Month: January 2023

Use of pyridinium chlorochromate and reusable polyaniline salt catalyst combination for the oxidation of indoles was written by Kumar, Chebolu Naga Sesha Sai Pavan;Devi, Chebrolu Lavanya;Rao, Vaidya Jayathirtha;Palaniappan, Srinivasan. And the article was included in Synlett in 2008.Application of 112656-95-8 This article mentions the following:

A novel method was described herein for the simple, convenient and efficient oxidation of indoles to isatins using pyridinium chlorochromate with the aid of polyaniline salt catalyst at room temperature or at reflux in dichloroethane. Interestingly, oxidation of 3-alkyl indoles by this procedure gave 3-hydroxy 3-alkyl oxo-indoles. On the other hand, indol-3-alkanols gave mixtures of isatins and 3-formyl indoles. This is the first example of use of polyaniline as a catalyst in oxidation reaction. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Application of 112656-95-8).

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

Development of Novel Mitochondrial Pyruvate Carrier Inhibitors to Treat Hair Loss was written by Liu, Xiaoguang;Flores, Aimee A.;Situ, Lisa;Gu, Wen;Ding, Hui;Christofk, Heather R.;Lowry, William E.;Jung, Michael E.. And the article was included in Journal of Medicinal Chemistry in 2021.HPLC of Formula: 827-01-0 This article mentions the following:

Herein, we report the synthesis and evaluation of novel analogs of UK-5099 both in vitro and in vivo for the development of mitochondrial pyruvate carrier (MPC) inhibitors to treat hair loss. A comprehensive understanding of the structure-activity relationship was obtained by varying four positions of the hit compound, namely, the alkyl group on the N1 position, substituents on the indole core, various aromatic and heteroaromatic core structures, and various Michael acceptors. The major discovery was that the inhibitors with a 3,5-bis(trifluoromethyl)benzyl group at the N1 position were shown to have much better activity than JXL001 (UK-5099) to increase cellular lactate production Addnl., analog JXL069, possessing a 7-azaindole heterocycle, was also shown to have significant MPC inhibition activity, which further increases the chem. space for drug design. Finally, more than 10 analogs were tested on shaved mice by topical treatment and promoted obvious hair growth on mice. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0HPLC of Formula: 827-01-0).

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) 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. 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.HPLC of Formula: 827-01-0

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

Synthesis of differentially protected azatryptophan analogs via Pd₂(dba)₃/XPhos catalyzed Negishi coupling of N-Ts azaindole halides with zinc derivative from Fmoc-protected tert-butyl (R)-2-amino-3-iodopropanoate was written by Nimje, Roshan Y.;Vytla, Devaiah;Kuppusamy, Prakasam;Velayuthaperumal, Rajeswari;Jarugu, Lokesh Babu;Reddy, China Anki;Chikkananjaiah, Nanjundaswamy Kanikahalli;Rampulla, Richard A.;Cavallaro, Cullen L.;Li, Jianqing;Mathur, Arvind;Gupta, Anuradha;Roy, Amrita. And the article was included in Journal of Organic Chemistry in 2020.Application In Synthesis of 3-Bromo-4-chloro-7-azaindole This article mentions the following:

Unnatural amino acids play an important role in peptide based drug discovery. Herein, we report a class of differentially protected azatryptophan derivatives synthesized from N-tosyl-3-haloazaindoles (I) (Pg = protective groups: Ts (tosyl), Fmoc (9-fluorenylmethoxycarbonyl), and tert-Bu) and Fmoc-protected tert-Bu iodoalanine (II) (Fmoc = 9-fluorenylmethoxycarbonyl) via a Negishi coupling. Through ligand screening, Pd₂(dba)₃/XPhos was found to be a superior catalyst for the coupling of 1 with the zinc derivative of 2 to give tert-Bu (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)propanoate derivatives (III) (Pg = protective groups: Ts, Fmoc, and tert-Bu; Fmoc = 9-fluorenylmethoxycarbonyl) in 69-91% isolated yields. In addition, we have demonstrated that the protecting groups, namely, Ts, Fmoc, and tert-Bu, can be easily removed selectively. In the experiment, the researchers used many compounds, for example, 3-Bromo-4-chloro-7-azaindole (cas: 1000340-39-5Application In Synthesis of 3-Bromo-4-chloro-7-azaindole).

3-Bromo-4-chloro-7-azaindole (cas: 1000340-39-5) 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. 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 3-Bromo-4-chloro-7-azaindole

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

Optimization of 2-aminothiazole derivatives as CCR4 antagonists was written by Wang, Xuemei;Xu, Feng;Xu, Qingge;Mahmud, Hossen;Houze, Jonathan;Zhu, Liusheng;Akerman, Michelle;Tonn, George;Tang, Liang;McMaster, Brian E.;Dairaghi, Daniel J.;Schall, Thomas J.;Collins, Tassie L.;Medina, Julio C.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2006.Related Products of 85696-95-3 This article mentions the following:

A series of 2-aminothiazole antagonists of the CCR4 receptor were synthesized and their affinity for the receptor evaluated using a [¹²⁵I]TARC (CCL17) displacement assay. Optimization of these compounds for potency and pharmacokinetic properties led to potent, orally bioavailable antagonists. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-indol-4-amine (cas: 85696-95-3Related Products of 85696-95-3).

1-Methyl-1H-indol-4-amine (cas: 85696-95-3) 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 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). Related Products of 85696-95-3

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

Effect of lipophilic substituents on some biological properties of indoles was written by Whitehead, Calvert W.;Whitesitt, Celia A.. And the article was included in Journal of Medicinal Chemistry in 1974.Related Products of 6639-06-1 This article mentions the following:

Addnl. data considered in abstracting and indexing are available from a source cited in the original document. The antimicrobial structure-activity relations for 400 simple indole derivatives were correlated. Of several (diarylmethyl)indoles, prepared by carbonium ion alkylation of selected indoles, 5-bromo-3-(diphenylmethyl)indole (I) [53924-07-5] was effective at 0.78-10 μg/ml against both gram-neg. and gram-pos. bacteria. Pharmacol. properties of the (diarylmethyl)indoles are described. In the experiment, the researchers used many compounds, for example, 3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1Related Products of 6639-06-1).

3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1) 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Related Products of 6639-06-1

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

Antibacterial and cytotoxic activity of 2,2¹-(5,5′-methylene bis (1,3,4-oxadiazole-5,2-diyl) bis (sulfanediyl) bis(N’-(2-oxoindolin-3-ylidene) acetohydrazides was written by Rani, S. Shobha;Agaiah, Bairi;Sarangapani, M.. And the article was included in International Journal of Chemical Sciences in 2010.Application In Synthesis of 7-Nitroindoline-2,3-dione This article mentions the following:

2,2¹-5,5′-Methylene bis(1,3,4-oxadiazole-5,2-diyl)bis(sulfanediyl)bis(N’-(2oxoindolin-3-ylidene) acetohydrazides) (VIa-o) have been synthesized by the condensation of 2-chloro-N¹(2-oxo-1,2-dihydro-3H-indole-3-ylidene)acetohydrazides (IVa-o) with the intermediate 5,5¹-methylene diyl bis(1,3,4-oxadiazole-2-thiol) (V). All the title compounds (VIa-o) were screened for cytotoxic activity using A-549 lung cancer and HT-29 colon cancer cell lines by MTT method and antimicrobial activity against B. subtilis, S. aureus, E. coli and S. typhi. The structures of newly synthesized compounds were established on the basis of elemental anal., IR, ¹H NMR and mass spectral data. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Application In Synthesis of 7-Nitroindoline-2,3-dione).

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.Application In Synthesis of 7-Nitroindoline-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

Photoinduced regioselective arylation of N-vinyllactams and methylthiazoles by tetrachlorophthalimides was written by Shen, Yong-Miao;Grampp, Guenter;Tao, Fei-Fei;He, Ning-De;Chen, Da-Qing;Ye, Miao. And the article was included in Journal of Photochemistry and Photobiology, A: Chemistry in 2013.Electric Literature of C8HBr4NO2 This article mentions the following:

Photoinduced reactions of 4,5,6,7-tetrahalophthalimides (1a-1h) with selected N-vinyllactams (N-vinylpyrrolidinone, N-vinylcaprolactam) and methylthiazoles resp. lead to dehydrohalogenative coupling reactions between the phthalimide and these heterocycles. These mild and metal-free coupling reactions result in regioselective and stereoselective arylation of the heterocycles by the phthalimide, with the Z-isomer as the main products. Reaction mechanism for the photo-reactions is discussed. In the experiment, the researchers used many compounds, for example, 4,5,6,7-Tetrabromoisoindoline-1,3-dione (cas: 24407-32-7Electric Literature of C8HBr4NO2).

4,5,6,7-Tetrabromoisoindoline-1,3-dione (cas: 24407-32-7) 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Electric Literature of C8HBr4NO2

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

Enantioselective N-Alkylation of Nitroindoles under Phase-Transfer Catalysis was written by Trubitson, Dmitri;Martonova, Jevgenija;Erkman, Kristin;Metsala, Andrus;Saame, Jaan;Koster, Kristjan;Jarving, Ivar;Leito, Ivo;Kanger, Tonis. And the article was included in Synthesis in 2020.Name: 6-Nitro-1H-indole This article mentions the following:

An asym. phase-transfer-catalyzed N-alkylation of substituted indoles I (R = 3-NO₂, 4-NO₂, 5-NO₂, 6-NO₂; R¹ = H, CN) with various Michael acceptors (E)-R²C(O)CH=CHR³ (R² = 4-BrC₆H₄, 2-furyl, 2-naphthyl, etc.; R³ = CH₃, CH(CH₃)₂, n-hexyl, C₆H₅, C(O)C₆H₅) and cyclohex-2-en-1-one was studied. Acidities of nitroindoles I were determined in acetonitrile by UV-Vis spectrophotometric titration There was essentially no correlation between acidity and reactivity in the aza-Michael reaction. The position of the nitro group on the indole ring was essential to control the stereoselectivity of the reaction. Michael adducts II were obtained in high yields and moderate enantioselectivities in the reaction between 4-nitroindole I and various Michael acceptors in the presence of cinchona alkaloid based phase-transfer catalysts. In addition to outlining the scope and limitations of the method, the geometries of the transition states of the reaction were calculated In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Name: 6-Nitro-1H-indole).

6-Nitro-1H-indole (cas: 4769-96-4) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Name: 6-Nitro-1H-indole

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

Catalytic asymmetric [3+2] cycloaddition of isomunchnones with methyleneindolinones was written by Wang, Kaixuan;Xu, Chaoran;Hu, Xinyue;Zhou, Yuqiao;Lin, Lili;Feng, Xiaoming. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2021.Electric Literature of C8H3F2NO2 This article mentions the following:

An efficient enantioselective [3+2] cycloaddition of isomunchnones with methyleneindolinones that are generated by an in situ intramol. addition of the carbonyl group to rhodium carbenes is realized with a chiral N,N’-dioxide/Zn(II) complex as a Lewis acid. A series of chiral oxa-bridged 3-spiropiperidines are obtained in high yields with excellent dr and excellent ee values. In the experiment, the researchers used many compounds, for example, 5,6-Difluoroindoline-2,3-dione (cas: 774-47-0Electric Literature of C8H3F2NO2).

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.Electric Literature of C8H3F2NO2

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 C3-cyanation of indoles by the combination of amine and ammonium was written by Liu, Bin;Wang, Jiehui;Zhang, Bo;Sun, Yang;Wang, Lei;Chen, Jianbin;Cheng, Jiang. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2014.Related Products of 90271-86-6 This article mentions the following:

A copper-promoted C3-cyanation of both the free N-H and N-protected indoles by N,N,N’,N’-tetramethyl-ethane-1,2-diamine (TMEDA) and ammonium is achieved. The iminium ion acts as the intermediate in this transformation, which is sequentially electrophilically attacked by indole and H₂O followed by hydrolysis to form the aldehyde. Then the reaction between the aldehyde and ammonium afforded nitriles. The reaction employs O₂ as a clean oxidant with good efficiency and functional group tolerance. Thus, it represents a facile and safe procedure leading to 3-cyano indoles. In the experiment, the researchers used many compounds, for example, 5-Bromo-3-cyanoindole (cas: 90271-86-6Related Products of 90271-86-6).

5-Bromo-3-cyanoindole (cas: 90271-86-6) 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). Related Products of 90271-86-6

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