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Molecules 2017, 22(11), 1739; doi:10.3390/molecules22111739

Design, Synthesis and Evaluation of Novel 2-Hydroxypyrrolobenzodiazepine-5,11-dione Analogues as Potent Angiotensin Converting Enzyme (ACE) Inhibitors

1
Key Laboratory of Resource Biology and Biotechnology in Western China, Ministry of Education, Northwest University, Xi’an 710069, China
2
Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi’an 710127, China
These authors contributed equally to this paper and share co-first authorship.
*
Author to whom correspondence should be addressed.
Received: 27 September 2017 / Revised: 9 October 2017 / Accepted: 9 October 2017 / Published: 3 November 2017
(This article belongs to the Section Medicinal Chemistry)
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Abstract

Under the guidance of combination of traditional Chinese medicine chemistry (CTCMC), this study describes the preparation of a phenolic acid/dipeptide/borneol hybrid consisting of phenolic acid and a bornyl moiety connected to the dipeptide N-terminal and C-terminal respectively. It also evaluates their angiotensin converting enzyme (ACE) inhibitory and synergistic antihypertensive activities. Briefly, a series of novel 2-hydroxypyrrolobenzodiazepine-5,11-dione analogues were prepared and investigated for their ability to inhibit ACE. The influence of the phenolic acid and bornyl moiety on subsite selectivity is also demonstrated. Among all the new compounds, two compounds—7a and 7g—reveal good inhibition potency in in vitro ACE-inhibitory tests. Interestingly, favorable binding results in molecular docking studies also supported the in vitro results. Additionally, the bioassay showed that oral administration of the two compounds displayed high and long-lasting antihypertensive activity both in acute antihypertensive tests and in therapeutic antihypertensive tests by non-invasive blood pressure measurements in spontaneously hypertensive rats. View Full-Text
Keywords: phenolic acid/dipeptide/borneol hybrid; ACE inhibitor; hypertension; combination of traditional Chinese medicine chemistry phenolic acid/dipeptide/borneol hybrid; ACE inhibitor; hypertension; combination of traditional Chinese medicine chemistry
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Sun, Y.; Bai, Y.; He, X.; Bai, Y.; Liu, P.; Zhao, Z.; Chen, X.; Zheng, X. Design, Synthesis and Evaluation of Novel 2-Hydroxypyrrolobenzodiazepine-5,11-dione Analogues as Potent Angiotensin Converting Enzyme (ACE) Inhibitors. Molecules 2017, 22, 1739.

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