category: indole-building-block This article mentions the following:

Unlike cyanine dyes, which are widely used as fluorescent probes and labels for biomedical applications squaraine dyes are less investigated. A series of monoreactive, water-soluble, squaraine dyes with two aromatic sulfo groups and up to 3 sulfobutyl groups was synthesized and the spectral properties of these dyes were compared to dicarbocyanines of identical structure. Compared to the cyanines in aqueous solutions the squaraine dyes absorb and emit at shorter wavelengths (630-636 nm/639-645 nm vs. 647-653 nm/665-672 nm), have higher molar absorptivities (284,000-333,000 M^-1 cm^-1vs. 242,000-260,000 M^-1 cm^-1), lower fluorescence quantum yields (4.3-9.4% vs. 27-32%) and lower fluorescence lifetimes (0.2-0.3 ns vs. 1.0-1.2 ns) but the quantum yields and lifetimes substantially increase when bound to proteins (Bovine Serum Albumin (BSA) or antibodies, IgG (IgG)). Squaraines with two aromatic sulfo groups show no aggregation tendency up to concentrations of 2 × 10^-4 M while the corresponding cyanine dye is free of aggregation up to 5 × 10^-4 M. The increase in the number of sulfobutyl groups bears a strong influence on the aggregation tendency of both dye classes upon covalent labeling to BSA and IgG resulting in increased quantum yields and lifetimes of the protein conjugates. Compared to cyanines, squaraine dyes exhibit higher photostabilities and much higher sensitivity of the quantum yields and fluorescence lifetimes toward the microenvironment and are therefore better suited as fluorescence sensors. In the experiment, the researchers used many compounds, for example, 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2Category: indole-building-block).

Fukuda, Yasumichi et al. published their research in Journal of Medicinal Chemistry in 1999 | CAS: 210345-56-5

Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5) 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.HPLC of Formula: 210345-56-5

Novel cyclopropapyrroloindole derivative (AT-3510) bearing methoxycarbonyl and trifluoromethyl groups was written by Fukuda, Yasumichi;Furuta, Hirosuke;Kusama, Yoshie;Ebisu, Hiroyuki;Oomori, Yasuo;Terashima, Shiro. And the article was included in Journal of Medicinal Chemistry in 1999.HPLC of Formula: 210345-56-5 This article mentions the following:

The seco-Cl 3-methoxycarbonyl-2-trifluoromethylcyclopropapyrroloindole (MCTFCPI) derivatives dl- and/or (S)-I [Ar = Q, Q₁, Q₂, Q₃, R = 4,5,6-(MeO)₃, 5,6,7-(MeO)₃, 5-MeO, etc., X = NH, O, CH, Y = CH, N] carrying various acyl moieties at the N6-position were synthesized along with their prodrugs (S)-II, and their antitumor activity was evaluated. Among these derivatives, AT-3510 [(S)-II (Ar = Q¹, R = 7-MeO, X = O)], the novel prodrug MCTFCPI derivative carrying a 5-(7-methoxybenzofuran-2-ylcarbonyl)aminoindole-2-carbonyl group at the N6-position, was found to exhibit more excellent antitumor activity against human tumor xenografts than the clin. trial candidates carzelesin and KW-2189 (III) and cisplatin. In the experiment, the researchers used many compounds, for example, Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5HPLC of Formula: 210345-56-5).

Dhawan, Sanjeev et al. published their research in Journal of Chemical and Pharmaceutical Research in 2016 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) 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). Recommanded Product: 2-(Phenylthio)isoindoline-1,3-dione

Strategies for chemical synthesis of pyrazolone derivatives and their bio-significance was written by Dhawan, Sanjeev;Narang, Rakesh;Khatik, Gopal L.;Chopra, Harish Kumar;Nayak, Surendra Kumar. And the article was included in Journal of Chemical and Pharmaceutical Research in 2016.Recommanded Product: 2-(Phenylthio)isoindoline-1,3-dione This article mentions the following:

Over the last few decades, pyrazolone derivatives have been used for various biochem. applications. Some of these derivatives such as metamizole, phenazone, aminopyrine and propyphenazone, are widely used as antiinflammatory and analgesics. Moreover, pyrazolones have been exhibited antioxidant, antibacterial, anticancer and several other biol. activities. Thus, keeping in view of their importance, synthetic strategies for existing as well as novel pyrazolone derivatives have been developed and explored their biochem. utility. As versatile features of pyrozaolones have emerged, so the aim of the present paper is to put chem. synthetic schemes and biol. advancements of pyrazolone derivatives together. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Recommanded Product: 2-(Phenylthio)isoindoline-1,3-dione).

Rogness, Donald C. et al. published their research in Tetrahedron Letters in 2009 | 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Quality Control of Methyl 5-bromo-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-bromo-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-bromo-1H-indole-2-carboxylate (cas: 210345-56-5Quality Control of Methyl 5-bromo-1H-indole-2-carboxylate).

Guan, Dongliang et al. published their research in Journal of Medicinal Chemistry in 2021 | 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.Reference of 827-01-0

Indole-Containing Amidinohydrazones as Nonpeptide, Dual RXFP3/4 Agonists: Synthesis, Structure-Activity Relationship, and Molecular Modeling Studies was written by Guan, Dongliang;Rahman, Toufiqur Md;Gay, Elaine A.;Vasukuttan, Vineetha;Mathews, Kelly M.;Decker, Ann M.;Williams, Alexander H.;Zhan, Chang-Guo;Jin, Chunyang. And the article was included in Journal of Medicinal Chemistry in 2021.Reference of 827-01-0 This article mentions the following:

Herein, the first structure-activity relationship studies of a series of novel nonpeptide amidinohydrazone-based agonists I [R¹ = H, 4-Me, 7-F, etc.; R² = H, Me; R³ = ; 4-ClC₆H₄, 3,4-di-ClC₆H₃, 2-thienyl, etc.; R⁴ = H, Me; n = 0,1,2,3], which were characterized by RXFP3 functional and radioligand binding assays was reported. Several potent and efficacious RXFP3 agonists compound I [R¹ = 5-CN-7-Me, R² = H, R³ = 4-CO₂MeC₆H₄, R⁴ = H, n = 2] were identified with EC₅₀ values <10 nM. These compounds also had high potency at RXFP4 but no agonist activity at RXFP1, demonstrating > 100-fold selectivity for RXFP3/4 over RXFP1. In vitro ADME and pharmacokinetic assessments revealed that the amidinohydrazone derivatives might have limited brain permeability. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Reference of 827-01-0).

Chaudhari, Chandan et al. published their research in Green Chemistry in 2020 | 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Application In Synthesis of 2-Phenylisoindolin-1-one

One-pot synthesis of pyrrolidones from levulinic acid and amines/nitroarenes/nitriles over the Ir-PVP catalyst was written by Chaudhari, Chandan;Shiraishi, Masaya;Nishida, Yoshihide;Sato, Katsutoshi;Nagaoka, Katsutoshi. And the article was included in Green Chemistry in 2020.Application In Synthesis of 2-Phenylisoindolin-1-one This article mentions the following:

The synthesis of pyrrolidones I (R = C₆H₅, CH₂C₆H₅, 4-FC₆H₄, etc.) via reductive amination of levulinic acid with aniline was examined over polypyrrolidone-stabilized metal nanoparticle catalysts. Among them, Ir metal was the most effective and applicable for the reductive amination of levulinic acid with nitroarenes R¹NO₂ (R¹ = C₆H₅, 4-CH₃OC₆H₄, 4-CH₃C₆H₄, 4-ClC₆H₄, 4-FC₆H₄)/nitriles R²CN (R² = C₆H₅, 4-CH₃OC₆H₄, 4-CH₃C₆H₄, 4-ClC₆H₄, 4-CF₃C₆H₄). Importantly, this catalyst was used for the one-pot synthesis of the anti-inflammatory drug indoprofen from 2-formylbenzoic acid and 2-(4-nitrophenyl)propanoic acid. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Application In Synthesis of 2-Phenylisoindolin-1-one).