22/02/2023 - Page 12 of 66 - Indole Building Blocks

Bartoccini, Francesca et al. published their research in Journal of Organic Chemistry in 2018 | CAS: 13523-92-7

1-Methyl-1H-indol-5-ol (cas: 13523-92-7) 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. 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 C9H9NO

Organocatalytic Aza-Friedel-Crafts/Lactonization Domino Reaction of Naphthols and Phenols with 2-Acetamidoacrylate to Naphtho- and Benzofuranones Bearing a Quaternary Center at the C3 Position was written by Bartoccini, Francesca;Mari, Michele;Retini, Michele;Bartolucci, Silvia;Piersanti, Giovanni. And the article was included in Journal of Organic Chemistry in 2018.Computed Properties of C9H9NO This article mentions the following:

N-Acetyl ketimine generated from Me 2-acetamidoacrylate was explored to develop an unprecedented domino aza-Friedel-Crafts/lactonization reaction with naphthols and phenols (including 5-hydroxyindoles). This novel method requires a catalyst loading of only 5 mol % of a phosphoric acid catalyst and provides a new series of 3-NHAc-naphtho- and benzofuranone derivatives bearing tetra-substituted stereogenic centers in moderate-to-good yields. The enantioselective variant using BINOL-derived phosphoric acids was also explored with 1-naphthol, providing the desired product with moderate enantioselectivities (up to 99:1 following recrystallization). In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-indol-5-ol (cas: 13523-92-7Computed Properties of C9H9NO).

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

Dubey, P. K. et al. published their research in Indian Journal of Heterocyclic Chemistry in 2006 | CAS: 10102-94-0

5-Bromo-1-methyl-1H-indole-3-carbaldehyde (cas: 10102-94-0) 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.Quality Control of 5-Bromo-1-methyl-1H-indole-3-carbaldehyde

Synthesis of N-alkyl/aralkyl derivatives of indole-3-aldehydes using TEBAC as phase transfer catalyst was written by Dubey, P. K.;Babu, Balaji;Narayana, M. Venkata. And the article was included in Indian Journal of Heterocyclic Chemistry in 2006.Quality Control of 5-Bromo-1-methyl-1H-indole-3-carbaldehyde This article mentions the following:

A simple and convenient procedure for the preparation of N-substituted derivatives of indoles and indole-3-aldehydes, in the presence of K₂CO₃ as a base and TEBAC as a phase transfer catalyst in acetonitrile medium at room temp is described. In the experiment, the researchers used many compounds, for example, 5-Bromo-1-methyl-1H-indole-3-carbaldehyde (cas: 10102-94-0Quality Control of 5-Bromo-1-methyl-1H-indole-3-carbaldehyde).

Xue, Chaoyi et al. published their research in Food Control in 2022 | CAS: 244-63-3

9H-Pyrido[3,4-b]indole (cas: 244-63-3) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.HPLC of Formula: 244-63-3

Ginger and curcumin can inhibit heterocyclic amines and advanced glycation end products in roast beef patties by quenching free radicals as revealed by electron paramagnetic resonance was written by Xue, Chaoyi;Deng, Peng;Quan, Wei;Li, Yong;He, Zhiyong;Qin, Fang;Wang, Zhaojun;Chen, Jie;Zeng, Maomao. And the article was included in Food Control in 2022.HPLC of Formula: 244-63-3 This article mentions the following:

This study investigated the inhibitory effects of ginger and curcumin on the formation of free and bound heterocyclic amines (HAs)1 and advanced glycation end products (AGEs) in roast beef patties. The underlying mechanism related to quenching free radical, alleviating lipid peroxidation and scavenging carbonyl intermediates was explored by ESR (EPR) and UPLC-MS/MS. Ginger (0.5%, 1.0%, 1.5%) and curcumin (0.005%, 0.010%, 0.015%) dose-dependently inhibited free and bound HAs and AGEs simultaneously. The maximum inhibition rates for free and bound HAs were 59.97% (0.015% curcumin) and 27.42% (1.5% ginger), and those for free and bound AGEs were 71.57% and 35.64% (1.5% ginger). EPR result indicated alkyl free radical and 1O2 were the pivotal free radicals for HAs and AGEs, and ginger and curcumin also dose-dependently reduced these radicals. Lipid peroxidation, active carbonyl intermediates-phenylacetaldehyde, glyoxal, and methylglyoxal were also inhibited by ginger and curcumin in a dose-dependent manner, probably due to quenching of free radical. In the experiment, the researchers used many compounds, for example, 9H-Pyrido[3,4-b]indole (cas: 244-63-3HPLC of Formula: 244-63-3).

Xu, Zhiping et al. published their research in Tetrahedron Letters in 2018 | 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Formula: C12H15N

Spiropyran-azobenzene-DBU system as solvent indicator was written by Xu, Zhiping;Li, Shen;Shen, Yujun;Chen, Meijun;Shao, Xusheng. And the article was included in Tetrahedron Letters in 2018.Formula: C12H15N This article mentions the following:

A dyad bearing azobenzene and spiropyran units was synthesized and its applications in indicating the polarity and protic or aprotic properties of a solvent were explored. The spiropyran-azobenzene derivative (SPAB) can be induced to different forms in different miscellaneous solvents accompanied with different color changes and spectral characteristics at the presence of organic base DBU. In a nonpolar or low-polar solvent, SPAB exists in thermostable spiropyran form with yellow color output. While in an aprotic polar solvent, the spiropyran part isomerized to merocyanine form giving a blue color. When SPAB is subjected to a protic solvent, the alkylation reaction occurs at the oxygen generating the alkylated-SPAB with red color. This solvent-dependent property can be used for discriminating solvent type. In the experiment, the researchers used many compounds, for example, 1,3,3-Trimethyl-2-methyleneindoline (cas: 118-12-7Formula: C12H15N).

Taylor, Dorothy L. et al. published their research in Journal of Pharmacy and Pharmacology in 1984 | CAS: 20315-68-8

6-Methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (cas: 20315-68-8) 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.HPLC of Formula: 20315-68-8

Effects of 6-methoxytetrahydro-尾-carboline on 5-hydroxytryptamine binding in rat brain was written by Taylor, Dorothy L.;Silverman, Peter B.;Ho, Beng T.. And the article was included in Journal of Pharmacy and Pharmacology in 1984.HPLC of Formula: 20315-68-8 This article mentions the following:

6-Methoxytetraydro-尾-carboline (I) [20315-68-8] competes for 5-HT聽聽[50-67-9] binding sites in rat brain in vitro and in vivo. The 尾-carboline is more active at the type 1, 5-HT, than the type 2, spiperone, receptors in vitro. Following injection into rats, I decreases 5-HT but not spiperone binding to the brain cortex. The ineffectiveness of I on spiperone binding in vivo corresponds with the results obtained in vitro. Thus, the effect of I on central 5-HT binding may be a significant aspect of its 5-hydroxytryptaminergic activity. In the experiment, the researchers used many compounds, for example, 6-Methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (cas: 20315-68-8HPLC of Formula: 20315-68-8).

Wang, Wei et al. published their research in Anhui Nongye Kexue in 2012 | CAS: 1016-47-3

N-(2-(1H-Indol-3-yl)ethyl)acetamide (cas: 1016-47-3) 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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Synthetic Route of C12H14N2O

Study on secondary metabolite of Trachelospermum jasminoides endophyte Myrothecium roridum (IFB-E009) was written by Wang, Wei;Jiang, Rong. And the article was included in Anhui Nongye Kexue in 2012.Synthetic Route of C12H14N2O This article mentions the following:

Eight compounds were isolated and identified from liquid fermentation products of Myrothecium roridum (IFB-E009) in Trachelospermum jasminoides, 1-4 were trichothecenes compounds, 5-6 were amides compounds, 7 was cyclic peptide, and 8 was uracil. As indicated by activity test, compound 1,4 showed activities to the human colon cancer cells SW1116. IC₅₀ were 25.68 and 38.93 渭mol/L, while the IC₅₀ of adriamycin was 5.31 渭mol. The study would provide theory and practice basis for the development and utilization of endophytes in pharmaceutical plants. In the experiment, the researchers used many compounds, for example, N-(2-(1H-Indol-3-yl)ethyl)acetamide (cas: 1016-47-3Synthetic Route of C12H14N2O).

Xia, Xiao-Feng et al. published their research in ACS Catalysis in 2022 | CAS: 57583-53-6

2,6-Dihydroxypyrrolo[3,4-f]isoindole-1,3,5,7(2H,6H)-tetraone (cas: 57583-53-6) 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). HPLC of Formula: 57583-53-6

Catalytic Desaturation and 尾-Fluorination of Aliphatic Amides Enabled by an Oxidative-Promoted Bond Destabilization was written by Xia, Xiao-Feng;Huang, Quan;Sun, Tian-Yu;Jiang, Yuqin;Ran, Guoxia. And the article was included in ACS Catalysis in 2022.HPLC of Formula: 57583-53-6 This article mentions the following:

The development of a desaturation and 尾-fluorination reaction of cyclic amides e.g., 1-benzoylpiperidine, which is achieved by an oxidative-promoted selective hydrogen atom-transfer/isomerization/electrophilic fluorination process was described. Moreover, the combination of an N-hydroxy catalyst and Selectfluor allows 伪, 尾-dehydrogenation and 纬-di-fluorination of N-aryl lactams I (R = H, 3-Me, 4-F, 4-Cl, 4-tBu) to be established. Furthermore, the present selective catalysis also works well for the C-N bond cleavage of acyclic amides R¹(R²)NC(O)C₆H₄-4-C(CH₃)₃ at the less-crowded site. The mechanism of this reaction has been carefully illustrated with exptl. and computational studies. In the experiment, the researchers used many compounds, for example, 2,6-Dihydroxypyrrolo[3,4-f]isoindole-1,3,5,7(2H,6H)-tetraone (cas: 57583-53-6HPLC of Formula: 57583-53-6).

Senwar, Kishna Ram et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2016 | CAS: 56341-41-4

5-Fluoroindolin-2-one (cas: 56341-41-4) 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. 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). Application of 56341-41-4

Design and synthesis of 4′-O-alkylamino-tethered-benzylideneindolin-2-ones as potent cytotoxic and apoptosis inducing agents was written by Senwar, Kishna Ram;Reddy, T. Srinivasa;Thummuri, Dinesh;Sharma, Pankaj;Bharghava, Suresh K.;Naidu, V. G. M.;Shankaraiah, Nagula. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2016.Application of 56341-41-4 This article mentions the following:

A series of new 4′-O-alkylamino-tethered-benzylideneindolin-2-one derivatives was synthesized and evaluated for their anti-proliferative activity against selected human cancer cell lines of lung (A549), prostate (DU-145), breast (BT549 and MDA-MB-231) and normal breast epithelial cells (MCF-10 脜). Gratifyingly, the compounds (Z)-5-chloro-3-(4′-(3-(2,6-dimethylmorpholino)propoxy)-3′-methoxybenzylidene)indolin-2-one , (Z)-5-chloro-3-(3′-methoxy-4′-(3-(4-(3-(trifluoromethyl)pyridin-2-yl)piperazin-1-yl)propoxy)benzylidene)indolin-2-one and (Z)-5-chloro-3-(3′-methoxy-4′-(3-(4-methylpiperazin-1-yl)propoxy)benzylidene)indolin-2-one exhibited potent cytotoxicity against breast cancer cell lines (BT549 and MDA-MB-231) with IC₅₀ values at 1.26-2.77 渭M, and are safer with lesser cytotoxicity on normal breast epithelial cells (MCF-10 脜). Further, experiments were conducted with these compounds (Z)-5-chloro-3-(4′-(3-(2,6-dimethylmorpholino)propoxy)-3′-methoxybenzylidene)indolin-2-one, (Z)-5-chloro-3-(3′-methoxy-4′-(3-(4-(3-(trifluoromethyl)pyridin-2-yl)piperazin-1-yl)propoxy)benzylidene)indolin-2-one and (Z)-5-chloro-3-(3′-methoxy-4′-(3-(4-methylpiperazin-1-yl)propoxy)benzylidene)indolin-2-one on MDA-MB-231 cancer cells to study the mechanism of growth inhibition and apoptosis inducing effect. Treatment of MDA-MB-231 cells with test compounds resulted in inhibition of cell migration through disorganization and disruption of F-actin capping protein. The flow-cytometry anal. results showed that the compound (Z)-5-Chloro-3-(3′-methoxy-4′-(3-(4-(3-(trifluoromethyl)pyridin-2-yl)piperazin-1-yl)propoxy)benzylidene)indolin-2-one arrested MDA-MB-231 cells in G0/G1 phase of cell cycle in a dose dependent manner. Hoechst staining study revealed that the test compounds inhibited tumor cell proliferation through induction of apoptosis. In addition, the mitochondrial membrane potential (D唯m) was affected and the increased level of reactive oxygen species (ROS) was noted in MDA-MB-231 cells. In the experiment, the researchers used many compounds, for example, 5-Fluoroindolin-2-one (cas: 56341-41-4Application of 56341-41-4).

Guo, Jing et al. published their research in Organic Chemistry Frontiers in 2017 | CAS: 16800-68-3

1-Acetylindolin-3-one (cas: 16800-68-3) 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Name: 1-Acetylindolin-3-one

Asymmetric amination of 2-substituted indolin-3-ones catalyzed by natural cinchona alkaloids was written by Guo, Jing;Lin, Zi-Hui;Chen, Kai-Bin;Xie, Ying;Chan, Albert S. C.;Weng, Jiang;Lu, Gui. And the article was included in Organic Chemistry Frontiers in 2017.Name: 1-Acetylindolin-3-one This article mentions the following:

The natural quinine-catalyzed enantioselective amination of 2-substituted indolin-3-ones with azodicarboxylates was developed. These reactions provided a broad spectrum of 2,2-disubstituted indolin-3-ones containing a nitrogen-attached quaternary stereocenter at the C2-position in extremely high yields and with excellent enantioselectivities. The readily available catalyst, broad substrate scope, and mild reaction conditions highlighted the practical utility of this process. In the experiment, the researchers used many compounds, for example, 1-Acetylindolin-3-one (cas: 16800-68-3Name: 1-Acetylindolin-3-one).

La Londe, R. L. et al. published their research in Angewandte Chemie, International Edition in 2010 | CAS: 34387-89-8

N-(tert-Butoxycarbonylamino)phthalimide (cas: 34387-89-8) 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Quality Control of N-(tert-Butoxycarbonylamino)phthalimide

Gold(I)-Catalyzed Enantioselective Synthesis of Pyrazolidines, Isoxazolidines, and Tetrahydrooxazines was written by La Londe, R. L.;Wang, Z. J.;Mba, M.;Lackner, A. D.;Toste, F. Dean. And the article was included in Angewandte Chemie, International Edition in 2010.Quality Control of N-(tert-Butoxycarbonylamino)phthalimide This article mentions the following:

Chiral ligands and chiral anions are employed in the gold(I)-catalyzed enantioselective intramol. additions of hydrazines and hydroxylamines to allenes. These complementary methods allow access to chiral vinyl isoxazolidines, oxazines, and differentially protected pyrazolidines. In the experiment, the researchers used many compounds, for example, N-(tert-Butoxycarbonylamino)phthalimide (cas: 34387-89-8Quality Control of N-(tert-Butoxycarbonylamino)phthalimide).