February 2023 - Page 96 of 117 - Indole Building Blocks

Blough, Bruce E. et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2014 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Computed Properties of C9H6ClNO

Alpha-ethyltryptamines as dual dopamine-serotonin releasers was written by Blough, Bruce E.;Landavazo, Antonio;Partilla, John S.;Decker, Ann M.;Page, Kevin M.;Baumann, Michael H.;Rothman, Richard B.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2014.Computed Properties of C9H6ClNO This article mentions the following:

The dopamine (DA), serotonin (5-HT), and norepinephrine (NE) transporter releasing activity and serotonin-2A (5-HT_2A) receptor agonist activity of a series of substituted tryptamines are reported. Three compounds, 7b, (+)-7d and 7f, were found to be potent dual DA/5-HT releasers and were >10-fold less potent as NE releasers. Addnl., these compounds had different activity profiles at the 5-HT_2A receptor. The unique combination of dual DA/5-HT releasing activity and 5-HT_2A receptor activity suggests that these compounds could represent a new class of neurotransmitter releasers with therapeutic potential. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Computed Properties of 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

O’Connell, E. J. Jr. et al. published their research in Photochemistry and Photobiology in 1971 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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. 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.Application In Synthesis of 2-Phenylisoindolin-1-one

Absorption and emission studies of electronic states of N-arylbenzamides was written by O’Connell, E. J. Jr.;Delmauro, M.;Irwin, J.. And the article was included in Photochemistry and Photobiology in 1971.Application In Synthesis of 2-Phenylisoindolin-1-one This article mentions the following:

Absorption and emission spectra of benzanilide, 1-naphthamide, N-phenylphthalimidine, naphthalene, BzNMePh and AcNHPh were obtained in solvents such as EtOH, benzene and 5:5:2 Et2O-isopentane-EtOH at 298 and 77掳K. Quantum yields were dependent on matrix viscosity and temperature Singlet-triplet splittings for the N-arylbenzamides, determined from the emission spectra, were small for 蟺,蟺* states (鈭?1500 cm-1). Phosphorescence maximum were blue-shifted relative to the fluorescence maximum Intersystem crossing efficiencies were consistent with S1 鈫?S0 radiationless decay. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Application In Synthesis of 2-Phenylisoindolin-1-one).

Papa, Veronica et al. published their research in Catalysis Science & Technology in 2020 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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. 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.Related Products of 5388-42-1

Homogeneous cobalt-catalyzed deoxygenative hydrogenation of amides to amines was written by Papa, Veronica;Cabrero-Antonino, Jose R.;Spannenberg, Anke;Junge, Kathrin;Beller, Matthias. And the article was included in Catalysis Science & Technology in 2020.Related Products of 5388-42-1 This article mentions the following:

The first general and efficient cobalt-catalyzed deoxygenative hydrogenation of amides, e.g., I to amines, e.g., II is presented. The optimal catalytic system based on a combination of [Co(NTf₂)₂] and (p-anisyl)triphos in the presence of [Me, ₃SiOTf] as acidic co-catalyst facilitates the direct hydrogenation of a broad range of amides, e.g., I to the corresponding amines e.g., II under mild conditions. A set of control experiments indicate that, after the initial reduction of the amide carboxylic group to the well-known hemiaminal intermediate, the reaction mainly proceeds through C-O bond cleavage though other pathways might be also involved to a minor extent. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Related Products of 5388-42-1).

Kim, Se Hun et al. published their research in Journal of Natural Products in 2015 | CAS: 1256359-99-5

tert-Butyl 5-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate (cas: 1256359-99-5) 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. 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 C20H28BNO5

Synthesis of Alocasin A was written by Kim, Se Hun;Sperry, Jonathan. And the article was included in Journal of Natural Products in 2015.Synthetic Route of C20H28BNO5 This article mentions the following:

Herein is reported a synthesis of alocasin A (I), an alkaloid component of Alocasia macrorrhiza, a herbaceous plant used in folk medicine throughout southern Asia. A double Suzuki-Miyaura cross-coupling reaction between a 3-borylindole and 2,5-dibromopyrazine was used to assemble the heteroaromatic framework of the natural product. Removal of the protecting groups gave a synthetic sample of I, the spectroscopic data of which matched those in the isolation report of this compound In the experiment, the researchers used many compounds, for example, tert-Butyl 5-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate (cas: 1256359-99-5Synthetic Route of C20H28BNO5).

Lewis, Frederick D. et al. published their research in Journal of Physical Chemistry A in 2002 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Reference of 5388-42-1

Temperature- and Conformation-Dependent Luminescence of Benzanilides was written by Lewis, Frederick D.;Liu, Weizhong. And the article was included in Journal of Physical Chemistry A in 2002.Reference of 5388-42-1 This article mentions the following:

The luminescence of benzanilide, N-methylbenzanilide, and two cyclic analogs has been investigated as a function of temperature both in microcrystals and in the glass-forming solvent methyltetrahydrofuran. Potential energy surfaces for small-amplitude geometric relaxation of the excited states and large amplitude twisting about the amide bond in the ground and excited states have been explored using AM1 and RCIS calculations, resp. ZINDO calculations have been used to probe the electronic configuration of the planar and twisted singlet and triplet states. Correlation of the spectroscopic and computational results indicates that at 77 K benzanilide phosphorescence occurs from a planar 蟺,蟺* triplet state whereas fluorescence occurs from a singlet state with partially relaxed geometry. At higher temperatures, large-amplitude geometric relaxation results in the formation of an intramol. charge-transfer (TICT) state that is twisted about the amide C-N bond. This TICT state is responsible for the weak Stokes-shifted fluorescence observed from benzanilide and N-methylbenzanilide in fluid solution Inhibition of amide twisting in cyclic derivatives precludes observation of TICT fluorescence. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Reference of 5388-42-1).

Lv, Leiyang et al. published their research in Journal of Organic Chemistry in 2018 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) 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.Electric Literature of C14H9NO2S

FeCl₃-Catalyzed Regio-Divergent Carbosulfenylation of Unactivated Alkenes: Construction of a Medium-Sized Ring was written by Lv, Leiyang;Li, Zhiping. And the article was included in Journal of Organic Chemistry in 2018.Electric Literature of C14H9NO2S This article mentions the following:

A FeCl₃-catalyzed regio-divergent carbosulfenylation of unactivated alkenes with electrophilic N-sulfenophthalimides has been developed. This protocol provides a straightforward and efficient access to various medium-sized rings, especially strained 7- and 8-membered carborings with a sulfur atom attached. The endo/exo selectivity in the reaction depends on the atom number of the chain between arene and alkene. Broad substrate scope, high yields, and gram-scale synthesis exemplified the utility and practicability of this protocol. In addition, this methodol. can be extended to the carboselenylation of isolated alkenes. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Electric Literature of C14H9NO2S).

Hennige, Hans et al. published their research in Chemische Berichte in 1988 | CAS: 110568-64-4

6-Nitroisoindolin-1-one (cas: 110568-64-4) 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. 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). Recommanded Product: 6-Nitroisoindolin-1-one

Studies on the chemistry of isoindoles and isoindolenines. XXVII. 3-Alkoxy-1H-isoindoles: syntheses and properties was written by Hennige, Hans;Kreher, Richard P.;Konrad, Michael;Jelitto, Frank. And the article was included in Chemische Berichte in 1988.Recommanded Product: 6-Nitroisoindolin-1-one This article mentions the following:

3-Alkoxy-1H-isoindoles I (R = H, 5-O₂N, 6-MeO, 5,6-Me₂, 4,7-Me₂, 5,6-Cl₂, 4,5,6,7-Cl₄; R¹ = Me, Et) were prepared from substituted 2,3-dihydro-1H-isoindol-1-ones by regiospecific O-alkylation with trialkyloxonium tetrafluoroborates or with trifluoromethanesulfonates, and subsequent NH deprotonation. According to the spectroscopic properties, the semicyclic alkyl imidates I exist exclusively in the benzenoid 1H structure; the tautomeric o-quinonoid 2H structure cannot be detected by spectroscopic means. In the experiment, the researchers used many compounds, for example, 6-Nitroisoindolin-1-one (cas: 110568-64-4Recommanded Product: 6-Nitroisoindolin-1-one).

Fang, Ling et al. published their research in Chemistry – A European Journal in 2009 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Reference of 14204-27-4

Highly Enantioselective Sulfenylation of 尾-Ketoesters: H-Bond Acceptor Catalysis was written by Fang, Ling;Lin, Aijun;Hu, Hongwen;Zhu, Chengjian. And the article was included in Chemistry – A European Journal in 2009.Reference of 14204-27-4 This article mentions the following:

The 伪,伪-diaryl prolinol catalyzed sulfenylation of 尾-ketoesters for the construction of quaternary carbon centers with excellent enantioselectivity and good yield was succeeded developed. Studies suggested that the activation mode involved a mol. interaction rather than a covalent bond. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Reference of 14204-27-4).

Oderinde, Martins S. et al. published their research in Journal of Organic Chemistry in 2021 | CAS: 210345-56-5

Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5) 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.Name: Methyl 5-bromo-1H-indole-2-carboxylate

Photocatalytic Dearomative Intermolecular [2 + 2] Cycloaddition of Heterocycles for Building Molecular Complexity was written by Oderinde, Martins S.;Ramirez, Antonio;Dhar, T. G. Murali;Cornelius, Lyndon A. M.;Jorge, Christine;Aulakh, Darpandeep;Sandhu, Bhupinder;Pawluczyk, Joseph;Sarjeant, Amy A.;Meanwell, Nicholas A.;Mathur, Arvind;Kempson, James. And the article was included in Journal of Organic Chemistry in 2021.Name: Methyl 5-bromo-1H-indole-2-carboxylate This article mentions the following:

Indole and indoline rings are important pharmacophoric scaffolds found in marketed drugs, agrochems., and biol. active mols. The [2 + 2] cycloaddition reaction is a versatile strategy for constructing architecturally interesting, sp³-rich cyclobutane-fused scaffolds with potential applications in drug discovery programs. A general platform for visible-light mediated intermol. [2 + 2] cycloaddition of indoles with alkenes has been realized. A substrate-based screening approach led to the discovery of tert-butyloxycarbonyl (Boc)-protected indole-2-carboxyesters as suitable motifs for the intermol. [2 + 2] cycloaddition reaction. Significantly, the reaction proceeds in good yield with a wide variety of both activated and unactivated alkenes, including those containing free amines and alcs., and the transformation exhibits excellent regio- and diastereoselectivity. Moreover, the scope of the indole substrate is very broad, extending to previously unexplored azaindole heterocycles that collectively afford fused cyclobutane containing scaffolds that offer unique properties with functional handles and vectors suitable for further derivatization. DFT computational studies provide insights into the mechanism of this [2 + 2] cycloaddition, which is initiated by a triplet-triplet energy transfer process. The photocatalytic reaction was successfully performed on a 100 g scale to provide the dihydroindole analog. In the experiment, the researchers used many compounds, for example, Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5Name: Methyl 5-bromo-1H-indole-2-carboxylate).

Priyanka, K. Blessi et al. published their research in World Journal of Pharmacy and Pharmaceutical Sciences in 2014 | CAS: 112656-95-8

7-Nitroindoline-2,3-dione (cas: 112656-95-8) 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.Computed Properties of C8H4N2O4

Synthesis and evaluation of new isatin derivatives for cytotoxic activity was written by Priyanka, K. Blessi;Manasa, C.;Sammaiah, G.. And the article was included in World Journal of Pharmacy and Pharmaceutical Sciences in 2014.Computed Properties of C8H4N2O4 This article mentions the following:

A series of semicarbazones I (R = 5-Br, 7-NO₂, 5-CH₃, etc.) was synthesized and screened for their cytotoxic activity by MTT assay method. All synthesized compounds I exhibited significant cytotoxicity in a concentration-dependent manner. The IC₅₀ values of all test compounds I were found to be between 19.27 and 52.45 mM for MCF-7 cell lines and between 14.10 and 31.6 mM for HeLa cell lines. All the synthesized compounds have shown moderate antioxidant activity. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Computed Properties of C8H4N2O4).