Anticancer Activity of 3,3′‐Diindolylmethane and the Molecular Mechanism Involved in Various Cancer Cell Lines

Abstract

Indole-3-carbinol is a natural compound present in cruciferous plants, which upon digestion, converts into 3,3'-diindolylmethane (DIM) under acidic pH of the stomach. In recent years, various methods have been developed to improve the synthesis of DIM and its analogs because of different pharmacological activities like anticancer, antimicrobial, anti-inflammatory, etc. Among them, DIMs anticancer activity by modulation of protein expression in cell signaling pathways and other factors has widely studied. This review describes the antiproli-ferative activity of DIMs and its mode of action, which resulted in apoptosis in various cancerous cells. We have performed a literature search on DIMs anticancer activity over the last ten years (2011-2020) and reported in this review. Several fascinating DIM attributes against cancer suggest it as a potential candidate for further drug development programs. This review will guide the medicinal chemist to find the mechanistic pathways involved in the inhibition of proliferation in cancerous cells by novel DIMs.

K2S2O8-glucose mediated oxidative coupling of alcohols with indoles for synthesis of bis(indolyl)methanes in water

“…Compound 1a was obtained as a brown solid (mp: 146-148 1C) with 92% yield. 1 H NMR (500 MHz, CDCl 3 ) d 7.87 (s, 2H), 7.44-7.19 (m, 11H), 7.04 (t, J = 7.5 Hz, 2H), 6.64 (s, 2H), 5.92 (s, 1H). 13 3,3 0 -((4-Isopropylphenyl)methylene)bis(1H-indole) (1d).…”

“…Compound 1d was obtained as a red solid (mp: 154-156 1C) with 83% yield. 1 This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022 3,3 0 -(Cyclopropylmethylene)bis(1H-indole) (2d). The representative general procedure mentioned above was followed.…”

“…Compound 2d was obtained as a red solid (mp: 154-156 1C) with 82% yield. 1 3,3 0 -(Phenylmethylene)bis(5-methoxy-1H-indole) (3d). The representative general procedure mentioned above was followed.…”

“…Compound 3d was obtained as a red solid (mp: 216-218 1C) with 82% yield. 1 H NMR (500 MHz, DMSO-d 6 ) d 10.61 (s, 2H), 7.34 (d, J = 7.5 Hz, 2H), 7.27-7.23 (m, 4H), 7.17-7.14 (m, 1H), 6.81 (d, J = 2.0 Hz, 2H), 6.70-6.68 (m, 4H), 5.71 (s, 1H), 3.57 (s, 6H). 13…”

“…Bis(indolyl)methanes (BIMs) are a key unit in bioactive metabolites of cruciferous plants, and marine and terrestrial microorganisms, 1 e.g., vibrindole A from Vibrio parahaemolyticus, 2 arsindoline A 3 and arsinoline B 4 from the bacterial strain CB101. 5 BIMs exhibit various bioactivities such as anticancer, 1 fibromyalgia treatment, 6 antistaphylococcal, 7 antileishmanial, 8 and antioxidant. 9 Because of their biological importance, several efficient methods for their syntheses have been developed.…”