10/02/2023 - Page 6 of 13 - Indole Building Blocks

Duan, Shengguo et al. published their research in Advanced Synthesis & Catalysis in 2020 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) 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.Formula: C9H6ClNO

Synthesis of Pyrido[2,3-b]indole Derivatives via Rhodium-Catalyzed Cyclization of Indoles and 1-Sulfonyl-1,2,3-triazoles was written by Duan, Shengguo;An, Yuehui;Xue, Bing;Chen, Yidian;Zhang, Wan;Xu, Ze-Feng;Li, Chuan-Ying. And the article was included in Advanced Synthesis & Catalysis in 2020.Formula: C9H6ClNO This article mentions the following:

Acyloxy-substituted 伪,尾-unsaturated imines generated in-situ from triazoles acts as aza-[4C] synthons and be trapped by indoles in a stepwise [4 + 2] cycloaddition reaction, thus providing rapid access to valuable pyrido[2,3-b]indoles in high yields. Attractive features of this reaction system included operational simplicity, readily available substrates, construction of sterically demanding quaternary centers and convenient derivatization using triflate. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Formula: C9H6ClNO).

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

Engvild, Kjeld C. et al. published their research in Physiologia Plantarum in 1978 | CAS: 1912-45-4

2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4) 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Name: 2-(5-Chloro-1H-indol-3-yl)acetic acid

Substituted indoleacetic acids tested in tissue cultures was written by Engvild, Kjeld C.. And the article was included in Physiologia Plantarum in 1978.Name: 2-(5-Chloro-1H-indol-3-yl)acetic acid This article mentions the following:

Monochloro substituted indole-3-acetic acids inhibited shoot induction in tobacco tissue cultures about as much as IAA. Dichloro substituted indole-3-acetic acids inhibited shoot formation less. Other substituted indoleacetic acids except 5-fluoro- and 5-bromoindole-3-acetic acid were less active than IAA. Callus growth was quite variable and not correlated with auxin strength measured in the Avena coleoptile test. In the experiment, the researchers used many compounds, for example, 2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4Name: 2-(5-Chloro-1H-indol-3-yl)acetic acid).

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).

Song, Bo et al. published their research in Dyes and Pigments in 2009 | CAS: 146368-07-2

1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2) 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. 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 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate

The synthesis and photostability of novel squarylium indocyanine dyes was written by Song, Bo;Zhang, Qian;Ma, Wen-Hui;Peng, Xiao-Jun;Fu, Xin-Mei;Wang, Bing-Shuai. And the article was included in Dyes and Pigments in 2009.Safety of 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate This article mentions the following:

Novel, water-soluble, squarylium indocyanine dyes with various N-substituents on 3H-indolenine were synthesized. The maxima of absorption and emission wavelengths of the dyes in different solvents were in the range 628-670 nm and exhibited neg. solvatochromism with increasing solvent polarity in protic solvents. Dyes with N-benzyl rings (such as N-benzyl, N-carboxylbenzyl and N-fluorobenzyl) displayed greater photostability than dyes containing N-alkyl groups (such as N-Et and N-carboxylpentanyl) in aqueous solution The electron-withdrawing group (such as carboxyl and fluoro group) on the N-benzyl group of cyanine dyes improved photostability compared to dyes that contained an electron-donating group (such as methyl). The fading constant k of the N-carboxylbenzyl dye was considerably lower than that of the N-carboxylpentanyl dye. In the experiment, the researchers used many compounds, for example, 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2Safety of 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate).

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).

Fang, Xinxin et al. published their research in Organic Chemistry Frontiers in 2017 | CAS: 4583-55-5

5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. 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.COA of Formula: C10H10BrN

Pd(II)-Catalyzed oxidative dearomatization of indoles: substrate-controlled synthesis of indolines and indolones was written by Fang, Xinxin;Gao, Shang;Wu, Zijun;Yao, Hequan;Lin, Aijun. And the article was included in Organic Chemistry Frontiers in 2017.COA of Formula: C10H10BrN This article mentions the following:

A Pd(II)-catalyzed oxidative Wacker-type cyclization/dearomatization of 2,3-disubstituted indoles with mol. oxygen as the oxidant was developed. This strategy provided straightforward access to diverse fused indolines bearing C2-oxygenated quaternary stereocenters with good functional group tolerance and high atom economy. Meanwhile, a Pd(II)-catalyzed oxidation/dearomatization of 2-substituted indoles was presented, which enabled the facile synthesis of indolones. In the experiment, the researchers used many compounds, for example, 5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5COA of Formula: C10H10BrN).

Kost, A. N. et al. published their research in Khimiya Geterotsiklicheskikh Soedinenii in 1965 | 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. 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.Product Details of 4583-55-5

Bromination of 2,3-dimethylindole was written by Kost, A. N.;Yudin, L. G.;Budylin, V. A.;Yaryshev, N. G.. And the article was included in Khimiya Geterotsiklicheskikh Soedinenii in 1965.Product Details of 4583-55-5 This article mentions the following:

Bromination of 2,3-dimethylindole (I) in concentrated H₂SO₄ containing Ag₂SO₄ gave 75% 5-bromo-2,3-dimethyl-indole (II), m. 138掳. Bromination of 1-acetyl-2,3-dimethyl-indole followed by hydrolysis gave 70% 5-bromo-2,3-dimethyl-indole (III), b₁₀ 135-7掳, n²⁰_D 1.5923, d₂₀ 0.9982. Dehydration of III with chloranil gave 45% II. II was also prepared in 70% yield by acid treatment of 2-butanone p-bromophenylhydrazone. Bromination in acid of 2,3-dimethylindoline gave 50% 6-bromo-2,3-dimethylindoline (IV), b₄ 132-4掳. Dehydration of IV with chloranil gave 37% 6-bromo-2,3-dimethylindole (V), m. 164掳. II and V could also be distinguished by ir bands at 590 cm.^-1 in II and 1326 cm.^-1 in V. 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).

Lopez-Mendoza, Pedro et al. published their research in Synthesis in 2021 | CAS: 6639-06-1

3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1) 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.SDS of cas: 6639-06-1

伪-Xanthylmethyl Ketones from 伪-Diazo ketones was written by Lopez-Mendoza, Pedro;Miranda, Luis D.. And the article was included in Synthesis in 2021.SDS of cas: 6639-06-1 This article mentions the following:

A simple and efficient method to obtain 伪-xanthylmethyl ketones from 伪-diazo ketones is described. The reaction proceeds through a protonation/nucleophilic substitution sequence in the presence of p-toluenesulfonic acid and potassium Et xanthogenate as the nucleophile. As 伪-diazo ketones can be readily synthesized from ubiquitous carboxylic acids, a broad variety of xanthates can be obtained, including examples from naturally occurring substrates. In the experiment, the researchers used many compounds, for example, 3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1SDS of cas: 6639-06-1).

Kona, Chandrababu Naidu et al. published their research in Organic Letters in 2021 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.SDS of cas: 14204-27-4

Sulfur-Directed C₇-Selective Alkenylation of Indoles under Rhodium Catalysis was written by Kona, Chandrababu Naidu;Nishii, Yuji;Miura, Masahiro. And the article was included in Organic Letters in 2021.SDS of cas: 14204-27-4 This article mentions the following:

In this report, a Rh-catalyzed C7-selective alkenylation of indole derivatives using a new sulfur directing group N-SCy is reported. A notable feature of this system is that the directing group is readily installed to the indoles and easily removed after the catalysis under mild conditions. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4SDS of cas: 14204-27-4).