144104-54-1

Basic information

• Product Name: 5-(2-THIENYL)-1H-INDOLE
• Synonyms: 5-(2-THIENYL)-1H-INDOLE;5-THIOPHEN-2-YL-1H-INDOLE;AKOS BAR-1293
• CAS NO: 144104-54-1
• Molecular Formula: C₁₂H₉NS
• Molecular Weight: 199.27
• Mol File: 144104-54-1.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-(2-THIENYL)-1H-INDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(2-THIENYL)-1H-INDOLE(144104-54-1)
• EPA Substance Registry System: 5-(2-THIENYL)-1H-INDOLE(144104-54-1)

Safety Data

• Hazardous Substances Data: 144104-54-1(Hazardous Substances Data)

Usage

General Description

5-(2-Thienyl)-1H-indole is a chemical compound with a molecular formula C12H9NS. It is a heterocyclic compound containing a thiophene ring fused to an indole ring, and it is classified as an indole derivative. 5-(2-THIENYL)-1H-INDOLE is a yellow solid at room temperature and is soluble in organic solvents, but insoluble in water. 5-(2-Thienyl)-1H-indole has found applications in various fields, including pharmaceuticals, agrochemicals, and materials science. It exhibits a range of biological activities, including antitumor and antimicrobial properties, making it a potential lead compound for the development of new drugs. Additionally, it can also be used as a building block for the synthesis of more complex organic molecules.

Upstream product

• 1003-09-4 2-bromothiophene 
• 144104-59-6 1H-indole-5-boronic acid 
• 3437-95-4 2-Iodothiophene 
• 16066-91-4 5-iodo-1H-indole 
• 1402550-72-4 1-methyldiphenylsilyl-5-(thien-2-yl)-1H-indole 
• 96-43-5 2-thienyl chloride 
• 269410-24-4 5-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole 
• 6165-68-0 thiophene boronic acid 
• 10075-50-0 5-bromo-1H-indole 
• 193978-23-3 2-thiopheneboronic acid pinacol ester 

Relevant articles and documents

Concatenating Suzuki Arylation and Buchwald–Hartwig Amination by A Sequentially Pd-Catalyzed One-Pot Process—Consecutive Three-Component Synthesis of C,N-Diarylated Heterocycles

The concatenation of Suzuki coupling and Buchwald-Hartwig amination in a consecutive multicomponent reaction opens a concise, modular and efficient one-pot approach to diversely functionalized heterocycles, as exemplified for 3,10-diaryl 10H-phenothiazines, 3,9-diaryl 9H-carbazoles, and 1,5-diaryl 1H-indoles, in high yields starting from simple staring materials. Moreover, this one-pot reaction is a sequentially palladium-catalyzed process that does not require additional catalyst loading after the first coupling step.

New 6- and 7-heterocyclyl-1H-indole derivatives as potent tubulin assembly and cancer cell growth inhibitors

We designed new 3-arylthio- and 3-aroyl-1H-indole derivatives 3–22 bearing a heterocyclic ring at position 5, 6 or 7 of the indole nucleus. The 6- and 7-heterocyclyl-1H-indoles showed potent inhibition of tubulin polymerization, binding of colchicine to tubulin and growth of MCF-7 cancer cells. Compounds 13 and 19 inhibited a panel of cancer cells and the NCI/ADR-RES multidrug resistant cell line at low nanomolar concentrations. Compound 13 at 50 nM induced 77% G2/M in HeLa cells, and at 20 nM caused 50% stable arrest of mitosis. As an inhibitor of HepG2 cells (IC50 = 20 nM), 13 was 4-fold superior to 19. Compound 13 was a potent inhibitor of the human U87MG glioblastoma cells at nanomolar concentrations, being nearly one order of magnitude superior to previously reported arylthioindoles. The present results highlight 13 as a robust scaffold for the design of new anticancer agents.

General suzuki coupling of heteroaryl bromides by using tri-tert-butylphosphine as a supporting ligand

A general procedure for the fast Suzuki coupling of major families of heteroaryl bromides was realized by using Pd(OAc)2/PtBu3 as the catalyst. Many couplings were finished within minutes at room temperature in n-butanol. Different from previous studies, three typical heteroaryl bromides were systematically examined in couplings of various heteroaryl and aryl boronic acids. A fast, general coupling of heteroaryl bromides is realized by using a single palladium catalyst supported by tri-tert-butylphosphine.