February 2023 - Page 4 of 117 - Indole Building Blocks

Saha, Goutam Kumar et al. published their research in Journal of the Bangladesh Chemical Society in 2000 | CAS: 96187-75-6

6-Chloro-5-methylindoline-2,3-dione (cas: 96187-75-6) 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.HPLC of Formula: 96187-75-6

Synthesis of thiazolo[2′,3′:3,4][1,2,4]triazino[5,6-b]indole from 4,5-disubstituted isatin was written by Saha, Goutam Kumar;Rashid, M. D. Abdur;Islam, M. D. Rabiul. And the article was included in Journal of the Bangladesh Chemical Society in 2000.HPLC of Formula: 96187-75-6 This article mentions the following:

Condensation of 4,5-disubstituted isatin (I) with thiosemicarbazide yields the corresponding thiosemicarbazone, which on cyclization with 4% KOH solution gives 1,2,4-triazino[5,6-b]indole-3-thione derivative (II). Reaction of II with 1,2-dibromoethane in DMF affords the desired compound (III). In the experiment, the researchers used many compounds, for example, 6-Chloro-5-methylindoline-2,3-dione (cas: 96187-75-6HPLC of Formula: 96187-75-6).

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

Mandal, Sumana et al. published their research in Organic Letters in 2020 | CAS: 6872-06-6

2-Methylindoline (cas: 6872-06-6) 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Computed Properties of C9H11N

Diastereoselective and Reversed Regioselective Annulations of N-Alkyl Anilines to Julolidines and Lilolidines was written by Mandal, Sumana;Saha, Subhajit;Jana, Chandan K.. And the article was included in Organic Letters in 2020.Computed Properties of C9H11N This article mentions the following:

A three-component annulation reaction of N-alkyl anilines, cyclic 1,3-dicarbonyl compounds, and aryl aldehydes to julolidines and lilolidines is reported. The 6蟺-electrocyclization enabled the annulation to proceed with reversed regioselectivity as compared with the annulation that occurs in the Povarov reaction. Both cyclic and acyclic N-alkyl anilines participated in the reaction to provide a wide range of julolidines and lilolidines as the single regio- and diastereoisomers in good to excellent yields. In the experiment, the researchers used many compounds, for example, 2-Methylindoline (cas: 6872-06-6Computed Properties of C9H11N).

Kumar, Mohit et al. published their research in Journal of Organic Chemistry in 2021 | CAS: 271-63-6

1H-Pyrrolo[2,3-b]pyridine (cas: 271-63-6) 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.HPLC of Formula: 271-63-6

Cu(II)-Catalyzed C-N, C-O, C-Cl, C-S, and C-Se Bond Formation via C(sp²)-H Activation Using 7-Azaindole as Intrinsic Directing Group was written by Kumar, Mohit. And the article was included in Journal of Organic Chemistry in 2021.HPLC of Formula: 271-63-6 This article mentions the following:

A general protocol has been developed for the construction of carbon-heteroatom (C-N, C-Cl, C-O, C-S & C-Se) bonds using the bench stable, earth-abundant, and environmentally benign copper catalyst. Only oxygen is sufficient to regenerate the copper catalyst. Control experiments suggested that the proto-demetalation step is reversible. Depending on the coupling partner the reaction follows either disproportionation or radical pathways to complete the catalytic cycle. The synthetic utility of the developed protocol has been demonstrated via various functional groups transformations. In the experiment, the researchers used many compounds, for example, 1H-Pyrrolo[2,3-b]pyridine (cas: 271-63-6HPLC of Formula: 271-63-6).

Pandit, Navin et al. published their research in Bioorganic & Medicinal Chemistry in 2022 | CAS: 61-54-1

2-(1H-Indol-3-yl)ethanamine (cas: 61-54-1) 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.Category: indole-building-block

Discovery of BET specific bromodomain inhibitors with a novel scaffold was written by Pandit, Navin;Yoo, Miyoun;Hyun Park, Tae;Kim, Jiin;Mi Kim, Seul;Myung Lee, Kyu;Kim, Yeongrin;Min Bong, Seoung;Il Lee, Byung;Jung, Kwan-Young;Hoon Park, Chi. And the article was included in Bioorganic & Medicinal Chemistry in 2022.Category: indole-building-block This article mentions the following:

Bromodomain and extra-terminal domain (BET) proteins have been considered as potent candidates for anti-cancer drug development. As epigenetic readers, they modulate gene expression by recognizing acetylated lysine residues on histones. Therefore, the pharmacol. inhibition of BET proteins has been extensively studied. Herein, we report the novel chem. scaffold of N-(pyridin-2-yl)-1H-benzo[d][1,2,3]triazol-5-amine as BET inhibitors using high-throughput screening assay. Through the anal. of structure-activity relationships, we developed a potent novel compound, which exhibited a better IC₅₀ value about 2-fold compared to iBet762 against the BRD4 bromodomain (BD). The addition of a sulfonyl group to the pyridine ring enhanced the inhibitory activity. Structural studies showed a clear electron d. map for the inhibitor and revealed the structural basis for the critical role of the sulfonyl group in the interaction with BRD4. In the experiment, the researchers used many compounds, for example, 2-(1H-Indol-3-yl)ethanamine (cas: 61-54-1Category: indole-building-block).

Uredi, Dilipkumar et al. published their research in Journal of Organic Chemistry in 2021 | CAS: 27421-51-8

1-Methyl-1H-indole-2-carbaldehyde (cas: 27421-51-8) 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Recommanded Product: 27421-51-8

Rapid Access to 3-Substituted Pyridines and Carbolines via a Domino, Copper-free, Palladium-Catalyzed Sonogashira Cross-Coupling/6蟺-Aza Cyclization Sequence was written by Uredi, Dilipkumar;Burra, Amarender Goud;Watkins, E. Blake. And the article was included in Journal of Organic Chemistry in 2021.Recommanded Product: 27421-51-8 This article mentions the following:

Herein, a one-pot, three-component method for the preparation of 3-substituted pyridines such as I [R = H, Me, Ph, tert-butoxycarbonyl; Ar = Ph, 2-MeC₆H₄, 3-quinolyl, etc.; R¹ = H, 6-Me, 8-Me, 5-MeO], II [R² = R² = H; R²R³ = HCCH=CHCH; X = S, O] and carbolines via copper-free, palladium-catalyzed Sonogashira cross-coupling with aryl iodides, followed by 6蟺-aza cyclization was reported. This arylation cross-coupling/annulation cascade provided easy access to substituted, fused pyridines I, II from readily available substrates in good yields (67-92%) with complete selectivity. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-indole-2-carbaldehyde (cas: 27421-51-8Recommanded Product: 27421-51-8).

Murar, Claudia E. et al. published their research in Journal of the American Chemical Society in 2014 | CAS: 4382-54-1

5-Methoxyindole-2-carboxylic acid (cas: 4382-54-1) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Related Products of 4382-54-1

KAHA Ligations That Form Aspartyl Aldehyde Residues as Synthetic Handles for Protein Modification and Purification was written by Murar, Claudia E.;Thuaud, Frederic;Bode, Jeffrey W.. And the article was included in Journal of the American Chemical Society in 2014.Related Products of 4382-54-1 This article mentions the following:

Aldehydes are widely recognized as valuable synthetic handles for the chemoselective manipulation of peptides and proteins. In this report, the authors show that peptides and small proteins containing the aspartic acid semialdehyde (Asa) side chain can be easily prepared by a chemoselective amide-forming ligation that results in the formation of the Asa residue at the ligation site. This strategy employs the 伪-ketoacid-hydroxylamine (KAHA) ligation in combination with a new isoxazolidine monomer that forms a side-chain aldehyde upon ligation. This monomer is easily prepared on a preparative scale by a catalytic, enantioselective approach and is readily introduced onto the N-terminus of a peptide segment by solid-phase peptide synthesis. The ligated product can be further functionalized by bioorthogonal reactions between the aldehyde residue and alkoxyamines or hydrazides. The authors demonstrated that glucagon aldehyde, an unprotected 29-mer peptide prepared by KAHA ligation, can be site specifically and chemoselectively modified with biotin, dyes, aliphatic oximes, and hydroxylamines. The authors further describe a simple and high recovery one-step purification process based on the capture of a 29-mer glucagon aldehyde and a 76-mer ubiquitin aldehyde by an alkoxyamine-functionalized polyethylene glycol resin. The peptide or protein was released from the resin by addition of a hydroxylamine to provide the corresponding oximes. In the experiment, the researchers used many compounds, for example, 5-Methoxyindole-2-carboxylic acid (cas: 4382-54-1Related Products of 4382-54-1).

Liu, Shuangping et al. published their research in LWT–Food Science and Technology in 2022 | CAS: 61-54-1

2-(1H-Indol-3-yl)ethanamine (cas: 61-54-1) 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.Quality Control of 2-(1H-Indol-3-yl)ethanamine

Heterologous expression and characterization of amine oxidases from Saccharopolyspora to reduce biogenic amines in huangjiu was written by Liu, Shuangping;Yao, Hongli;Sun, Mengfei;Zhou, Zhilei;Mao, Jian. And the article was included in LWT–Food Science and Technology in 2022.Quality Control of 2-(1H-Indol-3-yl)ethanamine This article mentions the following:

High content of biogenic amines in fermented food has adverse effects on the human body. Previous studies showed that biogenic amines could be reduced in some fermented foods using enzymes. However, this process was barely explored in alc. beverages. In this study, potential biogenic amine degarding genes were cloned from Saccharopolyspora hirsuta F1902 and Saccharopolyspora hordei F2002, and expressed in E. coli to study the enzymic activities of copper-containing amine oxidases named as CaoAShi and CaoASho in huangjiu. The degradation ratio of total biogenic amines by CaoAShi (31.72%) was higher than that of CaoASho (24.37%). CaoAShi and CaoASho had the highest degradation ratios of histamine, phenylethylamine, followed by tyramine, tryptamine or putrescine, and the smallest was cadaverine. The results indicated that CaoAShi had better biodegradability of biogenic amines than CaoASho in huangjiu (P < 0.05), and the two enzymes had the same amine substrate characteristics. These results provide new insights for the reduction of biogenic amines using amine oxidases, which is useful not only for huangjiu brewing industry, but also for other fermented food industries. In the experiment, the researchers used many compounds, for example, 2-(1H-Indol-3-yl)ethanamine (cas: 61-54-1Quality Control of 2-(1H-Indol-3-yl)ethanamine).

Zhao, Xu et al. published their research in Electrochimica Acta in 2009 | CAS: 15362-40-0

1-(2,6-Dichlorophenyl)-2-indolinone (cas: 15362-40-0) 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.COA of Formula: C14H9Cl2NO

Electro-oxidation of diclofenac at boron doped diamond: Kinetics and mechanism was written by Zhao, Xu;Hou, Yining;Liu, Huijuan;Qiang, Zhimin;Qu, Jiuhui. And the article was included in Electrochimica Acta in 2009.COA of Formula: C14H9Cl2NO This article mentions the following:

Diclofenac is a common antiinflammatory drug. Its electrochem. degradation at B doped diamond electrode was studied in aqueous solution The degradation kinetics and the intermediate products were studied. Electrooxidation was effective in inducing the degradation of diclofenac with 30 mg/L initial concentration, ensuring a mineralization degree of 72% after a 4 h treatment with the applied bias potential of 4.0 V. The effects of applied bias potential and addition of NaCl on diclofenac degradation were studied. Different degradation mechanisms of diclofenac were involved at various applied bias potentials. With the addition of NaCl, some chlorination intermediates including dichlorodiclofenac were identified, which lead to the total organic C increase compared with the electrolysis process without NaCl addition at the reaction initial period. The main intermediates including 2,6-dichlorobenzenamine, 2,5-dihydroxybenzyl alc., and HOBz are identified at the time of 2 h. 1-(2,6-Dichlorocyclohexa-2,4-dienyl)indolin-2-one were also identified. 1-(2,6-Dichlorocyclohexa-2,4-dienyl)indolin-2-one was also identified. These intermediates disappeared gradually with the extension of reaction time. Small mol. acids were identified finally. Based on these results, a degradation pathway of diclofenac is proposed. In the experiment, the researchers used many compounds, for example, 1-(2,6-Dichlorophenyl)-2-indolinone (cas: 15362-40-0COA of Formula: C14H9Cl2NO).

Ochiai, Eiji et al. published their research in Itsuu Kenkyusho Nempo in 1963 | CAS: 4662-03-7

2-(2-Phenyl-1H-indol-3-yl)acetic acid (cas: 4662-03-7) 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.Safety of 2-(2-Phenyl-1H-indol-3-yl)acetic acid

Synthesis of indole derivatives. I. 2-Phenylindole-3-acetic acid from quinoline was written by Ochiai, Eiji;Tamai, Yoshikazu. And the article was included in Itsuu Kenkyusho Nempo in 1963.Safety of 2-(2-Phenyl-1H-indol-3-yl)acetic acid This article mentions the following:

Into a solution of 4.88 g. 4-quinolyl(phenyl)acetonitrile in 15 cc. AcOH is introduced 3.8 cc. 33% H₂O₂, and the mixture heated 3 hrs., at 70掳 concentrated in vacuo, and extracted with CHCl₃ to give 3.65 g. 4-benzoylquinoline 1-oxide (I), m. 15-7掳 (decomposition). To a solution of 2.49 g. I in 30 cc. CHCl₃ is added a solution of 2.0 g. tosyl chloride in 20 cc. CHCl₃, the mixture heated 10 min., 20 cc. 8% NaOH added, and the mixture agitated 40 min. to give 2.1 g. 4-benzoylcarbostyril (II), needles, m. 263掳. A solution of 4 g. II in 80 cc. AcOH is subjected to catalytic reduction with 1 g. 40% Pd-C to give 3.1 g. 4-(伪-hydroxybenzyl)carbostyril, needles, H m. 251掳 (Me₂CO), and 0.2 g. 4-benzylcarbostyril (III), needles, m. 271掳 (MeOH). Catalytic reduction of 12 g. H by the use of Raney Ni under high pressure at 120掳 in MeOH gives two isomers of 4-(伪-hydroxybenzyl)-3,4-dihydrocarbostyril (IV), m. 183掳 (needles from MeOH), and m. 179掳 (needles from MeOH), as well as 0.2 g. 4-benzyl-3,4-dihydrocarbostyril (V), needles, m. 163掳 (MeOH). Catalytic reduction of III using Raney Ni under high pressure gives V. To a solution of 732 mg. CrO₃ in 5 cc. H₂O and 50 cc. AcOH is added a solution of 2.53 g. IV in 40 cc. AcOH, and the mixture heated 30 min. at 80掳 to give 2.04 g. 4-benzoyl-3,4dihydrocarbostyril (VI), prisms, m. 230掳 (MeOH);’ monoxime m. 165掳 (decomposition). VI (2.51 g.) is added to 40 g. EtOH containing 10 g. dry HCl gas and the mixture refluxed 25 hrs. to give 1.92 g. Et 2-phenylindole-3-acetate (VII), b₀.001 180-5掳. Reduction of 2.79 g. VII with LiAlH₄ in tetrahydrofuran solution gives 1.71 g. 2-phenyl3-(尾-hydroxyethyl)indole, needles, m. 144-6掳 (C₆H₆-ligroine). Heating 1.40 g. VII with 20% ethanolic HCl solution under refluxing gives 1.0 g. 2-phenylindole-3-acetic acid, leaves, m. 179掳 (C₆H₆). In the experiment, the researchers used many compounds, for example, 2-(2-Phenyl-1H-indol-3-yl)acetic acid (cas: 4662-03-7Safety of 2-(2-Phenyl-1H-indol-3-yl)acetic acid).

Purkait, Nibadita et al. published their research in Angewandte Chemie, International Edition in 2018 | CAS: 6872-06-6

2-Methylindoline (cas: 6872-06-6) 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.SDS of cas: 6872-06-6

Regiospecific N-Arylation of Aliphatic Amines under Mild and Metal-Free Reaction Conditions was written by Purkait, Nibadita;Kervefors, Gabriella;Linde, Erika;Olofsson, Berit. And the article was included in Angewandte Chemie, International Edition in 2018.SDS of cas: 6872-06-6 This article mentions the following:

A transition metal-free N-arylation of primary and secondary amines with diaryliodonium salts is presented. Both acyclic and cyclic amines are well tolerated, providing a large set of N-alkyl anilines. The methodol. is unprecedented among metal-free methods in terms of amine scope, the ability to transfer both electron-withdrawing and electron-donating aryl groups, and efficient use of resources, as excess substrate or reagents are not required. In the experiment, the researchers used many compounds, for example, 2-Methylindoline (cas: 6872-06-6SDS of cas: 6872-06-6).

2-Methylindoline (cas: 6872-06-6) 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.SDS of cas: 6872-06-6