Synlett
DOI: 10.1055/a-2616-5514
letter
Emerging Trends in Organic Chemistry: A Focus on India

Design, Synthesis, and Antifungal Activity of Isochroman-Fused Coumarins against Rhizoctonia solani

Kavita Kavita
a   Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi, 110007, India
,
Sumit Kumar
a   Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi, 110007, India
,
Prashant Kaushik
b   Division of Agricultural Chemicals, Indian Agricultural Research Institute, Delhi, 110012, India
,
Amita Dua
c   Department of Chemistry, Dyal Singh College, University of Delhi, Delhi, 110003, India
,
Najam Akhtar Shakil
b   Division of Agricultural Chemicals, Indian Agricultural Research Institute, Delhi, 110012, India
,
Brajendra K. Singh
a   Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi, 110007, India
› Author Affiliations

We appreciate the funding provided by the Institute of Emminence (IoE), University of Delhi which has contributed to further research and development. Kavita, Sumit Kumar thanks Council of Scientific and Industrial Research (CSIR), India for the award of Senior Research Fellowship.


We dedicate this article to the fond memory of our beloved Late Prof. Ashok K. Prasad

Abstract

This study presents the synthesis and antifungal assessment of novel isochroman-fused coumarin derivatives against Rhizoctonia solani. The compounds were synthesized using an efficient and environmentally benign approach and demonstrated strong in silico binding affinity to CYP51. In vitro assays further confirmed their antifungal activity, with one compound exhibiting the highest potency, achieving an ED50 value of 3.59 μM. These findings underscore the potential of isochroman-fused coumarins as eco-friendly rice sheath blight control agents.

Supporting Information



Publication History

Received: 10 March 2025

Accepted after revision: 19 May 2025

Accepted Manuscript online:
20 May 2025

Article published online:
02 July 2025

© 2025. Thieme. All rights reserved

Georg Thieme Verlag KG
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  • 38 General Procedure for the Synthesis of Isochroman-Fused Coumarins 4a–i 4-Hydroxy coumarins 1ah (1 equiv) and 2-bromobenzyl bromide 2a,b (1 equiv) were dissolved in propylene carbonate (5 mL) in the presence of potassium carbonate base (3 equiv) and 10 mol% PdCl2 as a catalyst in a 50 mL round-bottomed flask. The reaction mixture stirred for 4 h at 120 °C. Chloroform was then used to extract the resultant reaction mixture (3 × 30 mL) after the indication of completion of the reaction by TLC. The combined extracts were washed with brine solution, then dried using anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure under a vacuum resulting in the isolation of the crude product. The crude product thus obtained was purified by silica gel chromatography using ethyl acetate in petroleum ether as a gradient solvent system. The separated pure products were characterized by 1H, 13C NMR spectroscopy, mass spectroscopy, and IR spectroscopy.
  • 39 6H,11H-Isochromeno[4,3-c]chromen-11-one (4a) It was obtained as a white solid in 68% yield using 5% ethyl acetate in petroleum ether as an eluent, mp 105–107 °C; R ƒ = 0.4 (8% ethyl acetate in petroleum ether). IR (KBr): 1702, 1612, 1490, 1332, 1286, 1091, 913, 750 cm–1. 1H NMR (400 MHz, CDCl3): δ = 8.56 (1 H, d, J = 7.9 Hz), 7.86–7.88 (1 H, m), 7.57 (1 H, t, J = 8.4 Hz), 7.42 (1 H, t, J = 7.6 Hz), 7.32 (3 H, dt, J = 15.2, 7.7 Hz), 7.13 (1 H, d, J = 7.4 Hz), 5.41 (2 H, s). 13C NMR (100.6 MHz, CDCl3): δ = 161.3, 160.3, 153.0, 132.6, 129.2, 128.4, 127.5, 126.8, 125.0, 124.2, 124.1, 123.2, 116.7, 115.3, 102.8, 69.9. HRMS (ESI): m/z calcd for C16H11O3 [M + H]+: 251.0703; found: 251.0705.