04/01/2023 - Indole Building Blocks

Bogdanov, Andrei V. et al. published their research in ChemistrySelect in 2019 | CAS: 150560-58-0

5-Isopropylindoline-2,3-dione (cas: 150560-58-0) 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 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). SDS of cas: 150560-58-0

Synthesis and Biological Evaluation of New Isatin-Based QACs with High Antimicrobial Potency was written by Bogdanov, Andrei V.;Zaripova, Ilyuza F.;Voloshina, Alexandra D.;Sapunova, Anastasia S.;Kulik, Natalia V.;Bukharov, Sergey V.;Voronina, Julia K.;Vandyukov, Alexander E.;Mironov, Vladimir F.. And the article was included in ChemistrySelect in 2019.SDS of cas: 150560-58-0 This article mentions the following:

A simple and easy condensation reaction of aryl- or N-substituted isatins with Girard’s reagents P and T was described for the synthesis of water-soluble isatin-3-acylhydrazone-based quaternary ammonium compounds (QACs) I [R = H, F, Br; R¹ = H, Me, OMe, etc.; R² = H, Br; R³ = H, Et, NO₂, etc.; R⁴ = H, (3,5-ditert-butyl-4-hydroxy-phenyl)methyl; R⁵ = trimethylammonio, pyridinium-1-yl] with high yields. Synthesized compounds were evaluated for their antibacterial and antifungal activities against Gram-pos. bacteria (S. aureus 209p and B. cereus 8035) and yeast-like fungus C. albicans 855-653. Among them three compounds I [R = H; R¹ = Me, Et, F, Br; R² = H; R³ = H; R⁴ = (3,5-ditert-butyl-4-hydroxy-phenyl)methyl; R⁵ = pyridinium-1-yl] exhibited very promising antibacterial activities. The influence of the substituent’s nature as in the aromatic fragment as at position 1 on the activity was established. The structures of all novel compounds I were fully characterized using IR and NMR spectroscopies as well as XRD anal. In the experiment, the researchers used many compounds, for example, 5-Isopropylindoline-2,3-dione (cas: 150560-58-0SDS of cas: 150560-58-0).

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

Jaiswal, Komal et al. published their research in ACS Organic & Inorganic Au in 2022 | 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 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). Formula: C8H6N2O2

Dual Role of MoS₂ Quantum Dots in a Cross-Dehydrogenative Coupling Reaction was written by Jaiswal, Komal;Girish, Yarabahally R.;Behera, Pradipta;De, Mrinmoy. And the article was included in ACS Organic & Inorganic Au in 2022.Formula: C8H6N2O2 This article mentions the following:

Modern day research focuses on the development of greener and eco-friendlier protocols to fabricate biol. relevant targets with minimal waste generation. C-C bond formation reactions are of prime importance in this regard. In a typical photocatalytic hydrogen evolution reaction (HER) three components are used, viz, catalyst, photosensitizer and sacrificial amine donor. Among these, the photosensitizer and sacrificial amine donors are wasted at the end of the reaction. Considering these drawbacks, in this work, we have developed a methodol. targeted at the utilization of sacrificial amine donors for C-H functionalization with MoS₂ Quantum Dots (QDs) as the catalyst as well as photosensitizer. QDs indeed emerged to be an active participant in heterogeneous electron transfer (HET) process. This concept opens up new possibilities in the field of nanomaterial-based photomediated organic transformations without the aid of any external photosensitizers via a clean and sustainable protocol with no side product. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Formula: C8H6N2O2).

Witt, Jonathan O. et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2016 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Recommanded Product: 827-01-0

Synthesis and characterization of a series of chiral alkoxymethyl morpholine analogs as dopamine receptor 4 (D₄R) antagonists was written by Witt, Jonathan O.;McCollum, Andrea L.;Hurtado, Miguel A.;Huseman, Eric D.;Jeffries, Daniel E.;Temple, Kayla J.;Plumley, Hyekyung C.;Blobaum, Anna L.;Lindsley, Craig W.;Hopkins, Corey R.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2016.Recommanded Product: 827-01-0 This article mentions the following:

Herein, we report the synthesis and structure-activity relationship of a series of chiral alkoxymethyl morpholine analogs. Our efforts have culminated in the identification of (S)-2-(((6-chloropyridin-2-yl)oxy)methyl)-4-((6-fluoro-1H-indol-3-yl)methyl)morpholine(I) as a novel potent and selective dopamine D4 receptor antagonist with selectivity against the other dopamine receptors tested (<10% inhibition at 1 μM against D₁, D_2L, D_2S, D₃, and D₅). In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Recommanded Product: 827-01-0).

Kumar, Chebolu Naga Sesha Sai Pavan et al. published their research in Synlett in 2008 | CAS: 112656-95-8

7-Nitroindoline-2,3-dione (cas: 112656-95-8) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Application of 112656-95-8

Use of pyridinium chlorochromate and reusable polyaniline salt catalyst combination for the oxidation of indoles was written by Kumar, Chebolu Naga Sesha Sai Pavan;Devi, Chebrolu Lavanya;Rao, Vaidya Jayathirtha;Palaniappan, Srinivasan. And the article was included in Synlett in 2008.Application of 112656-95-8 This article mentions the following:

A novel method was described herein for the simple, convenient and efficient oxidation of indoles to isatins using pyridinium chlorochromate with the aid of polyaniline salt catalyst at room temperature or at reflux in dichloroethane. Interestingly, oxidation of 3-alkyl indoles by this procedure gave 3-hydroxy 3-alkyl oxo-indoles. On the other hand, indol-3-alkanols gave mixtures of isatins and 3-formyl indoles. This is the first example of use of polyaniline as a catalyst in oxidation reaction. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Application of 112656-95-8).

Liu, Xiaoguang et al. published their research in Journal of Medicinal Chemistry in 2021 | CAS: 827-01-0

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

Development of Novel Mitochondrial Pyruvate Carrier Inhibitors to Treat Hair Loss was written by Liu, Xiaoguang;Flores, Aimee A.;Situ, Lisa;Gu, Wen;Ding, Hui;Christofk, Heather R.;Lowry, William E.;Jung, Michael E.. And the article was included in Journal of Medicinal Chemistry in 2021.HPLC of Formula: 827-01-0 This article mentions the following:

Herein, we report the synthesis and evaluation of novel analogs of UK-5099 both in vitro and in vivo for the development of mitochondrial pyruvate carrier (MPC) inhibitors to treat hair loss. A comprehensive understanding of the structure-activity relationship was obtained by varying four positions of the hit compound, namely, the alkyl group on the N1 position, substituents on the indole core, various aromatic and heteroaromatic core structures, and various Michael acceptors. The major discovery was that the inhibitors with a 3,5-bis(trifluoromethyl)benzyl group at the N1 position were shown to have much better activity than JXL001 (UK-5099) to increase cellular lactate production Addnl., analog JXL069, possessing a 7-azaindole heterocycle, was also shown to have significant MPC inhibition activity, which further increases the chem. space for drug design. Finally, more than 10 analogs were tested on shaved mice by topical treatment and promoted obvious hair growth on mice. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0HPLC of Formula: 827-01-0).

Nimje, Roshan Y. et al. published their research in Journal of Organic Chemistry in 2020 | CAS: 1000340-39-5

3-Bromo-4-chloro-7-azaindole (cas: 1000340-39-5) 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Application In Synthesis of 3-Bromo-4-chloro-7-azaindole

Synthesis of differentially protected azatryptophan analogs via Pd₂(dba)₃/XPhos catalyzed Negishi coupling of N-Ts azaindole halides with zinc derivative from Fmoc-protected tert-butyl (R)-2-amino-3-iodopropanoate was written by Nimje, Roshan Y.;Vytla, Devaiah;Kuppusamy, Prakasam;Velayuthaperumal, Rajeswari;Jarugu, Lokesh Babu;Reddy, China Anki;Chikkananjaiah, Nanjundaswamy Kanikahalli;Rampulla, Richard A.;Cavallaro, Cullen L.;Li, Jianqing;Mathur, Arvind;Gupta, Anuradha;Roy, Amrita. And the article was included in Journal of Organic Chemistry in 2020.Application In Synthesis of 3-Bromo-4-chloro-7-azaindole This article mentions the following:

Unnatural amino acids play an important role in peptide based drug discovery. Herein, we report a class of differentially protected azatryptophan derivatives synthesized from N-tosyl-3-haloazaindoles (I) (Pg = protective groups: Ts (tosyl), Fmoc (9-fluorenylmethoxycarbonyl), and tert-Bu) and Fmoc-protected tert-Bu iodoalanine (II) (Fmoc = 9-fluorenylmethoxycarbonyl) via a Negishi coupling. Through ligand screening, Pd₂(dba)₃/XPhos was found to be a superior catalyst for the coupling of 1 with the zinc derivative of 2 to give tert-Bu (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)propanoate derivatives (III) (Pg = protective groups: Ts, Fmoc, and tert-Bu; Fmoc = 9-fluorenylmethoxycarbonyl) in 69-91% isolated yields. In addition, we have demonstrated that the protecting groups, namely, Ts, Fmoc, and tert-Bu, can be easily removed selectively. In the experiment, the researchers used many compounds, for example, 3-Bromo-4-chloro-7-azaindole (cas: 1000340-39-5Application In Synthesis of 3-Bromo-4-chloro-7-azaindole).

Wang, Xuemei et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2006 | CAS: 85696-95-3

1-Methyl-1H-indol-4-amine (cas: 85696-95-3) 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 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). Related Products of 85696-95-3

Optimization of 2-aminothiazole derivatives as CCR4 antagonists was written by Wang, Xuemei;Xu, Feng;Xu, Qingge;Mahmud, Hossen;Houze, Jonathan;Zhu, Liusheng;Akerman, Michelle;Tonn, George;Tang, Liang;McMaster, Brian E.;Dairaghi, Daniel J.;Schall, Thomas J.;Collins, Tassie L.;Medina, Julio C.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2006.Related Products of 85696-95-3 This article mentions the following:

A series of 2-aminothiazole antagonists of the CCR4 receptor were synthesized and their affinity for the receptor evaluated using a [¹²⁵I]TARC (CCL17) displacement assay. Optimization of these compounds for potency and pharmacokinetic properties led to potent, orally bioavailable antagonists. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-indol-4-amine (cas: 85696-95-3Related Products of 85696-95-3).

Whitehead, Calvert W. et al. published their research in Journal of Medicinal Chemistry in 1974 | CAS: 6639-06-1

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

Effect of lipophilic substituents on some biological properties of indoles was written by Whitehead, Calvert W.;Whitesitt, Celia A.. And the article was included in Journal of Medicinal Chemistry in 1974.Related Products of 6639-06-1 This article mentions the following:

Addnl. data considered in abstracting and indexing are available from a source cited in the original document. The antimicrobial structure-activity relations for 400 simple indole derivatives were correlated. Of several (diarylmethyl)indoles, prepared by carbonium ion alkylation of selected indoles, 5-bromo-3-(diphenylmethyl)indole (I) [53924-07-5] was effective at 0.78-10 μg/ml against both gram-neg. and gram-pos. bacteria. Pharmacol. properties of the (diarylmethyl)indoles are described. In the experiment, the researchers used many compounds, for example, 3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1Related Products of 6639-06-1).

Rani, S. Shobha et al. published their research in International Journal of Chemical Sciences in 2010 | CAS: 112656-95-8

7-Nitroindoline-2,3-dione (cas: 112656-95-8) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Application In Synthesis of 7-Nitroindoline-2,3-dione

Antibacterial and cytotoxic activity of 2,2¹-(5,5′-methylene bis (1,3,4-oxadiazole-5,2-diyl) bis (sulfanediyl) bis(N’-(2-oxoindolin-3-ylidene) acetohydrazides was written by Rani, S. Shobha;Agaiah, Bairi;Sarangapani, M.. And the article was included in International Journal of Chemical Sciences in 2010.Application In Synthesis of 7-Nitroindoline-2,3-dione This article mentions the following:

2,2¹-5,5′-Methylene bis(1,3,4-oxadiazole-5,2-diyl)bis(sulfanediyl)bis(N’-(2oxoindolin-3-ylidene) acetohydrazides) (VIa-o) have been synthesized by the condensation of 2-chloro-N¹(2-oxo-1,2-dihydro-3H-indole-3-ylidene)acetohydrazides (IVa-o) with the intermediate 5,5¹-methylene diyl bis(1,3,4-oxadiazole-2-thiol) (V). All the title compounds (VIa-o) were screened for cytotoxic activity using A-549 lung cancer and HT-29 colon cancer cell lines by MTT method and antimicrobial activity against B. subtilis, S. aureus, E. coli and S. typhi. The structures of newly synthesized compounds were established on the basis of elemental anal., IR, ¹H NMR and mass spectral data. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Application In Synthesis of 7-Nitroindoline-2,3-dione).

Shen, Yong-Miao et al. published their research in Journal of Photochemistry and Photobiology, A: Chemistry in 2013 | CAS: 24407-32-7

4,5,6,7-Tetrabromoisoindoline-1,3-dione (cas: 24407-32-7) 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.Electric Literature of C8HBr4NO2

Photoinduced regioselective arylation of N-vinyllactams and methylthiazoles by tetrachlorophthalimides was written by Shen, Yong-Miao;Grampp, Guenter;Tao, Fei-Fei;He, Ning-De;Chen, Da-Qing;Ye, Miao. And the article was included in Journal of Photochemistry and Photobiology, A: Chemistry in 2013.Electric Literature of C8HBr4NO2 This article mentions the following:

Photoinduced reactions of 4,5,6,7-tetrahalophthalimides (1a-1h) with selected N-vinyllactams (N-vinylpyrrolidinone, N-vinylcaprolactam) and methylthiazoles resp. lead to dehydrohalogenative coupling reactions between the phthalimide and these heterocycles. These mild and metal-free coupling reactions result in regioselective and stereoselective arylation of the heterocycles by the phthalimide, with the Z-isomer as the main products. Reaction mechanism for the photo-reactions is discussed. In the experiment, the researchers used many compounds, for example, 4,5,6,7-Tetrabromoisoindoline-1,3-dione (cas: 24407-32-7Electric Literature of C8HBr4NO2).