Potential for Aedes aegypti Larval Control and Environmental Friendliness of the Compounds Containing 2-Methyl-3,4-dihydroquinazolin-4-one Heterocycle

Hung Huy Nguyen; Cong Tien Nguyen; Huy Gia Ngo; Giang Thi Truc Nguyen; Phan Thi Thuy; William N Setzer; Ping-Chung Kuo; Ha Manh Bui

doi:10.1021/acsomega.3c01686

Potential for Aedes aegypti Larval Control and Environmental Friendliness of the Compounds Containing 2-Methyl-3,4-dihydroquinazolin-4-one Heterocycle

ACS Omega. 2023 Jul 5;8(28):25048-25058. doi: 10.1021/acsomega.3c01686. eCollection 2023 Jul 18.

Authors

Hung Huy Nguyen^{1

2}, Cong Tien Nguyen³, Huy Gia Ngo^{1

2}, Giang Thi Truc Nguyen^{3

4}, Phan Thi Thuy⁵, William N Setzer^{6

7}, Ping-Chung Kuo⁸, Ha Manh Bui⁹

Affiliations

¹ Center for Advanced Chemistry, Institute of Research and Development, Duy Tan University, 03 Quang Trung, Da Nang 55000, Vietnam.
² Department of Pharmacy, Duy Tan University, 03 Quang Trung, Da Nang 55000, Vietnam.
³ Department of Chemistry, Ho Chi Minh City University of Education, 280 An Duong Vuong Street, Ward 4, District 5, Ho Chi Minh City 70000, Vietnam.
⁴ Thanh Hoa High School, Thanh Hoa District, Long An Province 82906, Vietnam.
⁵ Faculty of Chemistry, College of Education, Vinh University 182 Le Duan, Vinh City, Nghe An Province 46000, Vietnam.
⁶ Aromatic Plant Research Center, 230 N 1200 E, Suite 100, Lehi, Utah 84043, United States.
⁷ Department of Chemistry, University of Alabama in Huntsville, Huntsville, Alabama 35899, United States.
⁸ School of Pharmacy, College of Medicine, National Cheng Kung University, Tainan 701, Taiwan.
⁹ Faculty of Environment, Saigon University, 273 An Duong Vuong Street, District 5, Ho Chi Minh City 70000, Vietnam.

Abstract

2-Methylquinazolin-4(3H)-one was prepared by the reaction of anthranilic acid, acetic anhydride, and ammonium acetate. The reaction of 2-methylquinazolin-4(3H)-one with N-aryl-2-chloroacetamides in acetone in the presence of potassium carbonate gave nine N-aryl-2-(2-methyl-4-oxoquinazolin-3(4H)-yl)acetamide compounds. The structures of these compounds were elucidated on the basis of their IR, ¹H nuclear magnetic resonance (NMR), ¹³C NMR, and high-resolution mass spectrometry (HR-MS) spectral data. These synthesized compounds containing the 2-methyl-3,4-dihydroquinazolin-4-one moiety exhibited activity against Aedes aegypti mosquito larvae with LC₅₀ values of 2.085-4.201 μg/mL after 72 h exposure, which is also confirmed using a quantitative structure-activity relationship (QSAR) model. Interestingly, these compounds did not exhibit toxicity to the nontarget organism Diplonychus rusticus. In silico molecular docking revealed acetylcholine binding protein (AChBP) and acetylcholinesterase (AChE) to be potential molecular targets. These data indicated the larvicidal potential and environmental friendliness of these N-aryl-2-(2-methyl-4-oxoquinazolin-3(4H)-yl)acetamide derivatives.