February 2023 - Page 107 of 117 - Indole Building Blocks

Ghorab, M. M. et al. published their research in Phosphorus, Sulfur and Silicon and the Related Elements in 1998 | CAS: 24407-32-7

4,5,6,7-Tetrabromoisoindoline-1,3-dione (cas: 24407-32-7) 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.Category: indole-building-block

Synthesis of some sulfur containing tetrahydrobenzo[b]thieno(pyridines, quinolines, oxazines and pyrimidines) as possible radioprotective and antineoplastic agents was written by Ghorab, M. M.;Nassar, O. M.;Hassan, A. Y.. And the article was included in Phosphorus, Sulfur and Silicon and the Related Elements in 1998.Category: indole-building-block This article mentions the following:

Synthesis of novel benzothienopyridines, benzothienoquinoline, benzothienoxazines and benzothienopyrimidines utilizing 2-methyl-5,6,7,8-tetrahydro-4H-3,1-benzothienoxazine-4-one are reported. Preliminary biol. studies of some compounds showed a promising radioprotection and antineoplastic activities. In the experiment, the researchers used many compounds, for example, 4,5,6,7-Tetrabromoisoindoline-1,3-dione (cas: 24407-32-7Category: indole-building-block).

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

Meyer, Kerstin U. et al. published their research in Journal of the Chemical Society, Perkin Transactions 1 in 2001 | CAS: 4583-55-5

5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5) 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Recommanded Product: 4583-55-5

Novel bis(tetrahydropyrrolo[3,4-b]carbazoles) linked with aliphatic chains: synthesis and structural aspects was written by Meyer, Kerstin U.;Pindur, Ulf. And the article was included in Journal of the Chemical Society, Perkin Transactions 1 in 2001.Recommanded Product: 4583-55-5 This article mentions the following:

Dehydrohalogenation of 2,3-bis(bromomethyl)-1H-indole-1-carboxylic acid Me ester gave 2,3-dihydro-2,3-bis(methylene)-1H-indole-1-carboxylic acid Me ester derivatives Diels-Alder reaction of these 2,3-dihydro-2,3-bis(methylene)-1H-indole-1-carboxylic acid Me ester derivatives with N,N‘-trimethylenedimaleimide, N,N‘-tetramethylenedimaleimide, or N,N‘-dodecamethylenedimaleimide gave 2,2’-(alkanediyl)bis[dioxopyrrolo[3,4-b]carbazolecarboxylate] derivatives (i.e., the title compounds containing aliphatic chain linkages). These conformationally highly flexible mols. represent an interesting class of compounds, believed to have an affinity towards DNA, as potential DNA ligands. Pharmacol. test data were not reported. In the experiment, the researchers used many compounds, for example, 5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5Recommanded Product: 4583-55-5).

Porter, William L. et al. published their research in Phytochemistry (Elsevier) in 1965 | CAS: 1912-45-4

2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Related Products of 1912-45-4

Molecular requirements for auxin activity. I. Halogenated indoles and indoleacetic acid was written by Porter, William L.;Thimann, Kenneth V.. And the article was included in Phytochemistry (Elsevier) in 1965.Related Products of 1912-45-4 This article mentions the following:

2-Chloroindoleacetic acid had 350% of the activity of indoleacetic acid (IAA) in the pea curvature test; the 2-bromo analog had 160% activity and the corresponding Me and Et esters were even more active. In a series of these and other IAA derivatives, the log of the growth activity is a linear function of the NH stretching frequency in the ir spectra and of the Hammett sigma value for the substituent. In the experiment, the researchers used many compounds, for example, 2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4Related Products of 1912-45-4).

Ma, Dengke et al. published their research in Angewandte Chemie, International Edition in 2019 | CAS: 4583-55-5

5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5) 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Computed Properties of C10H10BrN

Organocatalytic Enantioselective Functionalization of Unactivated Indole C(sp³)-H Bonds was written by Ma, Dengke;Zhang, Zhihan;Chen, Min;Lin, Zhenyang;Sun, Jianwei. And the article was included in Angewandte Chemie, International Edition in 2019.Computed Properties of C10H10BrN This article mentions the following:

Described here is a direct catalytic asym. functionalization of unactivated alkyl indoles using organocatalysis. In the presence of an effective chiral urea catalyst and a phosphoric acid additive, the intermol. C-C bond formation between alkyl indoles and trifluoropyruvates proceeded with high efficiency and enantiocontrol. Unlike previous asym. C(sp³-H) functionalizations of α-azaarenes, this process does not require the use of either a strong base or an electron-deficient substrate. The excellent enantiocontrol is particularly noteworthy in view of the severe background reaction as well as the complete inability of other types of catalysts evaluated. Control experiments, kinetic studies, and DFT calculations provided important insights into the mechanism. In the experiment, the researchers used many compounds, for example, 5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5Computed Properties of C10H10BrN).

Coyle, Robert et al. published their research in Journal of Organic Chemistry in 2014 | 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. 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

Tandem Reactions via Barton Esters with Intermolecular Addition and Vinyl Radical Substitution onto Indole was written by Coyle, Robert;McArdle, Patrick;Aldabbagh, Fawaz. And the article was included in Journal of Organic Chemistry in 2014.Category: indole-building-block This article mentions the following:

A one-pot initiator-free Barton ester decomposition with tandem radical addition onto alkyl propiolates or phenylacetylene with aromatic substitution of the resultant vinyl radical allows convenient access to new 9-substituted 6,7-dihydropyrido[1,2-a]indoles, e.g., I (X = Me, CHO, CN; R = Me, Et, t-Bu). Pr radical cyclizations compete when forming the expanded 7,8-dihydro-6H-azepino[1,2-a]indole system. 2-Thiopyridinyl S-radical is incorporated into aromatic adducts when using unsubstituted indole-1-alkanoic acid precursors. X-ray crystallog. on substitution products allows selectivity of the radical addition onto less reactive internal alkynes to be determined In the experiment, the researchers used many compounds, for example, 3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1Category: indole-building-block).

Oseka, Maksim et al. published their research in Organic Letters in 2016 | CAS: 112656-95-8

7-Nitroindoline-2,3-dione (cas: 112656-95-8) 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Synthetic Route of C8H4N2O4

Asymmetric Organocatalytic Wittig [2,3]-Rearrangement of Oxindoles was written by Oseka, Maksim;Kimm, Mariliis;Kaabel, Sandra;Jarving, Ivar;Rissanen, Kari;Kanger, Tonis. And the article was included in Organic Letters in 2016.Synthetic Route of C8H4N2O4 This article mentions the following:

A highly enantioselective organocatalytic [2,3]-rearrangement of oxindole derivatives is presented. The reaction was catalyzed by squaramide, and this provides access to 3-hydroxy 3-substituted oxindoles I and II (Ar = Ph, 4-ClC₆H₄, 3-ClC₆H₄, 2-ClC₆H₄, 4-MeOC₆H₄, 4-NO₂C₆H₄, 2-thienyl, 2-naphthyl, etc.; R¹ = H, 5-F, 7-F, 5-MeO, 5-Br, 7-NO₂, etc.; R² = H, Bn, Me, i-Pr, 4-MeC₆H₄CH₂) in high enantiomeric purities. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Synthetic Route of C8H4N2O4).

Foa, M. et al. published their research in Journal of Organometallic Chemistry in 1985 | 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Quality Control of 2-Phenylisoindolin-1-one

Cobalt-catalyzed carbonylation of aryl halides was written by Foa, M.;Francalanci, F.;Bencini, E.;Gardano, A.. And the article was included in Journal of Organometallic Chemistry in 1985.Quality Control of 2-Phenylisoindolin-1-one This article mentions the following:

Carbonylation of aromatic and heteroaromatic halides with a catalytic system of alkylcobalt carbonyl complexes, either preformed or made in situ, and bases such as alkoxides, NaOH, and K₂CO₃ in aliphatic alcs produced aromatic esters, acids, lactones, and lactams in high yield and under mild conditions. New anionic cobalt complexes were formed which were characterized by high reactivity toward aromatic halides. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Quality Control of 2-Phenylisoindolin-1-one).

Kovtunenko, V. A. et al. published their research in Khimiya Geterotsiklicheskikh Soedinenii in 1984 | CAS: 5388-42-1

1-Ethylthio-2R-isoindoles. An example of nonsynchronous addition in the Diels-Alder reaction was written by Kovtunenko, V. A.;Dobrenko, T. T.;Voitenko, Z. V.;Tyltin, A. K.;Babichev, F. S.. And the article was included in Khimiya Geterotsiklicheskikh Soedinenii in 1984.Product Details of 5388-42-1 This article mentions the following:

Treating isoindolinones I (R = Me, Ph, p-MeC₆H₄, p-MeOC₆H₄, X = O) with P₂S₅ in refluxing pyridine gave 53-70% I (X = S) which were converted to 50-80% indolium salts II by treatment with Meerwein’s reagent. Treating II with dry base gave 45-50% III which underwent an non-synchronous Diels-Alder addition with N-phenyl- or N-(p-methoxyphenyl)maleimides to give 90% adducts IV (R¹ = p-MeOC₆H₄ or Ph) or V. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Product Details of 5388-42-1).

Inoue, Kengo et al. published their research in Chemistry – A European Journal in 2021 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) 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.Application In Synthesis of 2-(Phenylthio)isoindoline-1,3-dione

“Snapshot” Trapping of Multiple Transient Azolyllithiums in Batch was written by Inoue, Kengo;Feng, Yuxuan;Mori, Atsunori;Okano, Kentaro. And the article was included in Chemistry – A European Journal in 2021.Application In Synthesis of 2-(Phenylthio)isoindoline-1,3-dione This article mentions the following:

Recent developments in flow microreactor technol. have allowed the use of transient organolithium compounds that cannot be realized in a batch reactor. However, trapping the transient aryllithiums in a halogen dance is still challenging. Herein is reported the trapping of such short-lived azolyllithiums in a batch reactor by developing a finely tuned in situ zincation using Zn halide diamine complexes. The reaction rate is controlled by the appropriate choice of diamine ligand. The reaction is operationally simple and can be performed at 0° with high reproducibility on a multigram scale. This method was applicable to a wide range of brominated azoles allowing deprotonative functionalization, which was used for the concise divergent syntheses of both constitutional isomers of biol. active azoles. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Application In Synthesis of 2-(Phenylthio)isoindoline-1,3-dione).

Gao, Xing et al. published their research in Synthesis in 2016 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. 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 14204-27-4

Chiral Iminophosphorane Organocatalyzed Asymmetric Sulfenylation of 3-Substituted Oxindoles: Substrate-Interrelated Enantioselectivities was written by Gao, Xing;Han, Jianwei;Wang, Limin. And the article was included in Synthesis in 2016.Application of 14204-27-4 This article mentions the following:

Catalytic asym. sulfenylation of 3-substituted oxindoles has been developed through efficient catalysis by tartaric acid derived chiral iminophosphoranes. With N-(phenylthio)phthalimide as the sulfur source, a wide range of optically active 3-phenylthiooxindoles were obtained in excellent yields (90-99%) and good enantiomeric excess (up to 90% ee). Interestingly, 3-aryl and 3-Me substituted oxindoles afforded sulfenylated products I (R¹ = Ph, Me, 2-naphthyl, 4-MeC₆H₄, 4-MeOC₆H₄, 4-FC₆H₄; R² = H, 5-Me, 5-MeO, 5-F, etc.) in S-configuration, whereas substituted oxindoles with 3-arylidene or 3-iso-Bu substituents gave the corresponding R-configured sulfenylated products II (R¹ = Bn, i-Bu, 4-MeC₆H₄CH₂, 4-MeOC₆H₄CH₂, 4-FC₆H₄CH₂; R² = H, 5-Me, 5-MeO, 5-F, etc). In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Application of 14204-27-4).