Tag: 238.08

Amberlyst-15 catalysed synthesis of novel indole derivatives under ultrasound irradiation: Their evaluation as serotonin 5-HT_2C receptor agonists was written by Reddy, Gangireddy Sujeevan;Kamaraj, Rajamanikkam;Hossain, Kazi Amirul;Kumar, Jetta Sandeep;Thirupataiah, B.;Medishetti, Raghavender;Sushma Sri, N.;Misra, Parimal;Pal, Manojit. And the article was included in Bioorganic Chemistry in 2021.Category: indole-building-block This article mentions the following:

A series of indole based novel Schiff bases I [R¹ = H, Me, prop-2-yn-1-yl, etc; R² = H, Br] was designed as potential agonists of 5-HT_2C receptor that was supported by docking studies in-silico. These compounds I were synthesized via Amberlyst-15 catalyzed condensation of an appropriate pyrazole based primary amine with the corresponding indole-3-aldehydes under ultrasound irradiation at ambient temperature A number of target Schiff bases I were obtained in good yields (77-87%) under mild conditions within 1 h. Notably, the methodol. afforded the corresponding pyrazolo[4,3-d]pyrimidin-7(4H)-one derivatives II [R³ = Et, n-Bu, benzyl; R⁴ = H, Br] when the primary amine was replaced by a secondary amine. Several Schiff bases I showed agonist activity when tested against human 5-HT_2C using luciferase assay in HEK293T cells in-vitro. The SAR (Structure-Activity-Relationship) studies suggested that the imine moiety was more favorable over its cyclic form i.e. the corresponding pyrazolopyrimidinone ring. The Schiff bases I [R¹ = Me, R² = H] (EC₅₀ 1.8 nM) and I [R¹ = Bn, R² = H] (EC₅₀ 5.7 nM) were identified as the most active compounds and were comparable with Lorcaserin (EC₅₀ 8.5 nM). Also like Lorcaserin, none of these compounds I were found to be PAM of 5-HT_2C. With 鈭?4 and 鈭?50 fold selectivity towards 5-HT_2C over 5-HT_2A and 5-HT_2B resp. the compound I [R¹ = Bn, R² = H] that reduced locomotor activity in zebrafish (Danio rerio) larvae model emerged as a promising hit mol. for further study. In the experiment, the researchers used many compounds, for example, 5-Bromo-1-methyl-1H-indole-3-carbaldehyde (cas: 10102-94-0Category: indole-building-block).

5-Bromo-1-methyl-1H-indole-3-carbaldehyde (cas: 10102-94-0) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Category: indole-building-block

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

Synthesis of (Z)-5-[(5-(2-(phenylsulfonyl-ethyl)-1H-indol-3-yl)methylene]thiazolidine-2,4-dione of potential pharmacological interest was written by Laxminarayana, Keetha;Rajendiran, Chinnapillai;Mukkanti, Khagga. And the article was included in Asian Journal of Chemistry in 2013.HPLC of Formula: 10102-94-0 This article mentions the following:

Formylation of 5-bromo-1H-indole under Vilsmeier-Hack formylation conditions using POCl₃ and DMF as a reagents under cooling conditions (0-5掳) followed by a simple process gave 5-bromo-1H-indole-3-carboxaldehyde. A condensation reaction of this aldehyde with 2,4-thiazolidinedione in toluene as a solvent in the presence of PTSA and TBAB as a phase transfer catalyst under stirring at room temperature for 10-30 min, then slowly raising the temperature to 105掳 and maintaining for 12-15 h gave (Z)-5-[(5-bromo-1-alkyl-1H-indol-3-yl)methylene]-2,4-thiazolidinedione. Further condensation of this intermediate with phenyl(vinyl)sulfone in the presence of palladium acetate as a catalyst and DMF as a solvent and heating to 100-105掳 for 16 h gave (5Z)-5-[1-alkyl-5-[(E)-2-[(phenylsulfonyl)vinyl]-1H-indol-3-yl]methylene]-2,4-thiazolidinedione derivatives Reduction of this compound in the presence of hydrogen gas, palladium-carbon as a catalyst in acetic acid medium and methanol as a solvent heating at 45-50掳 for 8 h gave (Z)-5-[1-alkyl-5-[2-[2-(phenylsulfonyl)ethyl]-1H-indol-3-yl]methylene]-2,4-thiazolidinedione derivatives These products could also be prepared by an alternate route and the products were characterized on the basis of spectral and anal. data. The title compounds thus formed included a thiazolidinedione indole sulfone (I). In the experiment, the researchers used many compounds, for example, 5-Bromo-1-methyl-1H-indole-3-carbaldehyde (cas: 10102-94-0HPLC of Formula: 10102-94-0).

5-Bromo-1-methyl-1H-indole-3-carbaldehyde (cas: 10102-94-0) belongs to indole derivatives. The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.HPLC of Formula: 10102-94-0

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