Category: 2591-98-2

2591-98-2, Name is 2-(1H-Indol-3-yl)acetaldehyde, belongs to indole-building-block compound, is a common compound. 2591-98-2. In an article, authors is Abu-Zaitoon, Yousef M., once mentioned the new application about 2591-98-2.

Investigation of the potential role of aldehyde oxidase in indole-3-acetic acid synthesis of developing rice grains

Aldehyde oxidase (AO) was proposed to convert indole-3-acetaldehyde (IAAld) to indole-3-acetic acid (IAA) primarily through the identification of endogenous IAAld and the efficient conversion of IAAld to IAA via AO. Involvement of AO in the production of IAA has been investigated in developing rice grains (OsAO). Analysis of phylogenetic tree, RT-PCR as well as online microarray data confirmed that rice inherited two groups of AO; OsAO1-3, and OsAO4. OsAO1-3 were found to be very similar and may arise as a result of recent duplication. RT-PCR analysis confirmed that OsAO1 but not OsAO2 or OsAO3 was expressed in the developing rice grains at 1, 7, and 21 days after flowering (DAF). Change in the expression of OsAO1 was found to be parallel to the previously reported abrupt change in IAA level between 4-7 DAF suggesting that OsAO1 may have a role in IAA synthesis at least in this system. The top 300 genes list created by co-expression analysis contained OsYUCCA9 and OsYUCCA11 which reported to have a significant role in IAA synthesis through the indole-3pyruvic acid (IPA) pathway. Lack of correlation between the two transcripts of OsAO4 and changes in IAA level may give a negative indication for the involvement of OsAO4 in de novo IAA synthesis.

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Reference£º
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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.2591-98-2,2-(1H-Indol-3-yl)acetaldehyde,as a common compound, the synthetic route is as follows.

At O0C under argon, lithium aluminum hydride (14 mg, 0.00036 mol) was added to a solution of intermediate 7 (74 mg, 0.00036 mol) in THF (1 ml). The mixture was stirred at 0C for 1 hour, quenched with a 5% solution of potassium hydrogen sulfate, and extracted twice with EtOAc. The organic layer was separated, washed with brine, dried (MgSO4), filtered, and the solvent was evaporated, to give the indole-3-yl acetaldehyde as an orange oil. A mixture of intermediate 9 (200 mg, 0.00074 mol) and sodium cyanoborohydride (64 mg, 0.0010 mol) in MeOH (2.3 ml) and acetic acid (2 drops) was added dropwise to a solution of the previous aldehyde (236 mg, 0.0015 mol) in MeOH (2 ml). The reaction mixture was stirred at room temperature for 16 hours. The reaction was quenched with water, made alkaline with a saturated solution of sodium hydrogen carbonate and extracted 3 times with EtOAc. The organic layer was separated, washed with brine, dried (MgSO4), filtered, and the solvent was evaporated. The residue was purified by column chromatography over silica gel (40-63 mum) (eluent: EtOAc/MeOH 100/0 to 90/10). The pure fractions were collected and the solvent was evaporated, yielding 190 mg (44 %) of compound 3 as an orange foam.1H NMR (300 MHz, CDCl3) delta 8.42 (d, IH, J=5.7), 8.08 (brs, IH), 7.79 (d, IH, J=2.4), 7.63 (d, IH, J=7.8), 7.40 (d, IH, J=8.1), 7.25-7.07 (m, 5H), 6.59 (s, IH), 6.48 (dd, IH, J=8.7. J=2.1), 4.00 (m, 5H), 3.48 (t, 2H, J=6.8), 3.12 (m, 4H). MS (ES+) w/z 413 (M+l).

2591-98-2, As the paragraph descriping shows that 2591-98-2 is playing an increasingly important role.

Reference£º
Patent; JANSSEN PHARMACEUTICA N.V.; WO2007/107545; (2007); A1;,
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