22/02/2023 - Page 11 of 66 - Indole Building Blocks

Levitskaya, Alina I. et al. published their research in Computational & Theoretical Chemistry in 2016 | CAS: 118-12-7

1,3,3-Trimethyl-2-methyleneindoline (cas: 118-12-7) 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.Category: indole-building-block

Nonlinear optical properties of chromophores with indolizine donors: Theoretical study was written by Levitskaya, Alina I.;Kalinin, Alexey A.;Fominykh, Olga D.;Vasilyev, Ilya V.;Balakina, Marina Yu.. And the article was included in Computational & Theoretical Chemistry in 2016.Category: indole-building-block This article mentions the following:

New class of nonlinear optical chromophores with donors containing indolizine moiety is proposed. Dipole moment and first hyperpolarizability values of the chromophores, which are analogs of FTC, CLD and OLD chromophores, containing 1-methyl-2-phenylindolizin-3-yl (MPI-3) or 3-methyl-2-phenylindolizin-1-yl (MPI-1) donors (instead of diethylaminophenyl), 3-cyano-2-dicyanomethylene-5,5-dimethyl-1,5-dihydrofuran-4-yl (TCF) acceptor, and 2,5-divinylthiophene, octatetraene and 2,2′-divinylbithiophene 蟺-electron bridge, are calculated by DFT technique. Chromophores with named donors and acceptors and 3,7-divinylquinoxalin-2-one 蟺-electron bridge are also studied. In most cases higher values of first hyperpolarizability were obtained for chromophores with MPI-3 donor, this being in accordance with the electron d. distribution in these fragments. The change of dimethylaniline donor fragment for indolizine one results in the growth of the first hyperpolarizability values. This observation holds also for chromophores with divinylquinoxalinone 蟺-electron bridge, in which higher values of first hyperpolarizability are obtained when the donor moiety is connected through vinylene group at position 3 rather than at position 7 of the quinoxalinone system. In the experiment, the researchers used many compounds, for example, 1,3,3-Trimethyl-2-methyleneindoline (cas: 118-12-7Category: indole-building-block).

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

Xu, Zhanwei et al. published their research in Journal of Organic Chemistry in 2012 | CAS: 27257-15-4

1-Methyl-1H-pyrrolo[2,3-b]pyridine (cas: 27257-15-4) 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. 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.Computed Properties of C8H8N2

Oxidative coupling of indoles with ethyl 2-(disubstituted amino)acetates: An approach to achieve indolylglycine derivatives was written by Xu, Zhanwei;Yu, Xiaoqiang;Feng, Xiujuan;Bao, Ming. And the article was included in Journal of Organic Chemistry in 2012.Computed Properties of C8H8N2 This article mentions the following:

An efficient method for the synthesis of indolylglycine derivatives is described. The oxidative coupling reactions of Et 2-(disubstituted amino)acetates with indoles proceeded smoothly in the presence of meta-chloroperoxybenzoic acid (mCPBA) under ambient conditions to produce indolylglycine derivatives in satisfactory to excellent yields. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-pyrrolo[2,3-b]pyridine (cas: 27257-15-4Computed Properties of C8H8N2).

Lee, Jong Seok et al. published their research in Bulletin of the Korean Chemical Society in 2013 | CAS: 1016-47-3

N-(2-(1H-Indol-3-yl)ethyl)acetamide (cas: 1016-47-3) 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 was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Quality Control of N-(2-(1H-Indol-3-yl)ethyl)acetamide

A concise and rapid approach to the marine natural product streptochlorin and its analogs was written by Lee, Jong Seok;Shin, Junho;Lee, Hyi-Seung;Shin, Hee Jae;Lee, Yeon-Ju. And the article was included in Bulletin of the Korean Chemical Society in 2013.Quality Control of N-(2-(1H-Indol-3-yl)ethyl)acetamide This article mentions the following:

The synthesis of the target compounds was achieved by a strategy involving a a van Leusen oxazole synthesis and a Gabriel-Robinson reaction (cyclodehydration). The title compounds thus formed included a streptochlorin analog (I) and related substances [3-(4-chloro-5-oxazolyl)-1H-indole, streptochlorin derivatives and analogs]. The synthesis of the target compounds was achieved using 3-formyl-1H-indole-1-carboxylic acid 1,1-dimethylethyl ester derivatives and 1-[(isocyanomethyl)sulfonyl]-4-methylbenzene (TosMIC) as starting materials. In the experiment, the researchers used many compounds, for example, N-(2-(1H-Indol-3-yl)ethyl)acetamide (cas: 1016-47-3Quality Control of N-(2-(1H-Indol-3-yl)ethyl)acetamide).

Huang, Zhi et al. published their research in Results in Chemistry in 2022 | CAS: 244-63-3

9H-Pyrido[3,4-b]indole (cas: 244-63-3) 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. 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: C11H8N2

Design, synthesis of N⁹– acyl substituted 尾-carboline derivatives containing 5-phenyl-2-furan moiety as potent anticancer agents was written by Huang, Zhi;Yang, Zhi-Kun;Chen, Si-Qing;Chen, Jian-Wei;Bao, Xiao-Ze;Ye, Xin-Yi;Wei, Bin;Cui, Zi-Ning;Li, Ya-Sheng;Wang, Hong. And the article was included in Results in Chemistry in 2022.COA of Formula: C11H8N2 This article mentions the following:

尾-Carbolines are of great interest due to their broad spectrum of biochem. effects and pharmaceutical functions, especially antitumor activity. The N⁹ position at 尾-carboline is a modification site for important antitumor activity. Several phenylfuran derivatives displayed significant antitumor activity in our previous work. Here, we designed and preparated a series of novel N⁹-acyl substituted 尾-carboline derivatives containing 5-phenyl-2-furan moiety as potent anticancer agents. All newly synthesized compounds and 尾-carboline were evaluated for antitumor activity on five cancer cells. 尾-Carboline had only weak antitumor activity, while the introduction of the phenylfuran fragment significantly improved the activity. The primary structure-activity relationship study showed that 4-substituted phenylfuran played a key role in anti-cancer activity and compound 8 displayed superior than Camptothecin in anti-proliferative activity against breast cancer cells MCF-7. Flow cytometry studied revealed that compounds 8 and 15 effectively mediated MCF-7 apoptosis. This study lays a working foundation for the research and development of new broad-spectrum antitumor drugs based on 尾-carboline and phenylfurans, compound 8 would be great promise as a hit antitumor candidate in the future study. In the experiment, the researchers used many compounds, for example, 9H-Pyrido[3,4-b]indole (cas: 244-63-3COA of Formula: C11H8N2).

Wang, Xixi et al. published their research in Nutrients in 2022 | CAS: 442-51-3

7-Methoxy-1-methyl-9H-pyrido[3,4-b]indole (cas: 442-51-3) 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Synthetic Route of C13H12N2O

Physicochemical Properties of the Soluble Dietary Fiber from Laminaria japonica and Its Role in the Regulation of Type 2 Diabetes Mice was written by Wang, Xixi;Zhang, Liping;Qin, Ling;Wang, Yanfeng;Chen, Fushan;Qu, Changfeng;Miao, Jinlai. And the article was included in Nutrients in 2022.Synthetic Route of C13H12N2O This article mentions the following:

Laminaria japonica is a large marine brown alga that is annually highly productive. However, due to its underutilization, its potential value is substantially wasted. For example, a lot of Laminaria japonica cellulose remains unused during production of algin. The soluble dietary fiber (SDF) was prepared from the byproducts of Laminaria japonica, and its physicochem. properties were explored. SDF exhibits good water-holding, oil-holding, water-absorbing swelling, glucose and cholesterol absorption capacity, and inhibitory activity of 伪-amylase and 伪-glucosidase. In addition, the beneficial effects of SDF in diabetic mice include reduced body weight, lower blood glucose, and relieved insulin resistance. Finally, the intestinal flora and metabolomic products were analyzed from feces using 16S amplicon and LC-MS/MS, resp. SDF not only significantly changed the composition and structure of intestinal flora and intestinal metabolites, but also significantly increased the abundance of beneficial bacteria Akkermansia, Odoribacter and Bacteroides, decreased the abundance of harmful bacteria Staphylococcus, and increased the content of bioactive substances in intestinal tract, such as harmine, magnolol, arachidonic acid, prostaglandin E2, urimorelin and azelaic acid. Taken together, these findings suggest that dietary intake of SDF alleviates type 2 diabetes mellitus disease, and provides an important theor. basis for SDF to be used as a functional food. In the experiment, the researchers used many compounds, for example, 7-Methoxy-1-methyl-9H-pyrido[3,4-b]indole (cas: 442-51-3Synthetic Route of C13H12N2O).

Lai, Zeng-Wei et al. published their research in Chinese Journal of Chemistry in 2017 | CAS: 773134-49-9

Methyl 7-methyl-1H-indole-3-carboxylate (cas: 773134-49-9) 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.Application of 773134-49-9

Asymmetric Synthesis of 3-Allyloxindoles and 3-Allenyloxindoles by Scandium(III)-Catalyzed Claisen Rearrangement Reactions was written by Lai, Zeng-Wei;Liu, Chuan;Sun, Hongbin;You, Shu-Li. And the article was included in Chinese Journal of Chemistry in 2017.Application of 773134-49-9 This article mentions the following:

Scandium-catalyzed asym. Claisen rearrangement reactions of 2-allyloxyindoles and 2-propargyloxyindoles provide a novel approach to diverse 3-allyloxindoles and 3-allenyloxindoles in excellent yields (up to 99%) and enantioselectivity (up to 99% ee) under mild reaction conditions. The scandium catalyst was derived from Sc(OTf)₃ and Pybox ligand. In the experiment, the researchers used many compounds, for example, Methyl 7-methyl-1H-indole-3-carboxylate (cas: 773134-49-9Application of 773134-49-9).

Kumar, Nag S. et al. published their research in Bioorganic & Medicinal Chemistry in 2014 | CAS: 475102-13-7

(5-Bromo-1-(tert-butoxycarbonyl)-1H-indol-2-yl)boronic acid (cas: 475102-13-7) 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. 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 and optimization of a new class of pyruvate kinase inhibitors as potential therapeutics for the treatment of methicillin-resistant Staphylococcus aureus infections was written by Kumar, Nag S.;Dullaghan, Edie M.;Finlay, B. Brett;Gong, Huansheng;Reiner, Neil E.;Jon Paul Selvam, J.;Thorson, Lisa M.;Campbell, Sara;Vitko, Nicholas;Richardson, Anthony R.;Zoraghi, Roya;Young, Robert N.. And the article was included in Bioorganic & Medicinal Chemistry in 2014.Category: indole-building-block This article mentions the following:

A novel series of bis-indoles derived from naturally occurring marine alkaloid cis-3,4-dihydrohamacanthin B (I) was synthesized and evaluated as inhibitors of methicillin-resistant Staphylococcus aureus (MRSA) pyruvate kinase (PK). PK is not only critical for bacterial survival which would make it a target for development of novel antibiotics, but it is reported to be one of the most highly connected ‘hub proteins’ in MRSA, and thus should be very sensitive to mutations and making it difficult for the bacteria to develop resistance. From the co-crystal structure of I bound to S. aureus PK we were able to identify the pharmacophore needed for activity. Consequently, we prepared simple direct linked bis-indoles such as 6,6′-dibromo-2,2′-biindolyl [II; R, R’ = 6,6′-dibromo (b)] that have similar anti-MRSA activity as compound I. Structure-activity relationship (SAR) studies on II led us to discover more potent compounds such as II [R, R’ = 6,5′-dibromo; 6-bromo-5′-chloro; 5,6,6′-tribromo; 5,6,5′-tribromo (c, d, k, m, resp.)] with enzyme inhibiting activities in the low nanomolar range that effectively inhibited the bacteria growth in culture with min. inhibitory concentrations (MIC) for MRSA as low as 0.5 渭g/mL. Some potent PK inhibitors, such as IIb, exhibited attenuated antibacterial activity and were found to be substrates for an efflux mechanism in S. aureus. Studies comparing a wild type S. aureus with a construct (S. aureus LAC 螖pyk::Erm^R) that lacks PK activity confirmed that bactericidal activity of IId was PK-dependant. In the experiment, the researchers used many compounds, for example, (5-Bromo-1-(tert-butoxycarbonyl)-1H-indol-2-yl)boronic acid (cas: 475102-13-7Category: indole-building-block).

Jiang, Shi-Fen et al. published their research in Organic Letters in 2018 | CAS: 20780-72-7

4-Bromoindoline-2,3-dione (cas: 20780-72-7) 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Formula: C8H4BrNO2

Switchable Access to 3-Carboxylate-4-quinolones and 1-Vinyl-3-carboxylate-4-quinolones via Oxidative Cyclization of Isatins and Alkynes was written by Jiang, Shi-Fen;Xu, Cheng;Zhou, Zhi-Wen;Zhang, Qin;Wen, Xiao-Hui;Jia, Feng-Cheng;Wu, An-Xin. And the article was included in Organic Letters in 2018.Formula: C8H4BrNO2 This article mentions the following:

Isatins underwent base-dependent oxidative cyclization or tandem oxidative cyclization and diastereoselective addition reactions with arylalkynoates such as PhC顚咰CO₂Me mediated by t-BuO₂H in DMSO to yield quinolinones such as I (with Cs₂CO₃ as base) or oxoquinolinylpropenoates such as II (with K₃PO₄ as base). In the experiment, the researchers used many compounds, for example, 4-Bromoindoline-2,3-dione (cas: 20780-72-7Formula: C8H4BrNO2).

Griesbeck, Axel G. et al. published their research in Journal of Organic Chemistry in 2000 | CAS: 3130-75-4

4-(1,3-Dioxoisoindolin-2-yl)butanoic acid (cas: 3130-75-4) 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Computed Properties of C12H11NO4

Photochemistry of MTM- and MTE-esters of 蠅-phthalimido carboxylic acids: Macrocyclization versus deprotection was written by Griesbeck, Axel G.;Oelgemoller, Michael;Lex, Johann. And the article was included in Journal of Organic Chemistry in 2000.Computed Properties of C12H11NO4 This article mentions the following:

The photolysis of linear methylthiomethyl (MTM) esters of 蠅-phthalimido carboxylic acids, Pht-(CH₂)_n-CO₂CH₂SCH₃ (I; Pht = phthalimido; n = 1, 2, 3, 5, 10), of methylthioethyl (MTE) esters Pht-(CH₂)_n-CO₂CH₂CH₂SCH₃ (II; Pht = phthalimido; n = 1, 3), and of two methyl-substituted esters Pht-CHMeCH₂CO₂CH₂SMe (III) and (S)-Pht-CHMeCO₂CH₂CH₂SMe (IV) resulted in photocyclization to give medium-sized and macrocyclic rings and in photochem. deprotection to give the free carboxylic acids. Photocyclization of I (n = 2, 3) gave the macrocyclic lactones V (n = 2, 3) in excellent yields whereas the substrates I (n = 1, 5, 10) with shorter as well as longer spacer groups gave preferentially deprotected carboxylic acid products. Subsequent photolysis of I (n = 1) gave N-methylphthalimide. Photolysis of the MTE esters II gave the macrocyclic lactones VI and VII. Thus, competition between cyclization and deprotection strongly depended on the chain length of the hydrocarbon linker between phthalimido chromophore and ester group. To examine the influence of the position of the ester group in the linker chain the model substrates III and IV with identical number of atoms separating electron donor and acceptor group were investigated. The more flexible MTE derivative IV cyclized to give a 4:1 diastereoisomeric mixture of 11(S)-cis/trans-indenooxathiaazacyclononanones VIII, whereas photolysis of the more reluctant MTM ester III gave cis-indenooxathiaazacyclononanone IX only after prolonged irradiation Thus, the methylthiomethyl group can function as a photolabile protecting group whereas the methylthioethyl group cannot be removed photochem. The distance dependence of the secondary reaction steps indicates that the primary electron transfer is not necessarily induced starting from close contact geometries. In the experiment, the researchers used many compounds, for example, 4-(1,3-Dioxoisoindolin-2-yl)butanoic acid (cas: 3130-75-4Computed Properties of C12H11NO4).

Velloso, Elizabeth Portugal et al. published their research in American Journal of Hypertension in 2016 | CAS: 136553-81-6

2-((3R,6S,9R,12R,17aS)-9-((1H-Indol-3-yl)methyl)-6-isobutyl-3-isopropyl-1,4,7,10,13-pentaoxohexadecahydro-1H-pyrrolo[1,2-a][1,4,7,10,13]pentaazacyclopentadecin-12-yl)acetic acid (cas: 136553-81-6) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Product Details of 136553-81-6

Identification of a novel agonist-like autoantibody in preeclamptic patients was written by Velloso, Elizabeth Portugal;Pimentel, Renata Lucia;Braga, Janaina F.;Cabral, Antonio Carlos Vieira;Reis, Zilma Silveira N.;Bader, Michael;Santos, Robson Augusto S.;Wallukat, Gerd. And the article was included in American Journal of Hypertension in 2016.Product Details of 136553-81-6 This article mentions the following:

BACKGROUND Recent studies have shown that preeclampsia (PE) is associated with the presence of autoantibodies (AABs) that activate the angiotensin II AT1 receptor, which could contribute to many of the symptoms of PE. METHODS To investigate the frequency and the targets of AABs in preeclamptic women (31 cases) and healthy pregnant normotensive women (29 cases) in Brazil, antibodies from serum samples were detected by a bioassay using spontaneously beating neonatal rat cardiomyocytes in culture. In the cardiomyocytes, the agonistic AABs induce a pos. or neg. chronotropic response, mimicking the corresponding receptor agonists. The specificity of the AAB response was identified by specific receptor antagonists. RESULTS Thirty preeclamptic patients (97%) presented AABs against the angiotensin II AT₁ receptor. The agonistic effect of the AAB was blocked by irbesartan and neutralized by a peptide corresponding to the second extracellular loop of this receptor. Strikingly, we discovered that all sera from the severe preeclamptic patients (16 cases) contained a novel agonist- like AAB directed against the endothelin-1 ETA receptor in addition to the AABs against the angiotensin II AT₁ receptor. This AAB was selectively blocked by the antagonist BQ-123, antagonized by the protein kinase C (PKC) inhibitor Calphostin C and neutralized by peptides corresponding to the second extracellular loop of the endothelin-1 ETA receptor subtype. CONCLUSIONS We described, for the first time, the presence of endothelin-1 ETA receptor AABs in PE. Our results suggest that the presence of both agonistic AABs may be involved in the pathogenesis of severe PE. In the experiment, the researchers used many compounds, for example, 2-((3R,6S,9R,12R,17aS)-9-((1H-Indol-3-yl)methyl)-6-isobutyl-3-isopropyl-1,4,7,10,13-pentaoxohexadecahydro-1H-pyrrolo[1,2-a][1,4,7,10,13]pentaazacyclopentadecin-12-yl)acetic acid (cas: 136553-81-6Product Details of 136553-81-6).