703-80-0 Usage
Description
3-Acetylindole is an organic compound that belongs to the indole family. It is characterized by the presence of an acetyl group attached to the indole nucleus. 3-Acetylindole is known for its diverse range of applications in various industries, particularly in the pharmaceutical and chemical sectors.
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 703-80-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 7,0 and 3 respectively; the second part has 2 digits, 8 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 703-80:
(5*7)+(4*0)+(3*3)+(2*8)+(1*0)=60
60 % 10 = 0
So 703-80-0 is a valid CAS Registry Number.
InChI:InChI=1/C10H9NO/c1-7(12)9-6-11-10-5-3-2-4-8(9)10/h2-6,11H,1H3
703-80-0Relevant articles and documents
Synthesis, biological evaluation and molecular modeling of imidazo[1,2-a]pyridine derivatives as potent antitubulin agents
Liu, Jin,Zuo, Daiying,Jing, Tongfei,Guo, Ming,Xing, Lingyun,Zhang, Wenyu,Zhao, Jianwen,Shen, Jiwei,Gong, Ping,Zhang, Dajun,Zhai, Xin
, p. 4088 - 4099 (2017)
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.
A radical addition and cyclization relay promoted by Mn(OAc)3?2H2O: Synthesis of 1,2-oxaphospholoindoles and mechanistic study
Xu, Meng-Meng,Kou, Lu-Yao,Bao, Xiao-Guang,Xu, Xiao-Ping,Ji, Shun-Jun
supporting information, p. 1915 - 1919 (2021/03/09)
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.
KOH-mediated stereoselective alkylation of 3-bromooxindoles for the synthesis of 3,3′-disubstituted oxindoles with two contiguous all carbon quaternary centres
Devi, Manju,Jadhav, Amol P.,Singh, Ravi P.
supporting information, p. 8445 - 8448 (2021/05/25)
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.
