Synthesis and antibacterial activities of a novel alkylide: 3-O-(3-aryl-2-propargyl) and 3-O-(3-aryl-2-propenyl)clarithromycin derivatives

Jian Hua Liang; Yue Ying Wang; He Wang; Xiao Li Li; Kun An; Ying Chun Xu; Guo Wei Yao

doi:10.1016/j.bmcl.2010.03.038

Synthesis and antibacterial activities of a novel alkylide: 3-O-(3-aryl-2-propargyl) and 3-O-(3-aryl-2-propenyl)clarithromycin derivatives

Jian Hua Liang^*, Yue Ying Wang, He Wang, Xiao Li Li, Kun An, Ying Chun Xu, Guo Wei Yao

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

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

11 Citations (Scopus)

Abstract

A series of novel 3-O-(3-aryl-E-2-propenyl)clarithromycin derivatives 8 and 3-O-(3-aryl-2-propargyl)clarithromycin derivatives 11 were designed, synthesized, and evaluated for their in vitro antibacterial activities. Compared with 8c and 11c (Ar was 5-pyrimidyl), 3-O-(3-(5′-pyrimidyl)-Z-1-propenyl) counterpart 6c displayed 4- to 64-fold more potent activities against erythromycin-susceptible Staphylococcus aureus and Streptococcus pneumoniae. Moreover, the activities of 6c, 8c, and 11c against erythromycin-resistant S. aureus and S. pneumoniae were in general 4-fold higher than those of the reference compound, clarithromycin and azithromycin.

Original language	English
Pages (from-to)	2880-2883
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	20
Issue number	9
DOIs	https://doi.org/10.1016/j.bmcl.2010.03.038
Publication status	Published - 1 May 2010

Keywords

Allyl
Erythromycin
Heck
Isomerization
Propargyl
Sonogashira

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10.1016/j.bmcl.2010.03.038

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@article{c3cec20101c34eb98604ef732bc96977,

title = "Synthesis and antibacterial activities of a novel alkylide: 3-O-(3-aryl-2-propargyl) and 3-O-(3-aryl-2-propenyl)clarithromycin derivatives",

abstract = "A series of novel 3-O-(3-aryl-E-2-propenyl)clarithromycin derivatives 8 and 3-O-(3-aryl-2-propargyl)clarithromycin derivatives 11 were designed, synthesized, and evaluated for their in vitro antibacterial activities. Compared with 8c and 11c (Ar was 5-pyrimidyl), 3-O-(3-(5′-pyrimidyl)-Z-1-propenyl) counterpart 6c displayed 4- to 64-fold more potent activities against erythromycin-susceptible Staphylococcus aureus and Streptococcus pneumoniae. Moreover, the activities of 6c, 8c, and 11c against erythromycin-resistant S. aureus and S. pneumoniae were in general 4-fold higher than those of the reference compound, clarithromycin and azithromycin.",

keywords = "Allyl, Erythromycin, Heck, Isomerization, Propargyl, Sonogashira",

author = "Liang, {Jian Hua} and Wang, {Yue Ying} and He Wang and Li, {Xiao Li} and Kun An and Xu, {Ying Chun} and Yao, {Guo Wei}",

year = "2010",

month = may,

day = "1",

doi = "10.1016/j.bmcl.2010.03.038",

language = "English",

volume = "20",

pages = "2880--2883",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

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TY - JOUR

T1 - Synthesis and antibacterial activities of a novel alkylide

T2 - 3-O-(3-aryl-2-propargyl) and 3-O-(3-aryl-2-propenyl)clarithromycin derivatives

AU - Liang, Jian Hua

AU - Wang, Yue Ying

AU - Wang, He

AU - Li, Xiao Li

AU - An, Kun

AU - Xu, Ying Chun

AU - Yao, Guo Wei

PY - 2010/5/1

Y1 - 2010/5/1

N2 - A series of novel 3-O-(3-aryl-E-2-propenyl)clarithromycin derivatives 8 and 3-O-(3-aryl-2-propargyl)clarithromycin derivatives 11 were designed, synthesized, and evaluated for their in vitro antibacterial activities. Compared with 8c and 11c (Ar was 5-pyrimidyl), 3-O-(3-(5′-pyrimidyl)-Z-1-propenyl) counterpart 6c displayed 4- to 64-fold more potent activities against erythromycin-susceptible Staphylococcus aureus and Streptococcus pneumoniae. Moreover, the activities of 6c, 8c, and 11c against erythromycin-resistant S. aureus and S. pneumoniae were in general 4-fold higher than those of the reference compound, clarithromycin and azithromycin.

AB - A series of novel 3-O-(3-aryl-E-2-propenyl)clarithromycin derivatives 8 and 3-O-(3-aryl-2-propargyl)clarithromycin derivatives 11 were designed, synthesized, and evaluated for their in vitro antibacterial activities. Compared with 8c and 11c (Ar was 5-pyrimidyl), 3-O-(3-(5′-pyrimidyl)-Z-1-propenyl) counterpart 6c displayed 4- to 64-fold more potent activities against erythromycin-susceptible Staphylococcus aureus and Streptococcus pneumoniae. Moreover, the activities of 6c, 8c, and 11c against erythromycin-resistant S. aureus and S. pneumoniae were in general 4-fold higher than those of the reference compound, clarithromycin and azithromycin.

KW - Allyl

KW - Erythromycin

KW - Heck

KW - Isomerization

KW - Propargyl

KW - Sonogashira

UR - http://www.scopus.com/inward/record.url?scp=77950860915&partnerID=8YFLogxK

U2 - 10.1016/j.bmcl.2010.03.038

DO - 10.1016/j.bmcl.2010.03.038

M3 - Article

C2 - 20356738

AN - SCOPUS:77950860915

SN - 0960-894X

VL - 20

SP - 2880

EP - 2883

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 9

ER -

Synthesis and antibacterial activities of a novel alkylide: 3-O-(3-aryl-2-propargyl) and 3-O-(3-aryl-2-propenyl)clarithromycin derivatives

Abstract

Keywords

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