20/02/2023 - Page 3 of 14 - Indole Building Blocks

Shi, Jingjing et al. published their research in Organic & Biomolecular Chemistry in 2014 | CAS: 4769-96-4

6-Nitro-1H-indole (cas: 4769-96-4) 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. 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 C8H6N2O2

Rhodium(III)-catalyzed regioselective C2-amidation of indoles with N-(2,4,6-trichlorobenzoyloxy)amides and its synthetic application to the development of a novel potential PPAR缂?modulator was written by Shi, Jingjing;Zhao, Guanguan;Wang, Xiaowei;Xu, H. Eric;Yi, Wei. And the article was included in Organic & Biomolecular Chemistry in 2014.Synthetic Route of C8H6N2O2 This article mentions the following:

A new and efficient method for the direct regioselective C2-amidation of various functionalized indoles with several N-(2,4,6-trichlorobenzoyloxy)amides via Rh(III)-catalyzed C-H activation/N-O cleavage/C-N formation using the pyrimidyl group as a readily installable and removable directing group has been developed. With this method, a variety of valuable 2-amido indoles can be easily prepared under mild conditions with broad functional group tolerance and excellent region-/site-specificities. The results from biol. evaluation showed that compound I had a partial PPAR缂?agonistic activity and a strong PPAR缂?binding affinity with an IC₅₀ value of 120.0 nM, along with a less pronounced adipocyte differentiation ability compared to the currently marketed anti-diabetic drug rosiglitazone, suggesting that further development of such a compound might be of great interest. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Synthetic Route of C8H6N2O2).

Referemce:
Indole alkaloid derivatives as building blocks of natural products from闂佽壈浜崹淇沜illus thuringiensis闂佽壈浜粋鍧闂佽壈浜崹淇沜illus velezensis闂佽壈浜粋鍧 their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Thapa, Pawan et al. published their research in Journal of Organic Chemistry in 2019 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Related Products of 5388-42-1

Isoindolinone Synthesis: Selective Dioxane-Mediated Aerobic Oxidation of Isoindolines was written by Thapa, Pawan;Corral, Esai;Sardar, Sinjinee;Pierce, Brad S.;Foss, Frank W.. And the article was included in Journal of Organic Chemistry in 2019.Related Products of 5388-42-1 This article mentions the following:

N-Alkyl and N-aryl-isoindolinones were prepared by a dioxane-mediated oxidation of isoindoline precursors. The transformation exhibits unique chemoselectivity for isoindonlines. A chiral tertiary (3闂?-benzylic position was not racemized during oxidation, and Me indoprofen was prepared by late stage oxidation Mechanistic studies suggest a selective H atom transfer, which avoids many known oxidation (by-)products of isoindolinones. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Related Products of 5388-42-1).

Chen, Meng-Nan et al. published their research in Tetrahedron 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Related Products of 774-47-0

Eosin Y-catalyzed one-pot synthesis of spiro[4H-pyran-oxindole] under visible light irradiation was written by Chen, Meng-Nan;Di, Jia-Qi;Li, Jiao-Mian;Mo, Li-Ping;Zhang, Zhan-Hui. And the article was included in Tetrahedron in 2020.Related Products of 774-47-0 This article mentions the following:

An efficient and simple synthetic approach was developed for the preparation of biol. interesting spiro[oxindole-3,4′-(4’H-pyran)] derivatives via visible light-mediated one-pot, three-component reaction of isatins, 1,3-dicarbonyl compounds and malononitrile by using an inexpensive organic dye, Na₂ eosin Y, as the photocatalyst in aqueous Et lactate at ambient temperature The substrate scope of this three-component reaction was expanded to linear 1,3-dicarbonyl compounds as viable starting materials. In the experiment, the researchers used many compounds, for example, 5,6-Difluoroindoline-2,3-dione (cas: 774-47-0Related Products of 774-47-0).

Thiele, J. et al. published their research in Justus Liebigs Annalen der Chemie in 1910 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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.Related Products of 5388-42-1

Condensation Products of o-Phthalaldehyde. II was written by Thiele, J.;Schneider, J.. And the article was included in Justus Liebigs Annalen der Chemie in 1910.Related Products of 5388-42-1 This article mentions the following:

Hydrindone oxalic acid (I) is prepared by adding 8 g. pyroracemic acid to a suspension of 12 g. phthalaldehyde in 750 cc. H₂O and treating gradually at 5闂?with 85 cc. 10% NaOH. Pale yellow needles, m. 211-2闂? Methyl ester, C₁₂H₁₀O₄, long, colorless needles, m. 99.5闂? The acid is resolved by NaOH+ Br into dibromohydrindone and (CO₂H)₂; by NaOH into hydrindone and (CO₂H)₂. A lactone-like acetate is obtained by the action of Ac₂O + H₂SO₄. C₁₅H₁₂O₆; color-less crystals, m. 149-50闂?(decompose). o-Phenylene-闁?闁?naphthyleneketone (II) is obtained by treating 2 g. 婵?hydrindone and 2 g. o-phthalaldehyde in absolute alc. with 5 drops MeOH +KOH. Bright yellow needles, m. 152闂? Hydrazone, C₂₃H₁₆N₂, yellow crystals, m. 174闂? Benzocycloheptadi濠殿噯绲鹃幑鏄絥edicarboxylic acid (III), crystals, m. 210闂? Diethyl ester, colorless leaves, m. 95.5闂? Monoethyl ester, white needles, m. 185闂? Phenylhydrazine addition product, C₂₃H₂₄O₅N₂, colorless needles, m. 138闂? Benzo-cycloheptadienonecarboxylic acid (IV), long needles, m. 172闂? Phenylphthalimidine (V), colorless leaves, m. 161闂? Phenylphthalimidine anil (VI), colorless needles, m. 142-3闂? Chloroplatinate, (C₂₀H₁₆N₂)₂.H₂PtCl₆, reddish yellow crystals, m. 212-3闂?(decompose). In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Related Products of 5388-42-1).

Yang, Zhen et al. published their research in Chemistry – A European Journal in 2019 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Recommanded Product: 2-(Phenylthio)isoindoline-1,3-dione

Photochemical, metal-free sigmatropic rearrangement reactions of sulfur ylides was written by Yang, Zhen;Guo, Yujing;Koenigs, Rene M.. And the article was included in Chemistry – A European Journal in 2019.Recommanded Product: 2-(Phenylthio)isoindoline-1,3-dione This article mentions the following:

Sigmatropic rearrangement reactions constitute one of the most fundamental reactions of carbenes. While state-of-the-art synthetic methods require the use of expensive precious metal catalysts, the application of visible light for the photolysis of 婵?aryldiazoacetates is much less investigated and provides an operationally simple entry to carbenes under mild reaction conditions. Herein, we report on blue-light induced sigmatropic rearrangement reactions of sulfur compounds with 婵?aryldiazoacetates. This process, depending on the substitution pattern of the sulfide, opens up formal insertion reactions of carbenes into S-N, S-C, or C-H bonds. 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).

Zhu, Li-Li et al. published their research in Journal of Organic Chemistry in 2022 | 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). Application of 14204-27-4

N²-Selective 闁?Thioalkylation of Benzotriazoles with Alkenes was written by Zhu, Li-Li;Tian, Lifang;Sun, Kunhui;Li, Yiwen;Liu, Guanglu;Cai, Bin;Zhang, Hui;Wang, Yahui. And the article was included in Journal of Organic Chemistry in 2022.Application of 14204-27-4 This article mentions the following:

Herein, N²-selective 闁?thioalkylation of benzotriazoles with unactivated alkenes and styrenes is reported. The N²-selective 闁?thioalkylation of benzotriazoles is highly stereospecific and works under simple and mild conditions, exhibiting excellent functional group tolerance. The high N²-selectivity is a consequence of the combination of hydrogen bonding and Lewis acid/base activation, which reverses the N²-position to be favored for alkylation. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Application of 14204-27-4).

Zhang, Lin-Lin et al. published their research in Organic Letters in 2018 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) 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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Category: indole-building-block

Remote Control of Axial Chirality: Synthesis of Spirooxindole-Urazoles via Desymmetrization of ATAD was written by Zhang, Lin-Lin;Zhang, Ji-Wei;Xiang, Shao-Hua;Guo, Zhen;Tan, Bin. And the article was included in Organic Letters in 2018.Category: indole-building-block This article mentions the following:

In the presence of a nonracemic bisthiourea, 3-vinylindoles and N-Boc alkylideneoxindoles underwent diastereoselective and enantioselective tandem Diels-Alder and ene reactions and desymmetrization with triazolinediones in hexane to yield spirooxindolecarbazolylurazoles such as I containing axial chirality in 49-84% yields, 3:1-10:1 dr at the atropisomeric axes, and in 93->99% ee. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Category: indole-building-block).

Ichimaru, Yoshimi et al. published their research in Bioorganic & Medicinal Chemistry in 2017 | CAS: 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.HPLC of Formula: 320734-35-8

5-Bromoindirubin 3′-(O-oxiran-2-ylmethyl)oxime: A long-acting anticancer agent and a suicide inhibitor for epoxide hydrolase was written by Ichimaru, Yoshimi;Fujii, Takeshi;Saito, Hiroaki;Sano, Makoto;Uchiyama, Taketo;Miyairi, Shinichi. And the article was included in Bioorganic & Medicinal Chemistry in 2017.HPLC of Formula: 320734-35-8 This article mentions the following:

Indirubin 3′-oxime (Indox I) suppresses cancer cell growth (IC₅₀: 15 濠电偞鎸鹃幏?towards HepG2 cells) and inhibits cell cycle-related kinases such as cyclin-dependent kinases and glycogen synthase kinase-3闁? The authors have previously reported that the conjugation of I with oxirane, a protein-reactive component, enhanced the cytotoxic activity of Indox as determined from the IC₅₀ value (1.7 濠电偞鎸鹃幏? of indirubin 3′-(O-oxiran-2-ylmethyl)oxime (Epox/Ind II). Here the authors prepared Epox/Ind derivatives with one or two halogen atoms or a methoxy group on the aromatic ring(s) of an Indox moiety and studied the structure-activity relationships of the substituent(s). It was found that bromine-substitution at the 5-position on II or any Epox/Ind derivative(s) having bromine on the aromatic ring except Epox/6′-Br-Ind was efficient to improving anticancer activity. Of the 22 Epox/Ind derivatives, 5-bromoindirubin 3′-(O-oxiran-2-ylmethyl)oxime (Epox/5-Br-Ind III) was the best anticancer agent in both short- (24 h) (IC₅₀: 0.67 濠电偞鎸鹃幏? and extended-duration (72 h) cultures. The high anticancer activity of III was partly due to it being a poor substrate and a suicide inhibitor for epoxide hydrolase as epoxide hydrolase was identified as the enzyme primarily responsible for the metabolism of III. In the experiment, the researchers used many compounds, for example, 7-Bromooxindole (cas: 320734-35-8HPLC of Formula: 320734-35-8).

Zhao, Shuai et al. published their research in Journal of Organic Chemistry in 2021 | CAS: 112656-95-8

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

Visible-Light-Mediated Cyclopropanation Reactions of 3-Diazooxindoles with Arenes was written by Zhao, Shuai;Chen, Xiang-Xiang;Gao, Nan;Qian, Mingcheng;Chen, Xin. And the article was included in Journal of Organic Chemistry in 2021.Reference of 112656-95-8 This article mentions the following:

The cyclopropanation reaction of 3-diazooxindoles with arenes was first accomplished using visible-light irradiation A series of spiro[norcaradiene-7,3′-indolin]-2′-ones, e.g., I, were synthesized for the first time in high yields and with excellent diastereoselectivities. The synthetic usefulness of this catalyst-free photochem. methodol. is illustrated by the further controllable rearrangement and epoxidation reactions. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Reference of 112656-95-8).

Kim, Seung Wook et al. published their research in Angewandte Chemie, International Edition in 2019 | CAS: 754214-56-7

7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7) 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

Regio- and Enantioselective Iridium-Catalyzed N-Allylation of Indoles and Related Azoles with Racemic Branched Alkyl-Substituted Allylic Acetates was written by Kim, Seung Wook;Schempp, Tabitha T.;Zbieg, Jason R.;Stivala, Craig E.;Krische, Michael J.. And the article was included in Angewandte Chemie, International Edition in 2019.Category: indole-building-block This article mentions the following:

Cyclometallated 闂?allyliridium C,O-benzoates modified with (S)-tol-BINAP, which are stable to air, water, and SiO₂, catalyze highly enantioselective N-allylations of indoles and related azoles. This reaction complements previously reported metal-catalyzed indole allylations in that complete levels of N vs. C3 and branched vs. linear regioselectivity are observed In the experiment, the researchers used many compounds, for example, 7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7Category: indole-building-block).