Research Progress in the Bioactivities of the Dithiocarbamates

doi:10.11944/j.issn.1000-0518.2015.02.140187

Chinese Journal of Applied Chemistry ›› 2015, Vol. 32 ›› Issue (2): 123-133.DOI: 10.11944/j.issn.1000-0518.2015.02.140187

• Review • Previous Articles Next Articles

Research Progress in the Bioactivities of the Dithiocarbamates

WANG Xiaojuan^*, LI Gaowei, MENG Tuanjie, LIU Lantao, ZHAO Wenxian^*

School of Chemistry and Chemical Engineering,Shangqiu Normal University,Shangqiu,He'nan 476000,China

Received:2014-05-23 Revised:2014-08-11 Published:2015-02-10 Online:2015-02-10
Contact: Corresponding author:ZHAO Wenxian, professor; Tel/Fax:0370-2595126; E-mail:zhwx5126@gmail.com; Research interests:organic methodology and medicinal chemistry
Supported by:
; Supported by the National Natural Science Foundation of China (Nos.21172139, 21202095) and the Education Department of He'nan Province Science and Technology Research Projects(No.13A150835, No.14A150055)

Abstract

CLC Number:

O626

WANG Xiaojuan ,LI Gaowei,MENG Tuanjie,LIU Lantao,ZHAO Wenxian . Research Progress in the Bioactivities of the Dithiocarbamates[J]. Chinese Journal of Applied Chemistry, 2015, 32(2): 123-133.

[1] Lai C S,Vassilev V P,Wang T M. Method for in Vivo Reduction of Nitric Oxide Levels and Compositions Useful Therefor:US Pat.5847004[P],1998.
[2] Hidaka S,Funakoshi T,Shimada H, et al . Comparative Effects of Diethyldithiocarbamate and n -Benzyl- D -Glucamine Dithiocarbamate on cis -Diamminedichloroplatinum-Induced Toxicity in Kidney and Gastrointestinal Tract in Rats[J]. J Appl Toxicol ,1995,15(4):267-273.
[3] Tandon S K,Singh S,Jain V K, et al . Chelation in Metal Intoxication XXXⅧ:Effect of Structurally Different Chelating Agents in Treatment of Nickel Intoxication in Rat [J]. Fundam Appl Toxicol ,1996,31(2):141-148.
[4] Imamura H,Ohtake N,Jona,H, et al . Structure-activity Relationships of trans -3,5-Disubstituted Pyrrolidinylthio-1 β -methylcarbapenems.Part 1:J-111,347 and Related Compounds[J]. Bioorg Med Chem Lett ,2000,10(2):109-113.
[5] Len C,Boulognemerlo A S,Posted D J. Synthesis and Antifungal Activity of Novel Bis(dithiocarbamate) Derivatives of Glycerol[J]. J Agric Food Chem ,1996,44(9):2856-2858.
[6] Menezes D C,Vieira F T,de Lima G M, et al . Tin(Ⅳ) Complexes of Pyrrolidinedithiocarbamate:Synthesis, Characterisation and Antifungal Activity[J]. Eur J Med Chem ,2005,40(12):1277-1282.
[7] Schreck R,Meier B,Mannel D N, et al . Dithiocarbamates as Potent Inhibitors of Nuclear Factor Kappa B Activation in Intact Cells[J]. J Exp Med ,1992,175:1181-1194.
[8] Ha T,Li Y,Gao X, et al . Attenuation of Cardiac Hypertrophy by Inhibiting both mTOR and NFκB Activation in vivo [J]. Free Radic Biol Med ,2005,39(12):1570-1580.
[9] Mehta G R,Liu J,Constantinou A, et al . Cancer Chemopreventive Activity of Brassinin, a Phytoalexin from Cabbage[J]. Carcinogenesis ,1995,16(2):399-404.
[10] Robert M M,Rajesh N,Jerome K, et al . Cancer Chemopreventive Activity of Sulforamate Derivatives[J]. Eur J Med Chem ,2006,41(1):121-124.
[11] Pedras M S,Loukaci A,Okanga F I. The Cruciferous Phytoalexins Brassinin and Cyclobrassinin are Intermediates in the Biosynthesis of Brassilexin[J]. Bioorg Med Chem Lett ,1998,8(21):3037-3038.
[12] Gaspari P,Banerjee T,Malachowski W P, et al . Structure-Activity Study of Brassinin Derivatives as Indoleamine 2,3-Dioxygenase Inhibitors[J]. J Med Chem ,2006,49(2):684-692.
[13] Péter C,István Z,Borbála R, et al . Isobrassinin and Its Analogues:Novel Types of Antiproliferative Agents[J]. Bioorg Med Chem Lett ,2006,16(24):6273-6276.
[14] Zhang Y,Kensler T W,Cho C G, et al . Anticarcinogenic Activities of Sulforaphane and Structurally Related Synthetic Norbornyl Isothiocyanates[J]. Proc Natl Acad Sci USA ,1994,91(8):3147-3150.
[15] Gerhäuser C,You M,Liu J F, et al . Cancer Chemopreventive Potential of Sulforamate, a Novel Analogue of Sulforaphane That Induces Phase 2 Drug-metabolizing Enzymes[J]. Cancer Res ,1997,57(2):272-278.
[16] WEI Jun,CHENG Tieming,LI Runtao. Improved Synthesis of Sulforamate, a Cancer-chemopreventive Compound[J]. Chinese J Med Chem ,2002,47(12):159-160(in Chinese). 卫军,程铁明,李润涛. 化学防癌化合物sulforamate的合成改进[J]. 中国药物化学杂志,2002,47(12):159-160.
[17] Kosmeder II J W,Hirschelman W H,Song L S, et al . Cancer Chemopreventive Activity of Oxomate:A Monfunctional Inducer of Phase Ⅱ Detoxification Enzymes[C]. 224th ACS National Meeting: Division of Medicinal Chemistry,2002:98.
[18] Hirschelman W H,Kosmeder II J W,Song L S, et al . Design and Lead Optimization of Oxomate:A Novel Phase II Enzyme Inducer[C]. 224th ACS National Meeting:Division of Medicinal Chemistry,2002:178.
[19] Hirschelman W H,Li Y M,van Breemen R B, et al . Synthesis of Oxomate Metabolites: Potential Chemopreventive Agents[C]. 225th ACS National Meeting:Division of Medicinal Chemistry,2003:86.
[20] Chen D,Dou Q P. New Uses for Old Copper-binding Drugs:Converting the Pro-angiogenic Copper to a Specific Cancer Cell Death Inducer[J]. Expert Opin Ther Targets ,2008,12(6):739-748.
[21] Chen D,Cui Q C,Yang H J, et al . Disulfiram, a Clinically Used Anti-Alcoholism Drug and Copper-Binding Agent, Induces Apoptotic Cell Death in Breast Cancer Cultures and Xenografts via Inhibition of the Proteasome Activity[J]. Cancer Res ,2006,66(21):10425-10433.
[22] Pang H,Chen D,Cui Q C, et al . Sodium Diethyldithiocarbamate, an Aids Progression Inhibitor and a Copper-Binding Compound, Has Proteasome-Inhibitory and Apoptosis-Inducing Activities in Cancer Cells[J]. Int J Mol Med ,2007,19(5):809-816.
[23] Ziegler-Heitbrock H W,Sternsdorf T,Liese J, et al . Pyrrolidine Dithiocarbamate Inhibits Nf-Kappa B Mobilization and Tnf Production in Human Monocytes[J]. J Immunol ,1993,151(12):6986-6993.
[24] Cen D,Brayton D,Shahandeh B, et al . Disulfiram Facilitates Intracellular Cu Uptake and Induces Apoptosis in Human Melanoma Cells[J]. J Med Chem ,2004,47(27):6914-6920.
[25] Verhaegen S,McGowan A J,Brophy A R, et al . Inhibition of Apoptosis by Antioxidants in the Human Hl-60 Leukemia Cell Line[J]. Biochem Pharmacol ,1995,50(7):1021-1029.
[26] Cao S L,Feng Y P,Jiang Y Y, et al . Synthesis and in Vitro Antitumor Activity of 4(3 H )-Quinazolinone Derivatives with Dithiocarbamate Side Chains[J]. Bioorg Med Chem Lett ,2005,15(7):1915-1917.
[27] Cao S L,Feng Y P,Zheng X L, et al . Synthesis of Substituted-benzylamino- and Heterocyclylmethylamino-carbodithioate Derivatives of 4(3 H )-Quinazolinone and Their Cytotoxic Activity[J]. Arch Pharm ,2006,339(5):250-254.
[28] Cao S L,Wang Y,Zhu L, et al . Synthesis and Cytotoxic Activity of N -((2-Methyl-4(3 H )-quinazolinon-6-yl) methyl) dithiocarbamates[J]. Eur J Med Chem ,2010,45(9):3850-3857.
[29] Cao S L,Han Y,Yuan C Z, et al . Synthesis and Antiproliferative Activity of 4-Substituted- Piperazine-1-Carbodithioate Derivatives of 2,4-Diaminoquinazoline[J]. Eur J Med Chem ,2013,64:401-409.
[30] Guo B B,Ge Z M,Cheng T M, et al . Synthesis and Anti-Tumor Activities of 1,4-Bis [3-(Amino-Dithiocarboxy) Propionyl] Piperazine Derivatives[J]. Acta Pharmaceutica Sinica ,2001,36(3):185-187.
[31] Li R T,Cheng T M,Cui J R. Study on the Synthesis and Anticancer Activity of Dithiocarbamate:US Pat.1328999[P],2002.
[32] JIANG Xiaomei,LING Xiaomei,LI Runtao, et al . Analysis of Hydrochloride 4-Methyl-piperazine-1-carbodithioc Acid 3-Cyano-3,3-diphenyl-propyl Ester and Its Metabolites in Rats by HPLC-ESI/ITMSn[J]. Acta Pharmaceut Sin ,2006,41(11):1084-1089(in Chinese). 姜小梅,凌笑梅,李润涛,等. HPLC-ESI/ITMS n 法分析大鼠体内4-甲基哌嗪-1-二硫代甲酸-(3-氰基-3,3-二苯基)丙酯盐酸盐及其主要代谢物[J]. 药学学报,2006,41(11):1084-1089.
[33] Zhang N,Guo W,Wang L, et al . Effect of TM208 on QGY-7703 Xenograft Tumor Growth[J]. Anticancer Drugs ,2008,19(6):593-598.
[34] Hou X L,Ge Z M,Wang T M, et al . Dithiocarbamic Acid Esters as Anticancer Agent.Part 1:4-Substituted-Piperazine-1-Carbodithioic Acid 3-Cyano-3,3-Diphenyl-Propyl Esters[J]. Bioorg Med Chem Lett ,2006,16(16):4214-4219.
[35] Ning M R,Li Liang,Li J. In Vitro Screening of Reversible and Time-Dependent Inhibition on Cyp3a by Tm208 and Tm209 in Rat Liver Microsomes[J]. Acta Pharmaceut Sin B ,2012,2(2):181-187.
[36] Kong D T,Ling,X M,Han F B, et al . Identification of the Metabolite and Cytochrome P450 Isoforms Involved in Rat Liver Microsomal Metabolism of TM208[J]. J Chin Pharm Sci ,2008,17:30-34.
[37] Zahrana M A H,Salemb T A R,Samaka R M, et al . Design, Synthesis and Antitumor Evaluation of Novel Thalidomide Dithiocarbamate and Dithioate Analogs against Ehrlich Ascites Carcinoma-Induced Solid Tumor in Swiss Albino Mice[J]. Bioorg Med Chem ,2008,16(22):9708-9718.
[38] Qian Y,Ma G Y,Yang Y, et al . Synthesis, Molecular Modeling and Biological Evaluation of Dithiocarbamates as Novel Antitubulin Agents[J]. Bioorg Med Chem ,2010,18(12):4310-4316.
[39] Huang W,Ding Y,Miao Y, et al . Synthesis and Antitumor Activity of Novel Dithiocarbamate Substituted Chromones[J]. Eur J Med Chem ,2009,44(9):3687-3696.
[40] Bacharaju K,Jambula S R,Sivan S, et al . Design, Synthesis, Molecular Docking and Biological Evaluation of New Dithiocarbamates Substituted Benzimidazole and Chalcones as Possible Chemotherapeutic Agents[J]. Bioorg Med Chem Lett ,2012,22(9):3274-3277.
[41] Wang X J,Xu H W,Guo L L, et al . Synthesis and in Vitro Antitumor Activity of New Butenolide-Containing Dithiocarbamates[J]. Bioorg Med Chem Lett ,2011,21(10):3074-3077.
[42] Wang X J,Xu H W,Guo L L, et al . Synthesis of Various Substituted Spiro- and Bicyclethiazolidine-2-Thiones by a Multicomponent Reaction and Biological Evaluation in Vitro [J]. Heterocycles ,2011,83(5):1005-1012.
[43] Duan Y,Ma Y,Zhang E, et al . Design and Synthesis of Novel 1,2,3-Triazole-Dithiocarbamate Hybrids as Potential Anticancer Agents[J]. Eur J Med Chem ,2013,62:11-19.
[44] Duan Y,ZhengY,Li X, et al . Design, Synthesis and Antiproliferative Activity Studies of Novel 1,2,3-Triazole Dithiocarbamate-Urea Hybrids[J]. Eur J Med Chem ,2013,64:99-110.
[45] Zheng Y C,Duan Y C,Ma J L, et al . Triazole-Dithiocarbamate Based Selective Lysine Specific Demethylase 1(Lsd1) Inactivators Inhibit Gastric Cancer Cell Growth, Invasion, and Migration[J]. J Med Chem ,2013,56(21):8543-8560.
[46] Ye X W,Zheng Y C,Duan Y C, et al . Synthesis and Biological Evaluation of Coumarin-1,2,3-Triazole Dithiocarbamate Hybrids as Potent Lsd1 Inhibitors[J]. Med Chem Comm ,2014,5(5):650-654.
[47] Ohtake N,Imamura H,Kiyonaga H, et al . Novel Dithiocarbamate Carbapenems1 with Anti-MRSA Activity[J]. Bioorg Med Chem Lett ,1997,7(13):1617-1622.
[48] Ren J L,Zhang E,Ye X W, et al . Design, Synthesis and Antibacterial Evaluation of Novel AHL Analogues[J]. Bioorg Med Chem Lett ,2013,23(14):4154-4156.
[49] Zou Y,Yu S,Li R, et al . Synthesis, Antifungal Activities and Molecular Docking Studies of Novel 2-(2,4-Difluorophenyl)-2-Hydroxy-3-(1 H -1,2,4-triazol-1-yl) Propyl Dithiocarbamates[J]. Eur J Med Chem ,2014,74:366-374.
[50] Horita Y,Takii T,Chiba T, et al . Synthesis of New Sugar Derivatives and Evaluation of Their Antibacterial Activities Against Mycobacterium Tuberculosis[J]. Bioorg Med Chem Lett ,2009,19(22):6313-6316.
[51] Güzel O,Salman A. Synthesis, Antimycobacterial and Antitumor Activities of New (1,1-Dioxido-3-Oxo-1,2-Benzisothiazol-2(3 H )-Yl)Methyl N , N -Disubstituted Dithiocarbamate/ O -Alkyldithiocarbonate Derivatives[J]. Bioorg Med Chem ,2006,14(23):7804-7815.
[52] Giglio J,Fern ndez S,Rey A, et al . Synthesis and Biological Characterisation of Novel Dithiocarbamate Containing 5-Nitroimidazole 99mTc-Complexes as Potential Agents for Targeting Hypoxia[J]. Bioorg Med Chem Lett ,2011,21(1):394-397.

Research Progress in the Bioactivities of the Dithiocarbamates

RichHTML

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 1

Recommended Articles

Metrics

Comments