Biological Activity and Solubility of 5-Methoxy-1,4-Benzoquinone Having Bromoheptyl and Bromodecyl Substituents in the n-Octanol/Water System

IF 0.8 Q3 MULTIDISCIPLINARY SCIENCES Makara Journal of Science Pub Date : 2021-01-01 DOI:10.7454/MSS.V25I1.1157
S. M. Ulfa, Fath Dwisari, Laras Pangesti, M. F. Rahman
{"title":"Biological Activity and Solubility of 5-Methoxy-1,4-Benzoquinone Having Bromoheptyl and Bromodecyl Substituents in the n-Octanol/Water System","authors":"S. M. Ulfa, Fath Dwisari, Laras Pangesti, M. F. Rahman","doi":"10.7454/MSS.V25I1.1157","DOIUrl":null,"url":null,"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-(7bromoheptyl)-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 sp and the absorption of C-Br because of the presence of the bromoheptyl and bromodecyl substituents. H-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 TSPO3a is lower than that of TSPO-3b, indicating that 3a has a higher activity for anti-inflammatory drug candidates than 3b.","PeriodicalId":18042,"journal":{"name":"Makara Journal of Science","volume":"9 1","pages":"3"},"PeriodicalIF":0.8000,"publicationDate":"2021-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Makara Journal of Science","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.7454/MSS.V25I1.1157","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"MULTIDISCIPLINARY SCIENCES","Score":null,"Total":0}
引用次数: 0

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-(7bromoheptyl)-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 sp and the absorption of C-Br because of the presence of the bromoheptyl and bromodecyl substituents. H-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 TSPO3a is lower than that of TSPO-3b, indicating that 3a has a higher activity for anti-inflammatory drug candidates than 3b.
查看原文
分享 分享
微信好友 朋友圈 QQ好友 复制链接
本刊更多论文
具有溴庚基和溴癸基取代基的5-甲氧基-1,4-苯醌在正辛醇/水体系中的生物活性和溶解度
化合物的生物活性和溶解度受其化学结构的影响。这些性质可以通过在母体骨架中取代烷基、烷氧基和/或卤代烷烃来改善。本研究通过脱羧反应合成了3-(7 -溴庚基)-2-甲基-5-甲氧基-1,4-苯醌(3a)和3-(10-溴癸基)-2-甲基-5-甲氧基-1,4-苯醌(3b)。将3a和3b与抗炎药百里醌(TQ)的溶解度和生物活性进行比较。成功地合成了化合物3a和3b,并用傅里叶变换红外(FTIR)和核磁共振(NMR)对其进行了分析。FTIR光谱显示,由于溴庚基和溴癸基取代基的存在,C-H - sp的强度和C-Br的吸收增加。H-NMR表明,在δ 1.29 ~ 3.40 ppm时,烯烃亚甲基发生了明显的化学位移。溶解度测试表明,3a和3b在正辛醇/水体系中的分配系数(log P)存在差异。3a和3b的logp值高于TQ的logp值,说明甲氧基、溴庚基和溴癸基支持溶解度的增加。生物活性测试表明,3a和3b与转运蛋白(TSPO)大分子的结合倾向高于与磷酸酶和紧张素同源物(PTEN)大分子的结合倾向。TSPO-3a和TSPO-3b的结合相互作用与TSPO-TQ相似,表明两种合成的化合物具有相当的活性。TSPO3a的结合能低于TSPO-3b,说明3a对抗炎候选药物的活性高于3b。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 去求助
来源期刊
Makara Journal of Science
Makara Journal of Science MULTIDISCIPLINARY SCIENCES-
CiteScore
1.30
自引率
20.00%
发文量
24
审稿时长
24 weeks
期刊最新文献
Assessment of Seasonal Variation in Heavy Metal Status of a Lotic Ecosystem in Federal Capital Territory, Abuja, North Central Nigeria An Inkjet-printed Graphene Oxide–poly(3,4-ethylenedioxythiophene) poly(styrene sulfonate) Electrode for Nitrite Detection in Water Enzymatic Screening and Genotypic Characterization of Thermophilic Bacteria from the Hot Springs of Sarawak, Malaysia Using In silico Tools to Analyze the 5ʹ Untranslated Regions of the Alcohol Dehydrogenase Gene from Arabidopsis thaliana and Omega Sequence Electro-optical Effect of 4-n-alkyl-sulfanyl-4' isothiocyanate-biphenyl Liquid Crystal Homologous Series Under Terahertz Frequency: A Theoretical Approach
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
已复制链接
已复制链接
快去分享给好友吧!
我知道了
×
扫码分享
扫码分享
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术
文献互助 智能选刊 最新文献 互助须知 联系我们:info@booksci.cn
Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。
Copyright © 2023 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1