Synthesis of some novel D-glucuronic acid acetylated derivatives as potential anti-tumor agents

Ahmed O.H. El-Nezhawy; Frady G. Adly; Ahmed F. Eweas; Atef G. Hanna; Yehya M. El-Kholy; Shahenaz H. El-Sayed; Tarek B.A. El-Naggar

doi:10.1002/ardp.201000367

Synthesis of some novel D-glucuronic acid acetylated derivatives as potential anti-tumor agents

Ahmed O.H. El-Nezhawy, Frady G. Adly, Ahmed F. Eweas, Atef G. Hanna, Yehya M. El-Kholy, Shahenaz H. El-Sayed, Tarek B.A. El-Naggar

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

8 Citations (Scopus)

Abstract

A structurally diverse series of Δ ^4,5-uronamide derivatives have been chemically synthesized starting from D-glucuronic acid itself by means of acetylation, activation, amide bond formation and base-catalyzed elimination protocols. Structure elucidation for all products along with optimization of the synthetic steps is described. The synthesized compounds were evaluated for their in-vitro anti-tumor activity against MCF-7, TK-10 and UACC-62 cell lines. The compounds 5, 11, 13, 15 and 16 were the most active against TK-10 cell line. On the other hand, the most active compounds against the MCF-7 cell line were 11 and 15. However, compounds 5, 7, 11, 13, 15 and 16 were the most active against the UACC-62 cell line.

Original language	English
Pages (from-to)	648-657
Number of pages	10
Journal	Archiv der Pharmazie
Volume	344
Issue number	10
DOIs	https://doi.org/10.1002/ardp.201000367
Publication status	Published - Oct 2011
Externally published	Yes

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@article{8435dbfde5604028b9c3eb0174878150,

title = "Synthesis of some novel D-glucuronic acid acetylated derivatives as potential anti-tumor agents",

abstract = "A structurally diverse series of Δ 4,5-uronamide derivatives have been chemically synthesized starting from D-glucuronic acid itself by means of acetylation, activation, amide bond formation and base-catalyzed elimination protocols. Structure elucidation for all products along with optimization of the synthetic steps is described. The synthesized compounds were evaluated for their in-vitro anti-tumor activity against MCF-7, TK-10 and UACC-62 cell lines. The compounds 5, 11, 13, 15 and 16 were the most active against TK-10 cell line. On the other hand, the most active compounds against the MCF-7 cell line were 11 and 15. However, compounds 5, 7, 11, 13, 15 and 16 were the most active against the UACC-62 cell line.",

keywords = "Amide linkage, Anti-tumor, D-Glucuronamide, D-Glucuronic acid, MCF-7, TK-10, UACC-62",

author = "El-Nezhawy, {Ahmed O.H.} and Adly, {Frady G.} and Eweas, {Ahmed F.} and Hanna, {Atef G.} and El-Kholy, {Yehya M.} and El-Sayed, {Shahenaz H.} and El-Naggar, {Tarek B.A.}",

year = "2011",

month = oct,

doi = "10.1002/ardp.201000367",

language = "English",

volume = "344",

pages = "648--657",

journal = "Archiv der Pharmazie",

issn = "0365-6233",

publisher = "Wiley-Blackwell",

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TY - JOUR

T1 - Synthesis of some novel D-glucuronic acid acetylated derivatives as potential anti-tumor agents

AU - El-Nezhawy, Ahmed O.H.

AU - Adly, Frady G.

AU - Eweas, Ahmed F.

AU - Hanna, Atef G.

AU - El-Kholy, Yehya M.

AU - El-Sayed, Shahenaz H.

AU - El-Naggar, Tarek B.A.

PY - 2011/10

Y1 - 2011/10

N2 - A structurally diverse series of Δ 4,5-uronamide derivatives have been chemically synthesized starting from D-glucuronic acid itself by means of acetylation, activation, amide bond formation and base-catalyzed elimination protocols. Structure elucidation for all products along with optimization of the synthetic steps is described. The synthesized compounds were evaluated for their in-vitro anti-tumor activity against MCF-7, TK-10 and UACC-62 cell lines. The compounds 5, 11, 13, 15 and 16 were the most active against TK-10 cell line. On the other hand, the most active compounds against the MCF-7 cell line were 11 and 15. However, compounds 5, 7, 11, 13, 15 and 16 were the most active against the UACC-62 cell line.

AB - A structurally diverse series of Δ 4,5-uronamide derivatives have been chemically synthesized starting from D-glucuronic acid itself by means of acetylation, activation, amide bond formation and base-catalyzed elimination protocols. Structure elucidation for all products along with optimization of the synthetic steps is described. The synthesized compounds were evaluated for their in-vitro anti-tumor activity against MCF-7, TK-10 and UACC-62 cell lines. The compounds 5, 11, 13, 15 and 16 were the most active against TK-10 cell line. On the other hand, the most active compounds against the MCF-7 cell line were 11 and 15. However, compounds 5, 7, 11, 13, 15 and 16 were the most active against the UACC-62 cell line.

KW - Amide linkage

KW - Anti-tumor

KW - D-Glucuronamide

KW - D-Glucuronic acid

KW - MCF-7

KW - TK-10

KW - UACC-62

UR - http://www.scopus.com/inward/record.url?scp=80054007351&partnerID=8YFLogxK

U2 - 10.1002/ardp.201000367

DO - 10.1002/ardp.201000367

M3 - Article

C2 - 21984015

AN - SCOPUS:80054007351

SN - 0365-6233

VL - 344

SP - 648

EP - 657

JO - Archiv der Pharmazie

JF - Archiv der Pharmazie

IS - 10

ER -

Synthesis of some novel D-glucuronic acid acetylated derivatives as potential anti-tumor agents

Abstract

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