Synthesis, characterization, and biological activities of new benzofuran derivatives

Kifah S.M. Salih; Mikdad T. Ayoub; Haythem A. Saadeh; Najim A. Al-Masoudi; Mohammad S. Mubarak

doi:10.3987/com-07-11052

Synthesis, characterization, and biological activities of new benzofuran derivatives

Kifah S.M. Salih, Mikdad T. Ayoub, Haythem A. Saadeh, Najim A. Al-Masoudi, Mohammad S. Mubarak

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

14 Citations (Scopus)

Abstract

A number of new benzofuran derivatives, ethyl 3-[(alkylamino)methyl]-6-methoxy-1-benzofuran-2-carboxylates (5a-i), were obtained via the reaction between ethyl 3-(bromomethyl)-6-methoxy-1-benzofuran-2-carboxylate (3) and amines or amino acid ethyl esters. In addition, 1,4-bis[(ethyl 6-methoxy-1-benzofuran-3-yl-2-carboxylate)methyl]piperazine (9), N,N′-diethyl-N,N′-bis[(6-methoxy-1-benzofuran-3-yl-2-carboxy late)methyl]but-2-ene-1,4-diamine (10) and 1,2-bis[(ethyl 6-methoxy-1-benzofuran-3-yl-2-carboxylate)methyl]- 1,2-dimethyl-hydrazine (11) were also obtained from the reaction of 3 with diamines. Their in vitro anti-HIV-1 (strain IIIB) and HIV-2 (strain ROD) activities of the synthesized compounds in human T-lymphocyte were tested; ethyl 3-bromomethyl-6-methoxycoumarlate displayed an ability to inhibit HIV-1 and HIV-2 replication in cell culture at non-toxic concentrations.

Original language	English
Pages (from-to)	1577-1587
Number of pages	11
Journal	Heterocycles
Volume	71
Issue number	7
DOIs	https://doi.org/10.3987/com-07-11052
Publication status	Published - Jul 1 2007
Externally published	Yes

Keywords

3-Bromomethyl-2-carbethoxy-6-methoxybenzofuran
Amino Acid Ethyl Ester
Benzofuran
Cyclization
HIV

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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10.3987/com-07-11052

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title = "Synthesis, characterization, and biological activities of new benzofuran derivatives",

abstract = "A number of new benzofuran derivatives, ethyl 3-[(alkylamino)methyl]-6-methoxy-1-benzofuran-2-carboxylates (5a-i), were obtained via the reaction between ethyl 3-(bromomethyl)-6-methoxy-1-benzofuran-2-carboxylate (3) and amines or amino acid ethyl esters. In addition, 1,4-bis[(ethyl 6-methoxy-1-benzofuran-3-yl-2-carboxylate)methyl]piperazine (9), N,N′-diethyl-N,N′-bis[(6-methoxy-1-benzofuran-3-yl-2-carboxy late)methyl]but-2-ene-1,4-diamine (10) and 1,2-bis[(ethyl 6-methoxy-1-benzofuran-3-yl-2-carboxylate)methyl]- 1,2-dimethyl-hydrazine (11) were also obtained from the reaction of 3 with diamines. Their in vitro anti-HIV-1 (strain IIIB) and HIV-2 (strain ROD) activities of the synthesized compounds in human T-lymphocyte were tested; ethyl 3-bromomethyl-6-methoxycoumarlate displayed an ability to inhibit HIV-1 and HIV-2 replication in cell culture at non-toxic concentrations.",

keywords = "3-Bromomethyl-2-carbethoxy-6-methoxybenzofuran, Amino Acid Ethyl Ester, Benzofuran, Cyclization, HIV",

author = "Salih, {Kifah S.M.} and Ayoub, {Mikdad T.} and Saadeh, {Haythem A.} and Al-Masoudi, {Najim A.} and Mubarak, {Mohammad S.}",

year = "2007",

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T1 - Synthesis, characterization, and biological activities of new benzofuran derivatives

AU - Salih, Kifah S.M.

AU - Ayoub, Mikdad T.

AU - Saadeh, Haythem A.

AU - Al-Masoudi, Najim A.

AU - Mubarak, Mohammad S.

PY - 2007/7/1

Y1 - 2007/7/1

N2 - A number of new benzofuran derivatives, ethyl 3-[(alkylamino)methyl]-6-methoxy-1-benzofuran-2-carboxylates (5a-i), were obtained via the reaction between ethyl 3-(bromomethyl)-6-methoxy-1-benzofuran-2-carboxylate (3) and amines or amino acid ethyl esters. In addition, 1,4-bis[(ethyl 6-methoxy-1-benzofuran-3-yl-2-carboxylate)methyl]piperazine (9), N,N′-diethyl-N,N′-bis[(6-methoxy-1-benzofuran-3-yl-2-carboxy late)methyl]but-2-ene-1,4-diamine (10) and 1,2-bis[(ethyl 6-methoxy-1-benzofuran-3-yl-2-carboxylate)methyl]- 1,2-dimethyl-hydrazine (11) were also obtained from the reaction of 3 with diamines. Their in vitro anti-HIV-1 (strain IIIB) and HIV-2 (strain ROD) activities of the synthesized compounds in human T-lymphocyte were tested; ethyl 3-bromomethyl-6-methoxycoumarlate displayed an ability to inhibit HIV-1 and HIV-2 replication in cell culture at non-toxic concentrations.

AB - A number of new benzofuran derivatives, ethyl 3-[(alkylamino)methyl]-6-methoxy-1-benzofuran-2-carboxylates (5a-i), were obtained via the reaction between ethyl 3-(bromomethyl)-6-methoxy-1-benzofuran-2-carboxylate (3) and amines or amino acid ethyl esters. In addition, 1,4-bis[(ethyl 6-methoxy-1-benzofuran-3-yl-2-carboxylate)methyl]piperazine (9), N,N′-diethyl-N,N′-bis[(6-methoxy-1-benzofuran-3-yl-2-carboxy late)methyl]but-2-ene-1,4-diamine (10) and 1,2-bis[(ethyl 6-methoxy-1-benzofuran-3-yl-2-carboxylate)methyl]- 1,2-dimethyl-hydrazine (11) were also obtained from the reaction of 3 with diamines. Their in vitro anti-HIV-1 (strain IIIB) and HIV-2 (strain ROD) activities of the synthesized compounds in human T-lymphocyte were tested; ethyl 3-bromomethyl-6-methoxycoumarlate displayed an ability to inhibit HIV-1 and HIV-2 replication in cell culture at non-toxic concentrations.

KW - 3-Bromomethyl-2-carbethoxy-6-methoxybenzofuran

KW - Amino Acid Ethyl Ester

KW - Benzofuran

KW - Cyclization

KW - HIV

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JO - Heterocycles

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ER -

Synthesis, characterization, and biological activities of new benzofuran derivatives

Abstract

Keywords

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