Theoretical and Natural Science

- The Open Access Proceedings Series for Conferences


Theoretical and Natural Science

Vol. 33, 08 March 2024


Open Access | Article

Proposed total synthesis of the potential antidiabetic compound 5,7-dihydroxy-6-(3-methybut-2-enyl)-isobenzofuran-(13H)-one

Kexin Li * 1
1 Shanxi Medical University

* Author to whom correspondence should be addressed.

Theoretical and Natural Science, Vol. 33, 24-28
Published 08 March 2024. © 2023 The Author(s). Published by EWA Publishing
This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Citation Kexin Li. Proposed total synthesis of the potential antidiabetic compound 5,7-dihydroxy-6-(3-methybut-2-enyl)-isobenzofuran-(13H)-one. TNS (2024) Vol. 33: 24-28. DOI: 10.54254/2753-8818/33/20240589.

Abstract

Insulin analogs are currently the most often prescribed medications for treating type 2 diabetes mellitus (T2DM). However, because of the inherent flaws of the medications and the restrictions of the administration methods, there is no comprehensive plan for managing diabetes. As a result, it’s crucial to research comprehensive treatment plans based on the available medications and the traits of T2DM. Natural products play as key role in drug discovery. Although many articles have been published on the antidiabetic potential of natural products, few natural product-based molecules have been approved for the treatment of T2DM. It has been established that the compound 5,7-dihydroxy-6-(3-methybut-2-enyl)-isobenzofuran-(13H)-one from Nigella glandulifera Freyn et Sint (N. glandulifera) possesses antidiabetic activity, but little attention has been dedicated to its total synthesis. Herein, we attempt to reveal a new total synthesis of 5,7-dihydroxy-6-(3-methybut-2-enyl)-isobenzofuran-(13H)-one. The synthesis is simple, with few steps, and has potential for industrialization.

Keywords

5, 7-dihydroxy-6-(3-methybut-2-enyl)-isobenzofuran-(13H)-one, Natural products, Total synthesis, T2DM, Antidiabetic activity

References

1. Li, Gang, and Hong‐Xiang Lou. “Strategies to Diversify Natural Products for Drug Discovery.” Medicinal research reviews 38, no. 4 (2018): 1255–1294.

2. Asma, Syeda Tasmia, Ulas Acaroz, Kálmán Imre, Adriana Morar, Syed Rizwan Ali Shah, Syed Zajif Hussain, Damla Arslan-Acaroz, et al. “Natural Products/Bioactive Compounds as a Source of Anticancer Drugs.” Cancers 14, no. 24 (2022): 6203–.

3. Blahova, Jana, Monika Martiniakova, Martina Babikova, Veronika Kovacova, Vladimira Mondockova, and Radoslav Omelka. “Pharmaceutical Drugs and Natural Therapeutic Products for the Treatment of Type 2 Diabetes Mellitus.” Pharmaceuticals 14, no. 8 (2021): 806.

4. Thomas, Celeste C., and Louis H. Philipson. “Update on Diabetes Classification.” The Medical clinics of North America 99, no. 1 (2015): 1–16.

5. Mishra, Vijay, Pallavi Nayak, Mayank Sharma, Aqel Albutti, Ameen S. S. Alwashmi, Mohammad Abdullah Aljasir, Noorah Alsowayeh, and Murtaza M. Tambuwala. “Emerging Treatment Strategies for Diabetes Mellitus and Associated Complications: An Update.” Pharmaceutics 13, no. 10 (2021): 1568–.

6. Chillarón, Juan J, Juana A Flores Le-Roux, David Benaiges, and Juan Pedro-Botet. “Type 1 Diabetes, Metabolic Syndrome and Cardiovascular Risk.” Metabolism, clinical and experimental 63, no. 2 (2014): 181–187.

7. DeFronzo, Ralph A. “Pathogenesis of Type 2 Diabetes Mellitus.” Medical Clinics of North America 88, no. 4 (2004): 787–835.

8. Standl, Eberhard, Kamlesh Khunti, Tina Birgitte Hansen, and Oliver Schnell. “The Global Epidemics of Diabetes in the 21st Century: Current Situation and Perspectives.” European journal of preventive cardiology 26, no. 2_suppl (2019): 7–14.

9. Yeung, Roseanne O, Yuying Zhang, Andrea Luk, Wenying Yang, Leorino Sobrepena, Kun-Ho Yoon, S R Aravind, et al. “Metabolic Profiles and Treatment Gaps in Young-Onset Type 2 Diabetes in Asia (The Jade Programme): A Cross-Sectional Study of a Prospective Cohort.” The Lancet Diabetes & Endocrinology 2, no. 12 (2014): 935–943.

10. Chatterjee, Sudesna, Kamlesh Khunti, and Melanie J Davies. “Type 2 Diabetes.” The Lancet (British edition) 389, no. 10085 (2017): 2239–2251.

11. Griffin, Stacy. “Insulin Treatment of Type 2 Diabetes: Considerations When Converting from Human Insulin to Insulin Analogs.” Annals of medicine (Helsinki) 45, no. 2 (2013): 129–140.

12. Padhi, Santwana, Amit Kumar Nayak, and Anindita Behera. “Type II Diabetes Mellitus: a Review on Recent Drug Based Therapeutics.” Biomedicine & pharmacotherapy 131 (2020): 110708–110708.

13. Zhao, Ruichen, Zhiguo Lu, Jun Yang, Liqun Zhang, Yan Li, and Xin Zhang. “Drug Delivery System in the Treatment of Diabetes Mellitus.” Frontiers in bioengineering and biotechnology 8 (2020): 880–880.

14. Jugran, Arun K., Sandeep Rawat, Hari P. Devkota, Indra D. Bhatt, and Ranbeer S. Rawal. “Diabetes and Plant‐derived Natural Products: From Ethnopharmacological Approaches to Their Potential for Modern Drug Discovery and Development.” Phytotherapy research 35, no. 1 (2021): 223–245.

15. Lv, Yan, Na Tian, Junsong Wang, Minghua Yang, and Lingyi Kong. “Metabolic Switching in the Hypoglycemic and Antitumor Effects of Metformin on High Glucose Induced HepG2 Cells.” Journal of pharmaceutical and biomedical analysis 156 (2018): 153–162.

16. Zheng, Yunliang, Qiao Zhang, and Xingjiang Hu. “A Comprehensive Review of Ethnopharmacological Uses, Phytochemistry, Biological Activities, and Future Prospects of Nigella Glandulifera.” Medicinal Chemistry Research 29, no. 7 (2020): 1168–1186.

17. Mir, Shabir Ahmad, Ahmad Firoz, Mohammed Alaidarous, Bader Alshehri, Abdul Aziz Bin Dukhyil, Saeed Banawas, Suliman A Alsagaby, et al. “Identification of SARS-CoV-2 RNA-Dependent RNA Polymerase Inhibitors from the Major Phytochemicals of Nigella Sativa: An in Silico Approach.” Saudi journal of biological sciences 29, no. 1 (2022): 394–401.

18. Li, Guo-Hong, Lei Li, Meng Duan, and Ke-Qin Zhang. “The Chemical Constituents of the Fungus Stereum Sp.” Chemistry & biodiversity 3, no. 2 (2006): 210–216.

19. Li, Qingqing, Jing Xu, Yiyu Chen, Wenli Xie, Gui Mei, Xueni Li, Yu Chen, and Guangzhong Yang. “Chemical Constituents from the Seeds of Nigella Glandulifera and Their Hypoglycemic Activities.” RSC advances 12, no. 30 (2022): 19445–19451.

20. Miyaura, Norio, and Akira Suzuki. “Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds.” Chemical reviews 95, no. 7 (1995): 2457–2483.

21. Sadamitsu, Yuta, Akira Okumura, Kodai Saito, and Tohru Yamada. “Kolbe-Schmitt Type Reaction Under Ambient Conditions Mediated by an Organic Base.” Chemical communications (Cambridge, England) 55, no. 66 (2019): 9837–984.

22. Zhang, Yang-Hui, Bing-Feng Shi, and Jin-Quan Yu. “Palladium(II)-Catalyzed Ortho Alkylation of Benzoic Acids with Alkyl Halides.” Angewandte Chemie (International ed.) 48, no. 33 (2009): 6097–6100.

23. Alam, Rauful, Tobias Vollgraff, Lars Eriksson, and Kálmán J Szabó. “Synthesis of Adjacent Quaternary Stereocenters by Catalytic Asymmetric Allylboration.” Journal of the American Chemical Society 137, no. 35 (2015): 11262–11265.

Data Availability

The datasets used and/or analyzed during the current study will be available from the authors upon reasonable request.

This work is licensed under a Creative Commons Attribution-ShareAlike 4.0 International License. Authors who publish this series agree to the following terms:

1. Authors retain copyright and grant the series right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgment of the work's authorship and initial publication in this series.

2. Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the series's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgment of its initial publication in this series.

3. Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (See Open Access Instruction).

Volume Title
Proceedings of the 2nd International Conference on Modern Medicine and Global Health
ISBN (Print)
978-1-83558-323-4
ISBN (Online)
978-1-83558-324-1
Published Date
08 March 2024
Series
Theoretical and Natural Science
ISSN (Print)
2753-8818
ISSN (Online)
2753-8826
DOI
10.54254/2753-8818/33/20240589
Copyright
08 March 2024
Open Access
This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited

Copyright © 2023 EWA Publishing. Unless Otherwise Stated