Category: 4382-54-1

Murar, Claudia E. et al. published their research in Journal of the American Chemical Society in 2014 | CAS: 4382-54-1

5-Methoxyindole-2-carboxylic acid (cas: 4382-54-1) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Related Products of 4382-54-1

KAHA Ligations That Form Aspartyl Aldehyde Residues as Synthetic Handles for Protein Modification and Purification was written by Murar, Claudia E.;Thuaud, Frederic;Bode, Jeffrey W.. And the article was included in Journal of the American Chemical Society in 2014.Related Products of 4382-54-1 This article mentions the following:

Aldehydes are widely recognized as valuable synthetic handles for the chemoselective manipulation of peptides and proteins. In this report, the authors show that peptides and small proteins containing the aspartic acid semialdehyde (Asa) side chain can be easily prepared by a chemoselective amide-forming ligation that results in the formation of the Asa residue at the ligation site. This strategy employs the 伪-ketoacid-hydroxylamine (KAHA) ligation in combination with a new isoxazolidine monomer that forms a side-chain aldehyde upon ligation. This monomer is easily prepared on a preparative scale by a catalytic, enantioselective approach and is readily introduced onto the N-terminus of a peptide segment by solid-phase peptide synthesis. The ligated product can be further functionalized by bioorthogonal reactions between the aldehyde residue and alkoxyamines or hydrazides. The authors demonstrated that glucagon aldehyde, an unprotected 29-mer peptide prepared by KAHA ligation, can be site specifically and chemoselectively modified with biotin, dyes, aliphatic oximes, and hydroxylamines. The authors further describe a simple and high recovery one-step purification process based on the capture of a 29-mer glucagon aldehyde and a 76-mer ubiquitin aldehyde by an alkoxyamine-functionalized polyethylene glycol resin. The peptide or protein was released from the resin by addition of a hydroxylamine to provide the corresponding oximes. In the experiment, the researchers used many compounds, for example, 5-Methoxyindole-2-carboxylic acid (cas: 4382-54-1Related Products of 4382-54-1).

5-Methoxyindole-2-carboxylic acid (cas: 4382-54-1) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Related Products of 4382-54-1

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

Morzyk-Ociepa, Barbara et al. published their research in Polyhedron in 2014 | CAS: 4382-54-1

5-Methoxyindole-2-carboxylic acid (cas: 4382-54-1) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Related Products of 4382-54-1

Crystal structure, infrared and EPR spectra and anticancer activity in vitro of the novel manganese(II) complexes of indolecarboxylic acids was written by Morzyk-Ociepa, Barbara;Kokot, Mariusz;Rozycka-Sokolowska, Ewa;Gielzak-Kocwin, Krystyna;Filip-Psurska, Beata;Wietrzyk, Joanna;Michalska, Danuta. And the article was included in Polyhedron in 2014.Related Products of 4382-54-1 This article mentions the following:

The new complexes of 5-methoxyindole-2-carboxylic acid (5-MeOI2CAH) and indole-2-carboxylic acid (I2CAH) with manganese(II): catena-poly[diaquamanganese(II)-bis(渭2-5-methoxyindole-2-carboxylato-O:O’)], [Mn(5-MeOI2CA)2(H2O)2]n (1) and catena-poly[diaquamanganese(II)-bis(渭2-indole-2-carboxylato-O:O’)], [Mn(I2CA)2(H2O)2]n (2) have been prepared A single crystal x-ray anal. of 1 shows that the complex crystallizes in the monoclinic system, space group P21/c. The 5-MeOI2CA anion acts as a bidentate bridging ligand coordinated to Mn(II) in an abnormal non-planar skew-skew mode, which differs from the coplanar syn-syn, syn-anti and anti-anti bridging modes commonly occurring in metal carboxylates. The FTIR and EPR spectroscopic studies of Mn(II) complexes are reported. In vitro cytotoxicities of 1, 2, 5-MeOI2CAH, I2CAH and their Zn(II) complexes have been evaluated by an MTT assay against the selected human leukemia cell lines: HL-60, MV-4-11, U937, Jurkat, KG-1, U2932 and murine melanoma B16-F0. The two manganese(II) complexes are cytotoxic and their antiproliferative activity against some cell lines (e.g. Jurkat derived from an acute T cell leukemia) is similar to that of cisplatin. In the experiment, the researchers used many compounds, for example, 5-Methoxyindole-2-carboxylic acid (cas: 4382-54-1Related Products of 4382-54-1).

5-Methoxyindole-2-carboxylic acid (cas: 4382-54-1) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Related Products of 4382-54-1

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

Downstream synthetic route of 4382-54-1

4382-54-1 5-Methoxyindole-2-carboxylic acid 20401, aindole-building-block compound, is more and more widely used in various.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4382-54-1,5-Methoxyindole-2-carboxylic acid,as a common compound, the synthetic route is as follows.

General procedure: A mixture of 5-methoxyindole-2-carboxylic acid 1 (20 g, 104.61 mmol) and sulfuric acid (16 mL) in EtOH (160 mL) was refluxed for 10 h. The reaction mixture was evaporated, neutralized to pH 7 with 2 N-NaOH and extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4, and evaporated under reduced pressure. The residue was purified by silica gel column chromatography using solvent CH2Cl2 and isolated by ether to give 5-methoxyindole-2-carboxylic acid ethyl ester (22.8 g, 99percent). Mp 157 ¡ãC; IR (ATR) vmax=3325, 1676 cm-1; Rf 0.39 (n-Hexane/EtOAc, 4:1); 1H NMR (300 MHz, CDCl3) delta 8.81 (br s, 1H), 7.31 (d, J=8.9 Hz, 1H), 7.16-7.05 (m, 2H), 7.00 (dd, J=9.0, 2.1 Hz), 4.40 (q, J=7.1 Hz, 2H), 3.85 (s, 3H), 1.41 (t, J=7.1 Hz, 3H). 13C NMR (75 MHz, CDCl3); delta 162.0, 154.7, 132.3, 127.9, 127.8, 116.7, 112.8, 108.2, 102.5, 60.9, 55.7, 14.4.

4382-54-1 5-Methoxyindole-2-carboxylic acid 20401, aindole-building-block compound, is more and more widely used in various.

Reference£º
Article; Pagire, Haushabhau S.; Chun, Hang-Suk; Bae, Myung Ae; Ahn, Jin Hee; Tetrahedron; vol. 69; 14; (2013); p. 3039 – 3044;,
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

Some tips on 4382-54-1

As the paragraph descriping shows that 4382-54-1 is playing an increasingly important role.

4382-54-1, 5-Methoxyindole-2-carboxylic acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(178-1) Under nitrogen atmosphere, to a solution of 5-methoxyindole-2-carboxylic acid (1.00 g) in Et2O (40 mL) was added LiAlH4 (280 mg) at 0 C., and the mixture was stirred under reflux for 3 hours. The mixture was treated with ethyl acetate, diluted with an aqueous hydrochloric acid solution, and extracted with ethyl acetate. The mixture was concentrated to give a crude alcohol compound (840 mg, 91%), which was dissolved in THF (10 mL), and stirred with MnO2 (4.20 g) at room temperature for 5 hours. The mixture was filtered on celite, and the filtrate was concentrated, and the residue was purified by silica gel column chromatography to give 5-methoxyindole-2-carbaldehyde (300 mg, 36%). 1H NMR (CDCl3, 400 MHz) delta 9.80 (s, 1H), 8.90 (brs, 1H), 7.34 (brd, 1H, J=8.9 Hz), 7.19 (dd, 1H, J=2.1 and 0.8 Hz), 7.11 (brs, 1H), 7.08 (dd, 1H, J=8.9 and 2.1 Hz), 3.86 (s, 3H).

As the paragraph descriping shows that 4382-54-1 is playing an increasingly important role.

Reference£º
Patent; Tokunaga, Teruhisa; Hume, William Ewan; Kitoh, Makoto; Nagata, Ryu; US2003/181496; (2003); 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