N-Arylsulfonylated C-Homoaporphines as a New Class of Antiplatelet and Antimicrobial Agents

Bharti Rajesh Kumar Shyamlal; Amol T Mahajan; Vikash Kumar; Aarohi Gupta; Rishabh Shrivastava Ronin; Manas Mathur; Janmejaya Sen; Sandeep Chaudhary

doi:10.1021/acsmedchemlett.4c00491

N-Arylsulfonylated C-Homoaporphines as a New Class of Antiplatelet and Antimicrobial Agents

ACS Med Chem Lett. 2024 Dec 23;16(1):116-125. doi: 10.1021/acsmedchemlett.4c00491. eCollection 2025 Jan 9.

Authors

Bharti Rajesh Kumar Shyamlal¹, Amol T Mahajan², Vikash Kumar¹, Aarohi Gupta^{1

3}, Rishabh Shrivastava Ronin⁴, Manas Mathur⁴, Janmejaya Sen², Sandeep Chaudhary^{1

2}

Affiliations

¹ Laboratory of Organic and Medicinal Chemistry, Department of Chemistry, Malaviya National Institute of Technology, Jawaharlal Nehru Marg, Jaipur 302017, India.
² Laboratory of Bioactive Heterocycles and Catalysis (BHC lab), Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research-Raebareli (Transit Campus), Bijnor-Sisendi Road, Near CRPF Base Camp, Sarojini Nagar, Lucknow 226002, India.
³ Department of Chemistry, University of Massachusetts Amherst, 710 North Pleasant Street, Amherst, Massachusetts 01003, United States.
⁴ School of Agriculture, Suresh Gyan Vihar University, Mahal Road, Jagatpura, Jaipur 303806, India.

PMID: 39811136
PMCID: PMC11726367 (available on 2026-01-09)
DOI: 10.1021/acsmedchemlett.4c00491

Abstract

A series of novel N-arylsulfonylated C-homoaporphine alkaloids were synthesized under microwave irradiation and evaluated for their in vitro antiplatelet and antimicrobial activities. Among the series, compounds 12a, 12c, 12e, 12f, 12h, 12j, 12k, 12m, and 12o demonstrated highly potent (∼3-fold) platelet aggregation inhibitory activity than acetylsalicylic acid (IC₅₀ = 21.34 μg/mL). Several N-arylsulfonylated C-homoaporphines also exhibited promising antimicrobial activity against various strains, including Macrophoma phaseolina, Trichoderma reesei, and Aspergillus niger, with minimum inhibitory concentrations (MIC) of 12.5, 6.25, and 12.5 μg/mL, respectively, comparable to Ketoconazole [MIC = 12.5 μg/mL (MP and AN strain); 6.25 μg/mL (TR strain)]. 12h showed potent antibacterial activity (IC₅₀ = 6.25 μg/mL against Escherichia coli and Bacillus subtilis) compared to Ampicillin (IC₅₀ = 12.5 μg/mL). After thorough structure-activity relationship (SAR) and in silico studies, C-homoaporphines were identified as a novel class of antiplatelet and antimicrobial agents.