Synthesis and antiparasitic evaluation of bis-2,5-[4-guanidinophenyl]thiophenes

Jose L. Gonzalez; Chad E. Stephens; Tanja Wenzler; Reto Brun; Farial A. Tanious; W. David Wilson; Todd Barszcz; Karl A. Werbovetz; David W. Boykin

doi:10.1016/j.ejmech.2006.11.006

Synthesis and antiparasitic evaluation of bis-2,5-[4-guanidinophenyl]thiophenes

Jose L. Gonzalez, Chad E. Stephens, Tanja Wenzler, Reto Brun, Farial A. Tanious, W. David Wilson, Todd Barszcz, Karl A. Werbovetz, David W. Boykin

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

57 Scopus citations

Abstract

A series of bis-2,5-[4-guanidinophenyl]thiophenes were prepared in a five step process starting from 2,5-bis[trimethylstannyl]thiophene. The compounds were evaluated in vitro against Trypanosoma brucei rhodesiense (T. b. r.), Plasmodium falciparum (P. f.), Leshmania donovani (L. d.) and Trypanasoma cruzi (T. c.), and in vivo against T. b. r. Certain compounds show promising in vitro activity against T. b. r. and P. f. and have superior in vivo activity against T. b. r. to that of pentamidine and furamidine.

Original language	English (US)
Pages (from-to)	552-557
Number of pages	6
Journal	European Journal of Medicinal Chemistry
Volume	42
Issue number	4
DOIs	https://doi.org/10.1016/j.ejmech.2006.11.006
State	Published - Apr 2007
Externally published	Yes

Keywords

Antiparasitic agents
Diguanidino thiophenes

ASJC Scopus subject areas

Pharmacology
Drug Discovery
Organic Chemistry

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10.1016/j.ejmech.2006.11.006

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title = "Synthesis and antiparasitic evaluation of bis-2,5-[4-guanidinophenyl]thiophenes",

abstract = "A series of bis-2,5-[4-guanidinophenyl]thiophenes were prepared in a five step process starting from 2,5-bis[trimethylstannyl]thiophene. The compounds were evaluated in vitro against Trypanosoma brucei rhodesiense (T. b. r.), Plasmodium falciparum (P. f.), Leshmania donovani (L. d.) and Trypanasoma cruzi (T. c.), and in vivo against T. b. r. Certain compounds show promising in vitro activity against T. b. r. and P. f. and have superior in vivo activity against T. b. r. to that of pentamidine and furamidine.",

keywords = "Antiparasitic agents, Diguanidino thiophenes",

author = "Gonzalez, {Jose L.} and Stephens, {Chad E.} and Tanja Wenzler and Reto Brun and Tanious, {Farial A.} and Wilson, {W. David} and Todd Barszcz and Werbovetz, {Karl A.} and Boykin, {David W.}",

note = "Funding Information: This work was supported by an award from the Bill and Melinda Gates Foundation and NIH grant GM61587. The technical assistance with the in vivo experiments by Guy Riccio (Swiss Tropical Institute) is greatly appreciated. ",

year = "2007",

month = apr,

doi = "10.1016/j.ejmech.2006.11.006",

language = "English (US)",

volume = "42",

pages = "552--557",

journal = "European Journal of Medicinal Chemistry",

issn = "0223-5234",

publisher = "Elsevier Masson SAS",

number = "4",

}

TY - JOUR

T1 - Synthesis and antiparasitic evaluation of bis-2,5-[4-guanidinophenyl]thiophenes

AU - Gonzalez, Jose L.

AU - Stephens, Chad E.

AU - Wenzler, Tanja

AU - Brun, Reto

AU - Tanious, Farial A.

AU - Wilson, W. David

AU - Barszcz, Todd

AU - Werbovetz, Karl A.

AU - Boykin, David W.

N1 - Funding Information: This work was supported by an award from the Bill and Melinda Gates Foundation and NIH grant GM61587. The technical assistance with the in vivo experiments by Guy Riccio (Swiss Tropical Institute) is greatly appreciated.

PY - 2007/4

Y1 - 2007/4

N2 - A series of bis-2,5-[4-guanidinophenyl]thiophenes were prepared in a five step process starting from 2,5-bis[trimethylstannyl]thiophene. The compounds were evaluated in vitro against Trypanosoma brucei rhodesiense (T. b. r.), Plasmodium falciparum (P. f.), Leshmania donovani (L. d.) and Trypanasoma cruzi (T. c.), and in vivo against T. b. r. Certain compounds show promising in vitro activity against T. b. r. and P. f. and have superior in vivo activity against T. b. r. to that of pentamidine and furamidine.

AB - A series of bis-2,5-[4-guanidinophenyl]thiophenes were prepared in a five step process starting from 2,5-bis[trimethylstannyl]thiophene. The compounds were evaluated in vitro against Trypanosoma brucei rhodesiense (T. b. r.), Plasmodium falciparum (P. f.), Leshmania donovani (L. d.) and Trypanasoma cruzi (T. c.), and in vivo against T. b. r. Certain compounds show promising in vitro activity against T. b. r. and P. f. and have superior in vivo activity against T. b. r. to that of pentamidine and furamidine.

KW - Antiparasitic agents

KW - Diguanidino thiophenes

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U2 - 10.1016/j.ejmech.2006.11.006

DO - 10.1016/j.ejmech.2006.11.006

M3 - Article

C2 - 17178177

AN - SCOPUS:34047175303

SN - 0223-5234

VL - 42

SP - 552

EP - 557

JO - European Journal of Medicinal Chemistry

JF - European Journal of Medicinal Chemistry

IS - 4

ER -

Synthesis and antiparasitic evaluation of bis-2,5-[4-guanidinophenyl]thiophenes

Abstract

Keywords

ASJC Scopus subject areas

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