2,4- and 2,5-disubstituted arylthiazoles: Rapid synthesis by C-H coupling and biological evaluation

Lilia Lohrey; Takahiro N. Uehara; Satoshi Tani; Junichiro Yamaguchi; Hans Ulrich Humpf; Kenichiro Itami

doi:10.1002/ejoc.201402129

2,4- and 2,5-disubstituted arylthiazoles: Rapid synthesis by C-H coupling and biological evaluation

Lilia Lohrey, Takahiro N. Uehara, Satoshi Tani, Junichiro Yamaguchi^*, Hans Ulrich Humpf, Kenichiro Itami

^*Corresponding author for this work

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

13 Citations (Scopus)

Abstract

Life-threatening infections caused by bacteria that have developed resistance to common antibiotics, such as methicillin-resistant Staphylococcus aureus (MRSA), have become a serious problem in hospitals and other areas all over the world. Thus, the development of an effective class of antibiotics against these bacteria is an urgent subject. Herein, we report a step-economical and diversity-oriented synthesis of a series of 2-arylidenehydrazinyl-4- arylthiazole and 2-arylidenehydrazinyl-5-arylthiazole analogues that utilizes C-H coupling methodologies. A library of 54 new congeners were synthesized and tested for their biological potential. Moreover, new knowledge regarding the structure-activity relationships (SARs) of these heterobiaryl compounds was collected.

Original language	English
Pages (from-to)	3387-3394
Number of pages	8
Journal	European Journal of Organic Chemistry
Volume	2014
Issue number	16
DOIs	https://doi.org/10.1002/ejoc.201402129
Publication status	Published - 2014 Jun
Externally published	Yes

Keywords

Antibiotics
C-H arylation
Cross-coupling
Structure-activity relationships
Thiazoles

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.201402129

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title = "2,4- and 2,5-disubstituted arylthiazoles: Rapid synthesis by C-H coupling and biological evaluation",

abstract = "Life-threatening infections caused by bacteria that have developed resistance to common antibiotics, such as methicillin-resistant Staphylococcus aureus (MRSA), have become a serious problem in hospitals and other areas all over the world. Thus, the development of an effective class of antibiotics against these bacteria is an urgent subject. Herein, we report a step-economical and diversity-oriented synthesis of a series of 2-arylidenehydrazinyl-4- arylthiazole and 2-arylidenehydrazinyl-5-arylthiazole analogues that utilizes C-H coupling methodologies. A library of 54 new congeners were synthesized and tested for their biological potential. Moreover, new knowledge regarding the structure-activity relationships (SARs) of these heterobiaryl compounds was collected.",

keywords = "Antibiotics, C-H arylation, Cross-coupling, Structure-activity relationships, Thiazoles",

author = "Lilia Lohrey and Uehara, {Takahiro N.} and Satoshi Tani and Junichiro Yamaguchi and Humpf, {Hans Ulrich} and Kenichiro Itami",

year = "2014",

month = jun,

doi = "10.1002/ejoc.201402129",

language = "English",

volume = "2014",

pages = "3387--3394",

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number = "16",

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T1 - 2,4- and 2,5-disubstituted arylthiazoles

T2 - Rapid synthesis by C-H coupling and biological evaluation

AU - Lohrey, Lilia

AU - Uehara, Takahiro N.

AU - Tani, Satoshi

AU - Yamaguchi, Junichiro

AU - Humpf, Hans Ulrich

AU - Itami, Kenichiro

PY - 2014/6

Y1 - 2014/6

N2 - Life-threatening infections caused by bacteria that have developed resistance to common antibiotics, such as methicillin-resistant Staphylococcus aureus (MRSA), have become a serious problem in hospitals and other areas all over the world. Thus, the development of an effective class of antibiotics against these bacteria is an urgent subject. Herein, we report a step-economical and diversity-oriented synthesis of a series of 2-arylidenehydrazinyl-4- arylthiazole and 2-arylidenehydrazinyl-5-arylthiazole analogues that utilizes C-H coupling methodologies. A library of 54 new congeners were synthesized and tested for their biological potential. Moreover, new knowledge regarding the structure-activity relationships (SARs) of these heterobiaryl compounds was collected.

AB - Life-threatening infections caused by bacteria that have developed resistance to common antibiotics, such as methicillin-resistant Staphylococcus aureus (MRSA), have become a serious problem in hospitals and other areas all over the world. Thus, the development of an effective class of antibiotics against these bacteria is an urgent subject. Herein, we report a step-economical and diversity-oriented synthesis of a series of 2-arylidenehydrazinyl-4- arylthiazole and 2-arylidenehydrazinyl-5-arylthiazole analogues that utilizes C-H coupling methodologies. A library of 54 new congeners were synthesized and tested for their biological potential. Moreover, new knowledge regarding the structure-activity relationships (SARs) of these heterobiaryl compounds was collected.

KW - Antibiotics

KW - C-H arylation

KW - Cross-coupling

KW - Structure-activity relationships

KW - Thiazoles

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ER -

2,4- and 2,5-disubstituted arylthiazoles: Rapid synthesis by C-H coupling and biological evaluation

Abstract

Keywords

ASJC Scopus subject areas

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