• 1. Nickel-catalysed chemoselective C-3 alkylation of indoles with alcohols through a borrowing hydrogen method
  Amreen K. Bains,Ayanangshu Biswas,Debashis Adhikari Chem. Commun. 2020 56 15442
• 2. Cobalt-catalysed CH-alkylation of indoles with alcohols by borrowing hydrogen methodology
  Bei Zhou,Zhuang Ma,Asma M. Alenad,Carsten Kreyenschulte,Stephan Bartling,Matthias Beller,Rajenahally V. Jagadeesh Green Chem. 2022 24 4566

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Indoles and derivatives 3-alkylindoles
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Indoles and derivatives Indoles 3-alkylindoles

Professional Introduction to 3-Benzyl-1H-indole (CAS No: 16886-10-5)

3-Benzyl-1H-indole, identified by the Chemical Abstracts Service Number (CAS No) 16886-10-5, is a significant heterocyclic compound that has garnered considerable attention in the field of pharmaceutical chemistry and medicinal biology. This compound belongs to the indole family, a class of molecules widely recognized for their diverse biological activities and pharmaceutical relevance. The structural motif of 3-Benzyl-1H-indole consists of a benzyl group attached to the 3-position of the indole ring, which imparts unique chemical and biological properties that make it a valuable scaffold for drug discovery and development.

The indole core is a privileged structure in medicinal chemistry, featuring a bicyclic system composed of a benzene ring fused to a pyrrole ring. This configuration endows indole derivatives with remarkable flexibility, allowing for diverse functionalization at multiple positions. Among these derivatives, 3-Benzyl-1H-indole has been extensively studied due to its potential pharmacological effects, which span across various therapeutic areas. The benzyl substitution at the 3-position not only enhances the solubility and metabolic stability of the molecule but also influences its interactions with biological targets.

Recent advancements in computational chemistry and molecular modeling have facilitated a deeper understanding of the pharmacophoric features of 3-Benzyl-1H-indole. Studies have demonstrated that the benzyl group can modulate the binding affinity and selectivity of indole derivatives by influencing electronic distributions and steric interactions. This has opened new avenues for designing novel compounds with improved pharmacokinetic profiles and reduced side effects.

In the realm of drug discovery, 3-Benzyl-1H-indole has been explored as a precursor for synthesizing more complex molecules with enhanced biological activity. For instance, researchers have leveraged this scaffold to develop inhibitors targeting enzymes involved in inflammatory pathways, such as cyclooxygenase (COX) and lipoxygenase (LOX). The benzyl-substituted indole derivatives exhibit promising anti-inflammatory properties, making them attractive candidates for treating chronic inflammatory diseases.

Moreover, the structural versatility of 3-Benzyl-1H-indole has been exploited in the development of anticancer agents. Preclinical studies have indicated that certain analogs of this compound can induce apoptosis in cancer cells by disrupting critical signaling pathways. The benzyl group plays a pivotal role in this process by facilitating optimal binding to target proteins, thereby modulating their function. These findings highlight the potential of 3-Benzyl-1H-indole as a lead compound for further derivatization to create next-generation anticancer therapies.

Another area where 3-Benzyl-1H-indole has shown promise is in neurodegenerative disease research. Indole derivatives are known to interact with neurotransmitter systems, suggesting their potential utility in treating conditions such as Alzheimer's disease and Parkinson's disease. The benzyl-substituted analogs have been found to cross the blood-brain barrier more efficiently, improving their therapeutic efficacy. Ongoing research aims to optimize these compounds to enhance their bioavailability and target specificity.

The synthesis of 3-Benzyl-1H-indole typically involves classical organic reactions such as Suzuki-Miyaura coupling or Buchwald-Hartwig coupling, which allow for the introduction of various substituents at strategic positions on the indole ring. These synthetic methodologies have enabled chemists to generate libraries of indole derivatives for high-throughput screening (HTS) experiments. The accessibility of starting materials and well-established synthetic routes makes 3-Benzyl-1H-indole an ideal candidate for medicinal chemists seeking to explore new drug candidates.

Recent publications have highlighted the role of 3-Benzyl-1H-indole in developing antimicrobial agents. The indole scaffold is known to exhibit broad-spectrum antimicrobial activity, and modifications such as benzyl substitution can enhance these properties. Researchers have reported that certain derivatives of 3-Benzyl-1H-indole demonstrate efficacy against multidrug-resistant bacteria, offering hope for addressing emerging antibiotic resistance challenges.

The pharmacokinetic profile of 3-Benzyl-1H-indole is another critical aspect that has been thoroughly investigated. Studies using in vitro and in vivo models have provided insights into its absorption, distribution, metabolism, and excretion (ADME) properties. The benzyl group contributes to improved oral bioavailability by enhancing lipophilicity while minimizing metabolic degradation. This balance makes 3-Benzyl-1H-indole an attractive scaffold for developing orally administered therapeutics.

In conclusion, 3-Benzyl-1H-indole (CAS No: 16886-10-5) represents a structurally intriguing and biologically relevant compound with significant potential in pharmaceutical applications. Its unique chemical properties, coupled with its versatility as a scaffold for drug design, position it as a cornerstone molecule in modern medicinal chemistry. As research continues to uncover new therapeutic applications and synthetic strategies, compounds derived from or inspired by 3-Benzyl-1H-indole are poised to play a crucial role in addressing unmet medical needs across multiple disease areas.

• 518-06-9(1H-Indole,3,3',3''-methylidynetris-)
• 5275-07-0(1H-Indole, 3-(4-pyridinylmethyl)-)
• 208-75-3(1,4-Methano-9H-carbazole)
• 1484-19-1(3-Ethyl-1H-indole)
• 159890-08-1(1H-Indole, 3,3'-methylenebis[5-methyl-)
• 5275-04-7(3-(pyridin-3-ylmethyl)-1H-indole)
• 5030-91-1(3-1-(1H-indol-3-yl)ethyl-1H-indole)
• 1968-05-4(3,3'-Diindolylmethane)
• 35173-74-1(3,3'-(phenylmethane-1,1-diyl)bis(1H-indole))
• 153474-33-0(3,3',3''-methanetriyltris(1H-indole))