18372-22-0 | - Indole Building Blocks

Zhang, Han-Cheng et al. published their research in Journal of Medicinal Chemistry in 2005 | CAS: 18372-22-0

Methyl 2-(1H-indol-3-yl)-2-oxoacetate (cas: 18372-22-0) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Recommanded Product: 18372-22-0

Novel Indolylindazolylmaleimides as Inhibitors of Protein Kinase C-尾: Synthesis, Biological Activity, and Cardiovascular Safety was written by Zhang, Han-Cheng;Derian, Claudia K.;McComsey, David F.;White, Kimberly B.;Ye, Hong;Hecker, Leonard R.;Li, Jian;Addo, Michael F.;Croll, Diane;Eckardt, Annette J.;Smith, Charles E.;Li, Quan;Cheung, Wai-Man;Conway, Bruce R.;Emanuel, Stuart;Demarest, Keith T.;Andrade-Gordon, Patricia;Damiano, Bruce P.;Maryanoff, Bruce E.. And the article was included in Journal of Medicinal Chemistry in 2005.Recommanded Product: 18372-22-0 This article mentions the following:

Novel indolylindazolylmaleimides were synthesized and examined for kinase inhibition. Low-nanomolar inhibitors of PKC-尾 with good to excellent selectivity vs other PKC isoenzymes and GSK-3尾 were identified. In a cell-based functional assay, the title compounds I [R = 2-naphthyl, 3-quinolinyl] effectively blocked IL-8 release induced by PKC-尾II (IC₅₀ = 20-25 nM). In cardiovascular safety assessment, representative lead compounds bound to the hERG channel with high affinity, potently inhibited ion current in a patch-clamp experiment, and caused a dose-dependent increase of QT_c in guinea pigs. In the experiment, the researchers used many compounds, for example, Methyl 2-(1H-indol-3-yl)-2-oxoacetate (cas: 18372-22-0Recommanded Product: 18372-22-0).

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Brief introduction of 18372-22-0

The synthetic route of 18372-22-0 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.18372-22-0,Methyl 2-(1H-indol-3-yl)-2-oxoacetate,as a common compound, the synthetic route is as follows.

In a three-necked flask, 47 mL lithium aluminum hydride (4.44 g, 117 mmol, 2.5 mol/L THF solution) was injected under Nitrogen at 0 C. 10.15 g (50 mmol) 1 was dissolved in 36 mL of dry THF. The above solution was added dropwise for a period of 1 h, then heated to 70 C for 4 hours. The reaction was complete and quenched by the Fisher treatment for a suspension. The suspension was filtered and the filter cake washed with ethyl acetate. The combined organic layer was wash with brine, dry over Na2SO4 and concentrated in vacuum. The residue was purified by flash silica gel column chromatography(ethyl acetate / petroleum ether, 25%) to obtain a white solid 2 (6.44 g, 80% yield)., 18372-22-0

The synthetic route of 18372-22-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Guo, Zhenbo; Xu, Yiming; Peng, Yujie; Haroon ur Rashid; Quan, Wei; Xie, Peng; Wu, Lichuan; Jiang, Jun; Wang, Lisheng; Liu, Xu; Bioorganic and Medicinal Chemistry Letters; vol. 29; 9; (2019); p. 1133 – 1137;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Downstream synthetic route of 18372-22-0

18372-22-0, As the paragraph descriping shows that 18372-22-0 is playing an increasingly important role.

To a suspension of compound 12 (1.17 g, 5.7 mmol) and compound 6 (586.5 mg, 2.9 mmol) in THF (50 mL) was added 1.0 M KOBut in THF (11.5 mL, 11.5 mmol) under nitrogen atmosphere. After stirring at ambient temperature for 5 h, thereaction mixture was quenched with 1 N HCl (50 mL) and extracted with EtOAc. The combined organic layer was washed with brine, dried over Na2SO4, and filtered. The solvent was removed in vacuo, and the crude product waspurified by column chromatography with (2:1 hexanes/acetone) to give 13 (726.0 mg, 71%) as an orange solid: mp 254 – 256 C; 1H NMR (DMSO-d6) delta 12.02 (s, 1H), 11.19 (s, 1H), 8.04 (d, J = 3.0 Hz, 1H), 7.73 (d, J = 2.0 Hz, 1H), 7.49 (dd, J = 2.0, 8.5 Hz, 1H), 7.43 (dd, J = 3.0, 8.5 Hz, 2H), 7.09-7.06 (m, 1H), 6.76-6.73 (m, 1H), 6.40(d, J = 8.0 Hz, 1H); HRMS (EI, m/z): calcd for C18H10N2O2Cl2 ([M]+) 356.0114, found 356.0126.

18372-22-0, As the paragraph descriping shows that 18372-22-0 is playing an increasingly important role.

Reference£º
Article; Wang, Min; Gao, Mingzhang; Miller, Kathy D.; Sledge, George W.; Hutchins, Gary D.; Zheng, Qi-Huang; Bioorganic and Medicinal Chemistry Letters; vol. 21; 1; (2011); p. 245 – 249;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles