Unexpected Reactions of Azido-p-Benzoquinone Derivatives Towards Lawesson’s Reagent and Molecular Docking Study as a Promising Anticancer Agent

Document Type : Original Article

Authors

1 Photochemistry Department, Industrial Research Division, national research Centre, Dokki, Cairo, Egypt

2 National Research Centre, Photochemistry Department, Industrial Chemical Division, 33 EL Bohouth st., Dokki, Giza 12622, Egypt

3 NRC_Photochemistry

Abstract

Synthesis of 1,3,2-benzo-aza-phosphole derivatives (3b-c) by reaction of lawesson’s Reagent (LR) 1b with 2-azido-p-benzoquinonedibenzenesulfonimine (2b-c) has been intercepted. The reaction of 2-azido-p-quinonediimine 4 with Lawesson’s Reagent (LR) (1a) and/or (1b) gave the corresponding compounds 6a and 6b. On the other hand, when 2,5-diazido 5 reacted with LR (1b) has led to the formation of the benzenesulfonamide 10. The disphospha-5-indacene adduct has been synthesized by the reaction of LR 1c with 5. Mechanisms accounting for the formation of these compounds are provided. All the synthesized compounds have been subjected to docking study using AutoDock Vina software in order to gain insights to their binding modes against cyclin-dependent protein kinase 2 (CDK-2, PDB:1DI8), receptor protein B-cell lymphoma 2 (BCL-2, PDB:2O2F), and Janus kinase 2 (Jak2, PDB:5AEP) that are highly involved in cell cycle and in cell apoptosis. These targets have been selected based on their key roles in cancer progression via the regulation of the cell cycle and DNA replication. Molecular-docking analyses have revealed that compound 12 and 6b are the best docked ligand against all tested targets. As it is displays the lowest binding energy and critical hydrogen bonds and hydrophobic interactions with these proteins.

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History

  • Receive Date: 29 September 2019
  • Revise Date: 17 November 2019
  • Accept Date: 21 November 2019

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