Pd/Cu-catalyzed access to novel 3-(benzofuran-2-ylmethyl) substituted (pyrazolo/benzo)triazinone derivatives: their<i>in silico</i>/<i>in vitro</i>evaluation as inhibitors of chorismate mutase (CM)

Reddy, Gangireddy Sujeevan; Shukla, Sharda; Bhuktar, Harshavardhan; Hossain, Kazi Amirul; Edwin, Rebecca Kristina; Giliyaru, Varadaraj Bhat; Misra, Parimal; Pal, Manojit

doi:10.1039/d2ra05255e

Cited by 8 publications

(3 citation statements)

References 43 publications

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“…Electronwithdrawing substituents on the phenyl ring diminished the yield of benzofuran derivatives and vice versa (Scheme 8). The reaction strategy involved the preparation of iodonium salt by using iodine followed by (triphenylphosphine-mediated) oxidative addition to generate intermediate C. 76 in 2022 availed the used of both palladium and copper by employing them as catalysts in Sonogashira coupling reaction between terminal alkynes 36/37 and iodophenols 35, which upon intramolecular cyclization resulted in the synthesis of benzofuran derivatives. In the developed approach, copper iodide was employed as a cocatalyst with the (PPh 3 )PdCl 2 catalyst in triethyl amine (base and solvent).…”

Section: Benzofuran Synthesis Via Palladium-based Catalystmentioning

confidence: 99%

“…Considering the utility of Pd- and Cu-catalyzed synthesis of benzofuran heterocycles, the Reddy group 76 in 2022 availed the used of both palladium and copper by employing them as catalysts in Sonogashira coupling reaction between terminal alkynes 36/37 and iodophenols 35 , which upon intramolecular cyclization resulted in the synthesis of benzofuran derivatives. In the developed approach, copper iodide was employed as a cocatalyst with the (PPh 3 )PdCl 2 catalyst in triethyl amine (base and solvent).…”

Section: Precedented Approachesmentioning

confidence: 99%

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A Comprehensive Review on Benzofuran Synthesis Featuring Innovative and Catalytic Strategies

Mushtaq,

Zahoor,

Ahmad

et al. 2024

ACS Omega

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Benzofurans have intrigued both pharmaceutical researchers and chemists owing to the medicinal usage of their derivatives against copious diseasecausing agents (i.e., bacteria, viruses, and tumors). These heterocyclic scaffolds are pervasively encountered in a number of natural products and drugs. The everincreasing utilization of benzofuran derivatives as pharmaceutical agents persuaded the chemists to devise novel and facile methodological approaches to assemble the biologically potent benzofuran nucleus. This review summarizes the current developments regarding the innovative synthetic routes and catalytic strategies to procure the synthesis of benzofuran heterocycles with their corresponding mechanistic details, reported by several research groups during 2021−2023.

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Section: Benzofuran Synthesis Via Palladium-based Catalystmentioning

confidence: 99%

Section: Precedented Approachesmentioning

confidence: 99%

A Comprehensive Review on Benzofuran Synthesis Featuring Innovative and Catalytic Strategies

Mushtaq,

Zahoor,

Ahmad

et al. 2024

ACS Omega

View full text Add to dashboard Cite

show abstract

“…[5,6] The absence of this enzyme [13] in animal as well as human has made it a promising pharmacological target for TB. Indeed, because of this feature we became interested in exploring CM for the identification of its inhibitors [14][15][16][17][18] that could be developed as potential antitubercular agents in future. In the current study we focused on the spiroindoline-3,2'-quinazoline framework A (Figure 1) for the identification of possible inhibitors of CM.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Docking and In Vitro Evaluation of Spiroindoline‐3,2’‐Quinazoline Derivatives

Addu,

Miriyala,

Kapavarapu

et al. 2023

ChemistrySelect

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The Wang‐OSO3H catalyzed synthesis of a series of spiroindoline‐3,2’‐quinazoline derivatives and their in silico and in vitro evaluation against MtbCM (Mycobacterium tuberculosis Chorismate Mutase) are disclosed. Initially, a library of small molecules based on spiroindoline‐3,2’‐quinazoline framework was constructed. The reaction of 2‐aminobenzamide with appropriate isatin derivatives in the presence of Wang‐OSO3H under ultrasound irradiation was used for this purpose. The reaction proceeded under mild conditions to afford the desired products in good yields within a short duration. With the use of heterogeneous catalyst, inexpensive solvent as reaction media, and ultrasound as the source of green energy the methodology appeared to be a useful alternative to the previously reported methods. The in silico docking of all the synthesized compounds into the MtbCM (PDB: 2FP2) revealed that the binding of these compounds took place on the external surface pockets of the MtbCM active site cavity mainly in two different clusters. Three compounds that interacted well with MtbCM also showed good (57–64 %) inhibition of MtbCM in vitro when tested at 10 μM. Based on in silico and in vitro studies along with the ADME predictions these three spiroindoline‐3,2’‐quinazoline derivatives were identified as pre‐hits.

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Wang resin catalysed sonochemical synthesis of pyrazolo[4,3-d]pyrimidinones and 2,3-dihydroquinazolin-4(1H)-ones: Identification of chorismate mutase inhibitors having effects on Mycobacterium tuberculosis cell viability

Shukla

Rao

Bhuktar

et al. 2023

Bioorganic Chemistry

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Pd/Cu-catalyzed access to novel 3-(benzofuran-2-ylmethyl) substituted (pyrazolo/benzo)triazinone derivatives: theirin silico/in vitroevaluation as inhibitors of chorismate mutase (CM)

Abstract: We report the Pd/Cu-catalyzed synthesis, in silico molecular docking, in vitro CM inhibition and computational ADME prediction of novel 3-(benzofuran-2-ylmethyl) substituted (pyrazolo/benzo)triazinone derivatives.

Cited by 8 publications

References 43 publications

A Comprehensive Review on Benzofuran Synthesis Featuring Innovative and Catalytic Strategies

A Comprehensive Review on Benzofuran Synthesis Featuring Innovative and Catalytic Strategies

Synthesis, Docking and In Vitro Evaluation of Spiroindoline‐3,2’‐Quinazoline Derivatives

Wang resin catalysed sonochemical synthesis of pyrazolo[4,3-d]pyrimidinones and 2,3-dihydroquinazolin-4(1H)-ones: Identification of chorismate mutase inhibitors having effects on Mycobacterium tuberculosis cell viability

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