Solventless Mechanosynthesis Of <i>Bis</i>(Indolyl)Methanes

Mhaldar, Shashank N.; Mandrekar, Ketan S.; Gawde, Mukund K.; Shet, Rajdatt V.; Tilve, Santosh G.

doi:10.1080/00397911.2018.1542732

Cited by 18 publications

(6 citation statements)

References 35 publications

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“…3,3′-Bisindolylmethane (BIM) and its functionalized class of natural products were originally isolated from cruciferous plants and terrestrial and marine organisms and shown to contain a broad array of medicinal properties. − Key members of this class of natural products include arundine, vibrindole A, streptindole, arsindoline A, tris(1 H -indol-3-yl)methane, and trisindoline (Figure ). − A unique structure of this bioactive intermediate contains two indole units which are responsible for exhibiting a range of essential biological activities such as anti-neurodegenerative, anti-inflammatory, anticancer, antibiotic, insecticidal, antimicrobial, antifungal, and antioxidant properties (Figure ). ,− Interestingly, some of these BIM derivatives are used as a sedatives in the treatment of AIDS, chronic fatigue, irritable bowel syndrome, and cancer, while bis(indolyl)arylmethane-bearing compounds are used as drugs for Parkinson’s disease, obesity, and bacterial and oncolytic viruses. ,− In addition, BIMs have also been found to have the potential to normalize abnormal cell growth associated with cervical dysplasia …”

Section: Introductionmentioning

confidence: 99%

Effective Synthesis and Biological Evaluation of Natural and Designed Bis(indolyl)methanes via Taurine-Catalyzed Green Approach

et al. 2022

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An ecofriendly, inexpensive, and efficient route for synthesizing 3,3′-bis(indolyl)methanes (BIMs) and their derivatives was carried out by an electrophilic substitution reaction of indole with structurally divergent aldehydes and ketones using taurine and water as a green catalyst and solvent, respectively, under sonication conditions. Using water as the only solvent, the catalytic process demonstrated outstanding activity, productivity, and broad functional group tolerance, affording the required BIM natural products and derivatives in excellent yields (59–90%). Furthermore, in silico based structure activity analysis of the synthesized BIM derivatives divulges their potential ability to bind antineoplastic drug target and spindle motor protein kinesin Eg5. The precise binding mode of BIM derivatives with the ATPase motor domain of Eg5 is structurally reminiscent with previously reported allosteric inhibitor Arry520, which is under phase III clinical trials. Nevertheless, detailed analysis of the binding poses indicates that BIM derivatives bind the allosteric pocket of the Eg5 motor domain more robustly than Arry520; moreover, unlike Arry520, BIM binding is found to be resistant to drug-resistant mutations of Eg5. Accordingly, a structure-guided mechanism of Eg5 inhibition by synthesized BIM derivatives is proposed.

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Section: Introductionmentioning

confidence: 99%

Effective Synthesis and Biological Evaluation of Natural and Designed Bis(indolyl)methanes via Taurine-Catalyzed Green Approach

et al. 2022

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“…The method was introduced as an eco-friendly solvent-free method for the synthesis of trisindoline in the presence of silica gel (SiO 2 ) as acid catalyst and grinding medium. 54 Trisindoline 3 was afforded after 7 h of grinding in 62% yield, compared to the grinding technique by mortar and pastel using nano-SiO 2 as a catalyst. 52 …”

Section: Synthesis Of Trisindolinesmentioning

confidence: 99%

Chemistry of trisindolines: natural occurrence, synthesis and bioactivity

et al. 2021

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“…In 2019, Mhaldar et al published a mechanochemical protocol, which avoided both the use of a solvent and catalyst, significantly decreasing toxic chemical waste production ( Scheme 76 ) [ 208 ]. In this methodology, the reactions performed with the ball-milling technique in the presence of SiO 2 , which played the role of both the grinding medium and the acid catalyst, due to its slightly acidic character (pH 6–7).…”

Section: Reviewmentioning

confidence: 99%

Green and sustainable approaches for the Friedel–Crafts reaction between aldehydes and indoles

Kolagkis,

Galathri,

Kokotos

2024

Beilstein J. Org. Chem.

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The synthesis of indoles and their derivatives, more specifically bis(indolyl)methanes (BIMs), has been an area of great interest in organic chemistry, since these compounds exhibit a range of interesting biological and pharmacological properties. BIMs are naturally found in cruciferous vegetables and have been shown to be effective antifungal, antibacterial, anti-inflammatory, and even anticancer agents. Traditionally, the synthesis of BIMs has been achieved upon the acidic condensation of an aldehyde with indole, utilizing a variety of protic or Lewis acids. However, due to the increased environmental awareness of our society, the focus has shifted towards the development of greener synthetic technologies, like photocatalysis, organocatalysis, the use of nanocatalysts, microwave irradiation, ball milling, continuous flow, and many more. Thus, in this review, we summarize the medicinal properties of BIMs and the developed BIM synthetic protocols, utilizing the reaction between aldehydes with indoles, while focusing on the more environmentally friendly methods developed over the years.

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Solventless Mechanosynthesis Of Bis(Indolyl)Methanes

Cited by 18 publications

References 35 publications

Effective Synthesis and Biological Evaluation of Natural and Designed Bis(indolyl)methanes via Taurine-Catalyzed Green Approach

Effective Synthesis and Biological Evaluation of Natural and Designed Bis(indolyl)methanes via Taurine-Catalyzed Green Approach

Chemistry of trisindolines: natural occurrence, synthesis and bioactivity

Green and sustainable approaches for the Friedel–Crafts reaction between aldehydes and indoles

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