Category: indole-building-block

Enantioselective Copper-Catalyzed Construction of Aryl Pyrroloindolines via an Arylation-Cyclization Cascade was written by Zhu, Shaolin;MacMillan, David W. C.. And the article was included in Journal of the American Chemical Society in 2012.Category: indole-building-block This article mentions the following:

An enantioselective arylation-cyclization cascade has been accomplished using a combination of diaryliodonium salts and asym. copper catalysis. These mild catalytic conditions provide a new strategy for the enantioselective construction of pyrroloindolines, an important alkaloid structural motif that is commonly found among biol. active natural products. In the experiment, the researchers used many compounds, for example, 4-Bromoindole-3-acetic Acid (cas: 89245-41-0Category: indole-building-block).

4-Bromoindole-3-acetic Acid (cas: 89245-41-0) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Category: 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

Tertiary Amine-Catalyzed Difluoromethylthiolation of Morita-Baylis-Hillman Carbonates of Isatins with Zard’s Trifluoromethylthiolation Reagent was written by Fan, Xing;Yang, Haibin;Shi, Min. And the article was included in Advanced Synthesis & Catalysis in 2017.Recommanded Product: 5-Isopropylindoline-2,3-dione This article mentions the following:

The authors report that a novel tertiary amine-catalyzed [3+2] annulation between Morita-Baylis-Hillman (MBH) carbonates derived from isatins with thiocarbonyl fluoride (F₂C=S) in situ generated from Zard’s reagent proceeds smoothly under mild conditions, affording difluoromethylthiolated spirocyclic oxindoles in good to excellent yields. Moreover, the asym. variant could be realized with a modified Cinchona alkaloid, giving the desired cyclic adducts, e.g., I (X-rays single crystal structure shown), in good to excellent yields with good enantioselectivities. In the experiment, the researchers used many compounds, for example, 5-Isopropylindoline-2,3-dione (cas: 150560-58-0Recommanded Product: 5-Isopropylindoline-2,3-dione).

5-Isopropylindoline-2,3-dione (cas: 150560-58-0) 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.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: 5-Isopropylindoline-2,3-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

Copper-Mediated Decarboxylative Coupling of 3-Indoleacetic Acids with Pyrazolones was written by Wen, Kangmei;Wu, Yinrong;Chen, Jiewen;Shi, Jie;Zheng, Mulin;Yao, Xingang;Tang, Xiaodong. And the article was included in ACS Omega in 2022.Electric Literature of C10H8ClNO2 This article mentions the following:

A copper-mediated decarboxylative coupling reaction of 3-indoleacetic acids with pyrazolones was described. This protocol realized new functionalization of pyrazolones under simple reaction conditions and exhibited high functional group compatibility and broad substrate scope. Notably, the products displayed antiproliferative activity against cancer cells. In the experiment, the researchers used many compounds, for example, 2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4Electric Literature of C10H8ClNO2).

2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Electric Literature of C10H8ClNO2

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

New indodicarbocyanine dyes for the biological microchip technology was written by Kuznetsova, V. E.;Vasiliskov, V. A.;Antonova, O. V.;Mikhailovich, V. M.;Zasedatelev, A. S.;Chudinov, A. V.. And the article was included in Russian Journal of Bioorganic Chemistry in 2008.Electric Literature of C13H17NO3S This article mentions the following:

New indodicarbocyanine dyes with the carboxybutyl group in position-3 of the indolenine fragment bearing Me and sulfonic groups in positions 5 and 7 of the cycle were synthesized in order to find the most effective fluorescent labels for the biol. microchip technol. The position of absorption and fluorescence maxima, the total charge of the dye mol., and water solubility depend on the location and the total amount of Me and sulfonic groups. The spectral characteristics of the dyes synthesized were determined The relative fluorescence efficiencies of the dyes at equal concentrations were measured at excitation wavelengths of 635 and 655 nm and emission wavelengths of 670 and 690 nm, resp. 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).

1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Electric Literature of C13H17NO3S

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

Selective reduction of carbonyl groups in the presence of low-valent titanium reagents was written by Lin, Wei;Hu, Ming-Hua;Feng, Xian;Fu, Lei;Cao, Cheng-Pao;Huang, Zhi-Bin;Shi, Da-Qing. And the article was included in Tetrahedron Letters in 2014.Reference of 774-47-0 This article mentions the following:

The chemoselective reduction of several structurally diverse compounds containing carbonyl groups was achieved in the presence of low-valent Ti reagents. This novel synthetic method provides easy access to highly selective reduction of carbonyl groups, and possesses several advantages including one-step procedure, convenient manipulation, good to excellent yields, and short reaction times. In the experiment, the researchers used many compounds, for example, 5,6-Difluoroindoline-2,3-dione (cas: 774-47-0Reference of 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. 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.Reference of 774-47-0

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

N-Thiolated β-lactam antibacterials: Effects of the N-organothio substituent on anti-MRSA activity was written by Heldreth, Bart;Long, Timothy E.;Jang, Seyoung;Reddy, G. Suresh Kumar;Turos, Edward;Dickey, Sonja;Lim, Daniel V.. And the article was included in Bioorganic & Medicinal Chemistry in 2006.Recommanded Product: 2-(Phenylthio)isoindoline-1,3-dione This article mentions the following:

A study on the structure-activity profiles of N-thiolated β-lactams 1 is reported which demonstrates the importance of the N-organothio moiety on antibacterial activity. Our results indicate that elongation of the N-alkylthio residue beyond two carbons, or extensive branching within the organothio substituent, diminishes antibacterial effects. Of the derivatives the authors examined, the N-sec-butylthio β-lactam derivative 5 g possesses the strongest growth inhibitory activity against methicillin-resistant Staphylococcus aureus strains. Sulfur oxidation state is important, as the N-sulfenyl and N-sulfinyl groups provide for the best antibacterial activity, while lactams bearing the N-sulfonyl or N-sulfonic acid functionalities have much weaker or no anti-MRSA properties. Stereochem. within the organothio chain does not seem to be a significant factor, although for N-sec-butylthio β-lactams, the 3R,4S-lactams (I, II) are more active than the 3S,4R-stereoisomers (III, IV) in agar diffusion experiments The N-methylthio lactams are the most sensitive to the presence of glutathione, followed by N-ethylthio and N-sec-butylthio lactams, which indicates that bioactivity and perhaps bacterial selectivity of the lactams may be related to the amount of organothiols in the bacterial cell. These results support the empirical model for the mechanism of action of the compounds in which the lactam transverses the bacterial membrane to deliver the organothio moiety to its cellular target. 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).

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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Recommanded Product: 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

Synthesis of monofluorinated C₄-building blocks based on methallyl chloride was written by Haufe, Guenter;Wessel, Ulrich;Schulze, Klaus;Alvernhe, Gerard. And the article was included in Journal of Fluorine Chemistry in 1995.HPLC of Formula: 14204-27-4 This article mentions the following:

Halofluorination of methallyl chloride using N-halosuccinimides in combination with triethylamine trishydrofluoride (Et₃N·3HF) gave in each case more than 98% of the Markovnikov products and <2% of the regioisomers in good yield. The formal addition of methanesulfenyl fluoride with the combination of dimethyl(methylthio)sulfonium fluoroborate (DMTSF) and Et₃N·3HF gave a 94:6 mixture of both regioisomers. Only small phenylsulfenyl fluorination of methallyl chloride has been observed when treated with N-phenylthiophthalimide (NPTP) and Olah’s reagent. With benzenesulfenyl chloride, 1,3-dichloro-2-methyl-2-(phenylthio)propane is formed which on treatment with Olah’s reagent at 0 °C or with Et₃N·3HF at 60 °C rearranges to 1,2-dichloro-2-methyl-3-(phenylthio)propane. Treatment of 1,3-dichloro-2-methyl-2-(phenylthio)propane with silver fluoride in methylene chloride at -30 °C gave 1-chloro-2-fluoro-2-methyl-3-(phenylthio)propane which was also obtained by reaction of 1-bromo-3-chloro-2-fluoro-2-methylpropane with thiophenolate. Chlorofluorination of methallylphenylthio ether using NCS/Et₃N·3HF failed, while corresponding reactions with NBS or NIS and Et₃N·3HF gave mainly the bromo- or iodo-fluorides with Markovnikov orientation in 61% or 35% yields. Related halofluorinations of methallylphenyl ether gave the halo fluorides in good yield. All attempts to obtain chromans or thiochromans bearing a 3-fluorine substituent by cyclization of these halofluorinated ethers or thio ethers failed using different Lewis acids. However, the benzyl protected o-allylphenol which was bromofluorinated with NBS/Et₃N·3HF in good yield gave on catalytic hydrogenation over Pd/C the 3-fluoro-2H-chroman in nearly quant. yield. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4HPLC of Formula: 14204-27-4).

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) 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.HPLC of Formula: 14204-27-4

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

Comparative Study of Novel Fluorescent Cyanine Nucleotides: Hybridization Analysis of Labeled PCR Products Using a Biochip was written by Shershov, V. E.;Lapa, S. A.;Kuznetsova, V. E.;Spitsyn, M. A.;Guseinov, T. O.;Polyakov, S. A.;Stomahin, A. A.;Zasedatelev, A. S.;Chudinov, A. V.. And the article was included in Journal of Fluorescence in 2017.COA of Formula: C13H17NO3S This article mentions the following:

This study investigated the synthesis and substrate properties of Cy5-labeled dUTP derivatives with different substituents, linkers between the dye unit and pyrimidine heterocycle and fluorophore charges. Fluorescently labeled nucleoside triphosphates were studied as substrates using multiplex PCR with Taq and Vent (exo-) DNA polymerases, the typical representatives of the A and B polymerase families. The efficiency of nucleotide incorporation during PCR was assessed with a multi-parameter hybridization anal. using a diagnostic DNA microarray. The hybridization anal. indirectly estimates the incorporation efficiency of dye-labeled nucleotides in multiplex PCR. Our results demonstrated higher efficiencies of substrates with elec. neutral dyes than electropos. and electroneg. Cy5 residues. In the experiment, the researchers used many compounds, for example, 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2COA of Formula: C13H17NO3S).

1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.COA of Formula: C13H17NO3S

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

Synthesis and antioxidant activity of 3-[4-(2,5-dimethylamino-1H-pyrrol-1-yl-phenyl)][1,3,4]-oxadiazino[6,5-b]substituted indole was written by Padma, Bairy;Gadea, Sammaiah. And the article was included in International Journal of Research in Pharmacy and Chemistry in 2020.Reference of 112656-95-8 This article mentions the following:

Fifteen new 3-[4-(2,5-di-Me amino-1H pyrrol-1-yl-phenyl)][1,3,4]-oxadiazino [6,5-b] substituted indoles I (R = 6-Cl, 8-Br, 6-F, etc.) have been synthesized. The chem. structures of the products I were confirmed by ¹HNMR, IR and mass spectral data. The compounds I were screened for antioxidant activity by standard DPPH assay method. IC₅₀ values of these compounds I were determined Compounds I (R = 8-F, 8-C(O)₂H, 8-C(O)₂Et) potent antioxidant and remaining compounds showed significant antioxidant activity. Ascorbic acid was taken as standard drug. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Reference of 112656-95-8).

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

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

Sulfuration reaction of glycine tert-butyl ester derivatives by phase transfer catalysis was written by Lu, Xieqin;Dong, Xiaoyang;Dai, Zhenya;You, Qidong. And the article was included in Hebei Yiyao in 2012.Quality Control of 2-(Phenylthio)isoindoline-1,3-dione This article mentions the following:

Sulfuration of glycine tert-Bu ester derivatives by phase transfer catalysis was tried to provide. The best condition was using TEBA as catalyst, 50% KOH as alk. and THF as solvent. α-Sulfuration reaction by phase transfer catalysis was successfully made, and ee in asymmetry could up to 70%. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Quality Control of 2-(Phenylthio)isoindoline-1,3-dione).

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