4769-96-4 | - Page 2 of 4 - Indole Building Blocks

Mino, Takashi et al. published their research in Organic & Biomolecular Chemistry in 2021 | 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Electric Literature of C8H6N2O2

Cinnamoyl amide type chiral P,olefin ligands for Pd-catalyzed reactions was written by Mino, Takashi;Fujisawa, Yohei;Yoshida, Shizuki;Hirama, Mitsuru;Akiyama, Takumu;Saito, Ryo;Yoshida, Yasushi;Kasashima, Yoshio;Sakamoto, Masami. And the article was included in Organic & Biomolecular Chemistry in 2021.Electric Literature of C8H6N2O2 This article mentions the following:

Cinnamoyl amide type chiral P,olefin ligands are synthesized. Authors successfully obtained separable diastereomers of I with axial chirality and demonstrated Pd-catalyzed asym. allylic substitution reactions of indoles using compound I as a chiral ligand with high enantioselectivities (up to 98% ee). In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Electric Literature of 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

Hikawa, Hidemasa et al. published their research in Organic Chemistry Frontiers in 2019 | CAS: 4769-96-4

6-Nitro-1H-indole (cas: 4769-96-4) 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. 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.Related Products of 4769-96-4

Platinum(II)-catalyzed dehydrative C3-benzylation of electron-deficient indoles with benzyl alcohols was written by Hikawa, Hidemasa;Matsuura, Yuuki;Kikkawa, Shoko;Azumaya, Isao. And the article was included in Organic Chemistry Frontiers in 2019.Related Products of 4769-96-4 This article mentions the following:

A synthetic strategy for the water-promoted direct dehydrative coupling of indoles I (R = H, Me; R¹ = 6-NO₂, 7-COOH, 5-CN, etc.; R² = H, COOH, phenyl) with benzyl alcs. ArC(OH)(R³)(R⁴) (Ar = C₆H₅, 4-MeOC₆H₄, 3-F₃CC₆H₄, CH=CHC₆H₅, etc.; R³ = Ph, 4-chlorophenyl, Me, etc.; R⁴ = H, Ph) catalyzed by PtCl₂(PhCN)₂ in 1,2-dichloroethane has been developed. Water mols. significantly accelerate C-C bond formation to construct 3-benzylindoles II, whereas the reaction proceeds slowly under anhydrous conditions. Comparative rate plots for reactions in the presence of H₂O and D₂O show a kinetic solvent isotope effect (KSIE) of 1.5. A Hammett study of the dehydrative reaction of para-substituted benzhydrols shows neg. 蟻 values, indicating a build-up of cationic charge during the rate-determining sp³ C-O bond cleavage step. This catalytic system can be used on the gram scale with simplified product isolation and catalysis is performed using 1 mol% of a Pt(II) catalyst with an addnl. mol. of water. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Related Products of 4769-96-4).

Yang, Ruchun et al. published their research in Journal of Organic Chemistry in 2020 | CAS: 4769-96-4

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 was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Formula: C8H6N2O2

DMSO/t-BuONa/O₂-Mediated Aerobic Dehydrogenation of Saturated N-Heterocycles was written by Yang, Ruchun;Yue, Shusheng;Tan, Wei;Xie, Yongfa;Cai, Hu. And the article was included in Journal of Organic Chemistry in 2020.Formula: C8H6N2O2 This article mentions the following:

Aromatic N-heterocycles such as quinolines I [R¹ = H, 8-Cl, 6-OMe, etc.; R² = H, 3-Me, 4-Ph, etc. X = N; Y = CH₂], isoquinolines I [R¹ = H; R² = H, 1-Ph; X = CH₂; Y = N] and indoles II [R¹ = H, 5-F, 4-Br, etc.; R² = H, 2-Me; Y = CH₂, N] were synthesized via a sodium tert-butoxide promoted oxidative dehydrogenation of the saturated heterocycles in DMSO solution This reaction proceeded under mild reaction conditions with a good functional group tolerance. Mechanistic studies suggested a radical pathway involved hydrogen abstraction of dimsyl radicals from the N-H bond or 伪-C-H of the substrates, and subsequent oxidation of the nitrogen or 伪-aminoalkyl radicals. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Formula: C8H6N2O2).

Jiang, Bo et al. published their research in Organic Chemistry Frontiers in 2017 | CAS: 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. 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 4769-96-4

Rhodium(II)-catalyzed intermolecular [3 + 2] annulation of N-vinyl indoles with N-tosyl-1,2,3-triazoles via an aza-vinyl Rh carbene was written by Jiang, Bo;Shi, Min. And the article was included in Organic Chemistry Frontiers in 2017.Product Details of 4769-96-4 This article mentions the following:

The rhodium(II)-catalyzed annulations of N-vinyl indole derivatives and N-tosyl-1,2,3-triazoles have been developed in this paper, providing a convenient, efficient and straightforward access to synthesize indoles containing a N-dihydropyrrole in moderate to good yields. Furthermore, the reaction of N-vinyl indoles with 2.5 equivalent of N-tosyl-1,2,3-triazoles gave C3-functionalized indoles containing a N-dihydropyrrole in moderate yields after reduction with NaBH₃CN in a one-pot manner. This finding gives a new synthetic protocol for the preparation of indoles containing a N-dihydropyrrole under mild conditions. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Product Details of 4769-96-4).

Mino, Takashi et al. published their research in Organic & Biomolecular Chemistry in 2016 | CAS: 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.Application of 4769-96-4

Chiral N-1-adamantyl-N-trans-cinnamylaniline type ligands: synthesis and application to palladium-catalyzed asymmetric allylic alkylation of indoles was written by Mino, Takashi;Nishikawa, Kenji;Asano, Moeko;Shima, Yamato;Ebisawa, Toshibumi;Yoshida, Yasushi;Sakamoto, Masami. And the article was included in Organic & Biomolecular Chemistry in 2016.Application of 4769-96-4 This article mentions the following:

Such chiral phosphine-internal olefin hybrid type ligands as N-1-adamantyl-N-cinnamylaniline derivatives 1 with C(aryl)-N(amine) bond axial chirality were synthesized and utilized for the palladium-catalyzed asym. allylic alkylation of indoles to afford the desired products in high enantioselectivities (up to 98% ee). In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Application of 4769-96-4).

Han, Xin 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. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Application of 4769-96-4

Synthesis and SARs of indole-based 伪-amino acids as potent HIV-1 non-nucleoside reverse transcriptase inhibitors was written by Han, Xin;Wu, Haoming;Wang, Wei;Dong, Chune;Tien, Po;Wu, Shuwen;Zhou, Hai-Bing. And the article was included in Organic & Biomolecular Chemistry in 2014.Application of 4769-96-4 This article mentions the following:

A series of non-nucleoside reverse transcriptase inhibitors derived from indole-based 伪-amino acids were designed and synthesized. Their inhibitory activities were detected by a TZM-bl cell assay on HIV virus type HIV-1_IIIB. The comprehensive understanding of the SAR was obtained by utilizing the variation of the substituents of the indole-based 伪-amino acids. From the screened compounds, the novel inhibitors (I) (R¹ = 5-Cl and 6-Br) were identified to be highly potent candidates with EC₅₀ values of 0.060 渭M and 0.045 渭M resp. (CC₅₀ values of 109.545 渭M and 49.295 渭M and SI values of 1825.8 and 1095.4). In most cases, the variation of substituents at different positions had a significant effect on the potency of activities. The results also indicate that the indole-based 伪-amino acids as efficient NNRTIs displayed comparable anti-HIV-1 activities to the reference drug NVP. We hope the identification of these indole-based amino acids as efficient NNRTIs of RT could stimulate researchers to develop more diversified anti-HIV drugs. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Application of 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Application of 4769-96-4

Prasad, Bagineni et al. published their research in Chemistry – A European Journal in 2018 | CAS: 4769-96-4

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

Flexible Versus Rigid G-Quadruplex DNA Ligands: Synthesis of Two Series of Bis-indole Derivatives and Comparison of Their Interactions with G-Quadruplex DNA was written by Prasad, Bagineni;Jamroskovic, Jan;Bhowmik, Sudipta;Kumar, Rajendra;Romell, Tajanena;Sabouri, Nasim;Chorell, Erik. And the article was included in Chemistry – A European Journal in 2018.Computed Properties of C8H6N2O2 This article mentions the following:

This work centered around how different design features of small mols. were affected the interactions with G4 DNA structures, exemplified by the development of synthetic methods to bis-indole scaffolds. The synthesized series of bis-indole scaffolds were structurally very similar but differ greatly in the flexibility of their core structures. The flexibility of the mols. proved to be an advantage compared to locking the compounds in the presumed bioactive G4 conformation. The flexible derivatives demonstrated similar or even improved G4 binding and stabilization in several orthogonal assays even though their entropic penalty of binding was higher. In addition, mol. dynamics simulations with the c-MYC G4 structure showed that the flexible compounds adapted better to the surrounding. This was reflected by an increased number of both stacking and polar interactions with both the residues in the G4 DNA structure and the DNA residues just upstream of the G4 structure. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Computed Properties of C8H6N2O2).

Fresia, Marvin et al. published their research in European Journal of Organic Chemistry in 2022 | CAS: 4769-96-4

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

Synthesis of Pyranocyclopentaindolines Representing the Western Sections of Janthitrem B, JBIR-137, and Shearinine G was written by Fresia, Marvin;Lindel, Thomas. And the article was included in European Journal of Organic Chemistry in 2022.Name: 6-Nitro-1H-indole This article mentions the following:

The synthesis of the ABCD tetracyclic partial structures of the fungal indole diterpenes janthitrem B, JBIR-137, and shearinine G is reported. The route starts from 5-formylated indoline that is coupled to a dihydropyran moiety, followed by Prins cyclization. A diene was obtained that was oxygenated in a divergent manner. The hydroxylated tetracyclic western half of janthitrem B was obtained in eight steps and 10% overall yield. We also share our experience with alternative approaches passing via alkynylated precursors. This includes the gold-catalyzed cycloisomerization of a 6-ethynyl-5-prenylindoline. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Name: 6-Nitro-1H-indole).

Wu, Zhiqiang et al. published their research in Green Chemistry in 2019 | CAS: 4769-96-4

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

Synthesis of bis(indolyl)methanes under dry grinding conditions, promoted by a Lewis acid-surfactant-SiO₂-combined nanocatalyst was written by Wu, Zhiqiang;Wang, Gang;Yuan, Shuo;Wu, Dan;Liu, Wanyi;Ma, Baojun;Bi, Shuxian;Zhan, Haijuan;Chen, Xiaoyan. And the article was included in Green Chemistry in 2019.Recommanded Product: 4769-96-4 This article mentions the following:

An in situ developed Lewis acid-surfactant-SiO₂-combined (LASSC) nanocatalyst was used, for the first time, as a green and effective promoting medium for the electrophilic activation of aldehydes RCHO (R = 4-nitrophenyl, 2,4-dichlorophenyl, 3,4-dihydroxyphenyl, etc.) under solvent-free and dry grinding conditions. The advantages of using the LASSC nanocatalyst include avoiding the generation of wastewater containing sodium dodecyl sulfate and the use of toxic reagents, excellent reusability of the catalyst, and obtaining a high yield of bis(indolyl)methanes I (R¹ = 6-NO₂, 2-Me, 3-Me, etc.). In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Recommanded Product: 4769-96-4).

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

Chen, Lingfeng et al. published their research in European Journal of Medicinal Chemistry in 2017 | 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 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

Structure-based design and synthesis of 2,4-diaminopyrimidines as EGFR L858R/T790M selective inhibitors for NSCLC was written by Chen, Lingfeng;Fu, Weitao;Feng, Chen;Qu, Rong;Tong, Linjiang;Zheng, Lulu;Fang, Bo;Qiu, Yinda;Hu, Jie;Cai, Yuepiao;Feng, Jianpeng;Xie, Hua;Ding, Jian;Liu, Zhiguo;Liang, Guang. And the article was included in European Journal of Medicinal Chemistry in 2017.Category: indole-building-block This article mentions the following:

Mutated epidermal growth factor receptor (EGFR) is a major driver of non-small cell lung cancer (NSCLC). The EGFRT790M secondary mutation has become a leading cause of clin.-acquired resistance to gefitinib and erlotinib. Herein, structure-based design approach to increase the potency and selectivity of the previously reported reversible EGFR inhibitor I, at the kinase and cellular levels has been reported. Three-step structure-activity relationship exploration led to promising compounds II (R¹ = Br; R² = 1-methyl-1H-indol-6-yl, 2,3-dihydro-1H-inden-5-yl; R³ = OMe; R⁴ = 4-methyl-1-piperazinyl) with unique chem. structure and binding mode from the other third-generation tyrosine kinase inhibitors. In a human NSCLC xenograft model, the above compounds exhibited dose-dependent tumor growth suppression without toxicity. These selective inhibitors are promising drug candidates for EGFRT790M-driven NSCLC. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Category: indole-building-block).