Category: 210345-56-5

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).

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

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

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).

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

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

Design, synthesis, and biological evaluation of novel trifluoromethyl indoles as potent HIV-1 NNRTIs with an improved drug resistance profile was written by Jiang, Hai-Xia;Zhuang, Dao-Min;Huang, Ying;Cao, Xing-Xin;Yao, Jian-Hua;Li, Jing-Yun;Wang, Jian-Yong;Zhang, Chen;Jiang, Biao. And the article was included in Organic & Biomolecular Chemistry in 2014.HPLC of Formula: 210345-56-5 This article mentions the following:

A novel series of trifluoromethyl indole derivatives have been designed, synthesized and evaluated for anti-HIV-1 activities in MT-2 cells. The hydrophobic constant, acute toxicity, carcinogenicity and mutagenicity were predicted. Trifluoromethyl indoles (I) and (II) showed extremely promising activities against WT HIV-1 with IC₅₀ values at the low nanomolar level, similar to efavirenz, better than nevirapine, and also possessed higher potency towards the drug-resistant mutant strain Y181C than nevirapine. Preliminary SAR and docking studies of detailed binding mode provided some insights for discovery of more potent NNRTIs. In the experiment, the researchers used many compounds, for example, Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5HPLC of Formula: 210345-56-5).

Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5) 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.HPLC of Formula: 210345-56-5

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

Simple syntheses of 5-fluoro/ chloro/ bromoindole-2-methanols and 5-fluoro/ chloro/ bromoindole-2-aldehydes was written by Narayana, B.;Ashalatha, B. V.;Raj, K. K. Vijaya. And the article was included in Organic Chemistry: An Indian Journal in 2006.Recommanded Product: Methyl 5-bromo-1H-indole-2-carboxylate This article mentions the following:

Efficient and simple methods for the syntheses of 5-haloindole-2-methanols and 5-haloindole-2-aldehydes have been described. 5-Haloindole-2-methanols were prepared by reduction of Me 5-haloindole-2-carboxylates with sodium borohydride in methanol/ THF media and 5-haloindole-2-aldehydes were prepared from the prepared 5-haloindole-2-methanols by oxidation with pyridinium chlorochromate or chromium trioxide-pyridine prepared in situ. The synthesized compounds were isolated in good yields and characterized by ¹H NMR, ¹³C NMR, FABMS and elemental anal. In the experiment, the researchers used many compounds, for example, Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5Recommanded Product: Methyl 5-bromo-1H-indole-2-carboxylate).

Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5) 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Recommanded Product: Methyl 5-bromo-1H-indole-2-carboxylate

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

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).

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

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

[Fe(F₂₀TPP)Cl] catalyzed intramolecular C-N bond formation for alkaloid synthesis using aryl azides as nitrogen source was written by Liu, Yungen;Wei, Jinhu;Che, Chi-Ming. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2010.Recommanded Product: 210345-56-5 This article mentions the following:

The syntheses of alkaloids including indoles, indolines, tetrahydroquinolines, dihydroquinazolinones and quinazolinones were accomplished in moderate to excellent yields via [Fe(F₂₀TPP)Cl] (I) catalyzed intramol. C-N bond formation using aryl azides as nitrogen source. E.g., dihydroquinazolinone derivative II was prepared with 83% yield by refluxing N₃-2-C₆H₄CON(CH₂Ph)₂ with I in (ClCH₂)₂. In the experiment, the researchers used many compounds, for example, Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5Recommanded Product: 210345-56-5).

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

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

New Arylthioindoles and Related Bioisosteres at the Sulfur Bridging Group. 4. Synthesis, Tubulin Polymerization, Cell Growth Inhibition, and Molecular Modeling Studies was written by La Regina, Giuseppe;Sarkar, Taradas;Bai, Ruoli;Edler, Michael C.;Saletti, Roberto;Coluccia, Antonio;Piscitelli, Francesco;Minelli, Lara;Gatti, Valerio;Mazzoccoli, Carmela;Palermo, Vanessa;Mazzoni, Cristina;Falcone, Claudio;Scovassi, Anna Ivana;Giansanti, Vincenzo;Campiglia, Pietro;Porta, Amalia;Maresca, Bruno;Hamel, Ernest;Brancale, Andrea;Novellino, Ettore;Silvestri, Romano. And the article was included in Journal of Medicinal Chemistry in 2009.HPLC of Formula: 210345-56-5 This article mentions the following:

A series of arylthioindoles, e.g., I (X = S, R¹ = H, CO₂Me, CO₂Et, R² = H, Cl, Br, OMe), the corresponding ketones I (X = CO) and diarylmethanes I (X = CH₂), as well as pyrrole II (Y = CH₂, CO, Z = CH, R³ = CO₂Et, R⁴ = R⁵ = H; etc.) and imidazole analogs II (Y = CO, Z = N, R³ = R⁵ = H, R⁴ = CO₂Et; etc.) were synthesized and their activity as tubulin polymerization and cancer cell growth inhibitors assessed. As growth inhibitors of MCF-7 cells, sulfur derivatives were superior or sometimes equivalent to the ketones, while methylene derivatives were substantially less effective. Indoles I (X = S, R¹ = H, R² = Br; X = S, CO, CH₂, R¹ = CO₂Me, R² = Br, OMe) showed ∼50% of inhibition on human HeLa and HCT116/chr3 cells at 0.5 μM, and these compounds inhibited the growth of HEK, M14, and U937 cells with IC₅₀‘s in the 78-220 nM range. While murine macrophage J744.1 cell growth was significantly less affected (20% at higher concentrations), four other non-transformed cell lines remained sensitive to these indoles. The effect of drug treatment on cell morphol. was examined by time-lapse microscopy. In a protocol set up to evaluate toxicity on the Saccharomyces cerevisiae BY4741 wild type strain, compounds I (X = S, R¹ = H, R² = Br) and II (Y = CH₂, Z = CH, R³ = CO₂H, R⁴ = R⁵ = H) strongly reduced cell growth, and I (X = CH₂, R¹ = CO₂Me, R² = Br; X = S, CO, R¹ = CO₂Me, R² = OMe) also showed significant inhibition. In the experiment, the researchers used many compounds, for example, Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5HPLC of Formula: 210345-56-5).

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

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