Synthesis, biological evaluation, and computational investigation of ethyl 2,4,6-trisubstituted-1,4-dihydropyrimidine-5-carboxylates as potential larvicidal agents against Anopheles arabiensis

References

• Agarwal, N., Srivastava, P., Raghuwanshi, S. K., Upadhyay, D. N., Sinha, S., Shukla, P. K., & Ji Ram, V. (2002). Chloropyrimidines as a new class of antimicrobial agents. Bioorganic & Medicinal Chemistry, 10(4), 869–874. https://doi.org/10.1016/s0968-0896(01)00374-1
   PubMed Web of Science ®Google Scholar
• Al-Shar’i, N., & Musleh, S. S. (2022). CHK1 kinase inhibition: Identification of allosteric hits using MD simulations, pharmacophore modeling, docking and MM-PBSA calculations. Molecular Diversity, 26(2), 903–921. https://doi.org/10.1007/s11030-021-10202-w
   PubMed Web of Science ®Google Scholar
• Al-Shar’i, N. A. (2021). Tackling COVID-19: Identification of potential main protease inhibitors via structural analysis, virtual screening, molecular docking and MM-PBSA calculations. Journal of Biomolecular Structure and Dynamics, 39(17), 6689–6704. https://doi.org/10.1080/07391102.2020.1800514
   PubMed Web of Science ®Google Scholar
• Al-Shar’i, N. A., & Alnabulsi, S. M. (2016). Explaining the autoinhibition of the SMYD enzyme family: A theoretical study. Journal of Molecular Graphics & Modelling, 68, 147–157. https://doi.org/10.1016/j.jmgm.2016.07.001
   PubMed Web of Science ®Google Scholar
• Bairagi, K. M., Venugopala, K. N., Mondal, P. K., Gleiser, R. M., Chopra, D., Garcia, D., Odhav, B., & Nayak, S. K. (2018). Larvicidal study of tetrahydropyrimidine scaffolds against Anopheles arabiensis and structural insight by single crystal X‐ray studies. Chemical Biology & Drug Design, 92(6), 1924–1932. https://doi.org/10.1111/cbdd.13351
   PubMed Web of Science ®Google Scholar
• Bairagi, K. M., Younis, N. S., Emeka, P. M., Venugopala, K. N., Alwassil, O. I., Khalil, H. E., Sangtani, E., Gonnade, R. G., Mohanlall, V., & Nayak, S. K. (2021). Chemistry, anti-diabetic activity and structural analysis of substituted dihydropyrimidine analogues. Journal of Molecular Structure, 1227, 129412. https://doi.org/10.1016/j.molstruc.2020.129412
   Web of Science ®Google Scholar
• Bhatt, S., Gething, P. W., Brady, O. J., Messina, J. P., Farlow, A. W., Moyes, C. L., Drake, J. M., Brownstein, J. S., Hoen, A. G., Sankoh, O., Myers, M. F., George, D. B., Jaenisch, T., Wint, G. R. W., Simmons, C. P., Scott, T. W., Farrar, J. J., & Hay, S. I. (2013). The global distribution and burden of dengue. Nature, 496(7446), 504–507. https://doi.org/10.1038/nature12060
   PubMed Web of Science ®Google Scholar
• Cheung, J., Mahmood, A., Kalathur, R., Liu, L., & Carlier, P. R. (2018). Structure of the G119S mutant acetylcholinesterase of the malaria vector Anopheles gambiae reveals basis of insecticide resistance. Structure (London, England : 1993), 26(1), 130–136.e132. https://doi.org/10.1016/j.str.2017.11.021
   PubMed Web of Science ®Google Scholar
• Chidambaram, S., Mostafa, A. A.-F., Abdulrahman Al-Askar, A., Sayed, S. R. M., Radhakrishnan, S., & Akbar, I. (2021). Green catalyst Cu(II)-enzyme-mediated eco-friendly synthesis of 2-pyrimidinamines as potential larvicides against Culex quinquefasciatus mosquito and toxicity investigation against non-target aquatic species. Bioorganic Chemistry, 109, 104697. https://doi.org/10.1016/j.bioorg.2021.104697
   PubMed Web of Science ®Google Scholar
• Chitikina, S. S., Buddiga, P., Deb, P. K., Mailavaram, R. P., Venugopala, K. N., Nair, A. B., Al-Jaidi, B., & Kar, S. (2020). Synthesis and anthelmintic activity of some novel (E)-2-methyl/propyl-4-(2-(substitutedbenzylidene)hydrazinyl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidines. Medicinal Chemistry Research, 29(9), 1600–1610. https://doi.org/10.1007/s00044-020-02586-5
   Web of Science ®Google Scholar
• Dharma Rao, B. D., Bhandary, S., Chopra, D., Venugopala, K. N., Gleiser, R. M., Kasumbwe, K., & Odhav, B. (2017). Synthesis and characterization of a novel series of 1,4-dihydropyridine analogues for larvicidal activity against Anopheles arabiensis. Chemical Biology & Drug Design, 90(3), 397–405. https://doi.org/10.1111/cbdd.12957
   PubMed Web of Science ®Google Scholar
• DiRienzo, J. A., Casanoves, F., Balzarini, M. G., Gonzalez, L., Tabalada, M., & Robledo, C. W. (2014). InfoStat version 2014. Group InfoStat, FCA. Universidad Nacional de. Retrieved Accessed February 12, 2022, from http://www.infostat.com.ar/.
   Google Scholar
• Dragovich, P. S., Fauber, B. P., Corson, L. B., Ding, C. Z., Eigenbrot, C., Ge, H., Giannetti, A. M., Hunsaker, T., Labadie, S., Liu, Y., Malek, S., Pan, B., Peterson, D., Pitts, K., Purkey, H. E., Sideris, S., Ultsch, M., VanderPorten, E., Wei, B., … Zhang, X. (2013). Identification of substituted 2-thio-6-oxo-1,6-dihydropyrimidines as inhibitors of human lactate dehydrogenase. Bioorganic & Medicinal Chemistry Letters, 23(11), 3186–3194. https://doi.org/10.1016/j.bmcl.2013.04.001
   PubMed Web of Science ®Google Scholar
• Dyer, D. H., Lovell, S., Thoden, J. B., Holden, H. M., Rayment, I., & Lan, Q. (2003). The structural determination of an insect sterol carrier protein-2 with a ligand-bound C16 fatty acid at 1.35-Å resolution*. The Journal of Biological Chemistry, 278(40), 39085–39091. https://doi.org/10.1074/jbc.M306214200
   PubMed Web of Science ®Google Scholar
• Finney, D. J. (1952). Probit analysis: A statistical treatment of the sigmoid response curve. 2nd ed. Cambridge University Press.
   Google Scholar
• Gorbalenya, A. E., Baker, S. C., Baric, R. S., de Groot, R. J., Drosten, C., Gulyaeva, A. A., Haagmans, B. L., Lauber, C., Leontovich, A. M., Neuman, B. W., Penzar, D., Perlman, S., Poon, L. L. M., Samborskiy, D. V., Sidorov, I. A., Sola, I., Ziebuhr, J., & Coronaviridae Study Group Of The International Committee On Taxonomy Of, V. (2020). The species Severe acute respiratory syndrome-related coronavirus: Classifying 2019-nCoV and naming it SARS-CoV-2. Nature Microbiology, 5(4), 536–544.
   PubMed Web of Science ®Google Scholar
• Inoue, M., Sumii, Y., & Shibata, N. (2020). Contribution of organofluorine compounds to pharmaceuticals. ACS Omega, 5(19), 10633–10640. https://doi.org/10.1021/acsomega.0c00830
   PubMed Web of Science ®Google Scholar
• Jindra, M., & Bittova, L. (2020). The juvenile hormone receptor as a target of juvenoid “insect growth regulators”. Archives of Insect Biochemistry and Physiology, 103(3), e21615. https://doi.org/10.1002/arch.21615
   PubMed Web of Science ®Google Scholar
• Kappe, C. O., & Stadler, A. (2004). The biginelli dihydropyrimidine synthesis. In Organic reactions. John Wiley & Sons, Inc.
   Google Scholar
• Kim, I. H., Pham, V., Jablonka, W., Goodman, W. G., Ribeiro, J. M. C., & Andersen, J. F. (2017). A mosquito hemolymph odorant-binding protein family member specifically binds juvenile hormone. The Journal of Biological Chemistry, 292(37), 15329–15339. https://doi.org/10.1074/jbc.M117.802009
   PubMed Web of Science ®Google Scholar
• Knutsson, S., Engdahl, C., Kumari, R., Forsgren, N., Lindgren, C., Kindahl, T., Kitur, S., Wachira, L., Kamau, L., Ekström, F., & Linusson, A. (2018). Noncovalent inhibitors of mosquito acetylcholinesterase 1 with resistance-breaking potency. Journal of Medicinal Chemistry, 61(23), 10545–10557. https://doi.org/10.1021/acs.jmedchem.8b01060
   PubMed Web of Science ®Google Scholar
• Lauro, G., Strocchia, M., Terracciano, S., Bruno, I., Fischer, K., Pergola, C., Werz, O., Riccio, R., & Bifulco, G. (2014). Exploration of the dihydropyrimidine scaffold for the development of new potential anti-inflammatory agents blocking prostaglandin E2 synthase-1 enzyme (mPGES-1). European Journal of Medicinal Chemistry, 80, 407–415. https://doi.org/10.1016/j.ejmech.2014.04.061
   PubMed Web of Science ®Google Scholar
• Mans, B. J., Calvo, E., Ribeiro, J. M., & Andersen, J. F. (2007). The crystal structure of D7r4, a salivary biogenic amine-binding protein from the malaria mosquito Anopheles gambiae. The Journal of Biological Chemistry, 282(50), 36626–36633. https://doi.org/10.1074/jbc.M706410200
   PubMed Web of Science ®Google Scholar
• Miller, B. R., McGee, T. D., Swails, J. M., Homeyer, N., Gohlke, H., & Roitberg, A. E. (2012). MMPBSA.py: An efficient program for end-state free energy calculations. Journal of Chemical Theory and Computation, 8(9), 3314–3321. https://doi.org/10.1021/ct300418h
   PubMed Web of Science ®Google Scholar
• Naidu, B. N., Sorenson, M. E., Patel, M., Ueda, Y., Banville, J., Beaulieu, F., Bollini, S., Dicker, I. B., Higley, H., Lin, Z., Pajor, L., Parker, D. D., Terry, B. J., Zheng, M., Martel, A., Meanwell, N. A., Krystal, M., & Walker, M. A. (2015). Synthesis and evaluation of C2-carbon-linked heterocyclic-5-hydroxy-6-oxo-dihydropyrimidine-4-carboxamides as HIV-1 integrase inhibitors. Bioorganic & Medicinal Chemistry Letters, 25(3), 717–720. https://doi.org/10.1016/j.bmcl.2014.11.060
   PubMed Web of Science ®Google Scholar
• Padmashali, B., Chidananda, B. N., Govindappa, B., Basavaraj, S. M., Chandrashekharappa, S., & Venugopala, K. N. (2019). Synthesis and characterization of novel 1, 6-dihydropyrimidine derivatives for their pharmacological properties. Journal of Applied Pharmaceutical Science, 9(5), 117–124.
   Google Scholar
• Patil, A. D., Kumar, N. V., Kokke, W. C., Bean, M. F., Freyer, A. J., De Brosse, C., Mai, S., Truneh, A., Faulkner, D. J., Carte, B., Breen, A. L., Hertzberg, R. P., Johnson, R. K., Westley, J. W., & Potts, B. C. M. (1995). Novel alkaloids from the sponge batzella Sp.: Inhibitors of HIV gp120-human CD4 binding. The Journal of Organic Chemistry, 60(5), 1182–1188. https://doi.org/10.1021/jo00110a021
   Web of Science ®Google Scholar
• Rovnyak, G. C., Atwal, K. S., Hedberg, A., Kimball, S. D., Moreland, S., Gougoutas, J. Z., O'Reilly, B. C., Schwartz, J., & Malley, M. F. (1992). Dihydropyrimidine calcium channel blockers. 4. Basic 3-substituted-4-aryl-1,4-dihydropyrimidine-5-carboxylic acid esters. Potent antihypertensive agents. Journal of Medicinal Chemistry, 35(17), 3254–3263. https://doi.org/10.1021/jm00095a023
   PubMed Web of Science ®Google Scholar
• Sakanashi, M., Yoshikawa, Y., Akiyoshi, R., Itoh, C., Kitamura, Y., Niho, T., & Ohnishi, H. (1983). Possible antiarrhythmic activities of trapidil. Arzneimittel-Forschung, 33(2), 215–217.
   PubMed Web of Science ®Google Scholar
• Sanchez-Borzone, M. E., Mariani, M. E., Miguel, V., Gleiser, R. M., Odhav, B., Venugopala, K. N., & Garcia, D. A. (2017). Membrane effects of dihydropyrimidine analogues with larvicidal activity. Colloids and Surfaces. B, Biointerfaces, 150, 106–113. https://doi.org/10.1016/j.colsurfb.2016.11.028
   PubMed Web of Science ®Google Scholar
• Sandeep, C., Venugopala, K. N., Nayak, S. K., Raquel, M. G., Daniel, A. G., Kumalo, H. M., Kulkarni, R. S., Fawzi, M. M., Rashmi, V., Mahendra, K. M., & Odhav, B. (2018). One-pot microwave assisted synthesis and structural elucidation of novel ethyl 3-substituted-7-methylindolizine-1-carboxylates with larvicidal activity against Anopheles arabiensis. Journal of Molecular Structure, 1156, 377–384. https://doi.org/10.1016/j.molstruc.2017.11.131
   Web of Science ®Google Scholar
• Tale, R. H., Rodge, A. H., Hatnapure, G. D., & Keche, A. P. (2011). The novel 3,4-dihydropyrimidin-2(1H)-one urea derivatives of N-aryl urea: Synthesis, anti-inflammatory, antibacterial and antifungal activity evaluation. Bioorganic & Medicinal Chemistry Letters, 21(15), 4648–4651. https://doi.org/10.1016/j.bmcl.2011.03.062
   PubMed Web of Science ®Google Scholar
• Taylor, E. A., Rinaldo-Matthis, A., Li, L., Ghanem, M., Hazleton, K. Z., Cassera, M. B., Almo, S. C., & Schramm, V. L. (2007). Anopheles gambiae purine nucleoside phosphorylase: Catalysis, structure, and inhibition. Biochemistry, 46(43), 12405–12415. https://doi.org/10.1021/bi7010256
   PubMed Web of Science ®Google Scholar
• Tratrat, C. (2020). Novel thiazole-based thiazolidinones as potent anti-infective agents: In silico PASS and toxicity prediction, synthesis, biological evaluation and molecular modelling. Combinatorial Chemistry & High Throughput Screening, 23(2), 126–140. https://doi.org/10.2174/1386207323666200127115238
   PubMed Web of Science ®Google Scholar
• Venugopala, K. N., Nayak, S. K., Gleiser, R. M., Sanchez‐Borzone, M. E., Garcia, D. A., & Odhav, B. (2016a). Synthesis, polymorphism, and insecticidal activity of methyl 4‐(4‐chlorophenyl)‐8‐iodo‐2‐. methyl‐6‐oxo‐1, 6‐dihydro‐4H‐pyrimido [2, 1‐b] quinazoline‐3‐carboxylate against Anopheles arabiensis mosquito. Chemical Biology & Drug Design, 88(1), 88–96. https://doi.org/10.1111/cbdd.12736
   PubMed Web of Science ®Google Scholar
• Venugopala, K. N., Rao, G. D., Bhandary, S., Pillay, M., Chopra, D., Aldhubiab, B. E., Attimarad, M., Alwassil, O. I., Harsha, S., & Mlisana, K. (2016b). Design, synthesis, and characterization of (1-(4-aryl)-1H-1, 2, 3-triazol-4-yl) methyl, substituted phenyl-6-methyl-2-oxo-1, 2, 3, 4-tetrahydropyrimidine-5-carboxylates against Mycobacterium tuberculosis. Drug Design, Development and Therapy, 10, 2681–2690. https://doi.org/10.2147/DDDT.S109760
   PubMed Web of Science ®Google Scholar
• Venugopala, K. N., Shinu, P., Tratrat, C., Deb, P. K., Gleiser, R. M., Chandrashekharappa, S., Chopra, D., Attimarad, M., Nair, A. B., Sreeharsha, N., Mahomoodally, F. M., Haroun, M., Kandeel, M., Asdaq, S. M. B., Mohanlall, V., Al-Shar’i, N. A., & Morsy, M. A. (2022). 1,2,3-Triazolyl-tetrahydropyrimidine conjugates as potential sterol carrier protein-2 inhibitors: larvicidal activity against the malaria vector Anopheles arabiensis and in silico molecular docking study. Molecules, 27(9), 2676. https://doi.org/10.3390/molecules27092676
   PubMed Web of Science ®Google Scholar
• WHO. (2022). https://www.who.int/news-room/fact-sheets/detail/malaria (visited on June 26, 2022).
   Google Scholar
• WHO. (1975). Manual on practical entomology. Geneva: WHO.
   Google Scholar