Category: 167015-84-1

Mu, Xin-Peng published the artcileStereoselective Synthesis of Cyclohepta[b]indoles by Visible-Light-Induced [2+2]-Cycloaddition/retro-Mannich-type Reactions, Application of tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, the publication is Angewandte Chemie, International Edition (2021), 60(20), 11211-11216, database is CAplus and MEDLINE.

A novel method for the concise synthesis of cyclohepta[b]indoles in high yields was developed. The method involves a visible-light-induced, photocatalyzed [2+2]-cycloaddition/ retro-Mannich-type reaction of enaminones such as I to yield cycloheptaindoles such as II. Exptl. and computational studies suggested that the reaction is a photoredox process initiated by single-electron oxidation of enaminones, which undergo subsequent cyclobutane formation and rapid fragmentation of the intermediate radical cations to form cyclohepta[b]indoles.

Angewandte Chemie, International Edition published new progress about 167015-84-1. 167015-84-1 belongs to indole-building-block, auxiliary class Indols, name is tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, and the molecular formula is C15H20N2O2, Application of tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Blackwell, J. Henry published the artcileVisible-Light-Mediated Carbonyl Alkylative Amination to All-Alkyl 伪-Tertiary Amino Acid Derivatives, Name: tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, the publication is Journal of the American Chemical Society (2021), 143(3), 1598-1609, database is CAplus and MEDLINE.

The all-alkyl 伪-tertiary amino acid scaffold represents an important structural feature in many biol. and pharmaceutically relevant mols. Syntheses of this class of mol., however, often involve multiple steps and require activating auxiliary groups on the nitrogen atom or tailored building blocks. A straightforward, single-step, and modular methodol. for the synthesis of all-alkyl 伪-tertiary amino esters was reported. This new strategy uses visible light and a silane reductant to bring about a carbonyl alkylative amination reaction that combines a wide range of primary amines, 伪-ketoesters, and alkyl iodides to form functionally diverse all-alkyl 伪-tertiary amino esters. Bronsted acid-mediated in situ condensation of primary amine and 伪-ketoester delivers the corresponding ketiminium species, which undergoes rapid 1,2-addition of an alkyl radical (generated from an alkyl iodide by the action of visible light and silane reductant) to form an aminium radical cation. Upon a polarity-matched and irreversible hydrogen atom transfer from electron rich silane, the electrophilic aminium radical cation is converted to an all-alkyl 伪-tertiary amino ester product. The benign nature of this process allows for broad scope in all three components and generates structurally and functionally diverse suite of 伪-tertiary amino esters that will likely have widespread use in academic and industrial settings.

Journal of the American Chemical Society published new progress about 167015-84-1. 167015-84-1 belongs to indole-building-block, auxiliary class Indols, name is tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, and the molecular formula is C15H20N2O2, Name: tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Danieli, Bruno published the artcileFormal enantioselective synthesis of tacamonine starting from asymmetrized 2-substituted propane-1,3-diols, COA of Formula: C15H20N2O2, the publication is Tetrahedron: Asymmetry (1999), 10(20), 4057-4064, database is CAplus.

2-Substituted propanediols monoacetates, derived from enzymic asymmetrization of the corresponding diols, have been obtained in high yields and enantiomeric excesses by using lipases and vinyl acetate as both solvent and acylating agent. These chiral building blocks have been transformed into the advanced intermediate I, useful for the enantioselective synthesis of tacamane alkaloids.

Tetrahedron: Asymmetry published new progress about 167015-84-1. 167015-84-1 belongs to indole-building-block, auxiliary class Indols, name is tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, and the molecular formula is C15H20N2O2, COA of Formula: C15H20N2O2.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Grover, Huck K. published the artcileThe Synthesis of 5,5-Disubstituted Piperidinones via a Reductive Amination-Lactamization Sequence: The Formal Synthesis of (±)-Quebrachamine, COA of Formula: C15H20N2O2, the publication is Synlett (2015), 26(6), 815-819, database is CAplus.

A preliminary investigation into the prospect of a common synthetic intermediate for the synthesis of a variety of indole alkaloids has led to a synthesis of substituted piperidinones and the corresponding piperidines. These common natural product cores are accessed via a reductive amination-lactamization sequence of di-Me 3-ethyl-3-formylpimelate. The synthetic utility of this initial study has been displayed in the formal synthesis of (±)-quebrachamine.

Synlett published new progress about 167015-84-1. 167015-84-1 belongs to indole-building-block, auxiliary class Indols, name is tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, and the molecular formula is C15H20N2O2, COA of Formula: C15H20N2O2.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Walpole, C. published the artcile2-Nitrophenylcarbamoyl-(S)-prolyl-(S)-3-(2-naphthyl)alanyl-N-benzyl-N- methylamide (SDZ NKT 343), a Potent Human NK₁ Tachykinin Receptor Antagonist with Good Oral Analgesic Activity in Chronic Pain Models, Application In Synthesis of 167015-84-1, the publication is Journal of Medicinal Chemistry (1998), 41(17), 3159-3173, database is CAplus and MEDLINE.

A lead compound which had sub-micromolar affinity for the rabbit NK₁ receptor but negligible affinity for rat NK₁ receptors, 2-MeOC₆H₄CH₂NHCS-Pro-NHCHPh₂, was discovered by directed screening. 2-Substitution in the ring of the benzylthiourea substituent in the initial lead was found to be important, and halogens (Cl, Br) in this position were found to improve affinity for the human receptor. The activity of a series of 2-halo-substituted benzylthioureas was then optimized by modification of the proline diphenylmethyl amide, guided by a simple conceptual model based on structural overlay between these early antagonists and NK₁ selective peptides. In this way, aromatic amino acid amides were identified which had improved affinity with respect to the starting diphenylmethyl (DPM) amides. The first sub-nanomolar ligand for the human NK₁ receptor which arose from this series, I, combined a 2-chlorobenzylthiourea unit with a 2-naphthylalanine amide. Contemporaneously it was discovered that the benzylthiourea unit could be simplified to a phenylthiourea providing that an appropriate 2-substituent was also incorporated. Combination of these two series gave 2-NO₂ phenylthiourea analogs which led directly to the analogous urea, II (SDZ NKT 343), a highly potent ligand for the human NK₁ receptor (K_i = 0.16 nM). In addition to its high in vitro potency, II proved to be a potent orally active analgesic in guinea pig models of chronic inflammatory and neuropathic pain. The nature of the 2-aryl substituent was found to be critical for oral activity in this series. Clin. evaluation of II as a novel analgesic agent is currently underway.

Journal of Medicinal Chemistry published new progress about 167015-84-1. 167015-84-1 belongs to indole-building-block, auxiliary class Indols, name is tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, and the molecular formula is C4H6BrFO2, Application In Synthesis of 167015-84-1.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Simpson, Levi S. published the artcileA cleavable scaffold strategy for the synthesis of one-bead one-compound cyclic peptoid libraries that can be sequenced by tandem mass spectrometry, SDS of cas: 167015-84-1, the publication is Tetrahedron Letters (2012), 53(18), 2341-2344, database is CAplus and MEDLINE.

Many macrocyclic depsipeptides or related compounds have interesting medicinal properties and often display more favorable pharmacokinetic properties than linear analogs. Therefore, there is considerable interest in the development of large combinatorial libraries of macrocyclic peptidomimetic compounds However, such mols. cannot be easily sequenced by tandem mass spectrometry, making it difficult to identify hits isolated from library screens using one bead one compound libraries. Here we report a strategy to solve this problem by placing a methionine in both the linker connecting the cyclic mol. to the bead as well as within the cycle itself. Treatment with CNBr both linearizes the mol. at a specific position and releases the mol. from the bead, making its characterization by tandem MALDI mass spectrometry straightforward.

Tetrahedron Letters published new progress about 167015-84-1. 167015-84-1 belongs to indole-building-block, auxiliary class Indols, name is tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, and the molecular formula is C23H23ClN2O4, SDS of cas: 167015-84-1.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles