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Nazare, Marc et al. published their research in Journal of Medicinal Chemistry in 2005 | CAS: 210345-56-5

Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Name: Methyl 5-bromo-1H-indole-2-carboxylate

Probing the Subpockets of Factor Xa Reveals Two Binding Modes for Inhibitors Based on a 2-Carboxyindole Scaffold: A Study Combining Structure-Activity Relationship and X-ray Crystallography was written by Nazare, Marc;Will, David W.;Matter, Hans;Schreuder, Herman;Ritter, Kurt;Urmann, Matthias;Essrich, Melanie;Bauer, Armin;Wagner, Michael;Czech, Joerg;Lorenz, Martin;Laux, Volker;Wehner, Volkmar. And the article was included in Journal of Medicinal Chemistry in 2005.Name: Methyl 5-bromo-1H-indole-2-carboxylate This article mentions the following:

Structure-activity relationships within a series of highly potent 2-carboxyindole-based factor Xa inhibitors incorporating a neutral P1 ligand are described with particular emphasis on the structural requirements for addressing subpockets of the factor Xa enzyme. Interactions with the subpockets were probed by systematic substitution of the 2-carboxyindole scaffold, in combination with privileged P1 and P4 substituents. Combining the most favorable substituents at the indole nucleus led to the discovery of a remarkably potent factor Xa inhibitor displaying a K_i value of 0.07 nM. X-ray crystallog. of inhibitors bound to factor Xa revealed substituent-dependent switching of the inhibitor binding mode and provided a rationale for the SAR obtained. These results underscore the key role played by the P1 ligand not only in determining the binding affinity of the inhibitor by direct interaction but also in modifying the binding mode of the whole scaffold, resulting in a nonlinear SAR. 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).

Referemce:
Indole alkaloid derivatives as building blocks of natural products from鑱紹acillus thuringiensis鑱絘nd鑱紹acillus velezensis鑱絘nd their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Bures, Jordi et al. published their research in Organic Letters in 2007 | 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Category: indole-building-block

Efficient preparation of N-phenylsulfenyl ketimines from oximes or nitro compounds without racemization of 浼?stereocenters was written by Bures, Jordi;Isart, Carles;Vilarrasa, Jaume. And the article was included in Organic Letters in 2007.Category: indole-building-block This article mentions the following:

As N-sulfenyl imines, e.g., I, could be readily transformed to their N-sulfinyl imines, N-sulfonyl imines , and N-sulfonyl oxaziridines, the very mild procedure developed to convert ketoximes and secondary nitro derivatives to N-arenesulfenyl ketimines constituted an efficient route to all these series of compounds The configuration of the 浼?stereocenters was retained. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Category: indole-building-block).

Marasek-Ciolakowska, Agnieszka et al. published their research in International Journal of Molecular Sciences in 2020 | CAS: 1912-45-4

2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. 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). Quality Control of 2-(5-Chloro-1H-indol-3-yl)acetic acid

Formation of the secondary abscission zone induced by the interaction of methyl jasmonate and auxin in Bryophyllum calycinum: relevance to auxin status and histology was written by Marasek-Ciolakowska, Agnieszka;Saniewski, Marian;Dziurka, Michal;Kowalska, Urszula;Goraj-Koniarska, Justyna;Ueda, Junichi;Miyamoto, Kensuke. And the article was included in International Journal of Molecular Sciences in 2020.Quality Control of 2-(5-Chloro-1H-indol-3-yl)acetic acid This article mentions the following:

The interaction of Me jasmonate (JA-Me) and indole-3-acetic acid (IAA) to induce the formation of the secondary abscission zone in the middle of internode segments of Bryophyllum calycinum was investigated in relation to auxin status and histol. When IAA at 0.1% (weight/weight, in lanolin) was applied to the segments, the formation of the secondary abscission zone at a few mm above the treatment in the apical direction was observed On the contrary, IAA at 0.5% (weight/weight, in lanolin) did not induce the formation of the secondary abscission zone. JA-Me at 0.5% (weight/weight, in lanolin) applied to the middle of internode segments kept in the normal (natural) or inverted positions also induced the formation of the secondary abscission zone below and above parts of the treatment. Comprehensive analyses of plant hormones revealed that the balance of the endogenous levels of IAA in both sides adjacent to the abscission zone was significantly disturbed when the secondary abscission formation was induced by the application of IAA. These results strongly suggest that an auxin gradient is important in the formation of the secondary abscission zone in the internode segments of B. calycinum, and IAA gradient results from polar IAA transport from the application site. Further possible mechanisms of the formation of the secondary abscission zone in the internode segments of B. calycinum are also discussed in the interaction of JA-Me and IAA. In the experiment, the researchers used many compounds, for example, 2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4Quality Control of 2-(5-Chloro-1H-indol-3-yl)acetic acid).

Cele, Zamani E. D. et al. published their research in European Journal of Organic Chemistry in 2015 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Product Details of 14204-27-4

Applied Enantioselective Aminocatalysis: 浼?Heteroatom Functionalization Reactions on the Carbapenem (灏?Lactam Antibiotic) Core was written by Cele, Zamani E. D.;Arvidsson, Per I.;Kruger, Hendrik G.;Govender, Thavendran;Naicker, Tricia. And the article was included in European Journal of Organic Chemistry in 2015.Product Details of 14204-27-4 This article mentions the following:

The carbapenem (灏?lactam antibiotic) scaffold serves as a useful nucleophile in organocatalytic diarylprolinol trimethylsilyl ether mediated 浼?heterofunctionalization reactions leading to the formation of diverse products that bear multiple stereocenters in high diastereoselectivity and moderate to good yields. Under optimized conditions the synthesis of the target compounds was achieved using (2S)-2-[diphenyl[(trimethylsilyl)oxy]methyl]pyrrolidine (chiral prolinol-silyl ether) as a catalyst. Starting materials included (5R,6S)-6-[(1R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (4-nitrophenyl)methyl ester, 1,2-diazenedicarboxylic acid, 1,2-bis(1,1-dimethylethyl) ester, N-(hydroxy)carbamic acid ester, (nitros)benzene,2-(phenylthio)-1H-isoindole-1,3(2H)-dione, 2-(phenylseleno)-1H-i-Isoindole-1,3(2H)-dione. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Product Details of 14204-27-4).

Najafi, Meysam et al. published their research in Monatshefte fuer Chemie in 2014 | CAS: 320734-35-8

7-Bromooxindole (cas: 320734-35-8) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Computed Properties of C8H6BrNO

On the antioxidant activity of ortho- and meta-substituted indolin-2-one derivatives was written by Najafi, Meysam. And the article was included in Monatshefte fuer Chemie in 2014.Computed Properties of C8H6BrNO This article mentions the following:

The antioxidant activity of ortho- and meta-substituted indolin-2-one derivatives was investigated in the gas phase and water. The reaction enthalpies of the individual steps of three antioxidant mechanisms of the studied derivatives were calculated and compared with the corresponding values of indolin-2-one. The results show that electron-withdrawing substituents increase the bond dissociation enthalpy and ionization potential, whereas electron-donating substituents increase the proton affinity. The indolin-2-one derivatives with the lowest bond dissociation enthalpy, ionization potential, and proton affinity values were identified as the compounds with high antioxidant activity. The results show that indolin-2-one derivatives with substituents in the ortho position are promising potential novel antioxidants. The results also show that the protective role of indolin-2-one derivatives occurs via hydrogen atom transfer and a sequential proton loss electron transfer mechanism in the gas phase and water, resp. The calculated reaction enthalpies of the substituted indolin-2-ones are linearly dependent on the Hammett constants and E_HOMO such that the latter can be utilized in the selection of suitable substituents for the synthesis of novel antioxidants based on indolin-2-one. In the experiment, the researchers used many compounds, for example, 7-Bromooxindole (cas: 320734-35-8Computed Properties of C8H6BrNO).

Prey, V. et al. published their research in Monatshefte fuer Chemie in 1958 | 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. 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). Electric Literature of C14H11NO

1-Thiophthalide was written by Prey, V.;Kondler, P.. And the article was included in Monatshefte fuer Chemie in 1958.Electric Literature of C14H11NO This article mentions the following:

Treatment of 1-thiophthalide (I) with PhNH₂ at 190鎺?in a bomb tube resulted in a rearrangement to 2-thiophthalide (II). The mechanism of the rearrangement is discussed. Phthalide (6.7 g.) and 11.1 g. P₂S₅ in xylene refluxed 1 hr., the mixture filtered hot, the filtrate steam distilled, the residue cooled, the oily product filtered off, pressed, and recrystallized twice from absolute EtOH gave 4.5 g. I, m. 108-9鎺? mol. weight 148.6. Proof of structure was supported by hydrolysis of I to phthalide, m. 73鎺? detection of the CS group by treatment of I with 0.5N alc. KOH and several drops of 30% H₂O₂, warming, cooling, acidifying, and adding BaCl₂ to obtain BaSO₄, and detection of the CS group by Grote’s test (C.A. 25, 5876). I treated with HgCl₂ 1 in Et₂O 15 parts gave I-Hg Cl₂ adduct (III), decompose 185鎺? III treated with saturated aqueous KI decomposed with the formation of HgS. I (2.0 g.) and 5.0 g. freshly distilled PhNH₂ refluxed 5 hrs. at 185鎺? cooled, the precipitate filtered off, and washed with dilute HCl and dried gave 1.02 g. N-phenylphthalimidine (IV), m. 165鎺? from the filtrate was obtained 0.7 g. addnl. IV. I (2.0 g.) and 5.0 g. PhNH₂ heated 3 hrs. at 190鎺?in a bomb tube, the mixture treated with dilute HCl, the oily precipitate dried in vacuo, taken up in EtOH, filtered, EtOH removed from the filtrate, and the product recrystallized from tetrahydrofuran with C and then from H₂O gave 1.65 g. II, white needles, m. 57-8鎺? I and PhNH₂ heated 3 hrs. at 240鎺?in a bomb tube gave 94% IV, m. 164鎺? II (2.0 g.) and 5.0 g. PhNH₂ refluxed 12 hrs. at 185鎺? cooled, the mixture treated with 50 cc. 20% HCl, and the resulting precipitate crystallized from EtOH gave 1.8 g. unchanged II, m. 57-8鎺? II (2 g.) and 5.0 g. PhNH₂ heated 3 hrs. at 190鎺?gave 95% unchanged II, but this mixture heated 3 hrs. at 240鎺?gave 2.45 g. IV, m. 164-5鎺? IV (2.0 g.) and 5.0 g. PhNH₂ contained in a bomb tube treated with dry H₂S with cooling at -78鎺? the tube sealed, and heated 3 hrs. at 190鎺?gave only unchanged IV. A similar result was obtained by heating at 240鎺? I (2.0 g.) and 5.8 g. PhNHMe refluxed 4.5 hrs. gave only 1.8 g. unchanged I. A similar result was obtained by heating 3 hrs. at 190鎺? Similar unsuccessful results were obtained using I and PhNMe, I being recovered. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Electric Literature of C14H11NO).

Woldegiorgis, Alemayehu Gashaw et al. published their research in Organic Letters in 2022 | CAS: 320734-35-8

7-Bromooxindole (cas: 320734-35-8) 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 was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Application of 320734-35-8

Asymmetric [3 + 3] Annulation to Construct Trifluoromethylated Pyrazolo[3,4-b]pyridin-6-ones via Chiral Phosphoric Acid and MgSO₄ Synergistic Catalysis was written by Woldegiorgis, Alemayehu Gashaw;Han, Zhao;Lin, Xufeng. And the article was included in Organic Letters in 2022.Application of 320734-35-8 This article mentions the following:

A novel asym. Friedel-Crafts alkylation/transamidation tandem reaction for the enantio- and diastereoselective synthesis of pyrazolo[3,4-b]pyridin-6-ones I (R = H, Me, Cl; R¹ = H, OMe, Br, Cl, F; R² = H, Me, Br, F; R³ = H, Br; R⁴ = Boc, Cbz; R⁵ = H, Et, i-Pr; R⁶ = Ph, 3-bromophenyl, 1H-benzo[d]imidazol-2-yl, etc.; R⁷ = Me, Et, i-Pr, Ph) bearing a -CF₃ unit via synergistic chiral phosphoric acid and MgSO₄ catalysis was developed. This [3 + 3] annulation protocol allows the formation of trifluoromethylated pyrazolo[3,4-b]pyridin-6-ones I with two adjacent tertiary stereocenters in moderate to high yields (up to 90%), enantioselectivities (up to 97% ee), and diastereoselectivities (up to >20:1 dr). In the experiment, the researchers used many compounds, for example, 7-Bromooxindole (cas: 320734-35-8Application of 320734-35-8).

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

Nazare, Marc et al. published their research in Journal of Medicinal Chemistry in 2005 | CAS: 210345-56-5

Bures, Jordi et al. published their research in Organic Letters in 2007 | CAS: 14204-27-4

Efficient preparation of N-phenylsulfenyl ketimines from oximes or nitro compounds without racemization of α-stereocenters was written by Bures, Jordi;Isart, Carles;Vilarrasa, Jaume. And the article was included in Organic Letters in 2007.Category: indole-building-block This article mentions the following:

As N-sulfenyl imines, e.g., I, could be readily transformed to their N-sulfinyl imines, N-sulfonyl imines , and N-sulfonyl oxaziridines, the very mild procedure developed to convert ketoximes and secondary nitro derivatives to N-arenesulfenyl ketimines constituted an efficient route to all these series of compounds The configuration of the α-stereocenters was retained. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Category: indole-building-block).