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Synthesis of Chiral 3,3ʹ-Disubstituted (S)-BINOL Derivatives via the Kumada and Suzuki Coupling and Their Antibacterial Activity

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Abstract

A new series of 3,3ʹ-disubstituted chiral (S)-BINOL derivatives 6a–6k has been synthesized via the Kumada and Suzuki–Miyaura coupling reactions using (S)-BINOL as the initial compound. The Kumada coupling has been found to be superior in terms of yields and reaction time. All the synthesized compounds have been screened for their antibacterial activity against Gram-positive and Gram-negative organisms using Penicillin and Streptomycin as standards. The most potent antibacterial activity has been determined for compounds 6a,6b, 6c, and 6d with MIC values ranging from 1.17 to 4.68 μg/mL against all bacterial strains tested. Molecular docking studies has presented an insight into the binding pattern of the top active ligands with the respective target protein.

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Funding

We acknowledge Department of Science and Technology (DST) (DST-SERB-ECR/2016/000288) India for providing the financial assistance and Gandhi Institute of Technology (GITAM) University for providing the facility. We would like to thank Prof.G.A.Rama Rao, Principal SoS, (GITAM), for his voluble suggestions while preparing the manuscript. The author RS thank CSIR-HRDG for the award of CSIR-SRAship [13(8906-A)/2017-pool].

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Authors and Affiliations

  1. Department of Chemistry, Gitam University, Rudraram Mandal, Sangareddy District, Patancheru, 502329, Hyderabad, Telangana, India

    A. Reddy Ankireddy, K. Paidikondala & R. Gundla

  2. Department of Chemistry, JNT University, Kukatpally, 500085, Hyderabad, Telangana, India

    R. Syed & Ch. Venkata Ramana Reddy

  3. Stem Cell Research Division, National Institute of Nutrition (NIN), Indian Council of Medical Research (ICMR), 500007, Hyderabad, Telangana, India

    T. Ganapathi

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  1. A. Reddy Ankireddy
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  2. K. Paidikondala
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  3. R. Syed
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  4. R. Gundla
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  5. Ch. Venkata Ramana Reddy
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  6. T. Ganapathi
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Correspondence to R. Gundla.

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Ankireddy, A.R., Paidikondala, K., Syed, R. et al. Synthesis of Chiral 3,3ʹ-Disubstituted (S)-BINOL Derivatives via the Kumada and Suzuki Coupling and Their Antibacterial Activity. Russ J Gen Chem 90, 1507–1517 (2020). https://doi.org/10.1134/S1070363220080198

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