Day: February 10, 2023

Asymmetric [3 + 3] Annulation to Construct Trifluoromethylated Pyrazolo[3,4-b]pyridin-6-ones via Chiral Phosphoric Acid and MgSO₄ Synergistic Catalysis was written by Woldegiorgis, Alemayehu Gashaw;Han, Zhao;Lin, Xufeng. And the article was included in Organic Letters in 2022.Application of 320734-35-8 This article mentions the following:

A novel asym. Friedel-Crafts alkylation/transamidation tandem reaction for the enantio- and diastereoselective synthesis of pyrazolo[3,4-b]pyridin-6-ones I (R = H, Me, Cl; R¹ = H, OMe, Br, Cl, F; R² = H, Me, Br, F; R³ = H, Br; R⁴ = Boc, Cbz; R⁵ = H, Et, i-Pr; R⁶ = Ph, 3-bromophenyl, 1H-benzo[d]imidazol-2-yl, etc.; R⁷ = Me, Et, i-Pr, Ph) bearing a -CF₃ unit via synergistic chiral phosphoric acid and MgSO₄ catalysis was developed. This [3 + 3] annulation protocol allows the formation of trifluoromethylated pyrazolo[3,4-b]pyridin-6-ones I with two adjacent tertiary stereocenters in moderate to high yields (up to 90%), enantioselectivities (up to 97% ee), and diastereoselectivities (up to >20:1 dr). In the experiment, the researchers used many compounds, for example, 7-Bromooxindole (cas: 320734-35-8Application of 320734-35-8).

7-Bromooxindole (cas: 320734-35-8) 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.Application of 320734-35-8

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

[Fe(F₂₀TPP)Cl]-Catalyzed Amination with Arylamines and {[Fe(F₂₀TPP)(NAr)](PhI=NAr)}⁺. Intermediate Assessed by High-Resolution ESI-MS and DFT Calculations was written by Liu, Yungen;Chen, Guo-Qiang;Tse, Chun-Wai;Guan, Xianguo;Xu, Zheng-Jiang;Huang, Jie-Sheng;Che, Chi-Ming. And the article was included in Chemistry – An Asian Journal in 2015.Recommanded Product: 167631-84-7 This article mentions the following:

Amination of C-H bonds catalyzed by transition metal complexes via nitrene/imide insertion is an appealing strategy for C-N bond formation, and the use of iminoiodinanes, or their in situ generated forms from PhI(OAc)₂+primary amides (such as sulfonamides, sulfamates, and carbamates), as nitrogen sources for the amination reaction was well documented. A metal catalyst+PhI(OAc)₂+primary arylamines amination protocol was developed using [Fe(F₂₀TPP)Cl] (H₂F₂₀TPP=meso-tetrakis(pentafluorophenyl)porphyrin) as a catalyst. This catalytic method is applicable for both intra- and intermol. amination of sp² and sp³ C-H bonds (>27 examples), affording the amination products, including natural products such as rutaecarpine, in moderate-to-good yields. ESI-MS anal. and DFT calculations lend support for the involvement of {[Fe(F₂₀TPP)(NC₆H₄-p-NO₂)](PhI=NC₆H₄-p-NO₂)}^+. intermediate in the catalysis. In the experiment, the researchers used many compounds, for example, Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7Recommanded Product: 167631-84-7).

Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Recommanded Product: 167631-84-7

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

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

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

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

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

Selective halogen-lithium exchange in bromophenylalkyl halides was written by Parham, William E.;Jones, Lawrence D.;Sayed, Yousry A.. And the article was included in Journal of Organic Chemistry in 1976.Reference of 5388-42-1 This article mentions the following:

Exchange of the aryl halide atom in o-BrC6H4CH2Cl, o-BrC6H4(CH2)2Br, and o-BrC6H4(CH2)3Cl for Li was carried out with BuLi in THF-hexane at -100掳. The stable lithio derivatives reacted with a variety of electrophiles; e.g., o-LiC6H4CH2Cl (I) with H2O, cyclohexanone, or PhNCO at low temperature gave, resp., PhCH2Cl, II, and III. I with H2O at room temperature gave 9,10-dihydroanthracene (not benzocyclopropene). Benzocyclobutene was formed from o-LiC6H4(CH2)2Br under similar conditions. O-halobenzyl bromides were lithiated at the benzyl bromine atom and underwent subsequent coupling to bibenzyl. O-BrC6H4(CH2)3Br with BuLi underwent intramol. coupling to indan. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Reference of 5388-42-1).

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Reference of 5388-42-1

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

Ir-Catalyzed Reversible Acceptorless Dehydrogenation/Hydrogenation of N-Substituted and Unsubstituted Heterocycles Enabled by a Polymer-Cross-Linking Bisphosphine was written by Zhang, Deliang;Iwai, Tomohiro;Sawamura, Masaya. And the article was included in Organic Letters in 2020.Formula: C8H6N2O2 This article mentions the following:

In the presence of a catalyst generated from [Ir(cod)Cl]₂ and the crosslinked polystyrene-bound diphosphine PS-DPPBz, indolines and selected partially saturated five- and six-membered nitrogen heterocycles underwent reversible acceptorless dehydrogenation to give aromatic nitrogen heterocycles. The method was used for the dehydrogenation of N-substituted indolines with various nitrogen substituents and substituents with various electronic and steric effects. Under 40 atm. of H₂, indoles and a quinoline, isoquinoline, and quinoxaline underwent hydrogenation in the presence of the resin-bound iridium catalyst to yield partially saturated nitrogen heterocycles. A reaction pathway involving oxidative addition of an N-adjacent C(sp³)-H bond to a bisphosphine-coordinated Ir(I) center is proposed for the dehydrogenation of N-substituted substrates. 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 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.Formula: C8H6N2O2

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

Concise synthesis of carbazole-1,4-quinones and evaluation of their antiproliferative activity against HCT-116 and HL-60 cells was written by Nishiyama, Takashi;Hatae, Noriyuki;Yoshimura, Teruki;Takaki, Sawa;Abe, Takumi;Ishikura, Minoru;Hibino, Satoshi;Choshi, Tominari. And the article was included in European Journal of Medicinal Chemistry in 2016.Quality Control of Methyl 5-fluoro-1H-indole-2-carboxylate This article mentions the following:

A convenient synthesis of carbazole-1,4-quinone alkaloid koeniginequinones A and B using a tandem ring-closing metathesis with the dehydrogenation reaction sequence under an O₂ atmosphere as an important step is reported. Using this method, carbazole-1,4-quinones substituted at the 5-, 6-, 7-, and/or 8-positions I (R¹ = R² = H, CH₃; R³ = H, 6-OCH₃, 5,6-(OCH₃)₂, 7-CH₃, 6-NO₂, etc.; R⁴ = H, MOM) have been synthesized. Moreover, 24 compounds, including koeniginequinones A and B, have been evaluated for their antiproliferative activity against HCT-116 and HL-60 cells, and the 6-nitro analog exhibited the most potent activity against both tumor cell types. 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).

Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. 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.Quality Control of 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

Oxidative cleavage reaction of substituted indoles catalyzed by plant cell cultures was written by Takemoto, Masumi;Iwakiri, Yasutaka;Tanaka, Kiyoshi. And the article was included in Heterocycles in 2007.Application of 4583-55-5 This article mentions the following:

We have developed a novel method for the oxidative cleavage of indole carbon double bonds in the presence of H₂O₂ using plant cell cultures as peroxidase. The oxidative method has some advantage, as features such as mild reactions, good yields, easy work-up, and safety. In the experiment, the researchers used many compounds, for example, 5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5Application of 4583-55-5).

5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5) 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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Application of 4583-55-5

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