Category: indole-building-block

Asymmetric Synthesis of Structurally Sophisticated Spirocyclic Pyrano[2,3-c]pyrazole Derivatives Bearing a Chiral Quaternary Carbon Center was written by Yang, Xiaoqun;Sun, Jun;Huang, Xuan;Jin, Zhichao. And the article was included in Organic Letters in 2022.Recommanded Product: 5,6-Difluoroindoline-2,3-dione This article mentions the following:

A carbene-catalyzed enantio- and diastereoselective [2 + 4] cycloaddition reaction is developed for quick and efficient access to structurally complex multicyclic pyrano[2,3-c]pyrazole mols. I (R = Me, Ph, 1-naphthyl, etc.; R¹ = H, Me, F; R² = H, Br, F; R³ = H, Me; R⁴ = Me, Bn, Ac, H; R⁵ = Me, Ph, 2-chlorophenyl). The reaction tolerates a broad scope of substrates bearing various substitution patterns, with the multicyclic pyrano[2,3-c]pyrazole products I afforded in generally good to excellent yields and optical purities. The chiral mols. obtained from this approach have found promising applications in the development of novel bactericides for plant protection. In the experiment, the researchers used many compounds, for example, 5,6-Difluoroindoline-2,3-dione (cas: 774-47-0Recommanded Product: 5,6-Difluoroindoline-2,3-dione).

5,6-Difluoroindoline-2,3-dione (cas: 774-47-0) 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.Recommanded Product: 5,6-Difluoroindoline-2,3-dione

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

Asymmetric sulfenylation of 3-CF₃-Oxindoles through organocatalysis with a quinidine derivative was written by E, Yidan;Yuan, Teng;Yin, Liang;Xu, Youjun. And the article was included in Tetrahedron Letters in 2017.Synthetic Route of C14H9NO2S This article mentions the following:

An asym. sulfenylation of 3-CF₃-oxindoles catalyzed by a quinidine derivative was described. 3-CF₃-oxindoles with electro-donating groups led to corresponding products in good yield and with good enantioselectivity while 3-CF₃-oxindoles bearing electro-withdrawing groups were not competent substrates due to its significant decomposition at the optimal reaction conditions. As for the sulfenylation reagents based on thiophenol, both electro-donating groups and electro-withdrawing groups were well tolerated. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Synthetic Route of C14H9NO2S).

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 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). Synthetic Route of C14H9NO2S

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

Cyanine dye labeling reagents: Sulfoindocyanine succinimidyl esters was written by Mujumdar, Ratnakar B.;Ernst, Lauren A.;Mujumdar, Swati R.;Lewis, Christopher J.;Waggoner, Alan S.. And the article was included in Bioconjugate Chemistry in 1993.Computed Properties of C13H17NO3S This article mentions the following:

The synthesis and properties of a series of new fluorescent labeling reagents based on sulfoindocyanine dyes are described. They contain succinimidyl ester reactive groups and can be readily conjugated to antibodies, avidin, DNA, lipids, polymers, and other amino-group-containing materials. The labeling reagents are water soluble, pH insensitive, and show much reduced dye aggregation under labeling conditions. One of the reagents, Cy3, can be excited with the 488-, 514-, and 532-nm laser lines and is optimally excited with the 546-nm mercury arc line. Another, Cy5, can be excited with the 633-nm HeNe and 647-nm Kr laser lines available with many flow cytometers and confocal laser-scanning microscopes. New laser diodes emitting near 650 nm should also be excellent excitation sources for Cy5. In the experiment, the researchers used many compounds, for example, 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2Computed Properties of C13H17NO3S).

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

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

Discovery of Novel Schizocommunin Derivatives as Telomeric G-Quadruplex Ligands That Trigger Telomere Dysfunction and the Deoxyribonucleic Acid (DNA) Damage Response was written by Che, Tong;Chen, Shuo-Bin;Tu, Jia-Li;Wang, Bo;Wang, Yu-Qing;Zhang, Yan;Wang, Jing;Wang, Zeng-Qing;Zhang, Ze-Peng;Ou, Tian-Miao;Zhao, Yong;Tan, Jia-Heng;Huang, Zhi-Shu. And the article was included in Journal of Medicinal Chemistry in 2018.Reference of 774-47-0 This article mentions the following:

Telomeric G-quadruplex targeting and telomere maintenance interference are emerging as attractive strategies for anticancer therapies. Here, a novel mol. scaffold is explored for telomeric G-quadruplex targeting. A series of novel schizocommunin derivatives was designed and synthesized as potential telomeric G-quadruplex ligands. The interaction of telomeric G-quadruplex DNA with the derivatives was explored by biophys. assay. The cytotoxicity of the derivatives toward cancer cell lines was evaluated by the Me thiazolyl tetrazolium (MTT) assay. Among the derivatives, compound 16 showed great stabilization ability toward telomeric G-quadruplex DNA and good cytotoxicity toward cancer cell lines. Further cellular experiments indicated that 16 could induce the formation of telomeric G-quadruplex in cells, triggering a DNA damage response at the telomere and causing telomere dysfunction. These effects ultimately provoked p53-mediated cell cycle arrest and apoptosis, and suppressed tumor growth in a mouse xenograft model. Our work provides a novel scaffold for the development of telomeric G-quadruplex ligands. 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 could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Reference of 774-47-0

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

Visible-light induced divergent dearomatization of indole derivatives: controlled access to cyclobutane-fused polycycles and 2-substituted indolines was written by Zhuang, Weihui;Cheng, Yuan-Zheng;Huang, Xu-Lun;Huang, Qiufeng;Zhang, Xiao. And the article was included in Organic Chemistry Frontiers in 2021.Recommanded Product: Methyl 5-fluoro-1H-indole-2-carboxylate This article mentions the following:

A photocatalytic protocol for the divergent dearomative functionalization of indole derivatives was reported. Under the irradiation of visible light, either dimerization or reduction occurred selectively by modifying the reaction conditions, leading to the formation of the corresponding cyclobutane-fused polycycles and 2-substituted indolines in good yields with exclusive selectivity. 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).

Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes.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: Methyl 5-fluoro-1H-indole-2-carboxylate

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

Parameterization of Acyclic Diaminocarbene Ligands Applied to a Gold(I)-Catalyzed Enantioselective Tandem Rearrangement/Cyclization was written by Niemeyer, Zachary L.;Pindi, Suresh;Khrakovsky, Dimitri A.;Kuzniewski, Christian N.;Hong, Cynthia M.;Joyce, Leo A.;Sigman, Matthew S.;Toste, F. Dean. And the article was included in Journal of the American Chemical Society in 2017.Formula: C10H8ClNO2 This article mentions the following:

Computed descriptors for acyclic diaminocarbene ligands are developed in the context of a gold catalyzed enantioselective tandem [3,3]-sigmatropic rearrangement-[2+2]-cyclization. Surrogate structures enable the rapid identification of parameters that reveal mechanistic characteristics. The observed selectivity trends are validated in a robust multivariate anal. facilitating the development of a highly enantioselective process. In the experiment, the researchers used many compounds, for example, 2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4Formula: 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.Formula: C10H8ClNO2

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

Diverse ring opening of thietanes and other cyclic sulfides: an electrophilic aryne activation approach was written by Zheng, Tianyu;Tan, Jiajing;Fan, Rong;Su, Shuaisong;Liu, Binbin;Tan, Chen;Xu, Kun. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2018.Recommanded Product: 6-Nitro-1H-indole This article mentions the following:

An electrophilic aryne-activated ring opening protocol of one or two heteroatom containing saturated sulfur heterocycles was reported. This three-component transformation proceeded under mild reaction conditions and displayed exceptional generality of nucleophiles (C, O, S, N and F centered nucleophiles), giving structurally diverse thioethers in good yields. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Recommanded Product: 6-Nitro-1H-indole).

6-Nitro-1H-indole (cas: 4769-96-4) 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: 6-Nitro-1H-indole

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

Electron transfer from guanosine to the lowest triplet excited state of 4-nitroindole through hydrogen-bonded complex was written by Ye, Zhao;Du, Yong;Pan, Xinghang;Zheng, Xuming;Xue, Jiadan. And the article was included in Journal of Photochemistry and Photobiology, A: Chemistry in 2021.Product Details of 4769-96-4 This article mentions the following:

The photochem. reaction of 4-nitroindole and guanosine was studied with the transient absorption spectroscopy as guanine is an effective hole trap during the charge transfer in DNA, and 4-nitroindole is a universal base. Excitation of 4-nitroindole generates the lowest triplet excited state 4-nitroindole (³HN-NO₂) within 10 ns in the quantum yield 0.41. ³HN-NO₂ has increased basicity compared to its ground state. Consequently, its nitro group exhibits the hydrogen bond accepting ability. ³HN-NO₂ can interact with guanosine (G) to form the hydrogen-bonded ³HN-NO₂…G complex with the rate constant k = (8.7 卤 0.3)x10⁹ M^-1路s^-1. The hydrogen-bonded complex is identified based on the blue shift evolvement of the absorption maximum of ³HN-NO₂ in alc. solutions The reduction potential of ³HN-NO₂ is Ered(³HN-NO₂) = 1.23 V vs. SCE. The electron transfer occurs in the ³HN-NO₂…G complex and generates G+bul and HN-NO₂-鈥?followed by the proton transfer from N₁ and N₂ of G producing radicals HN-NO₂H鈥? G(N₁-H)鈥?and G(N₂-H)鈥? In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Product Details of 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Product Details of 4769-96-4

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

Synthesis of a new near-IR fluorescent reagent and study on its in-situ dimer’s interaction with DNA was written by Zheng, Hong;Li, Dong-Hui;Wu, Min;Chen, Qiu-Ying;Xu, Jin-Gou. And the article was included in Gaodeng Xuexiao Huaxue Xuebao in 1999.Reference of 146368-07-2 This article mentions the following:

A new anionic Near-IR fluorescent cyanine dye was synthesized and its absorption and fluorescence spectra in water and in the solution of cationic surfactant-hexadecyltrimethyl-ammonium bromide (CTAB) were studied. The results showed that the maximum excitation wavelength and emission wavelength were 765 nm and 795 nm in water, resp. In the presence of low concentration of CTAB, the dye formed ionic associate with CTAB was made higher to form the pre-micellar aggregation, the fluorescence intensity decreased dramatically because of forming a low-fluorescent in-situ dimeric dye. When the concentration of CTAB was above the critical micelle concentration (cmc), the dimeric dye dissociated, and the fluorescence intensity of Near-IR cyanine was restored, and the maximum emission wavelength was bathochromated from 795 nm to 812 nm. The possibility of using low-fluorescent in-situ dimeric dye as a Near-IR region fluorescent probe for DNA was also studied. In the experiment, the researchers used many compounds, for example, 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2Reference of 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. 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 146368-07-2

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

Photoactive electron donor-acceptor complex platform for Ni-mediated C(sp³)-C(sp²) bond formation was written by Kammer, Lisa Marie;Badir, Shorouk O.;Hu, Ren-Ming;Molander, Gary A.. And the article was included in Chemical Science in 2021.Recommanded Product: 14204-27-4 This article mentions the following:

A dual photochem./nickel-mediated decarboxylative strategy for the assembly of C(sp₃)-C(sp₂) linkages was disclosed. Under light irradiation at 390 nm, com. available and inexpensive Hantzsch ester (HE) functions as a potent organic photoreductant to deliver catalytically active Ni(0) species through single-electron transfer (SET) manifolds. As part of its dual role, the Hantzsch ester effects a decarboxylative-based radical generation through electron donor-acceptor (EDA) complex activation. This homogeneous, net-reductive platform bypasses the need for exogenous photocatalysts, stoichiometric metal reductants, and additives. Under this cross-electrophile paradigm, the coupling of diverse C(sp₃)-centered radical architectures (including primary, secondary, stabilized benzylic, 伪-oxy, and 伪-amino systems) with (hetero)aryl bromides was accomplished. The protocol proceeded under mild reaction conditions in the presence of sensitive functional groups and pharmaceutically relevant cores. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Recommanded Product: 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Recommanded Product: 14204-27-4

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