Novel hybrids of natural isochroman-4-one bearing N-substituted isopropanolamine as potential antihypertensive candidates

Renren Bai; Xiaojing Huang; Xue Yang; Wen Hong; Yiqun Tang; Hequan Yao; Jieyun Jiang; Jie Liu; Mingqin Shen; Xiaoming Wu; Jinyi Xu

doi:10.1016/j.bmc.2013.02.044

Novel hybrids of natural isochroman-4-one bearing N-substituted isopropanolamine as potential antihypertensive candidates

Renren Bai, Xiaojing Huang, Xue Yang, Wen Hong, Yiqun Tang, Hequan Yao, Jieyun Jiang, Jie Liu, Mingqin Shen, Xiaoming Wu, Jinyi Xu

Research output: Contribution to journal › Article › peer-review

12 Scopus citations

Abstract

A series of novel hybrids of natural isochroman-4-one bearing isopropanolamine moiety were designed, synthesized and evaluated for their antihypertensive activity. It was found that compound IIId, prepared by hybridizing N-isopropyl substituted isopropanolamine functionality to a phenolic oxygen of isochroman-4-one, exhibited potent β₁-adrenoceptor blocking effect comparable to the well-known antihypertensive drug propranolol. Additionally, IIId significantly reduced the systolic and diastolic blood pressure in SHRs by over 40%, which was obviously stronger than the lead compounds 7,8-dihydroxy-3-methyl-isochroman-4-one (XJP) and its analogue XJP-B. Overall, IIId may be a promising antihypertensive candidate for further investigation.

Original language	English
Pages (from-to)	2495-2502
Number of pages	8
Journal	Bioorganic and Medicinal Chemistry
Volume	21
Issue number	9
DOIs	https://doi.org/10.1016/j.bmc.2013.02.044
State	Published - May 1 2013

Bibliographical note

Funding Information:
This study was financially supported by a grant from ‘Eleventh Five-Year’ Major Innovation Projects for New Drug Candidates (No. 2009ZX09103-128 ), Project for Research and Innovation of Graduates in Colleges and Universities of Jiangsu Province ( CXZZ11-0798 ), Fundamental Research Funds for the Central Universities ( JKY2011027 ) and Project Program of State Key Laboratory of Natural Medicines, China Pharmaceutical University ( JKGQ201115 ).

Funding

This study was financially supported by a grant from ‘Eleventh Five-Year’ Major Innovation Projects for New Drug Candidates (No. 2009ZX09103-128 ), Project for Research and Innovation of Graduates in Colleges and Universities of Jiangsu Province ( CXZZ11-0798 ), Fundamental Research Funds for the Central Universities ( JKY2011027 ) and Project Program of State Key Laboratory of Natural Medicines, China Pharmaceutical University ( JKGQ201115 ).

Funders	Funder number
Project for Research and Innovation of Graduates in Colleges and Universities of Jiangsu Province	CXZZ11-0798
State Key Laboratory of Natural Medicines, China Pharmaceutical University	JKGQ201115
Fundamental Research Funds for the Central Universities	JKY2011027

Keywords

Antihypertensive activity
Hybrids
Isochroman-4-one
Isopropanolamine
β-Adrenoceptor blockers

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmc.2013.02.044

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title = "Novel hybrids of natural isochroman-4-one bearing N-substituted isopropanolamine as potential antihypertensive candidates",

abstract = "A series of novel hybrids of natural isochroman-4-one bearing isopropanolamine moiety were designed, synthesized and evaluated for their antihypertensive activity. It was found that compound IIId, prepared by hybridizing N-isopropyl substituted isopropanolamine functionality to a phenolic oxygen of isochroman-4-one, exhibited potent β1-adrenoceptor blocking effect comparable to the well-known antihypertensive drug propranolol. Additionally, IIId significantly reduced the systolic and diastolic blood pressure in SHRs by over 40%, which was obviously stronger than the lead compounds 7,8-dihydroxy-3-methyl-isochroman-4-one (XJP) and its analogue XJP-B. Overall, IIId may be a promising antihypertensive candidate for further investigation.",

keywords = "Antihypertensive activity, Hybrids, Isochroman-4-one, Isopropanolamine, β-Adrenoceptor blockers",

author = "Renren Bai and Xiaojing Huang and Xue Yang and Wen Hong and Yiqun Tang and Hequan Yao and Jieyun Jiang and Jie Liu and Mingqin Shen and Xiaoming Wu and Jinyi Xu",

note = "Funding Information: This study was financially supported by a grant from {\textquoteleft}Eleventh Five-Year{\textquoteright} Major Innovation Projects for New Drug Candidates (No. 2009ZX09103-128 ), Project for Research and Innovation of Graduates in Colleges and Universities of Jiangsu Province ( CXZZ11-0798 ), Fundamental Research Funds for the Central Universities ( JKY2011027 ) and Project Program of State Key Laboratory of Natural Medicines, China Pharmaceutical University ( JKGQ201115 ).",

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doi = "10.1016/j.bmc.2013.02.044",

language = "English",

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T1 - Novel hybrids of natural isochroman-4-one bearing N-substituted isopropanolamine as potential antihypertensive candidates

AU - Bai, Renren

AU - Huang, Xiaojing

AU - Yang, Xue

AU - Hong, Wen

AU - Tang, Yiqun

AU - Yao, Hequan

AU - Jiang, Jieyun

AU - Liu, Jie

AU - Shen, Mingqin

AU - Wu, Xiaoming

AU - Xu, Jinyi

N1 - Funding Information: This study was financially supported by a grant from ‘Eleventh Five-Year’ Major Innovation Projects for New Drug Candidates (No. 2009ZX09103-128 ), Project for Research and Innovation of Graduates in Colleges and Universities of Jiangsu Province ( CXZZ11-0798 ), Fundamental Research Funds for the Central Universities ( JKY2011027 ) and Project Program of State Key Laboratory of Natural Medicines, China Pharmaceutical University ( JKGQ201115 ).

PY - 2013/5/1

Y1 - 2013/5/1

N2 - A series of novel hybrids of natural isochroman-4-one bearing isopropanolamine moiety were designed, synthesized and evaluated for their antihypertensive activity. It was found that compound IIId, prepared by hybridizing N-isopropyl substituted isopropanolamine functionality to a phenolic oxygen of isochroman-4-one, exhibited potent β1-adrenoceptor blocking effect comparable to the well-known antihypertensive drug propranolol. Additionally, IIId significantly reduced the systolic and diastolic blood pressure in SHRs by over 40%, which was obviously stronger than the lead compounds 7,8-dihydroxy-3-methyl-isochroman-4-one (XJP) and its analogue XJP-B. Overall, IIId may be a promising antihypertensive candidate for further investigation.

AB - A series of novel hybrids of natural isochroman-4-one bearing isopropanolamine moiety were designed, synthesized and evaluated for their antihypertensive activity. It was found that compound IIId, prepared by hybridizing N-isopropyl substituted isopropanolamine functionality to a phenolic oxygen of isochroman-4-one, exhibited potent β1-adrenoceptor blocking effect comparable to the well-known antihypertensive drug propranolol. Additionally, IIId significantly reduced the systolic and diastolic blood pressure in SHRs by over 40%, which was obviously stronger than the lead compounds 7,8-dihydroxy-3-methyl-isochroman-4-one (XJP) and its analogue XJP-B. Overall, IIId may be a promising antihypertensive candidate for further investigation.

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KW - β-Adrenoceptor blockers

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Novel hybrids of natural isochroman-4-one bearing N-substituted isopropanolamine as potential antihypertensive candidates

Abstract

Bibliographical note

Funding

Keywords

ASJC Scopus subject areas

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