Synthesis and anticancer activity of new ((Furan-2-yl)-1,3,4-thiadiazolyl)-1,3,4-oxadiazole acyclic sugar derivatives

Asmaa F. Kassem; Ibrahim F. Nassar; Mohammed T. Abdel-Aal; Hanem M. Awad; Wael A. El-Sayed

doi:10.1248/cpb.c19-00280

Synthesis and anticancer activity of new ((Furan-2-yl)-1,3,4-thiadiazolyl)-1,3,4-oxadiazole acyclic sugar derivatives

Asmaa F. Kassem
, Ibrahim F. Nassar
, Mohammed T. Abdel-Aal
, Hanem M. Awad
, Wael A. El-Sayed

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

77 Scopus citations

Abstract

New sugar hydrazones incorporating furan and/or 1,3,4-thiadiazole ring systems were synthesized by reaction of the corresponding hydrazide with different aldose sugars. Heterocyclization of the formed hydrazones afforded the derived acyclic nucleoside analogues possessing the 1,3,4-oxadiazoline as modified nucleobase via acetylation followed by the heterocyclization process. The anticancer activity of the synthesized compounds was studied against human liver carcinoma cell (HepG-2) and at human normal retina pigmented epithelium cells (RPE-1). High activities were revealed by compounds 3, 12 and 14 with IC50 values near to that of the reference drug doxorubicin.

Original language	English
Pages (from-to)	888-895
Number of pages	8
Journal	Chemical and Pharmaceutical Bulletin
Volume	67
Issue number	8
DOIs	https://doi.org/10.1248/cpb.c19-00280
State	Published - 2019
Externally published	Yes

Keywords

1,3,4-oxadiazole
Acyclic nucleoside
Anticancer
Hydrazone
Sugar
Thiadiazole

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1248/cpb.c19-00280

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title = "Synthesis and anticancer activity of new ((Furan-2-yl)-1,3,4-thiadiazolyl)-1,3,4-oxadiazole acyclic sugar derivatives",

abstract = "New sugar hydrazones incorporating furan and/or 1,3,4-thiadiazole ring systems were synthesized by reaction of the corresponding hydrazide with different aldose sugars. Heterocyclization of the formed hydrazones afforded the derived acyclic nucleoside analogues possessing the 1,3,4-oxadiazoline as modified nucleobase via acetylation followed by the heterocyclization process. The anticancer activity of the synthesized compounds was studied against human liver carcinoma cell (HepG-2) and at human normal retina pigmented epithelium cells (RPE-1). High activities were revealed by compounds 3, 12 and 14 with IC50 values near to that of the reference drug doxorubicin.",

keywords = "1,3,4-oxadiazole, Acyclic nucleoside, Anticancer, Hydrazone, Sugar, Thiadiazole",

author = "Kassem, \{Asmaa F.\} and Nassar, \{Ibrahim F.\} and Abdel-Aal, \{Mohammed T.\} and Awad, \{Hanem M.\} and El-Sayed, \{Wael A.\}",

note = "Publisher Copyright: {\textcopyright} 2019 The Pharmaceutical Society of Japan.",

year = "2019",

doi = "10.1248/cpb.c19-00280",

language = "English",

volume = "67",

pages = "888--895",

journal = "Chemical and Pharmaceutical Bulletin",

issn = "0009-2363",

publisher = "Pharmaceutical Society of Japan",

number = "8",

}

TY - JOUR

T1 - Synthesis and anticancer activity of new ((Furan-2-yl)-1,3,4-thiadiazolyl)-1,3,4-oxadiazole acyclic sugar derivatives

AU - Kassem, Asmaa F.

AU - Nassar, Ibrahim F.

AU - Abdel-Aal, Mohammed T.

AU - Awad, Hanem M.

AU - El-Sayed, Wael A.

PY - 2019

Y1 - 2019

N2 - New sugar hydrazones incorporating furan and/or 1,3,4-thiadiazole ring systems were synthesized by reaction of the corresponding hydrazide with different aldose sugars. Heterocyclization of the formed hydrazones afforded the derived acyclic nucleoside analogues possessing the 1,3,4-oxadiazoline as modified nucleobase via acetylation followed by the heterocyclization process. The anticancer activity of the synthesized compounds was studied against human liver carcinoma cell (HepG-2) and at human normal retina pigmented epithelium cells (RPE-1). High activities were revealed by compounds 3, 12 and 14 with IC50 values near to that of the reference drug doxorubicin.

AB - New sugar hydrazones incorporating furan and/or 1,3,4-thiadiazole ring systems were synthesized by reaction of the corresponding hydrazide with different aldose sugars. Heterocyclization of the formed hydrazones afforded the derived acyclic nucleoside analogues possessing the 1,3,4-oxadiazoline as modified nucleobase via acetylation followed by the heterocyclization process. The anticancer activity of the synthesized compounds was studied against human liver carcinoma cell (HepG-2) and at human normal retina pigmented epithelium cells (RPE-1). High activities were revealed by compounds 3, 12 and 14 with IC50 values near to that of the reference drug doxorubicin.

KW - 1,3,4-oxadiazole

KW - Acyclic nucleoside

KW - Anticancer

KW - Hydrazone

KW - Sugar

KW - Thiadiazole

UR - https://www.scopus.com/pages/publications/85070572869

U2 - 10.1248/cpb.c19-00280

DO - 10.1248/cpb.c19-00280

M3 - Article

C2 - 31366838

AN - SCOPUS:85070572869

SN - 0009-2363

VL - 67

SP - 888

EP - 895

JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

IS - 8

ER -

Synthesis and anticancer activity of new ((Furan-2-yl)-1,3,4-thiadiazolyl)-1,3,4-oxadiazole acyclic sugar derivatives

Abstract

Keywords

UN SDGs

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