Day: November 17, 2022

Williams, John D. published the artcilePotent and broad-spectrum antibacterial activity of indole-based bisamidine antibiotics: Synthesis and SAR of novel analogs of MBX 1066 and MBX 1090, Recommanded Product: Ethyl 6-cyano-1H-indole-2-carboxylate, the main research area is indole bisamidine preparation antibacterial antibiotic; Amidine; Antibacterial; Antibiotic; Broad-spectrum; Cadogan–Sundberg reaction; Imidazoline; Indole; McMurry reductive homocoupling reaction; Reissert indole synthesis; Tetrahydropyrimidine.

The prevalence of drug-resistant bacteria in the clinic has propelled a concerted effort to find new classes of antibiotics that will circumvent current modes of resistance. The authors have previously described a set of bisamidine antibiotics that contains a core composed of two indoles and a central linker. The first compounds of the series, MBX 1066 and MBX 1090, have potent antibacterial properties against a wide range of Gram-pos. and Gram-neg. bacteria. The authors have conducted a systematic exploration of the amidine functionalities, the central linker, and substituents at the indole 3-position to determine the factors involved in potent antibacterial activity. Some of the newly synthesized compounds have even more potent and broad-spectrum activity than MBX 1066 and MBX 1090.

Bioorganic & Medicinal Chemistry published new progress about Antibacterial agents. 104291-81-8 belongs to class indole-building-block, name is Ethyl 6-cyano-1H-indole-2-carboxylate, and the molecular formula is C12H10N2O2, Recommanded Product: Ethyl 6-cyano-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

Knepper, Kerstin published the artcileBartoli Indole Synthesis on Solid Supports, HPLC of Formula: 57663-18-0, the main research area is indolecarboxylate Bartoli synthesis solid phase.

Bartoli indole synthesis was performed on solid supports. Starting from Merrifield resin, immobilization of five nitrobenzoic acids was performed. Addition of four different alkenyl Grignard reagents and basic cleavage leads to substituted Me indolecarboxylates in excellent purities. Features of this reaction are the stability of halide groups, ester moieties, and tolerance of o,o’-unsubstituted nitro resins. Heck and Sonogashira reactions are also possible with immobilized indoles.

Organic Letters published new progress about Solid phase synthesis. 57663-18-0 belongs to class indole-building-block, name is Methyl 2-methyl-1H-indole-5-carboxylate, and the molecular formula is C11H11NO2, HPLC of Formula: 57663-18-0.

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

Golovko, T. V. published the artcileNew synthesis of pyrido[4,3-b]indoles (γ-carbolines) on the basis of indolin-2-one lactim ether, Category: indole-building-block, the main research area is indolinone lactim ether malononitrile condensation; oxindole lactim ether malononitrile condensation; pyridoindole preparation; gamma carboline preparation; pyrimidocarboline preparation.

Condensation of indolin-2-one (oxindole) lactim ether with H2C(CN)2 leads to 2-dicyanomethylidene-2,3-dihydroindole. Subsequent reaction with DMF di-Et acetal [or HC(OEt)3] and further cyclization affords 4-cyanopyrido[4,3-b]indoles (γ-carbolines). 3-Amino-4-cyanopyrido[4,3-b]indole was used in the synthesis of substituted pyrimido[4,5-c]-γ-carbolines.

Russian Chemical Bulletin published new progress about Condensation reaction. 1009-27-4 belongs to class indole-building-block, name is 2-Ethoxy-1H-indole, and the molecular formula is C10H11NO, Category: 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

Jiang, Zhigan published the artcileScaffold hopping of sampangine: discovery of potent antifungal lead compound against Aspergillus fumigatus and Cryptococcus neoformans, Recommanded Product: 4-(Benzyloxy)-1-methyl-1H-indole, the main research area is antifungal sampangine derivative; Antifungal activity; Sampangine; Scaffold hopping.

Discovery of novel antifungal agents against Aspergillus fumigatus and Cryptococcus neoformans remains a significant challenge in current antifungal therapy. Here, the antifungal natural product sampangine (I) was used as the lead compound for novel antifungal drug discovery. D-ring scaffold hopping derivatives were designed and synthesized to improve antifungal activity and water solubility Among them, the thiophene derivative S2 showed broad-spectrum antifungal activity, particularly for Aspergillus fumigatus and Cryptococcus neoformans. Moreover, compound S2 also revealed better water solubility than sampangine, which represents a promising antifungal lead compound for further structural optimization.

Bioorganic & Medicinal Chemistry Letters published new progress about Aspergillus fumigatus. 13523-93-8 belongs to class indole-building-block, name is 4-(Benzyloxy)-1-methyl-1H-indole, and the molecular formula is C16H15NO, Recommanded Product: 4-(Benzyloxy)-1-methyl-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

Boger, Dale L. published the artcileCC-1065 CBI analogs: an example of enhancement of DNA alkylation efficiency through introduction of stabilizing electrostatic interactions, Category: indole-building-block, the main research area is CC1065 CBI analog preparation DNA alkylation.

The three trimethylammonium salts I (R1 and R2 and R3 = H or NMe3+) proved to be 100 times more efficient at alkylating DNA than I (R1 and R2 and R3 = H) and exhibited DNA alkylation efficiencies identical to that of (+)-CC-1065. In addition, the agents I (R1 and R2 = H and R3 = NMe3+) and I (R1 and R3 = H and R2 = NMe3+) exhibited DNA alkylation selectivities identical to that of I (R1 and R2 and R3 = H). This may be attributed to spatially well-defined stabilizing electrostatic interactions between the pos. charged trimethylammonium salt lying on the peripheral face of the agents and the bracketing, neg. charged phosphates located in the DNA backbone that enhance the DNA noncovalent binding affinity without affecting DNA binding or alkylation selectivity. The agent I (R2 and R3 = H and R1 = NMe3+) exhibited an altered and more discriminating AT-rich adenine N3 alkylation selectivity than the other agents that may be attributed to the groove placement of the large trimethylammonium salt.

Bioorganic & Medicinal Chemistry published new progress about Biochemical alkylation. 136818-66-1 belongs to class indole-building-block, name is Methyl 6-nitro-1H-indole-2-carboxylate, and the molecular formula is C10H8N2O4, Category: 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

Kulagowski, Janusz J. published the artcile3-[[4-(4-Chlorophenyl)piperazin-1-yl]methyl]-1H-pyrrolo[2,3-b]pyridine: An Antagonist with High Affinity and Selectivity for the Human Dopamine D4 Receptor, Category: indole-building-block, the main research area is dopamine D4 receptor chlorophenylpiperazinylmethyl pyrrolopyridine.

A topol. similarity search of the Merck sample collection using known dopamine agonists and antagonists as probe structures identified indole I as having modest binding selectivity for cloned human dopamine D4 receptors over D2 and D3 subtypes. Optimization of the amino side chain and introduction of a nitrogen atom into the indole nucleus resulted in L-745,870 (II), having high D4 affinity (Ki 0.43 nM) with 2200 and >5000-fold selectivity over D2 and D3 receptors, resp. Also identified in the course of this work was the piperidinol III which demonstrated the opposite selectivity, being 100-fold binding selective for the D2 receptor.

Journal of Medicinal Chemistry published new progress about Dopamine D4 antagonists. 5654-92-2 belongs to class indole-building-block, name is N,N-Dimethyl-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)methanamine, and the molecular formula is C10H13N3, Category: 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

Zhao, He published the artcileIndoline and piperazine containing derivatives as a novel class of mixed D2/D4 receptor antagonists. Part 1: Identification and structure-activity relationships, SDS of cas: 41910-64-9, the main research area is dopamine receptor antagonist indoline piperazine derivative preparation SAR.

Optimization of the lead compound 2-[-4-(4-chlorobenzyl)piperazin-1-yl]-1-(2,3-dihydroindol-1-yl)ethanone by systematic structure-activity relation (SAR) studies leads to two potent compounds 2-[-4-(4-chlorobenzyl)piperazin-1-yl]-1-(2-methyl-2,3-dihydroindol-1-yl)ethanone and 2-[-4-(4-chlorobenzyl)piperazin-1-yl]-1-(2-methy-2,3-dihydroindol-1-yl)ethanone. Synthesis and structure-activity relationship as mixed D2/D4 receptor antagonists are reported.

Bioorganic & Medicinal Chemistry Letters published new progress about Dopamine D2 antagonists. 41910-64-9 belongs to class indole-building-block, name is 4-Chloroindoline, and the molecular formula is C8H8ClN, SDS of cas: 41910-64-9.

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

Qin, Hui published the artcileA Mild and Direct C(sp3)-S Cross-Coupling of Oxindoles with Thiols: Synthesis of Unsymmetrical 3-Thiooxindoles, Computed Properties of 71293-59-9, the main research area is thiooxindole preparation coupling oxindole thiol.

Herein, an operationally simple and mild strategy to construct sulfenation of oxindoles with a series of thiols in the absence of transition metals was developed. This methodol. provides an efficient way to directly form a C-S bond at the C-3 position of oxindoles under mild reaction conditions with a cheap and common solvent and base in moderate to good yields.

Journal of Organic Chemistry published new progress about Cross-coupling reaction. 71293-59-9 belongs to class indole-building-block, name is 5,6-Dichloroindolin-2-one, and the molecular formula is C8H5Cl2NO, Computed Properties of 71293-59-9.

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

Koenig, Stefan G. published the artcileCopper-Catalyzed Synthesis of Indoles and Related Heterocycles in Renewable Solvents, Recommanded Product: Ethyl 6-cyano-1H-indole-2-carboxylate, the main research area is copper catalyst cross coupling acetamidoacetate bromobenzaldehyde renewable solvent; indolecarboxylate preparation green chem; fused heterocycle preparation green chem.

An efficient one-pot cascade to indoles and related fused heterocycles has been demonstrated in renewable solvents (EtOAc, 2-methyltetrahydrofuran), thereby eliminating the previously required dipolar aprotic solvent. The copper-catalyzed reaction proceeds with a range of bromobenzaldehydes to give products in good yields. E.g., in presence of CuI and Cs2CO3 under nitrogen in EtOAc, cross-coupling of 2-BrC6H4CHO and Et acetamidoacetate gave 59% indole derivative (I). In addition, the external ligand-free cross-coupling methodol. provides convenient access to an investigational treatment for central nervous system disorders.

ACS Sustainable Chemistry & Engineering published new progress about Cross-coupling reaction. 104291-81-8 belongs to class indole-building-block, name is Ethyl 6-cyano-1H-indole-2-carboxylate, and the molecular formula is C12H10N2O2, Recommanded Product: Ethyl 6-cyano-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

Lillich, Felix F. published the artcileStructure-Based Design of Dual Partial Peroxisome Proliferator-Activated Receptor γ Agonists/Soluble Epoxide Hydrolase Inhibitors, Safety of Methyl 2-methyl-1H-indole-5-carboxylate, the main research area is antitumor structure activity relationship epoxide hydrolase inhibitor.

A dual partial PPARγ agonist/sEH inhibitor using a structure-guided approach was designed. Exhaustive structure-activity relationship studies lead to the successful optimization of the designed lead. Crystal structures of one representative compound with both targets revealed potential points for optimization. The optimized compounds exhibited favorable metabolic stability, toxicity, selectivity, and desirable activity in adipocytes and macrophages.

Journal of Medicinal Chemistry published new progress about Adipocyte, preadipocyte. 57663-18-0 belongs to class indole-building-block, name is Methyl 2-methyl-1H-indole-5-carboxylate, and the molecular formula is C11H11NO2, Safety of Methyl 2-methyl-1H-indole-5-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