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Open AccessArticle

Design, Synthesis and Biological Evaluation of Nitrate Derivatives of Sauropunol A and B as Potent Vasodilatory Agents

1
State Key Laboratory of Natural Medicines and Department of Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing 210009, China
2
National Certified Enterprise Technology Center, Disha Pharmaceutical Group Co., Ltd., Weihai 264205, China
3
Faculty of Pharmacy, Kinki University, 3-4-1 Kowakae, Higashi-Osaka, Osaka 577-8502, Japan
*
Authors to whom correspondence should be addressed.
Molecules 2019, 24(3), 583; https://doi.org/10.3390/molecules24030583
Received: 20 December 2018 / Revised: 27 January 2019 / Accepted: 28 January 2019 / Published: 6 February 2019
(This article belongs to the Section Bioorganic Chemistry)
A group of nitrate derivatives of naturally occurring sauropunol A and B were designed and synthesized. Nitric oxide (NO) releasing capacity and vasodilatory capacity studies were performed to explore the structure-activity relationship of resulted nitrates. Biological evaluation of these compounds revealed that most of the synthesized mononitrate derivatives demonstrated superior releasing capacity than isosorbide mononitrate (ISMN), and 2MNS-6 even demonstrated stronger NO releasing capacity than isosorbide dinitrate (ISDN). Two dinitrates, DNS-1 and DNS-2, showed higher NO releasing capacity than ISDN. Evaluation of inhibitory activities to the contractions in mesenteric artery rings revealed that 2MNS-8 and DNS-2 showed stronger vasorelaxation activities than ISDN. High level of NO and soluble guanylyl cyclase (sGC) may be essential for the potent vasodilatory effect of DNS-2. The vasodilatory effects of DNS-2 may result from cellular signal transduction of NO-sGC-cGMP. DNS-2 was found to be the most potent sauropunol-derived nitrate vasodilatory agent for further pharmaceutical investigation against cardiovascular diseases. View Full-Text
Keywords: vasodilatory agents; NO releasing capacity; sauropunol A and B; NO donor; Sauropus rostratus vasodilatory agents; NO releasing capacity; sauropunol A and B; NO donor; Sauropus rostratus
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MDPI and ACS Style

Lu, L.; Rao, X.; Cong, R.; Zhang, C.; Wang, Z.; Xu, J.; Tanabe, G.; Muraoka, O.; Wu, X.; Xie, W. Design, Synthesis and Biological Evaluation of Nitrate Derivatives of Sauropunol A and B as Potent Vasodilatory Agents. Molecules 2019, 24, 583.

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