88321-08-8

Usage

InChI:InChI=1/C20H18N2O2/c1-13(23)24-12-18(16-10-21-19-8-4-2-6-14(16)19)17-11-22-20-9-5-3-7-15(17)20/h2-11,18,21-22H,12H2,1H3

Upstream product

• 120-72-9 indole 
• 108-24-7 acetic anhydride 
• 141-46-8 Glycolaldehyde 
• 200347-50-8 1-benzyloxy-2,2-di(3'-indolyl)ethane 
• 111-15-9 2-ethoxyethyl acetate 
• 95331-90-1 2,2-di(1H-indol-3-yl)ethan-1-ol 
• 75-36-5 acetyl chloride 
• 924-44-7 glyoxylic acid ethyl ester 
• 66638-22-0 O-acetyl-L-serine hydrochloride 
• 30934-97-5 2,2-dimethoxyethanol 
• 577-19-5 2-nitrophenyl bromide 
• 64-19-7 acetic acid 
• 1445721-33-4 2,2-bis(7-bromo-1H-indole-3-yl)ethanol 
• 1445721-32-3 methyl bis(7-bromo-1H-indole-3-yl)acetate 

Relevant academic research and scientific papers

STRUCTURE ELUCIDATION OF STREPTINDOLE, A NOVEL GENOTOXIC METABOLITE ISOLATED FROM INTESTINAL BACTERIA

The structure of genotoxic metabolite, streptindole, isolated from inestinal bacteria (Streptococcus faecium IB 37) has been established as 2,2-di(3-indolyl) ethyl acetate by spectroscopic and synthetic methods.

Application of alkaloid streptindole and derivatives thereof in prevention and control of plant viruses and pathogenic bacteria

The invention relates to an application of alkaloid streptindole and derivatives thereof in control of plant virus pathogens. It is found that streptindole and derivatives I-1 to I-14 thereof show good anti-plant virus pathogen activity for the first time

Streptindole and Its Derivatives as Novel Antiviral and Anti-Phytopathogenic Fungus Agents

Plant diseases caused by plant viruses and pathogens seriously affect the production and storage of food crops. With the emergence of drug resistance, it is very difficult to control. Natural products are the source of new drug discovery. Here, the natural product streptindole was found to have good antiviral activity against tobacco mosaic virus (TMV) and fungicidal activities against 14 kinds of phytopathogenic fungi. A series of derivatives of streptindole were designed, synthesized, and evaluated for their antiviral and fungicidal activities. Compounds 4, 5, 11, 12c, 12d, 13d, and 13i-13l showed higher anti-TMV activities than ribavirin (inhibitory rate: 38, 37, and 40% at 500 μg/mL for inactivation, curative, and protection activity in vivo, respectively), among which compound 12d (inhibitory rate: 57, 55, and 53% at 500 μg/mL for inactivation, curative, and protection activity in vivo, respectively) with excellent antiviral activity was further evaluated for the mode of action. The mechanism research revealed that 12d can break the three-dimensional structure of TMV coat protein (CP) through hydrogen bonds, thus inhibiting the assembly of virus particles. The molecular docking result showed that compound 12d did exhibit strong interaction with TMV CP. The derivatives of streptindole also displayed broad-spectrum fungicidal activities. The current study provided valuable insights into the antiviral and fungicidal activities of streptindole derivatives.

(Thio)urea-catalyzed friedel-crafts reaction: Synthesis of bis(indolyl)-methanes

Bis(indolyl)methane derivatives (BIMs) were synthesized in moderate to good yields by (thio)urea catalyzed electrophilic substitution of indole (2) with various aldehydes 1. Reactions were performed under conventional and microwave (MW) heating, either using 1,2-dichloroetane as solvent or without solvent. The procedure using microwave heating was also applied to the synthesis of the natural products vibrindole A (3n), arsindoline A (3i), arundine (3o) and tris(1H-indol-3-yl)methane (3j). Additionally, the synthesis of streptindole was carried out via intermediate 3g. This methodology is well suited for the synthesis of bis(indolyl)methanes: it offers good yields of products, low sensitivity to moisture and oxygen, high tolerance to different functional groups on the aldehydes such as al-kynes and trimethylsilane, and simplicity in operation

One-pot total synthesis of streptindole, arsindoline B and their congeners through tandem decarboxylative deaminative dual-coupling reaction of amino acids with indoles

This paper described a decarboxylative deaminative dual-coupling reaction of amino acids with indoles to afford BIM scaffolds and its further application to the one-pot total synthesis of natural products. This method featured a stimulating example of activating amino acids in one pot as multi-carbon building blocks for transformation into final targets which are equipped with amino acid side chain backbones. This journal is

Eco-friendly synthesis of condensed nitrogen heterocycles: A brief experience from our group

In order to develop eco-friendly syntheses of condensed nitrogen heterocycles, solvent-free syntheses on solid acidic catalysts and aqueous reactions using a phase transfer catalyst (PTC) were successfully carried out. The catalysts used were (i) TLC-grade silica gel G (SiO2), (ii) SiO2 doped with 10 mol% phosphoric acid (H3PO 4-SiO2), (iii) Montmorillonite K10 clay (K10), (iv) acid-washed K10 clay (acid-clay), (v) K10 doped with one equivalent (with respect to substrate) of tosic acid (TsOH-K10) and (vi) cetylpyridinium bromide (CPB) (5 mol%) as the PTC. The reactions were carried out at room temperature (rt), at 60-70°C (oven) or under microwave irradiation (MWI).

One-pot construction of 3,3′-bisindolylmethanes through Bartoli indole synthesis

A one-pot approach to 3,3′-bisindolylmethane derivatives from nitrobenzene derivatives through the Bartoli indole synthesis was developed, in which the acid used to quench the reaction markedly affected its outcome. Quenching the reaction with concd HCl produced 3,3′-bisindolylmethane in contrast to the formation of 7-substituted indole by quenching with NH 4Cl.

One-pot synthesis of symmetric and unsymmetric 1,1-bis-indolylmethanes via tandem iron-catalyzed C-H bond oxidation and C-O bond cleavage

(Chemical Equation Presented) The reactions of indoles with ethers give a variety of symmetric and unsymmetric 1,1-bis-indolylmethane derivatives via iron-catalyzed C-H bond oxidation and C-O bond cleavage. 2009 American Chemical Society.

A mild and environmentally friendly scandium(III) trifluoromethanesulfonate-catalyzed synthesis of bis(3′-indolyl)alkanes and bis(3′-indolyl)-1-deoxyalditols

Bis(3′-indolyl)alkanes and bis(3′-indolyl) derivatives containing a 1-deoxyalditol moiety were synthesized in the presence of 5 mol % of scandium(III) trifluoromethanesulfonate [Sc(OTf)3] in CH 3CN or EtOH-H2O mixture as a

A Facile and Efficient Synthesis of 2,2-Bis(3′/2′ -indolyl)ethylamines and Three Bisindolic Natural Products

A simple and efficient synthesis of bis(indolyl)ethylamines and three bisindolic natural products, viz. hallucinogenic 6, genotoxic 7 and the alkanoic acid 8 has been developed by the reaction of indoles with appropriate carbonyl compounds on montmorillonite K10 clay.