Synthesis and Anti-tumor Activities of Novel 18β-Glycyrrhetinic Acid Derivatives Attaching Dithiocarbamate Units

被引：5

作者：

Chen Couxi ^{[1
]}

Li Xueqiang ^{[1
,2
]}

Li Tiancai ^{[1
]}

Zhou Xuezhang ^{[3
]}

机构：

[1] Ningxia Univ, Sch Chem & Chem Engn, Yinchuan 750021, Peoples R China

[2] Ningxia Dev Ctr Nat Prod & Medicat, Yinchuan 750021, Peoples R China

[3] Ningxia Univ, Key Lab Minist Educ Protect & Utilizat Special Bi, Yinchuan 750021, Peoples R China

来源：

ACTA CHIMICA SINICA | 2012年 / 70卷 / 07期

基金：

中国国家自然科学基金;

关键词：

18 beta-glycyrrhetinic acid; dithiocarbamates; synthesis; anti-tumor activity; GLYCYRRHETINIC ACID; GLYCYRRHIZIC ACID; LEUKEMIA-CELLS; INHIBITORS; APOPTOSIS;

D O I：

10.6023/A1111051

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Ten new 18 beta-glycyrrhetinic acid derivatives with dithiocarbamate units were prepared by amidation of 18 beta-glycyrrhetinic acid and piperazine followed with one-pot condensation of the amide, CS2 and alkyl halides in the presence of potassium carbonate in CHCl3. The structures of all the new compounds were identified by NMR spectra, IR and HRMS technology. Anti-tumor activities of the 18 beta-glycyrrhetinic acid derivatives against human hepatoma SMMC-7721 cell lines were evaluated by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) method. They were found to inhibit the liver cancer cell proliferation and induce apoptosis as the lowest IC50 value was only 14.42 mu g/mL.

引用

页码：852 / 858

页数：7

共 33 条

[1] Cytotoxic, antioxidant activities and structure activity relationship of some newly synthesized terpenoidal oxaliplatin analogs [J].

Amr, Abd El-Galil E. ;

Ali, Korany A. ;

Abdalla, Mohamed M. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (02) :901-907

[2] Straightforward and highly efficient catalyst-free one-pot synthesis of dithiocarbamates under solvent-free conditions [J].

Azizi, Najmedin ;

Aryanasab, Fezzeh ;

Saidi, Mohammad R. .

ORGANIC LETTERS, 2006, 8 (23) :5275-5277

[3] Determination of dithiocarbamate fungicide residues in food by a spectrophotometric method using a vertical disulfide reaction system [J].

Caldas, ED ;

Conceiçao, MH ;

Miranda, MCC ;

de Souza, LCKR ;

Lima, JF .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2001, 49 (10) :4521-4525

[4] Pyrrolidine dithiocarbamate inhibition of luteolin-induced apoptosis through up-regulated phosphorylation of Akt and caspase-9 in human leukemia HL-60 cells [J].

Cheng, An-Chin ;

Huang, Tzou-Chi ;

Lai, Ching-Shu ;

Kuo, Jen-Min ;

Huang, Ying-Tang ;

Lo, Chih-Yu ;

Ho, Chi-Tang ;

Pan, Min-Hsiung .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2006, 54 (12) :4215-4221

[5] Synthesis and antitumor activity of ring A modified glycyrrhetinic acid derivatives [J].

Csuk, Rene ;

Schwarz, Stefan ;

Siewert, Bianka ;

Kluge, Ralph ;

Stroehl, Dieter .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (11) :5356-5369

[6] Glycyrrhizic acid alters Kaposi sarcoma-associated herpesvirius latency, triggering p53-mediated apoptosis in transformed B lymphocytes [J].

Curreli, F ;

Friedman-Kien, AE ;

Flore, O .

JOURNAL OF CLINICAL INVESTIGATION, 2005, 115 (03) :642-652

[7] ANTIULCER ACTIVITIES OF LICORICE AND ITS DERIVATIVES IN EXPERIMENTAL GASTRIC LESION-INDUCED BY IBUPROFEN IN RATS [J].

DEHPOUR, AR ;

ZOLFAGHARI, ME ;

SAMADIAN, T ;

KOBARFARD, F ;

FAIZI, M ;

ASSARI, M .

INTERNATIONAL JOURNAL OF PHARMACEUTICS, 1995, 119 (02) :133-138

[8]

[冯文宇 FENG Wen-yu], 2010, [中成药, Chinese Traditional Patent Medicine], V32, P189

[9] Nanosized polymetallic resorcinarene-based host assemblies that strongly bind fullerenes [J].

Fox, O. Danny ;

Cookson, James ;

Wilkinson, Emma J. S. ;

Drew, Michael G. B. ;

MacLean, Elizabeth J. ;

Teat, Simon J. ;

Beer, Paul D. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :6990-7002

[10] Fabrication of Asymmetric Molecular Junctions by the Oriented Assembly of Dithiocarbamate Rectifiers [J].

Gao, Deqing ;

Scholz, Frank ;

Nothofer, Heinz-Georg ;

Ford, William E. ;

Scherf, Ullrich ;

Wessels, Jurina M. ;

Yasuda, Akio ;

von Wrochem, Florian .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (15) :5921-5930

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