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All Journal Journal of Tropical Life Science : International Journal of Theoretical, Experimental, and Applied Life Sciences JURNAL KIMIA SAINS DAN APLIKASI Teknotan: Jurnal Industri Teknologi Pertanian Jurnal Ilmu Kimia Universitas Brawijaya Bulletin of Chemical Reaction Engineering & Catalysis Journal of Innovation and Applied Technology Jurnal Pembangunan dan Alam Lestari Natural B The Journal of Pure and Applied Chemistry Research Jurnal Penelitian Pendidikan IPA (JPPIPA) Indonesian Journal of Chemistry Indonesian Food Science and TechnologyJournal Media Akuakultur Makara Journal of Science Bulletin of Chemical Reaction Engineering & Catalysis
Siti Mariyah Ulfa
Department Of Chemistry, Faculty Of Mathematics And Natural Sciences, Brawijaya University, Jl. Veteran, Malang 65145, Indonesia
Agriculture, Biological Sciences & Forestry Biochemistry, Genetics & Molecular Biology Chemical Engineering, Chemistry & Bioengineering Chemistry Civil Engineering, Building, Construction & Architecture Computer Science & IT Control & Systems Engineering Decision Sciences, Operations Research & Management Education Engineering Environmental Science Materials Science & Nanotechnology Medicine & Pharmacology Physics Other

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Journal : Makara Journal of Science

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Biological Activity and Solubility of 5-Methoxy-1,4-Benzoquinone Having Bromoheptyl and Bromodecyl Substituents in the n-Octanol/Water System Ulfa, Siti Mariyah; Dwisari, Fath; Pangesti, Laras; Rahman, Mohammad Farid
Makara Journal of Science Vol. 25, No. 1
Publisher : UI Scholars Hub

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Abstract

The biological activity and solubility of compounds are influenced by its chemical structure. These properties can be improved by substituting alkyl, alkoxy, and/or haloalkane in the parent skeleton. In this research, the synthesis of 3-(7-bromoheptyl)-2-methyl-5-methoxy-1,4-benzoquinone (3a) and 3-(10-bromodecyl)-2-methyl-5-methoxy-1,4-benzoquinone (3b) was achieved through the decarboxylation reaction. The solubility and biological activity of 3a and 3b were compared with that of thymoquinone (TQ), which acts as an anti-inflammatory agent. Compounds 3a and 3b were successfully synthesized and analyzed using Fourier Transform Infra-Red (FTIR) and Nuclear Magnetic Resonance (NMR). The FTIR spectrum showed the increasing intensity of C-H sp3 and the absorption of C-Br because of the presence of the bromoheptyl and bromodecyl substituents. 1H-NMR showed the prominent chemical shift of olefinic methylene at δ 1.29–3.40 ppm. The solubility test showed the differences in the partition coefficient (log P) of 3a and 3b in the n-octanol/water system. The log P values of 3a and 3b are higher than those of TQ, indicating that methoxy, bromoheptyl, and bromodecyl support the increase in solubility. Biological activity test using the in silico approach showed that 3a and 3b have a higher tendency to bind with the translocator protein (TSPO) macromolecule than the phosphatase and tensin homolog (PTEN) macromolecule. The binding interactions of TSPO-3a and TSPO-3b, similar to that of TSPO-TQ, showed that both synthesized compounds have comparable activity. The binding energy of TSPO-3a is lower than that of TSPO-3b, indicating that 3a has a higher activity for anti-inflammatory drug candidates than 3b.
Co-Authors A.A. Ketut Agung Cahyawan W Adam Mahfud Ade Cintyia Sally Al zamzami, Ilham Misbakudin Alma Miranda Amaniyah, Amaniyah Amin, Abd Aziz Amini, Helda Wika Andi Kurniawan Andi Kurniawan Anggayasti, Wresti L. Anjani, Ryzki Martha Arda Rista Lestari Caterina Widya Astutik Chairulita Putri Kusumaningsih Dinia Rizqi Dwijayanti Dwi Susanti, Yogita Ayu Edi Priyo Utomo Edi Priyo Utomo Edi Priyo Utomo Efani, Anton Eka Novitasari Elvina Dhiaul Iftitah Elvina Dhiaul Iftitah Elvina Dhiaul Iftitah Esya, Firdausy Amalina Fadlilah, Lilik Nur Fath Dwisari Fatma, Aliya Galisong, Ridwan Danuarta Grahadi, Rahmat Gunawan, Firza Rajasa Hapsari, Febriyana Rizky Helda Wika Amini Hermanto, Feri Eko Hidayatul Mustafidah Hideki Okamoto Hideki Okamoto Iftitah, Elvina Dhiaul Indah Nur Pramesti Inra Sari Kamila, Fairuz Sarah Karimah Karimah Kyosuke Satake Kyosuke Satake Lisa Aulia, Lisa Listianingsih, Lia Lukman Hakim Lutfi Ni’matus Salamah Luthfia Ayu Dhea Maharani Pertiwi Koentjoro Mahfuzh Huda Masruri Masruri Masruri Masruri Masruri Moehammad, Khibar Syiar Moh. Farid Rahman Mohammad Elham Firdaus Mohammad Farid Rahman Mohammad Farid Rahman Momodou Salieu Sowe Momodou Salieu Sowe Nashi Widodo Nisa', Khibrun Nur Ikhtiarini Nuraini Uswatun Chasana Pangesti, Laras Pramudia, Zulkisam Pratama, Safreno Panggih Pratiwi, Rahmania Tulus Setya Prihartini, Dita Puspitasari, Rizka Dwitya Rachmat Triandi Tjahjanto Rizka Fauzia Ohorella Rizqi Alima Fabri, Ahmad Rosyadah, Nuraini Safitri, Anna Salamah, Lutfi Ni’matus Suratmo, Suratmo SUTRISNO Sutrisno, Sutrisno Utomo, Edi Priyo Wardani, Eris Agustin Warsito Warsito Warsito Warsito Widia Edy Kuncoro Widodo Widodo Widyananda, Muhammad Hermawan Yanuar, Adi Tiya Yosua Yosua Yulistian, Dhoni Prielananta Yusnawan, Eriyanto Yusuf Hendrawan Zahara, Izaz Aqeiluz