DOI: https://doi.org/10.14710/jksa.23.5.142-146

Effect of methyl substituent on the solubility of 1,4-benzoquinone derivatives in n-octanol/water system

Department of Chemistry, Faculty of Mathematics and Natural Sciences, Brawijaya University, Malang, Indonesia

Received: 28 Oct 2019; Revised: 26 Apr 2020; Accepted: 27 Apr 2020; Published: 31 May 2020.
Open Access Copyright 2020 Jurnal Kimia Sains dan Aplikasi under http://creativecommons.org/licenses/by-sa/4.0.

Citation Format:
Cover Image
Abstract
The solubility of the compound is a crucial task for new drug design. Quinone is a promising candidate to develop as a new drug. In this research, the synthesis of 1,4-benzoquinone derivatives, that is, 2-(5-bromoamyl)-3,5-dimethyl-1,4-benzoquinone (2a) and 2-(5-bromoamyl)-5-methyl-1,4-benzoquinone (2b) were carried out by decarboxylation and insertion reaction of alkyl bromides. The product 2a and 2b are purified using SiO2 gel column chromatography and analyzed by UV-Visible, FT-IR, and NMR. The yield of 2a is 13.75%, and 2b is 4.04%. The solubility of 2a and 2b, expressed by log P, is measured in the n-octanol/water (3:7 (v/v)) system by the shake flask method. The log P of 2a and 2b are 2.99 and 1.36, respectively. It is showed that the log P of 2a is higher compared to 2b. The presence of two methyl substituents on the quinone ring of 2a supports the increase of hydrophobicity of the compound in the n-octanol/water system.
Fulltext View|Download
Keywords: 1,4-benzoquinone; decarboxylation; bioavailability; coefficient partition
Funding: Brawijaya University

Article Metrics:

Article Info
Section: Research Articles
Language : EN
Recent articles
Molecular Docking and Chemical Analysis of Alcohol Compounds (C16-C20) Bound to InhA Receptors as Mycobactericidal Candidates Utilization of Jengkol Peel (Pithecellobium jiringa (Jack) Prain) as Lead (II) Ions Bio-sorbent with Column Method Production of Micro Crystalline Cellulose from Tapioca Solid Waste: Effect of Acid Concentration on its Physico-chemical Properties Validation of High-Performance Liquid Chromatography Method for Determination of Vitamin B1 in Powder Milk Polymerization Domain Translated from 0.9 kb Gene Fragment of DNA Polymerase I from a Thermo-Halophilic PLS A Strain More recent articles
Most cited articles
Pengelolaan Alat Bahan dan Laboratorium Kimia Skrining Metabolit Sekunder Bakteri Endofit yang Berfungsi sebagai Antidiabetes dari Daun Mimba (Azadirachta Indica) Chitosan succinate/PVA-PEG Membrane: Preparation, Characterization and Permeation Ability Test on Creatinine Modifikasi Zeolit Alam dengan Ligan EDTA untuk Adsorpsi Ion Logam Pb2+ dan Cd2+ Profil Kandungan Protein dan Tekstur Tahu Akibat Penambahan Fitat pada Proses Pembuatan Tahu More cited articles
  1. Chern Chiuh Woo, Alan Prem Kumar, Gautam Sethi and Kwong Huat Benny Tan, Thymoquinone: Potential cure for inflammatory disorders and cancer, Biochemical Pharmacology, 83, 4, (2012), 443-451 https://doi.org/10.1016/j.bcp.2011.09.029
  2. Regine Schneider-Stock, Isabelle H. Fakhoury, Angela M. Zaki, Chirine O. El-Baba and Hala U. Gali-Muhtasib, Thymoquinone: fifty years of success in the battle against cancer models, Drug Discovery Today, 19, 1, (2014), 18-30 https://doi.org/10.1016/j.drudis.2013.08.021
  3. Mohammad Rashidmayvan, Majid Mohammadshahi, Seyed Saeed Seyedian and Mohammad Hossein Haghighizadeh, The effect of Nigella sativa oil on serum levels of inflammatory markers, liver enzymes, lipid profile, insulin and fasting blood sugar in patients with non-alcoholic fatty liver, Journal of Diabetes & Metabolic Disorders, 18, 2, (2019), 453-459 https://doi.org/10.1007/s40200-019-00439-6
  4. Mohammed Bule, Shekoufeh Nikfar, Mohsen Amini and Mohammad Abdollahi, The antidiabetic effect of thymoquinone: A systematic review and meta-analysis of animal studies, Food Research International, 127, (2020), 108736 https://doi.org/10.1016/j.foodres.2019.108736
  5. Khalid M. Alkharfy, Ajaz Ahmad, Rao M. A. Khan and Waleed M. Al-Shagha, Pharmacokinetic plasma behaviors of intravenous and oral bioavailability of thymoquinone in a rabbit model, European Journal of Drug Metabolism and Pharmacokinetics, 40, 3, (2015), 319-323 https://doi.org/10.1007/s13318-014-0207-8
  6. Okiemute Rosa Johnson-Ajinwo, Imran Ullah, Haddijatou Mbye, Alan Richardson, Paul Horrocks and Wen-Wu Li, The synthesis and evaluation of thymoquinone analogues as anti-ovarian cancer and antimalarial agents, Bioorganic & Medicinal Chemistry Letters, 28, 7, (2018), 1219-1222 https://doi.org/10.1016/j.bmcl.2018.02.051
  7. Fath Dwisari, Arie Srihardyastutie and Siti Mariyah Ulfa, Synthesis of 2-methyl-5-methoxy-1,4-benzoquinone and In-silico Activity Profiling Toward Cytochrome P450-3A4, IOP Conference Series: Materials Science and Engineering, 546, (2019), 062005 http://dx.doi.org/10.1088/1757-899X/546/6/062005
  8. Andriani Furoida and Siti Mariyah Ulfa, Synthesis of 3-(7-triphenylphosphonioheptyl)-2,6-dimethyl-1,4-benzoquinone) and The Activity Test Toward Glycogen Phosphorylase Enzyme: In silico Approach, IOP Conference Series: Materials Science and Engineering, 546, (2019), 062008 http://dx.doi.org/10.1088/1757-899X/546/6/062008
  9. Novia Eka Setyatama, Siti Mariyah Ulfa and Hideki Okamoto, Synthesis and Activity Analysis of 3-(10-Bromodecyl)-5-isopropyl-2-methyl-1,4-benzoquinone: In-silico Approach, 1st International Conference in One Health (ICOH 2017), (2017) https://doi.org/10.2991/icoh-17.2018.24
  10. Christopher A. Lipinski, Franco Lombardo, Beryl W. Dominy and Paul J. Feeney, Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings, Advanced Drug Delivery Reviews, 46, 1, (2001), 3-26 https://doi.org/10.1016/S0169-409X(00)00129-0
  11. Y. N. Antonenko, A. V. Avetisyan, L. E. Bakeeva, B. V. Chernyak, V. A. Chertkov, L. V. Domnina, O. Yu Ivanova, D. S. Izyumov, L. S. Khailova, S. S. Klishin, G. A. Korshunova, K. G. Lyamzaev, M. S. Muntyan, O. K. Nepryakhina, A. A. Pashkovskaya, O. Yu Pletjushkina, A. V. Pustovidko, V. A. Roginsky, T. I. Rokitskaya, E. K. Ruuge, V. B. Saprunova, I. I. Severina, R. A. Simonyan, I. V. Skulachev, M. V. Skulachev, N. V. Sumbatyan, I. V. Sviryaeva, V. N. Tashlitsky, J. M. Vassiliev, M. Yu Vyssokikh, L. S. Yaguzhinsky, A. A. Zamyatnin and V. P. Skulachev, Mitochondria-targeted plastoquinone derivatives as tools to interrupt execution of the aging program. 1. Cationic plastoquinone derivatives: Synthesis and in vitro studies, Biochemistry (Moscow), 73, 12, (2008), 1273-1287 https://doi.org/10.1134/S0006297908120018
  12. Siti Mariyah Ulfa, Shoimatus Sholikhah and Edi Priyo Utomo, Synthesis of Thymoquinone derivatives and its activity analysis: In-silico approach, AIP Conference Proceedings, (2017) https://doi.org/10.1063/1.4978175
  13. Axel Andrés, Martí Rosés, Clara Ràfols, Elisabeth Bosch, Sonia Espinosa, Víctor Segarra and Josep M. Huerta, Setup and validation of shake-flask procedures for the determination of partition coefficients (logD) from low drug amounts, European Journal of Pharmaceutical Sciences, 76, (2015), 181-191 https://doi.org/10.1016/j.ejps.2015.05.008
  14. Wilbes Mbiya, Itai Chipinda, Paul D. Siegel, Morgen Mhike and Reuben H. Simoyi, Substituent Effects on the Reactivity of Benzoquinone Derivatives with Thiols, Chemical Research in Toxicology, 26, 1, (2013), 112-123 https://doi.org/10.1021/tx300417z
  15. Donald L. Pavia, Gary M. Lampman, George S. Kriz and James A. Vyvyan, Introduction to Spectroscopy, Cengage Learning, 2008
  16. Igor V. Tetko and Vsevolod Yu Tanchuk, Application of Associative Neural Networks for Prediction of Lipophilicity in ALOGPS 2.1 Program, Journal of Chemical Information and Computer Sciences, 42, 5, (2002), 1136-1145 https://doi.org/10.1021/ci025515j
  17. John E. A. Comer, High‐Throughput Measurement of log D and pKa, in: Drug bioavailability: Estimation of solubility, permeability, absorption and bioavailability, 2003, pp. 21-45 https://doi.org/10.1002/3527601473.ch2
  18. David J. Triggle and John B. Taylor, Comprehensive Medicinal Chemistry II, Elsevier Science, 2006

Last update:

  1. Facile synthesis of 5-Isopropyl-2,3-dimethylbenzene-1,4-diol by Friedel-Crafts and Determination of Partition Coefficient in n- Octanol/Water

    Siti Mariyah Ulfa, Alma Miranda, Fath Dwisari, Mohammad Farid Rahman. Jurnal Kimia Sains dan Aplikasi, 25 (1), 2022. doi: 10.14710/jksa.25.1.7-12

Last update: 2024-11-20 13:05:22

No citation recorded.