Synthesis of a novel water-soluble NMDA receptor antagonist

The acid catalyzed reaction of electron rich heterocyclic compounds such as indole and pyroles with p-dimethyl aminobenzaldehyde is known as the Ehrlich test 12. Generally 3,3`-bis (indolyl) methanes are synthesized by an analogous reaction to the Ehrlich test, where indole reacts with aliphatic or aromatic aldehydes or ketones in the presence of an acid catalyst to produce azafulvenium salt which undergoes further addition reaction with a second indole molecule to produce bis (indolyl) methanes.

20/12/2017 · Highly Efficient Synthesis of Bis ..

Highly Efficient Method for Synthesis of Bis ..

Curtius-like Rearrangement of an Iron–Nitrenoid …

In conclusion, a simple, efficient, green, and eco-friendly procedure is described in this study for the synthesis of bis(indolyl)methanes in the presence of PEG-OP(O)Cl2. This protocol provides a low cost procedure for the synthesis of these compounds and also evaluated their anticancer activity.

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Cell cytotoxicity was measured using the MTT assay. Cancer cells in the exponential growth phase were cultured at a density of 1 × 105 cells/well in 96-well plates. After treatment with various concentration of synthesized bis(indolyl)methanes for 24 h, MTT solution (5.0 mg/mL in phosphate-buffered saline) was added (10 μL/well), and the plates were incubated for another 4 h at 37 °C. Purple formazan crystals were dissolved in 100 μL DMSO per well. After 10 min, the reaction products were colorimetrically quantified at 570 nm with subtraction of the background absorbance at 630 nm by scanning with a microplate reader. Cell viability was determined as a ratio of treated cells to untreated cells (control at 0 μM). A stock solution of compound was prepared in DMSO, and the final concentration of this solvent was kept constant at 0.1%. The control group received DMSO alone. The IC50 (the concentration of each substance required for 50% inhibition of tumor activity) was calculated according to standard method. All experiments were performed in triplicate.


to Formaldehyde for the Synthesis of 3,3′-Bisindolylmethanes ..

Tungstosilicic acid hydrate was employed as an efficient catalyst for the synthesis of bisindolylmethanes 4 using the Friedel-Crafts reaction of N-sulfonyl tryptamine 5 with various aromatic aldehydes, except 3-formylindole. In the excluding case, tris-indolylmethane 7 was formed via a sequential addition-elimination-addition process. The bioactivity test revealed that the phenolic hydroxyl group plays an important role in cytotoxicity; it demonstrated that ortho- and para-hydroxy bis-indolylmethane (BIM) analogs (4b and 4d) displayed cytotoxic potency toward HepG2 (human hepatocellular liver carcinoma cell line) and MOLT-3 (human lymphoblastic leukemia cell line) cancer cell lines. Significantly, both analogs showed slightly higher inhibitory efficacy than the control drug, etoposide, in HepG2 cells, and the analog 4d exhibited the most potent activity against MOLT-3 cell lines, with an IC50 value of 1.62 μg/mL.

of Bisindolylmethanes and Their Cytotoxicity Properties ..

Mechanism of the Reaction:
The common route for the synthesis of bis (indolyl) methanes is electrophilic substitution reaction of indoles with the aromatic or aliphatic aldehyde and ketones catalyzed by protic acids or Lewis acids. However, Lewis acids are required in excess because it is destroyed by the presence of even small amount of moisture or when trapped by nitrogen present in heterocycles.

The present method for the synthesis of bisindolylmethanes in ..

In continuation of our research and interest in the development of novel synthetic methodologies [], herein we report an efficient method for the synthesis of bisindolylmethanes catalyzed by PEG-OPOCl2 (). To date, it is the first feasible method for electrophilic substitution at 3-position of indole with various aryl/heteroaryl aldehydes in PEG-OP(O)Cl2 medium. It has great advantages including simple and mild experimental conditions, less reaction time, cost-effectiveness due to recyclability of PEG-OP(O)Cl2 and applicability to various substituted aryl, and heterocyclic aldehyde substrates. It is an innovative and efficient approach to synthesize bisindolylmethanes while avoiding hazardous solvents.

General & Introductory Chemistry

The common route for the synthesis of bis (indolyl) methanes is electrophilic substitution reaction of indoles with the aromatic or aliphatic aldehyde and ketones catalyzed by protic acids or Lewis acids. However, Lewis acids are required in excess because it is destroyed by the presence of even small amount of moisture or when trapped by nitrogen present in heterocycles.