5416-80-8 Usage
Description
2-Methylindole-3-carboxaldehyde is an organic compound with the chemical formula C9H7NO. It is a brown powder that can be oxidatively activated via N-heterocyclic carbene organocatalysis to generate heterocyclic ortho-quinodimethane as a key intermediate. 2-Methylindole-3-carboxaldehyde has a wide range of applications across different industries due to its unique chemical properties and reactivity.
Uses
Used in Pharmaceutical Industry:
2-Methylindole-3-carboxaldehyde is used as a reactant for the preparation of tryptophan dioxygenase inhibitors, specifically pyridyl-ethenyl-indoles, which have potential as anticancer immunomodulators. These inhibitors can modulate the immune system and exhibit inhibitory effects on tumor growth and progression.
Used in Chemical Sensors:
In the field of chemical sensors, 2-Methylindole-3-carboxaldehyde is utilized as a reactant for the preparation of fluorescent sensors, such as BODIPY. These sensors are essential for detecting and measuring various chemical and biological substances, providing valuable information for research and industrial applications.
Used in Antimicrobial Applications:
2-Methylindole-3-carboxaldehyde is also used as a reactant for the preparation of antimicrobial agents against methicillin-resistant Staphylococcus aureus (MRSA). MRSA is a significant concern in healthcare settings, and the development of new antimicrobial agents is crucial for combating drug-resistant bacteria.
Used in G Protein-Coupled Receptor Antagonists:
2-Methylindole-3-carboxaldehyde is employed as a reactant in the synthesis of G protein-coupled receptor (GPCR) CRTh2 antagonists. These antagonists play a role in modulating immune responses and have potential applications in treating asthma and other inflammatory conditions.
Used in Inhibitors of PI3 Kinase-α:
2-Methylindole-3-carboxaldehyde is also used in the preparation of inhibitors of PI3 kinase-α, which are involved in various cellular processes, including cell growth, survival, and metabolism. Inhibiting this enzyme can have therapeutic implications in cancer treatment and other diseases.
Used in Antitubercular Agents:
2-Methylindole-3-carboxaldehyde is used as a reactant for the preparation of antitubercular agents, which are essential for treating tuberculosis, a severe bacterial infection caused by Mycobacterium tuberculosis.
Used in Anti-Inflammatory Agents:
2-Methylindole-3-carboxaldehyde is utilized in the synthesis of anti-inflammatory agents, which can help reduce inflammation and alleviate pain and swelling associated with various conditions, such as arthritis and other autoimmune diseases.
Used in Mycobacterium tuberculosis Protein Tyrosine Phosphatase B:
2-Methylindole-3-carboxaldehyde is used as a reactant in the preparation of Mycobacterium tuberculosis protein tyrosine phosphatase B inhibitors. These inhibitors can potentially disrupt the bacterial cell's signaling pathways, leading to the inhibition of bacterial growth and aiding in the treatment of tuberculosis.
Used in Glucocorticoid Receptor Ligands:
2-Methylindole-3-carboxaldehyde is also used in the synthesis of glucocorticoid receptor ligands, which can modulate the activity of the glucocorticoid receptor, playing a role in various physiological processes, including immune response and inflammation.
Used in Agents Stimulating Neurite Outgrowth:
2-Methylindole-3-carboxaldehyde is employed as a reactant for the preparation of agents that stimulate neurite outgrowth. These agents can promote the growth and development of nerve cells, which can be beneficial in the treatment of neurodegenerative diseases and nerve damage.
Synthesis Reference(s)
Chemical and Pharmaceutical Bulletin, 31, p. 2892, 1983 DOI: 10.1248/cpb.31.2892
Check Digit Verification of cas no
The CAS Registry Mumber 5416-80-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,4,1 and 6 respectively; the second part has 2 digits, 8 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 5416-80:
(6*5)+(5*4)+(4*1)+(3*6)+(2*8)+(1*0)=88
88 % 10 = 8
So 5416-80-8 is a valid CAS Registry Number.
InChI:InChI=1/C10H9NO/c1-7-9(6-12)8-4-2-3-5-10(8)11-7/h2-6,11H,1H3
5416-80-8Relevant articles and documents
Naked-eye fluorescent sensor for Cu(II) based on indole conjugate BODIPY dye
Tümay, Sureyya O.,Okutan, Elif,Sengul, Ibrahim F.,?zcan, Emrah,Kandemir, Hakan,Doruk, Tu?rul,?etin, Metin,?o?ut, Bünyemin
, p. 161 - 171 (2016)
Graphical abstract A novel indole mono-styryl BODIPY was synthesised and characterized for the colorimetric recognition of Cu2+. It was also revealed from this study 3 can passively diffuse through cell membrane and stain both bacterial and mammalian cells even in very low concentrations. BODIPY-indole 3 retains inside the cells in cytometry and can be further modified for other applications.
Triphenylphosphine/1,2-Diiodoethane-Promoted Formylation of Indoles with N, N -Dimethylformamide
Lin, Jin-Hong,Xiao, Ji-Chang,Zhu, Yu-Rong
supporting information, (2021/11/22)
Despite intensive studies on the synthesis of 3-formylindoles, it is still highly desirable to develop efficient methods for the formylation of indoles, due to the shortcomings of the reported methods, such as inconvenient operations and/or harsh reaction conditions. Here, we describe a Ph3P/ICH2CH2I-promoted formylation of indoles with DMF under mild conditions. A Vilsmeier-type intermediate is readily formed from DMF promoted by the Ph3P/ICH2CH2I system. A onestep formylation process can be applied to various electron-rich indoles, but a hydrolysis needs to be carried out as a second step in the case of electron-deficient indoles. Convenient operations make this protocol attractive.
First discovery of pimprinine derivatives and analogs as novel potential herbicidal, insecticidal and nematicidal agents
Zhang, Ming-Zhi,Mulholland, Nick,Seville, Anne,Hough, Gemma,Smith, Nicholas,Dong, Hong-Qiang,Zhang, Wei-Hua,Gu, Yu-Cheng
supporting information, (2020/12/21)
Pimprinine and streptochlorin are indole natural products produced by many species of organisms, and they are reported to possess a wide range of biological activities, such as anticancer, antiviral, antifungal activity and so on. In this study, three series of pimprinine derivatives or analogs were efficiently synthesized under the optimized methods. Biological assays conducted at Syngenta firstly indicated the pimprinine derivatives or analogs possessed potential herbicidal and insecticidal activity, and this is highlighted by compounds 21g, 21h, 21i, 21j, 21l, 22h, 22i and 23h, they possessed significant biological activity as well as broad spectrum. Meanwhile, compounds with benzothiophene-oxazole core (21h, 22h and 23h), showed effective nematicidal activity in primary screening. Compounds 21g and 21i were identified as the most promising lead structures for further study.
Copper-catalyzed synthesis and anticancer activity evaluation of indolo[1,2-a]quinoline derivatives
Borwornpinyo, Suparerk,Chuanopparat, Nutthawat,Jearawuttanakul, Kedchin,Kanjanasirirat, Phongthon,Ngernmeesri, Paiboon,Rattanarat, Hassayaporn,Seemakhan, Sawinee,Thanetchaiyakup, Adisak
, (2021/09/14)
A simple and effective one-pot synthesis of substituted indolo[1,2-a]quinolines has been developed. The desired products were obtained in up to 98% yield when substituted 2-methyindoles were treated with 2-iodobenzaldehyde in the presence of Cs2CO3, CuI and L-proline. Our mechanistic study confirmed that the reaction sequence involved an intermolecular Knoevenagel reaction followed by an intramolecular Ullmann-type coupling reaction. Moreover, some of the synthesized compounds were found to be active against human breast (MCF-7) and colorectal (HCT-116) cancer cells with IC50 values of 27.96 μM and in the range of 6.21–46.91 μM, respectively.
