Design, synthesis and antitumor activity of novel D-Glucuronic acid derivatives

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

doi:10.2174/157340611797928398

Design, synthesis and antitumor activity of novel D-Glucuronic acid derivatives

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

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

6 Citations (Scopus)

Abstract

A series of D-glucuronic acid derivatives were chemically synthesized including acetylated and deacetylated glucuronamides, as well as N-glucuronides starting from the D-glucuronic acid itself by means of protection/deprotection, activation and condensation protocols. Structure elucidation of all products along with optimization of the synthetic steps is described. The synthesized compounds were evaluated for their in vitro antitumor activity against MCF-7, TK-10 and UACC-62 cell lines. The compounds 4, 5, 7, 8, 14, 16 and 18 were the most active against TK-10 cell line. On the other hand, the most active compounds against the MCF-7 cell line were 9, 18 and 20. However, compounds 7-10 13-15 and 17 were the most active against the UACC-62 cell line.

Original language	English
Pages (from-to)	624-638
Number of pages	15
Journal	Medicinal Chemistry
Volume	7
Issue number	6
DOIs	https://doi.org/10.2174/157340611797928398
Publication status	Published - Nov 2011
Externally published	Yes

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title = "Design, synthesis and antitumor activity of novel D-Glucuronic acid derivatives",

abstract = "A series of D-glucuronic acid derivatives were chemically synthesized including acetylated and deacetylated glucuronamides, as well as N-glucuronides starting from the D-glucuronic acid itself by means of protection/deprotection, activation and condensation protocols. Structure elucidation of all products along with optimization of the synthetic steps is described. The synthesized compounds were evaluated for their in vitro antitumor activity against MCF-7, TK-10 and UACC-62 cell lines. The compounds 4, 5, 7, 8, 14, 16 and 18 were the most active against TK-10 cell line. On the other hand, the most active compounds against the MCF-7 cell line were 9, 18 and 20. However, compounds 7-10 13-15 and 17 were the most active against the UACC-62 cell line.",

keywords = "Amide linkage, Antitumor, 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-Syed, {Shahenaz H.} and El-Naggar, {Tarek B.A.}",

year = "2011",

month = nov,

doi = "10.2174/157340611797928398",

language = "English",

volume = "7",

pages = "624--638",

journal = "Medicinal Chemistry",

issn = "1573-4064",

publisher = "Bentham Science Publishers B.V.",

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TY - JOUR

T1 - Design, synthesis and antitumor activity of novel D-Glucuronic acid derivatives

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-Syed, Shahenaz H.

AU - El-Naggar, Tarek B.A.

PY - 2011/11

Y1 - 2011/11

N2 - A series of D-glucuronic acid derivatives were chemically synthesized including acetylated and deacetylated glucuronamides, as well as N-glucuronides starting from the D-glucuronic acid itself by means of protection/deprotection, activation and condensation protocols. Structure elucidation of all products along with optimization of the synthetic steps is described. The synthesized compounds were evaluated for their in vitro antitumor activity against MCF-7, TK-10 and UACC-62 cell lines. The compounds 4, 5, 7, 8, 14, 16 and 18 were the most active against TK-10 cell line. On the other hand, the most active compounds against the MCF-7 cell line were 9, 18 and 20. However, compounds 7-10 13-15 and 17 were the most active against the UACC-62 cell line.

AB - A series of D-glucuronic acid derivatives were chemically synthesized including acetylated and deacetylated glucuronamides, as well as N-glucuronides starting from the D-glucuronic acid itself by means of protection/deprotection, activation and condensation protocols. Structure elucidation of all products along with optimization of the synthetic steps is described. The synthesized compounds were evaluated for their in vitro antitumor activity against MCF-7, TK-10 and UACC-62 cell lines. The compounds 4, 5, 7, 8, 14, 16 and 18 were the most active against TK-10 cell line. On the other hand, the most active compounds against the MCF-7 cell line were 9, 18 and 20. However, compounds 7-10 13-15 and 17 were the most active against the UACC-62 cell line.

KW - Amide linkage

KW - Antitumor

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=80755159517&partnerID=8YFLogxK

U2 - 10.2174/157340611797928398

DO - 10.2174/157340611797928398

M3 - Article

C2 - 22313302

AN - SCOPUS:80755159517

SN - 1573-4064

VL - 7

SP - 624

EP - 638

JO - Medicinal Chemistry

JF - Medicinal Chemistry

IS - 6

ER -

Design, synthesis and antitumor activity of novel D-Glucuronic acid derivatives

Abstract

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