5-[(1-Benzyl-1H-1,2,3-triazol-4-yl)meth-yl]-5H-dibenzo[b,f]azepine.

Acta Crystallogr Sect E Struct Rep Online

Department of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India.

Published: November 2013

AI Article Synopsis

Article Abstract

In the title compound, C24H20N4, the azepine ring adopts a boat conformation. The dihedral angle between the benzene rings fused to the azepine ring is 49.40 (9)°. The triazole ring makes a dihedral angle of 77.88 (9)° with the terminal phenyl ring. In the crystal, mol-ecules are linked via C-H⋯π inter-actions and a parallel slipped π-π inter-action [centroid-centroid distance = 3.7324 (9), normal distance = 3.4060 (6) and slippage = 1.526 Å], forming a three-dimensional network.

Download full-text PDF

Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3885037PMC
http://dx.doi.org/10.1107/S1600536813030547DOI Listing

Publication Analysis

Top Keywords

azepine ring
8
dihedral angle
8
5-[1-benzyl-1h-123-triazol-4-ylmeth-yl]-5h-dibenzo[bf]azepine title
4
title compound
4
compound c24h20n4
4
c24h20n4 azepine
4
ring
4
ring adopts
4
adopts boat
4
boat conformation
4

Similar Publications

Reactivity of Anomalous Aziridines for Versatile Access to High Fsp Amine Chemical Space.

Acc Chem Res

January 2025

Department of Chemistry, University of Wisconsin, 1101 University Avenue, Madison, Wisconsin 53706, United States.

ConspectusThe manipulation of strained rings is a powerful strategy for accessing the valuable chemical frameworks present in natural products and active pharmaceutical ingredients. Aziridines, the smallest N-containing heterocycles, have long served as building blocks for constructing more complex amine-containing scaffolds. Traditionally, the reactivity of typical aziridines has been focused on ring-opening by nucleophiles or the formation of 1,3-dipoles.

View Article and Find Full Text PDF

Bioinspired Synthesis of (-)-Hunterine A: Deciphering the Key Step in the Biogenetic Pathway.

Chemistry

December 2024

Organocatalysis Research Group, Institute of Organic Chemistry, HUN-REN Research Centre for Natural Sciences, 2. Magyar tudósok krt., H-1117, Budapest, Hungary.

A concise, bioinspired, and enantioselective synthesis of (-)-hunterine A, an odd 6/7/6/6/5 pentacyclic natural product, is described. The key step in the synthesis of this complex structure is an interim-template directed 6-exo selective epoxide ring-opening reaction, which is interwoven with a hydrolysis step of the indolenine hemiaminal template to create the unusual 7-membered azepine bridge motif. Our work not only refines the previously proposed biogenetic pathway, but also reveals the possible stereochemical prerequisite of the unique skeletal rearrangement, which provides a vantage point for understanding how (-)-hunterine A is likely to be generated in nature.

View Article and Find Full Text PDF

Selectively Extending the Curved Side of N-Doped Hexa-peri- hexabenzocoronene.

Chemistry

December 2024

School of Chemical Science and Technology & Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan University, Kunmimg, 650500, PR China.

A curved nanographene, conceptually by insertion of nitrogen into a trapezoidal planar nanographene at the edge was synthesized by π-extension of the nitrogen-doped hexa-peri-hexabenzocoronene. This N-doped nanographene exhibited a π-electronic concave face containing a nonaromatic azepine ring in the middle with a size of 14.0 Å length and 4.

View Article and Find Full Text PDF

Riluzole, the first clinically approved treatment for amyotrophic lateral sclerosis (ALS), represents a successful example of a drug endowed with a multimodal mechanism of action. In recent years, different series of riluzole-based compounds have been reported, including several agents acting as Multi-Target-Directed Ligands (MTLDs) endowed with neuroprotective effects. Aiming at identical twin structures inspired by riluzole (2a-c), a synthetic procedure was planned, but the reactivity of the system took a different path, leading to the serendipitous isolation of benzo[b][1,4]thiazepines 3a-c and expanded intermediates N-cyano-benzo[b][1,4]thiazepines 4a-c, which were fully characterized.

View Article and Find Full Text PDF

Regulated induced proximity targeting chimeras-RIPTACs-A heterobifunctional small molecule strategy for cancer selective therapies.

Cell Chem Biol

August 2024

Department of Molecular, Cellular, & Developmental Biology, Yale University, New Haven, CT, USA; Department of Pharmacology, Yale University, New Haven, CT, USA; Department of Chemistry, Yale University, New Haven, CT, USA. Electronic address:

Article Synopsis
  • RIPTACs (Regulated Induced Proximity Targeting Chimeras) are innovative small molecules designed to create stable complexes between a target protein found in tumor cells and a widely expressed essential protein, leading to cancer cell death.
  • This approach targets proteins that are specifically expressed in cancer cells without needing them to be the main drivers of the disease, thus offering a new strategy for cancer treatment.
  • In the study, RIPTACs were engineered with ligands linked to various effector molecules, demonstrating selective accumulation in target-expressing cells and effectively inducing an anti-proliferative effect.
View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!