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 journalArticle

4 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 languageEnglish
Pages (from-to)624-638
Number of pages15
JournalMedicinal Chemistry
Volume7
Issue number6
DOIs
Publication statusPublished - Nov 2011
Externally publishedYes

Fingerprint

Glucuronic Acid
Cell Line
Glucuronides
MCF-7 Cells

Cite this

El-Nezhawy, A. O. H., Adly, F. G., Eweas, A. F., Hanna, A. G., El-Kholy, Y. M., El-Syed, S. H., & El-Naggar, T. B. A. (2011). Design, synthesis and antitumor activity of novel D-Glucuronic acid derivatives. Medicinal Chemistry, 7(6), 624-638. https://doi.org/10.2174/157340611797928398
El-Nezhawy, Ahmed O.H. ; Adly, Frady G. ; Eweas, Ahmed F. ; Hanna, Atef G. ; El-Kholy, Yehya M. ; El-Syed, Shahenaz H. ; El-Naggar, Tarek B.A. / Design, synthesis and antitumor activity of novel D-Glucuronic acid derivatives. In: Medicinal Chemistry. 2011 ; Vol. 7, No. 6. pp. 624-638.
@article{300f140212d84ba7becb32e5e71c48c9,
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 = "11",
doi = "10.2174/157340611797928398",
language = "English",
volume = "7",
pages = "624--638",
journal = "Medicinal Chemistry",
issn = "1573-4064",
publisher = "Bentham Science Publishers B.V.",
number = "6",

}

El-Nezhawy, AOH, Adly, FG, Eweas, AF, Hanna, AG, El-Kholy, YM, El-Syed, SH & El-Naggar, TBA 2011, 'Design, synthesis and antitumor activity of novel D-Glucuronic acid derivatives', Medicinal Chemistry, vol. 7, no. 6, pp. 624-638. https://doi.org/10.2174/157340611797928398

Design, synthesis and antitumor activity of novel D-Glucuronic acid derivatives. / El-Nezhawy, Ahmed O.H.; Adly, Frady G.; Eweas, Ahmed F.; Hanna, Atef G.; El-Kholy, Yehya M.; El-Syed, Shahenaz H.; El-Naggar, Tarek B.A.

In: Medicinal Chemistry, Vol. 7, No. 6, 11.2011, p. 624-638.

Research output: Contribution to journalArticle

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

VL - 7

SP - 624

EP - 638

JO - Medicinal Chemistry

JF - Medicinal Chemistry

SN - 1573-4064

IS - 6

ER -

El-Nezhawy AOH, Adly FG, Eweas AF, Hanna AG, El-Kholy YM, El-Syed SH et al. Design, synthesis and antitumor activity of novel D-Glucuronic acid derivatives. Medicinal Chemistry. 2011 Nov;7(6):624-638. https://doi.org/10.2174/157340611797928398