Month: January 2023

A General Strategy Toward Aromatic 1,2-Ambiphilic Synthons: Palladium-Catalyzed ortho-Halogenation of PyDipSi-Arenes was written by Dudnik, Alexander S.;Chernyak, Natalia;Huang, Chunhui;Gevorgyan, Vladimir. And the article was included in Angewandte Chemie, International Edition in 2010.Name: 5-Bromo-2,3-dimethyl-1H-indole This article mentions the following:

1,2-Amphiphilic aromatic and heteroaromatic synthons were prepared by conversion of haloarenes to aryl(2-pyridinyl)diisopropylsilanes, halogenating these on the aromatic ring, and replacement of the pyridinyldiisopropylsilyl group. In the experiment, the researchers used many compounds, for example, 5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5Name: 5-Bromo-2,3-dimethyl-1H-indole).

5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5) 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.Name: 5-Bromo-2,3-dimethyl-1H-indole

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

Chemometric and molecular modeling study of 1H-indole-3-acetic acid derivatives with auxin activity was written by Kiralj, Rudolf;Ferreira, Marcia M. C.. And the article was included in Croatica Chemica Acta in 2005.Recommanded Product: 2-(5-Chloro-1H-indol-3-yl)acetic acid This article mentions the following:

Quant. Structure-Activity Relationship (QSAR) study on 22 1H-indole-3-acetic acid derivatives with auxin activity was performed by Principal Component Anal. (PCA), Hierarchical Cluster Anal. (HCA), Partial Least Squares Regression (PLS) and Multiple Linear Regression (MLR). Mol. geometry of the auxins was optimized at MMFF94 and ab initio B3LYP 6-31G** levels. Modeling of complexes of some auxin mols. with the auxin binding protein 1 (ABP1) was also carried out. Parsimonius PLS and MLR models for prediction of optimal and half-optimal auxin concentrations for Avena L. Sativa coleoptile elongation were obtained with 15 auxins in the training set. HCA and PCA on data for the half-optimal concentration exhibit auxin clustering with respect to substituent type and position, biol. activity, and the size of the active site pockets of ABP1. Mol. graphics of ABP1 – NAA derivative complexes and of the coordination spheres around NAA (1-naphthalenic acid) hydrogen atoms in the ABP1 – NAA complex agrees well with the chemometrics/QSAR results. In the experiment, the researchers used many compounds, for example, 2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4Recommanded Product: 2-(5-Chloro-1H-indol-3-yl)acetic acid).

2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4) 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.Recommanded Product: 2-(5-Chloro-1H-indol-3-yl)acetic acid

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

N’-[(5-Chloro-1H-indol-3-yl)methylene]-3,4,5-trihydroxybenzohydrazide was written by Khaledi, Hamid;Mohd Ali, Hapipah;Ng, Seik Weng. And the article was included in Acta Crystallographica, Section E: Structure Reports Online in 2009.Computed Properties of C9H6ClNO This article mentions the following:

The two aromatic parts of the title compound, C₁₆H₁₃ClN₃O₄, are connected through a conjugated -CH=N-NH-C(O)- fragment, giving an almost planar mol. (r.m.s. deviation 0.08 Å). In the crystal structure, adjacent mols. are linked by N-H···O and O-H···O hydrogen bonds into a three-dimensional network. Crystallog. data are given. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Computed Properties of C9H6ClNO).

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) 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. 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

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

eCF309: a potent, selective and cell-permeable mTOR inhibitor was written by Fraser, Craig;Carragher, Neil O.;Unciti-Broceta, Asier. And the article was included in MedChemComm in 2016.Recommanded Product: 7-Azaindole-5-boronic Acid Pinacol Ester This article mentions the following:

Kinase inhibitors capable of blocking the phosphorylation of protein substrates with high selectivity are essential to probe and elucidate the etiol. role of such mols. and their signalling pathways. By addressing these biochem. questions in disease relevant cell-based and in vivo models, strong pharmacol. evidence can be generated towards validating or disproving a target hypothesis. Pharmacol. studies can also provide fundamental information to identify appropriate biomarkers and rational drug combination strategies and thereby facilitate clin. translation. However, due to the high number of kinases encoded by the human genome (>500) and their highly conserved catalytic domains, the development of such an elite class of inhibitors-a.k.a. high-quality chem. probes-represents a major challenge. Through a ligand-based inhibitor design, focused library synthesis and phenotypic screening to prioritize compounds with potent cell activity, we recently identified a cell cycle inhibitor with micromolar potency that inhibits mTOR kinase activity. Following a rapid lead optimization campaign, we report the development of eCF309, an mTOR inhibitor displaying low nanomolar potency both in vitro and in cells and an excellent selectivity profile (S-score (35%) = 0.01 at 10 μM). In the experiment, the researchers used many compounds, for example, 7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7Recommanded Product: 7-Azaindole-5-boronic Acid Pinacol Ester).

7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7) 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. 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: 7-Azaindole-5-boronic Acid Pinacol Ester

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

Auxin-binding site in wheat shoots: interactions between indol-3-ylacetic acid and its halogenated derivatives was written by Zazimalova, Eva;Kutacek, M.. And the article was included in Biologia Plantarum in 1985.Product Details of 1912-45-4 This article mentions the following:

The specificity of IAA-binding site from wheat shoots was investigated in an attempt to confirm its receptor function. Several monofluoro-, monochloro-, dichloro-, and monobromo-substituted indol-3-ylacetic acids were allowed to displace ¹⁴C-IAA from the binding site. Displacement abilities of these halogenated IAAs were closely related to their activities in wheat coleoptile straight growth biotest. This finding indirectly confirms the physiol. significance of this binding site. In the experiment, the researchers used many compounds, for example, 2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4Product Details of 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). Product Details of 1912-45-4

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

Derivatization of a rigid meso-substituted heptamethine cyanine dye was written by Shershov, Valeriy E.;Kuznetsova, Viktoriya E.;Miftakhov, Rinat A.;Lapa, Sergey A.;Stomahin, Andrey A.;Timofeev, Edward N.;Grechishnikova, Irina V.;Zasedatelev, Alexander S.;Chudinov, Alexander V.. And the article was included in Mendeleev Communications in 2021.Product Details of 146368-07-2 This article mentions the following:

A novel electroneutral rigid meso-sulfophenyloxy substituted heptamethine dye was synthesized in six steps. Selective derivatization of one sulfonamide group with octanedioic acid introduced the carboxy end group attached through the hexamethylene linker, which provided the dye solubility in water. Absorbance of the dye in the near IR region makes it promising for covalent labeling of biomols. In the experiment, the researchers used many compounds, for example, 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2Product Details of 146368-07-2).

1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2) 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Product Details of 146368-07-2

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

Access to Polycyclic Sulfonyl Indolines via Fe(II)-Catalyzed or UV-Driven Formal [2 + 2 + 1] Cyclization Reactions of N-((1H-indol-3-yl)methyl)propiolamides with NaHSO₃ was written by Lu, Lin;Luo, Chenguang;Peng, Hui;Jiang, Huanfeng;Lei, Ming;Yin, Biaolin. And the article was included in Organic Letters in 2019.Computed Properties of C11H11NO This article mentions the following:

A variety of structurally novel polycyclic sulfonyl indolines were synthesized via FeCl₂-catalyzed or UV-driven intramol. formal [2 + 2 + 1] dearomatizing cyclization reactions of N-(1H-indol-3-yl)methylpropiolamides with NaHSO₃ in an aqueous medium. The reactions involve the formation of one C-C bond and two C-S bonds in a single step. In the experiment, the researchers used many compounds, for example, 1,4-Dimethyl-1H-indole-3-carbaldehyde (cas: 170489-16-4Computed Properties of C11H11NO).

1,4-Dimethyl-1H-indole-3-carbaldehyde (cas: 170489-16-4) 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.Computed Properties of C11H11NO

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

Synthesis of indole and carbazole derivatives by condensation of α-hydroxyketones and aromatic amines was written by Roth, H. J.;Lepke, P.. And the article was included in Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft in 1972.Quality Control of 5-Bromo-2,3-dimethyl-1H-indole This article mentions the following:

Thirty title compounds [I; R = R1 = Me or Ph or RR1 = (CH2)4; R2 = H, 5-OH, 6-OH, 5-HO2C, 6-HO2C, 5-EtO2C, 5-MeO, 6-MeS, 5-Me, 7-Me, 4,7-Me2, 6,5-BrMe, 5-Cl, 5-Br, or 6-Cl or the naphthyl analogs] were prepared in 21-92% yield by condensation of R2C6H4NH2 and RCH(OH)COR1. The products were determined by NMR. In the experiment, the researchers used many compounds, for example, 5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5Quality Control of 5-Bromo-2,3-dimethyl-1H-indole).

5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5) 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.Quality Control of 5-Bromo-2,3-dimethyl-1H-indole

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

Antibacterial activity of MreB inhibitors against gram (-) bacteria was written by Sagong, Hye Yeon;Rosado-Lugo, Jesus D.;Bryan, Eric J.;Ferrer-Gonzalez, Edgar;Wang, Yiling;Cao, Yanlu;Parhi, Ajit K.;Pilch, Daniel S.;LaVoie, Edmond J.. And the article was included in Medicinal Chemistry Research in 2022.SDS of cas: 210345-56-5 This article mentions the following:

MreB is a cytoskeleton protein present in rod-shaped bacteria that is both essential for bacterial cell division and highly conserved. Because most Gram (-) bacteria require MreB for cell division, chromosome segregation, cell wall morphogenesis, and cell polarity, it is an attractive target for antibacterial drug discovery. As MreB modulation is not associated with the activity of antibiotics in clin. use, acquired resistance to MreB inhibitors is also unlikely. Compounds, such as A22and CBR-4830, are known to disrupt MreB function by inhibition of ATPase activity. However, the toxicity of these compounds has hindered efforts to assess the in vivo efficacy of these MreB inhibitors. The present study further examines the structure-activity of analogs related to CBR-4830 as it relates to relative antibiotic activity and improved drug properties. These data reveal that certain analogs have enhanced antibiotic activity. In addition, we evaluated several representative analogs (9, 10, 14, 26, and 31) for their abilities to target purified E. coli MreB (EcMreB) and inhibit its ATPase activity. Except for 14, all these analogs were more potent than CBR-4830 as inhibitors of the ATPase activity of EcMreB with corresponding IC₅₀ values ranging from 6 ± 2 to 29 ± 9 μM. In the experiment, the researchers used many compounds, for example, Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5SDS of cas: 210345-56-5).

Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5) 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.SDS of cas: 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

Catalyst-Free Decarbonylative Trifluoromethylthiolation Enabled by Electron Donor-Acceptor Complex Photoactivation was written by Lipp, Alexander;Badir, Shorouk O.;Dykstra, Ryan;Gutierrez, Osvaldo;Molander, Gary A.. And the article was included in Advanced Synthesis & Catalysis in 2021.Name: 2-(Phenylthio)isoindoline-1,3-dione This article mentions the following:

A catalyst- and additive-free decarbonylative trifluoromethylthiolation of aldehyde feedstocks has been developed. This operationally simple, scalable, and open-to-air transformation is driven by the selective photoexcitation of electron donor-acceptor (EDA) complexes, stemming from the association of 1,4-dihydropyridines (donor) with N-(trifluoromethylthio)phthalimide (acceptor), to trigger intermol. single-electron transfer events under ambient- and visible light-promoted conditions. Extension to other electron acceptors enables the synthesis of thiocyanates and thioesters, as well as the difunctionalization of [1.1.1]propellane. The mechanistic intricacies of this photochem. paradigm are elucidated through a combination of exptl. efforts and high-level quantum mech. calculations [dispersion-corrected (U)DFT, DLPNO-CCSD(T), and TD-DFT]. This comprehensive study highlights the necessity for EDA complexation for efficient alkyl radical generation. Computation of subsequent ground state pathways reveals that S_H2 addition of the alkyl radical to the intermediate radical EDA complex is extremely exergonic and results in a charge transfer event from the dihydropyridine donor to the N-(trifluoromethylthio)phthalimide acceptor of the EDA complex. Exptl. and computational results further suggest that product formation also occurs via S_H2 reaction of alkyl radicals with 1,2-bis(trifluoromethyl)disulfane, generated in-situ through combination of thiyl radicals. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Name: 2-(Phenylthio)isoindoline-1,3-dione).

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.Name: 2-(Phenylthio)isoindoline-1,3-dione

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