703-80-0

Basic information

• Product Name: 3-Acetylindole
• Synonyms: TIMTEC-BB SBB003977;IFLAB-BB F1727-0313;1-(1H-INDOL-3-YL)ETHANONE;3-ACETYL-2,3-BENZOPYRROLE;3-ACETYL-1-BENZAZOLE;3-ACETYLINDOLE;3-INDOLYL METHYL KETONE;AKOS BBS-00004490
• CAS NO: 703-80-0
• Molecular Formula: C₁₀H₉NO
• Molecular Weight: 159.18
• EINECS: 211-875-5
• Product Categories: ACETYLGROUP;Indoles and derivatives;IndoleDerivative;Pyrroles & Indoles;Indole;Heterocyclic Compounds;Indoles;Simple Indoles;Pyrroles & Indoles;Building Blocks;C10;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 703-80-0.mol

Chemical Properties

• Melting Point: 188-192 °C(lit.)
• Boiling Point: 284.68°C (rough estimate)
• Flash Point: 163.7 °C
• Appearance: Yellow to light brown/Powder
• Density: 1.1202 (rough estimate)
• Vapor Pressure: 0.000132mmHg at 25°C
• Refractive Index: 1.6070 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: DMSO; Dichloromethane; Methanol
• PKA: 15.38±0.30(Predicted)
• BRN: 122579
• CAS DataBase Reference: 3-Acetylindole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Acetylindole(703-80-0)
• EPA Substance Registry System: 3-Acetylindole(703-80-0)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: OB4520000
• HazardClass: IRRITANT
• Hazardous Substances Data: 703-80-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Acetylindole is used as a reactant for the preparation of various indole derivatives with antitumor activities. It serves as a key intermediate in the synthesis of several anticancer agents, including Oncrasin-1 derivatives, which are known to inhibit the C-terminal domain of RNA polymerase II.
3-Acetylindole is also used as a reactant in the preparation of endothelin-1 antagonists, which are compounds that block the action of endothelin-1, a potent vasoconstrictor peptide involved in various physiological processes.
In addition, 3-Acetylindole is utilized in the development of inhibitors targeting the hepatitis C NS3/4A serine protease, an enzyme crucial for the replication of the hepatitis C virus.
Used in Antimicrobial Applications:
3-Acetylindole is used as an antibacterial agent against multidrug-resistant (MDR) Staphylococcus aureus strains, a significant concern in the field of infectious diseases.
3-Acetylindole also serves as a reactant in the preparation of antimalarial agents, which are essential in combating malaria, a widespread and life-threatening disease.
Furthermore, it is used in the development of anti-bovine viral diarrhea virus (BVDV) agents, which are crucial in controlling the spread of this viral disease in cattle.
3-Acetylindole is also employed in the synthesis of HIV-1 integrase inhibitors, which are vital in the treatment and management of HIV/AIDS.
Used in Anti-inflammatory Applications:
3-Acetylindole is used as a reactant for the preparation of inhibitors of NF-κB transcription regulation, which play a significant role in the regulation of TNF-α cytokine release, a key mediator of inflammation.
Used in Antifungal Applications:
3-Acetylindole can be used as an anti-fungal agent, providing a potential solution for combating fungal infections.

Purification Methods

Recrystallise the indole from MeOH or *C6H6 containing a little EtOH. The phenylureido derivative has m 154o. [Baker J Chem Soc 461 1946, Beilstein 21/8 V 297.]

InChI:InChI=1/C10H9NO/c1-7(12)9-6-11-10-5-3-2-4-8(9)10/h2-6,11H,1H3

Upstream product

• 91-22-5 quinoline 
• 99055-69-3 1-indol-3-yl-ethanone-hydrazone 
• 79-16-3 N-methyl-acetamide 
• 120-72-9 indole 
• 1563-90-2 N,N-dibutylacetamide 
• 108-24-7 acetic anhydride 
• 562-90-3 tetraacetoxysilane 
• 1477-50-5 Indole-2-carboxylic acid 
• 64-19-7 acetic acid 
• 17537-64-3 1,3-diacetyl-1H-indole 
• 75-36-5 acetyl chloride 
• 127-19-5 N,N-dimethyl acetamide 
• 576-15-8 N-acetylindole 
• 550-44-7 N-methylphthalimide 

Downstream Products

• 83-34-1 3-Methylindole 
• 24955-83-7 3-(β-dimethylamino)propionylindole 
• 88636-52-6 1-(1-ethyl-1H-indol-3-yl)ethan-1-one 
• 1484-19-1 3-ethyl-1H-indole 
• 38470-64-3 (2E)-1-(1H-indol-3-yl)-3-phenylprop-2-en-1-one 
• 90539-81-4 1-(1-benzoyl-1H-indol-3-yl)ethanone 
• 51842-50-3 ethyl 4-(1H-indol-3-yl)-2,4-dioxobutanoate 
• 103205-15-8 1-indol-3-yl-ethanol 
• 771-50-6 1H-indole-3-carboxylic acid 
• 114554-24-4 4-(2-aminophenyl)-3-methylpyrazole 
• 54921-44-7 3-(α,α-ethylenedithioethyl)indole 
• 93315-38-9 3-acetyl-1-benzyl-1H-indole 
• 113143-39-8 Benzoic acid [1-(1H-indol-3-yl)-eth-(E)-ylidene]-hydrazide 
• 103871-32-5 benzyl 3-acetyl-1H-indole-1-carboxylate 

Relevant articles and documents

Synthesis, biological evaluation and molecular modeling of imidazo[1,2-a]pyridine derivatives as potent antitubulin agents

Two series of novel 5,7-diarylimidazo[1,2-a]pyridine-8-carbonitrile derivatives (3a–3q and 7a–7n) were designed by modification of CA-4 pharmacophore to develop colchicine targeted antitubulin agents. All compounds were efficiently synthesized and evaluated for their cytotoxicity against five selected cancer cell lines (HT-29, H460, A549, MKN-45 and SMMC-7721) which got an insight in structure and activity relationships (SARs). Several molecules (7e, 7f, 7h–7j and 7m) were disclosed to exhibit promising antiproliferative activity with IC50 values in double-digit nanomolar degree. Optimization toward these compounds led to the discovery of a promising lead 7e, which showed noteworthy potency with IC50 value ranging from 0.01 to 3.2?μM superior to CA-4 and Crolibulin. Importantly, immunofluorescence staining and colchcine competitive binding assay revealed that microtubule dynamics was disrupted by 7e by binding at the colchicine site of tubulin. Moreover, molecular docking studies suggested the binding of this mimic at colchcine-binding site is similar to Crolibulin, as was in conformity with the observed SARs for these compounds.

Natural product Pimprinine derivative as well as preparation method and application thereof

The invention discloses a Pimprinine derivative as shown in a formula III in the description. The invention also discloses a preparation method of the Pimprinine derivative, and a series of Pimprinine derivatives are synthesized by taking Pimprinine as a lead, combining the structural characteristics of Pimprinine, taking cheap and easily available indole as a raw material, modifying and transforming different sites of a framework structure of the indole and introducing different substituent groups. The Pimprinine derivative disclosed by the invention has good bactericidal activity, shows efficient and/or broad-spectrum bactericidal activity, and can be applied to crop diseases caused by fungi, bacteria and viruses.

A radical addition and cyclization relay promoted by Mn(OAc)3?2H2O: Synthesis of 1,2-oxaphospholoindoles and mechanistic study

Novel and efficient Mn(OAc)3?2H2O promoted radical addition-[4 + 1] cyclization relay of 3-indolymethanols and phosphites was disclosed, which afforded 1,2-oxaphospholoindole derivatives in moderate to good yields. Based on the experimental and computational studies, a mechanism involving radical addition and intramolecular cyclization cascade was proposed.

Sulfonimide photo-acid generator with high acid yield

The invention discloses a sulfonimide photo-acid generator with high acid yield. The sulfonimide photo-acid generator has a structure as shown in a general formula (A) in the description. The acid generator has high sensitivity to active energy rays with the wavelength of 300-450nm, particularly 365nm (I rays) and 405nm (H rays), and is good in solubility and strong in acidity.

KOH-mediated stereoselective alkylation of 3-bromooxindoles for the synthesis of 3,3′-disubstituted oxindoles with two contiguous all carbon quaternary centres

The stereoselective synthesis of 3,3′-disubstituted oxindoles having all-carbon quaternary stereocenters has been achieved using KOH as a base with an excellent diastereomeric ratio (98?:?2). The practicability of the present methodology has been validated with the synthesis of a series of substrates in good to excellent yields. The aesthetic simplicity, accessibility, and eco-friendly base (KOH) have prompted the broader application of the present methodology in organic synthesis.

Rh(III)-Catalyzed [5 + 1] Annulation of Indole-enaminones with Diazo Compounds to Form Highly Functionalized Carbazoles

A novel Rh(III)-catalyzed C-H activation/annulation cascade of indole-enaminones with diazo compounds was reported to construct diversely functionalized carbazole frameworks. The most notable characteristic is that this transformation could smoothly furnish a novel [5 + 1] cyclization product with good to excellent yields (up to 95%), accompanied by the thorough removal of acetyl and N,N-dimethyl groups of two substrates from the target products, rather than the normally expected [4 + 2] cyclization products.

Cascade Reaction to Selectively Synthesize Multifunctional Indole Derivatives by IrIII-Catalyzed C?H Activation

An effective and condition-controlled way to synthesize with high selectivity a variety of functionalized indoles with potent biological properties has been developed. Notably, 2,4-dialkynyl indole products were obtained by direct double C?H bond alkynylation, whereas alkynyl at the C4 position could convert to carbonyl to generate 2-alkynyl-3,4-diacetyl indoles fast and effectively. Additionally, a one-pot relay catalytic reaction led to 2,5-di-alkynyl-3,4-diacetyl indoles when using a carbonyl group as the directing group and by controlling the type and quantity of additives. A possible mechanism was proposed based on many studies including deuterium-exchange experiments, the necessary conditions of product conversion, and the effect of water on the reaction.

Z-Selective Fluoroalkenylation of (Hetero)Aromatic Systems by Iodonium Reagents in Palladium-Catalyzed Directed C?H Activation

The direct and catalytic incorporation of fluorine containing molecular motifs into organic compounds resulting high-value added chemicals represents a rapidly evolving part of synthetic methodologies, thus this area is in the focus of pharmaceutical and agrochemical research. Herein we report a stereoselective procedure for direct fluorovinylation of aromatic and heteroaromatic scaffolds. This methodology development has been realized by palladium-catalyzed ortho C?H activation reaction of aniline derivatives featuring the regioselectivity via directing groups such as secondary of tertiary amides, ureas or ketones. The application of non-symmetrical aryl(fluoroalkenyl)-iodonium salts as fluoroalkenylating agents allowed mild reaction conditions in general for this transformation. The scope and limitations have been thoroughly investigated and the feasibility has been demonstrated by more than 50 examples.

Synthesis and antibacterial evaluation of (E)-1-(1H-indol-3-yl) ethanone O-benzyl oxime derivatives against MRSA and VRSA strains

Infections caused due to multidrug resistant organisms have emerged as a constant menace to human health. Even though numerous antibiotics are currently available for treating infectious diseases, a great number of bacterial strains have acquired resistance to many of them. Among these, infections caused due to Staphylococcus aureus are predominant in adult and paediatric population. Indole is a prominent chemical scaffold found in many pharmacologically active natural products and synthetic drugs. A number of oxime ether containing compounds have attracted attention of researchers owing to their interesting biological properties. Current work details the synthesis of indole containing oxime ether derivatives and their evaluation for antimicrobial activity against a panel of bacterial and mycobacterial strains. Synthesized compounds demonstrated good to moderate activity against drug-resistant S. aureus including resistant to vancomycin. Among all, compound 5h was found to possess potent activity against susceptible as well as MRSA and VRSA strains of S. aureus with MIC of 1 μg/mL and 2–4 μg/mL respectively. In addition, compound 5h was found to be non-toxic to Vero cells and exhibited good selectivity index of >40. Further, 5h, E-9a and E-9b possessed good biofilm inhibition against S. aureus. With these assuring biological properties, synthesized compounds could be potential prospective antimicrobial agents.

Site-Specific Oxidation of (sp3)C-C(sp3)/H Bonds by NaNO2/HCl

A site-specific oxidation of (sp3)C-C(sp3) and (sp3)C-H bonds in aryl alkanes by the use of NaNO2/HCl was explored. The method is chemical-oxidant-free, transition-metal-free, uses water as the solvent, and proceeds under mild conditions, making it valuable and attractive to synthetic organic chemistry.