Analysis of Quantitative Structure-Activity Relationship (QSAR) Of 1,8-Napthalymide-4-Aminoquinoline Derivatives as Antimalarial Compounds

Ika Nur Fitriani*  -  Universitas Islam Negeri Walisongo Semarang, Indonesia
Muhammad Sholahudin  -  Department of Chemistry, Faculty of Science and Technology, Universitas Islam Negeri Walisongo Semarang, Indonesia
Adi Tiara Zikri  -  Department of Material Science and Engineering, Chonnam National University, Republic of Korea, Korea, Republic of

(*) Corresponding Author

QSAR analysis from derivative compounds of 1,8-naphthalimide-4-aminoquinoline has been carried out with the aim of knowing the quantitative relationship between structure and activity based on the log IC50 value. The modelling was made with two dimensions and geometric optimization is carried out. The AM1 semi-empirical method was used to optimize the geometry of the total energy of 25 compounds. The descriptors in the QSAR calculation were dipole moment, atomic net charge, ELUMO, EHOMO, SAG, SAA, hydration energy, polarizability, and log P. The descriptors were used to find quantitative equations of the relationship between the structure and antimalarial activity.

Keywords: AM1; antimalarial; QSAR; 1,8-naphthalimide-4-aminoquinoline; derivative compounds

  1. Armunanto, R. and Sudiono, S. (2010) ‘Relation of Electronic Structures With Their Antimalarial Activities on Artemisinin Derivatives’, Indonesian Journal of Chemistry, 4(3), pp. 212–217. doi: 10.22146/ijc.21856.
  2. Block, J. H. and Beale, J. M. (2011) Organic Medicinal and Pharmaceutical Chemistry. 12th edn. Philadelphia: Lippincott Williams & Wilkins.
  3. FDA (2020) FDA cautions against use of hydroxychloroquine or chloroquine for COVID-19 outside of the hospital setting or a clinical trial due to risk of heart rhythm problems.
  4. Garcia, M. L. et al. (2022) ‘QSAR studies on benzothiophene derivatives as Plasmodium falciparum N-myristoyltransferase inhibitors: Molecular insights into affinity and selectivity’, Drug Development Research, 83(2), pp. 264–284. doi: 10.1002/ddr.21646.
  5. Hamzah, N., Rauf, A. and Anam, A. (2014) ‘Studi Hubungan Kuantitatif Struktur-Aktivitas (HKSA) dan Docking Molekuler Senyawa Turunan Oxabicycloheptene Sulfonamide (OBHS) sebagai Antagonis Reseptor Estrogen-α pada Terapi Kanker Leher Rahim (Serviks)’, 2, pp. 39–45.
  6. Kesar, S. et al. (2019) ‘Quantitative Structure-Activity Relationship Analysis of Selective Rho Kinase Inhibitors as Neuro-regenerator Agents’, Turkish Journal of Pharmaceutical Sciences, 16(2), pp. 141–154. doi: 10.4274/tjps.galenos.2018.70288.
  7. MAG (2018) World Malaria Day 2018.
  8. De Oliveira, D. B. and Gaudio, A. C. (2001) ‘BuildQSAR: A new computer program for QSAR analysis’, Quantitative Structure-Activity Relationships, 19(6), pp. 599–601. doi: 10.1002/1521-3838(200012)19:6<599::AID-QSAR599>3.0.CO;2-B.
  9. Piekuś-Słomka, N., Zapadka, M. and Kupcewicz, B. (2022) ‘Methoxy and methylthio-substituted trans-stilbene derivatives as CYP1B1 inhibitors – QSAR study with detailed interpretation of molecular descriptors’, Arabian Journal of Chemistry, 15(11). doi: 10.1016/j.arabjc.2022.104204.
  10. Rakhman, K. A. et al. (2019) ‘Kajian Senyawa Turunan Benzopirazin sebagai Antimalaria Menggunakan Metode HKSA dan MLR’, EduChemia (Jurnal Kimia dan Pendidikan), 4(2), p. 112. doi: 10.30870/educhemia.v4i2.4989.
  11. Shalini et al. (2020) ‘Functionalized Naphthalimide-4-aminoquinoline Conjugates as Promising Antiplasmodials, with Mechanistic Insights’, ACS Medicinal Chemistry Letters, 11(2), pp. 154–161. doi: 10.1021/acsmedchemlett.9b00521.
  12. Siswanta, D. and Nugraha, G. (2017) ‘Pemodelan dan Analisis QSAR Turunan Metilkarbamat sebagai Insektisida menggunakan Metode Semiempirik Austin Model 1’, 1, pp. 43–49.
  13. Swinney, D. C. (2011) Molecular Mechanism of Action (MMoA) in Drug Discovery. 1st edn, Annual Reports in Medicinal Chemistry. 1st edn. Elsevier Inc. doi: 10.1016/B978-0-12-386009-5.00009-6.
  14. Tilley, L., Loria, P. and Foley, M. (2003) ‘Chloroquine and Other Quinoline Antimalarials’, Antimalarial Chemotherapy, pp. 87–121. doi: 10.1385/1-59259-111-6:87.
  15. WHO (2021) World Malaria Report 2021, Angewandte Chemie International Edition, 6(11), 951–952.
  16. Yulianto, T. (2014) ‘Hubungan Kuantitatif Struktur dan Aktivitas Antikanker Senyawa Turunan Bakteriofeoforbid A’, thesis.

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WJC: Walisongo Journal of Chemistry
Published by the Department of Chemistry
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ISSN: 2549-385X (Print)
ISSN: 2621-5985 (Online)




 

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