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Nishiyama, Takashi et al. published their research in European Journal of Medicinal Chemistry in 2016 | CAS: 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. 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

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).

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

Zhang, Deliang et al. published their research in Organic Letters in 2020 | 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Formula: C8H6N2O2

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).

Yang, Xiaoqun et al. published their research in Organic Letters in 2022 | CAS: 774-47-0

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

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).

Che, Tong et al. published their research in Journal of Medicinal Chemistry in 2018 | 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. 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

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).

Zhuang, Weihui et al. published their research in Organic Chemistry Frontiers in 2021 | CAS: 167631-84-7

Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7) 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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Recommanded Product: Methyl 5-fluoro-1H-indole-2-carboxylate

Visible-light induced divergent dearomatization of indole derivatives: controlled access to cyclobutane-fused polycycles and 2-substituted indolines was written by Zhuang, Weihui;Cheng, Yuan-Zheng;Huang, Xu-Lun;Huang, Qiufeng;Zhang, Xiao. And the article was included in Organic Chemistry Frontiers in 2021.Recommanded Product: Methyl 5-fluoro-1H-indole-2-carboxylate This article mentions the following:

A photocatalytic protocol for the divergent dearomative functionalization of indole derivatives was reported. Under the irradiation of visible light, either dimerization or reduction occurred selectively by modifying the reaction conditions, leading to the formation of the corresponding cyclobutane-fused polycycles and 2-substituted indolines in good yields with exclusive selectivity. In the experiment, the researchers used many compounds, for example, Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7Recommanded Product: Methyl 5-fluoro-1H-indole-2-carboxylate).

Zheng, Tianyu et al. published their research in Chemical Communications (Cambridge, United Kingdom) in 2018 | 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 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). Recommanded Product: 6-Nitro-1H-indole

Diverse ring opening of thietanes and other cyclic sulfides: an electrophilic aryne activation approach was written by Zheng, Tianyu;Tan, Jiajing;Fan, Rong;Su, Shuaisong;Liu, Binbin;Tan, Chen;Xu, Kun. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2018.Recommanded Product: 6-Nitro-1H-indole This article mentions the following:

An electrophilic aryne-activated ring opening protocol of one or two heteroatom containing saturated sulfur heterocycles was reported. This three-component transformation proceeded under mild reaction conditions and displayed exceptional generality of nucleophiles (C, O, S, N and F centered nucleophiles), giving structurally diverse thioethers in good yields. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Recommanded Product: 6-Nitro-1H-indole).

Ye, Zhao et al. published their research in Journal of Photochemistry and Photobiology, A: Chemistry in 2021 | 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.Product Details of 4769-96-4

Electron transfer from guanosine to the lowest triplet excited state of 4-nitroindole through hydrogen-bonded complex was written by Ye, Zhao;Du, Yong;Pan, Xinghang;Zheng, Xuming;Xue, Jiadan. And the article was included in Journal of Photochemistry and Photobiology, A: Chemistry in 2021.Product Details of 4769-96-4 This article mentions the following:

The photochem. reaction of 4-nitroindole and guanosine was studied with the transient absorption spectroscopy as guanine is an effective hole trap during the charge transfer in DNA, and 4-nitroindole is a universal base. Excitation of 4-nitroindole generates the lowest triplet excited state 4-nitroindole (³HN-NO₂) within 10 ns in the quantum yield 0.41. ³HN-NO₂ has increased basicity compared to its ground state. Consequently, its nitro group exhibits the hydrogen bond accepting ability. ³HN-NO₂ can interact with guanosine (G) to form the hydrogen-bonded ³HN-NO₂…G complex with the rate constant k = (8.7 卤 0.3)x10⁹ M^-1路s^-1. The hydrogen-bonded complex is identified based on the blue shift evolvement of the absorption maximum of ³HN-NO₂ in alc. solutions The reduction potential of ³HN-NO₂ is Ered(³HN-NO₂) = 1.23 V vs. SCE. The electron transfer occurs in the ³HN-NO₂…G complex and generates G+bul and HN-NO₂-鈥?followed by the proton transfer from N₁ and N₂ of G producing radicals HN-NO₂H鈥? G(N₁-H)鈥?and G(N₂-H)鈥? In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Product Details of 4769-96-4).

Qiao, Yu et al. published their research in Advanced Synthesis & Catalysis in 2018 | 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Computed Properties of C8H6N2O2

Copper-Catalyzed Successive C-C bond formations on Indoles or Pyrrole: A Convergent Synthesis of Symmetric and Unsymmetric Hydroxyl Substituted N-H Carbazoles was written by Qiao, Yu;Wu, Xin-Xing;Zhao, Yupeng;Sun, Yongqing;Li, Baoguo;Chen, Shufeng. And the article was included in Advanced Synthesis & Catalysis in 2018.Computed Properties of C8H6N2O2 This article mentions the following:

A copper-catalyzed successive C-C bond formations on indoles and pyrrole approach for the direct synthesis of hydroxyl substituted N-H carbazoles is described. The current process represents an atom-economical method for the preparation of both sym. and unsym. densely substituted and hydroxyl containing N-H carbazoles from easily accessible starting materials without the need for expensive metals and harsh reaction conditions. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Computed Properties of C8H6N2O2).

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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Computed Properties of C8H6N2O2

Lu, Lin et al. published their research in Tetrahedron in 2015 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) 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

Iodine-catalyzed C3-formylation of indoles via C-N bond cleavage of tertiary amines under aerobic conditions was written by Lu, Lin;Xiong, Qiheng;Guo, Shengmei;He, Tianqiang;Xu, Feng;Gong, Jiuhan;Zhu, Zheng;Cai, Hu. And the article was included in Tetrahedron in 2015.Category: indole-building-block This article mentions the following:

A novel route was developed for the C3-formation of indoles using iodine as the catalyst. This transformation involves the cleavage of the C-N bond of tertiary amines by the Cross-Dehydrogenative Coupling reaction (CDC), and is well tolerated by a range of 1H-indoles under aerobic conditions. Moreover, this method can be applied to gram-scale synthesis. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Category: indole-building-block).

Wang, Qinghui et al. published their research in European Journal of Medicinal Chemistry in 2018 | 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. 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.Safety of 6-Nitro-1H-indole

Synthesis and biological evaluation of indole-based UC-112 analogs as potent and selective survivin inhibitors was written by Wang, Qinghui;Arnst, Kinsie E.;Xue, Yi;Lei, Zi-Ning;Ma, Dejian;Chen, Zhe-Sheng;Miller, Duane D.;Li, Wei. And the article was included in European Journal of Medicinal Chemistry in 2018.Safety of 6-Nitro-1H-indole This article mentions the following:

The extensive structural modification of the recently discovered selective survivin inhibitor UC-112 and the synthesis of thirty-three new analogs I [R = (5-fluoro-1H-indazol-1-yl)methyl, 7-fluoro-indol-1-ylmethyl, 2-methyl-5-methoxy-indol-1-ylmethyl, etc.] have been reported. The structure-activity relationship (SAR) study indicated that replacement of the benzyloxy moiety in UC-112 with an indole moiety was preferred to other moieties. Among these UC-112 analogs, I (R = 5-fluoro-indol-1-ylmethyl, 5-nitro-indol-1-ylmethyl, 6-chloro-indol-1-ylmethyl, 6-methoxy-indol-1-ylmethyl) showed the most potent antiproliferative activities. Interestingly, they were more potent against the P-glycoprotein overexpressing cancer cell lines compared with the parental cancer cell lines. Mechanistic studies confirmed that new analogs maintained their unique selectivity against survivin among the IAP family members. In vivo study using I (R = 5-fluoro-indol-1-ylmethyl) in a human A375 melanoma xenograft model revealed that it effectively inhibited melanoma tumor growth without observable acute toxicity. Collectively, this study strongly supports the further preclin. development of selective survivin inhibitors based on the UC-112 scaffold. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Safety of 6-Nitro-1H-indole).