February 2023 - Page 110 of 117 - Indole Building Blocks

Geng, Kaijun et al. published their research in Organic Chemistry Frontiers in 2016 | 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Recommanded Product: 2-Phenylisoindolin-1-one

Rhodium-catalyzed oxidative coupling of N-acyl anilines with alkynes using an acylamino moiety as the traceless directing group was written by Geng, Kaijun;Fan, Zhoulong;Zhang, Ao. And the article was included in Organic Chemistry Frontiers in 2016.Recommanded Product: 2-Phenylisoindolin-1-one This article mentions the following:

A rhodium-catalyzed oxidative annulation of N-acyl anilines with alkynes was developed by using the acylamino group as a traceless directing group for the first time. Various N-acyl anilines and para- or meta-substituted diphenylacetylenes were well tolerated, and a series of 1,2,3,4-tetrasubstituted naphthalenes were readily synthesized in good to excellent yields. Meanwhile, this method also provided a new strategy for the N-dearylation of N-phenylamides. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Recommanded Product: 2-Phenylisoindolin-1-one).

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

Jiang, Zhi et al. published their research in Organic & Biomolecular Chemistry in 2022 | CAS: 16732-64-2

4-Bromo-1H-indole-2-carboxylic acid (cas: 16732-64-2) 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.Computed Properties of C9H6BrNO2

Palladium oxidative addition complex-enabled synthesis of amino-substituted indolyl-4(3H)-quinazolinones and their antitumor activity evaluation was written by Jiang, Zhi;Zhao, Dan-Dan;Hu, Yu-Tao;Rao, Yong;Guo, Shi-Yao;Xu, Yao-Hao;Li, Qingjiang;Huang, Zhi-Shu. And the article was included in Organic & Biomolecular Chemistry in 2022.Computed Properties of C9H6BrNO2 This article mentions the following:

A palladium-mediated amination of halogen-containing indolyl-4(3H)-quinazolinones such as I (R = Br) with a variety of primary and secondary amines, e.g., morpholine via the corresponding palladium oxidative addition complexes was reported. The protocol allows the facile synthesis of indolyl-4(3H)-quinazolinone derivatives with amino groups at all the positions of the benzene ring such as I (R = 4-morpholinyl) in moderate to good yields with mild reaction conditions and good functional group tolerance. Furthermore, the antitumor activity of these products was evaluated. In the experiment, the researchers used many compounds, for example, 4-Bromo-1H-indole-2-carboxylic acid (cas: 16732-64-2Computed Properties of C9H6BrNO2).

Saint-Louis, Carl Jacky et al. published their research in Organic & Biomolecular Chemistry in 2017 | CAS: 110568-64-4

6-Nitroisoindolin-1-one (cas: 110568-64-4) 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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.COA of Formula: C8H6N2O3

Synthesis, computational, and spectroscopic analysis of tunable highly fluorescent BN-1,2-azaborine derivatives containing the N-BOH moiety was written by Saint-Louis, Carl Jacky;Shavnore, Renee N.;McClinton, Caleb D. C.;Wilson, Julie A.;Magill, Lacey L.;Brown, Breanna M.;Lamb, Robert W.;Webster, Charles Edwin;Schrock, Alan K.;Huggins, Michael T.. And the article was included in Organic & Biomolecular Chemistry in 2017.COA of Formula: C8H6N2O3 This article mentions the following:

Nine new polycyclic aromatic BN-1,2-azaborine analogs containing the N-BOH moiety were synthesized using a convenient two-step, one-pot procedure. Characterization of the prepared compounds show the luminescence wavelength and the quantum yields of the azaborines were tunable by controlling the power and location of the donor and acceptor substituents on the chromophore. UV-visible spectroscopy and d. functional theory (DFT) computations revealed that the addition of electron-donating moieties to the isoindolinone hemisphere raised the energy of the HOMO, resulting in the reduction of the HOMO-LUMO gap. The addition of an electron-accepting moiety to the isoindolinone hemisphere and an electron-donating group to the boronic acid hemisphere decreased the HOMO-LUMO gap considerably, leading to emission properties from partial intramol. charge transfer (ICT) states. The combined effect of an acceptor on the isoindolinone side and a donor on the boronic acid side (strong acceptor-π-donor) gave the most red-shifted absorption. The polycyclic aromatic BN-1,2-azaborines emitted strong fluorescence in solution and in the solid-state with the largest red-shifted emission at 640 nm and a Stokes shift of Δλ = 218 nm, or Δν = 8070 cm^-1. In the experiment, the researchers used many compounds, for example, 6-Nitroisoindolin-1-one (cas: 110568-64-4COA of Formula: C8H6N2O3).

Joule, J. A. et al. published their research in Science of Synthesis in 2001 | CAS: 16732-64-2

4-Bromo-1H-indole-2-carboxylic acid (cas: 16732-64-2) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Reference of 16732-64-2

Product class 13: indole and its derivatives was written by Joule, J. A.. And the article was included in Science of Synthesis in 2001.Reference of 16732-64-2 This article mentions the following:

A review of preparation of indoles and its derivatives Covered reactions include cyclization, ring transformation, aromatization and substituent modifications. Subclasses covered include 1H-indol-1-ols, 1,3-dihydro-2H-indol-2-ones, and 1,2-dihydro-3H-indol-3-ones. In the experiment, the researchers used many compounds, for example, 4-Bromo-1H-indole-2-carboxylic acid (cas: 16732-64-2Reference of 16732-64-2).

Zhao, Fei et al. published their research in Bioorganic & Medicinal Chemistry in 2016 | CAS: 754214-56-7

7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7) 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Related Products of 754214-56-7

Discovery and optimization of a series of imidazo[4,5-b]pyrazine derivatives as highly potent and exquisitely selective inhibitors of the mesenchymal-epithelial transition factor (c-Met) protein kinase was written by Zhao, Fei;Zhang, Jing;Zhang, Leduo;Hao, Yu;Shi, Chen;Xia, Guangxin;Yu, Jianxin;Liu, Yanjun. And the article was included in Bioorganic & Medicinal Chemistry in 2016.Related Products of 754214-56-7 This article mentions the following:

Aberrant c-Met activation has been implicated in multiple tumor oncogenic processes and drug resistance. In this study, a series of imidazo[4,5-b]pyrazine derivatives was designed and synthesized, and their inhibitory activities were evaluated in vitro. Structure-activity relationship (SAR) was investigated systematically and docking anal. was performed to elucidate the binding mode, leading to the identification of the most promising compound 1D-2 (I) which exhibited significant inhibitory effect on both enzymic (IC₅₀ = 1.45 nM) and cellular (IC₅₀ = 24.7 nM in H1993 cell line) assays, as well as exquisite selectivity and satisfactory metabolic stability in human and rat liver microsomes. In the experiment, the researchers used many compounds, for example, 7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7Related Products of 754214-56-7).

Liddle, John et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2021 | CAS: 90322-37-5

2-Oxoindoline-4-carboxylic acid (cas: 90322-37-5) 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Synthetic Route of C9H7NO3

The development of highly potent and selective small molecule correctors of Z α₁-antitrypsin misfolding was written by Liddle, John;Pearce, Andrew C.;Arico-Muendel, Christopher;Belyanskaya, Svetlana;Brewster, Andrew;Brown, Murray;Chung, Chun-wa;Denis, Alexis;Dodic, Nerina;Dossang, Anthony;Eddershaw, Peter;Klimaszewska, Diana;Haq, Imran;Holmes, Duncan S.;Jagger, Alistair;Jakhria, Toral;Jigorel, Emilie;Lind, Ken;Messer, Jeff;Neu, Margaret;Olszewski, Allison;Ronzoni, Riccardo;Rowedder, James;Rudiger, Martin;Skinner, Steve;Smith, Kathrine J.;Trottet, Lionel;Uings, Iain;Zhu, Zhengrong;Irving, James A.;Lomas, David A.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2021.Synthetic Route of C9H7NO3 This article mentions the following:

α1-Antitrypsin deficiency is characterized by the misfolding and intracellular polymerization of mutant α1-antitrypsin protein within the endoplasmic reticulum (ER) of hepatocytes. Small mols. that bind and stabilize Z α₁-antitrypsin were identified via a DNA-encoded library screen. A subsequent structure-based optimization led to a series of highly potent, selective and cellular active α1-antitrypsin correctors, e.g., I. In the experiment, the researchers used many compounds, for example, 2-Oxoindoline-4-carboxylic acid (cas: 90322-37-5Synthetic Route of C9H7NO3).

Rani, B. Shoba et al. published their research in World Journal of Pharmacy and Pharmaceutical Sciences in 2016 | CAS: 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 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). HPLC of Formula: 112656-95-8

Cytotoxic, antioxidant and anti-inflammatory activity of N-(6-benzoyl-1H-benzo [d]imidazol-2-yl)-2-(2-oxosubtituted indolin-3-ylidene) hydrazine carboxamides was written by Rani, B. Shoba;Priyanka, K. Blessi;Harikiran, L.;Sammaiah, G.. And the article was included in World Journal of Pharmacy and Pharmaceutical Sciences in 2016.HPLC of Formula: 112656-95-8 This article mentions the following:

In the present study novel series of N-(6-benzoyl-1H-benzo[d]imidazol-2-yl)-2-(2-oxosubstitutedindolin-3-ylidene) hydrazine carboxamides (III a-m) have been synthesized in good yields and characterized by IR, NMR and mass spectral analyses. The compounds were evaluated for their preliminary in vitro cytotoxic activity against HCT-116 (colon ) and HepG2 (hepatocellular) cancer cell lines by standard MTT assay, antioxidant activity by standard DPPH assay method and also were screened for in vitro anti-inflammatory activity by TMPD assay method. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8HPLC of Formula: 112656-95-8).

Zhang, Huiming et al. published their research in Youji Huaxue in 2014 | CAS: 4769-96-4

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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Product Details of 4769-96-4

Synthesis of 3-indolyl-substituted benzoboroxole via Friedel-Crafts reaction in water was written by Zhang, Huiming;Shen, Shaochun;Yang, Xiaodi;Sun, Xingwen. And the article was included in Youji Huaxue in 2014.Product Details of 4769-96-4 This article mentions the following:

A highly efficient and catalyst free approach for the synthesis of 3-indolyl-substituted benzoboroxole via Friedel-Crafts reaction in water was developed successfully using readily accessible 2-formylbenzeneboronic acid and indole as the starting material and water as solvent at room temperature An array of desired 3-indolyl-substituted benzoboroxoles was synthesized in moderate to near quant. yield. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Product Details of 4769-96-4).

Gao, Shang et al. published their research in Organic & Biomolecular Chemistry in 2016 | CAS: 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Product Details of 4583-55-5

Pd(II)-catalyzed intramolecular oxidative Heck dearomative reaction: approach to thiazole-fused pyrrolidinones with a C2-azaquarternary center was written by Gao, Shang;Yang, Chi;Huang, Yue;Zhao, Lei;Wu, Xiaoming;Yao, Hequan;Lin, Aijun. And the article was included in Organic & Biomolecular Chemistry in 2016.Product Details of 4583-55-5 This article mentions the following:

A Pd(II)-catalyzed intramol. oxidative Heck dearomative reaction for the construction of thiazole-fused pyrrolidinones with a C2-azaquarternary center and C3-exo-double bond has been achieved for the first time. The reaction exhibited good functional group tolerance and gram-scale capacity. In the experiment, the researchers used many compounds, for example, 5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5Product Details of 4583-55-5).

Mussari, Christopher P. et al. published their research in ACS Medicinal Chemistry Letters in 2020 | CAS: 90271-86-6

5-Bromo-3-cyanoindole (cas: 90271-86-6) 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.Formula: C9H5BrN2

Discovery of Potent and Orally Bioavailable Small Molecule Antagonists of Toll-like Receptors 7/8/9 (TLR7/8/9) was written by Mussari, Christopher P.;Dodd, Dharmpal S.;Sreekantha, Ratna Kumar;Pasunoori, Laxman;Wan, Honghe;Posy, Shana L.;Critton, David;Ruepp, Stefan;Subramanian, Murali;Watson, Andrew;Davies, Paul;Schieven, Gary L.;Salter-Cid, Luisa M.;Srivastava, Ratika;Tagore, Debarati Mazumder;Dudhgaonkar, Shailesh;Poss, Michael A.;Carter, Percy H.;Dyckman, Alaric J.. And the article was included in ACS Medicinal Chemistry Letters in 2020.Formula: C9H5BrN2 This article mentions the following:

The toll-like receptor (TLR) family is an evolutionarily conserved component of the innate immune system, responsible for the early detection of foreign or endogenous threat signals. In the context of autoimmunity, the unintended recognition of self-motifs as foreign promotes initiation or propagation of disease. Overactivation of TLR7 and TLR9 have been implicated as factors contributing to autoimmune disorders such as psoriasis, arthritis, and lupus. In our search for small mol. antagonists of TLR7/9, 7f(I) was identified as possessing excellent on-target potency for human TLR7/9 as well as for TLR8, with selectivity against other representative TLR family members. Good pharmacokinetic properties and a relatively balanced potency against TLR7 and TLR9 in mouse systems (systems which lack functional TLR8) made this an excellent in vivo tool compound, and efficacy from oral dosing in preclin. models of autoimmune disease was demonstrated. In the experiment, the researchers used many compounds, for example, 5-Bromo-3-cyanoindole (cas: 90271-86-6Formula: C9H5BrN2).