Efficient, straightforward, catalyst-free synthesis of medicinally important S-alkyl/benzyl dithiocarbamates under green conditions

被引:18
作者
Asadipour, Ali [1 ,2 ]
Shams, Zeynab [1 ,2 ]
Eskandari, Khalil [1 ,2 ]
Moshafi, Mohammad-Hassan [3 ]
Faghih-Mirzaei, Ehsan [1 ,2 ]
Pourshojaei, Yaghoub [1 ,2 ,4 ]
机构
[1] Kerman Univ Med Sci, Fac Pharm, Dept Med Chem, Kerman, Iran
[2] Kerman Univ Med Sci, Pharmaceut Res Ctr, Kerman, Iran
[3] Kerman Univ Med Sci, Sch Pharm, Dept Pharmaceut Sci, Kerman, Iran
[4] Kerman Univ Med Sci, Inst Neuropharmacol, Neurosci Res Ctr, Kerman, Iran
关键词
Dithiocarbamate; Alkyl halide; Amine; Catalyst-free; Ethanol-aqueous medium; ONE-POT SYNTHESIS; AMINE SIDE-CHAIN; ANTICHOLINESTERASE ACTIVITY; BENZYLBARBITUROCOUMARIN DERIVATIVES; CARBAMATE DERIVATIVES; CARBON-DISULFIDE; DESIGN; DECOMPOSITION; INHIBITORS; COMPLEXES;
D O I
10.1007/s11164-017-3167-1
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Green synthesis of some novel dithiocarbamate derivatives substituted by aliphatic and aromatic groups as potentially interesting, medicinally important organic compounds via efficient one-pot, catalyst-free reaction is described. In this reaction, dithiocarbamate derivatives are obtained from condensation reaction between primary or secondary amines, carbon disulfide, and alkyl or benzyl halides in one pot and ethanol-aqueous medium. Among aliphatic and aromatic amines, the results generally show that reaction of aliphatic amines with alkyl or benzyl halides led to desired products in highest yields. Also, among aliphatic amines, those which reacted with benzyl halides showed better yields than those that reacted with alkyl halides. Use of environmentally benign solvents is one of the advantages of this procedure. Also, obtaining products in good yield via catalyst-free reaction using a facile, inexpensive, and practical approach can be considered other advantages of this procedure. Target products are very important compounds, because their analogs have been applied in pharmaceutical, chemical, and rubber industries.
引用
收藏
页码:1295 / 1304
页数:10
相关论文
共 46 条
[1]   Ruthenium catalysed one-pot synthesis of S-allyl and cinnamyl dithiocarbamates using allyl and cinnamyl acetates in water [J].
Ahammed, Sabir ;
Saha, Amit ;
Ranu, Brindaban C. .
RSC ADVANCES, 2012, 2 (15) :6329-6335
[2]  
[Anonymous], 1981, SYNTHESIS
[3]   A highly efficient synthesis of dithiocarbamates in green reaction media [J].
Azizi, Najmadin ;
Gholibeglo, Elham .
RSC ADVANCES, 2012, 2 (19) :7413-7416
[4]   Cyclic ammonium salts of dithiocarbamic acid: stable alternative reagents for the synthesis of S-alkyl carbodithioates from organyl thiocyanates in water [J].
Biswas, Kinkar ;
Ghosh, Sujit ;
Ghosh, Pranab ;
Basu, Basudeb .
JOURNAL OF SULFUR CHEMISTRY, 2016, 37 (04) :361-376
[5]   Facile synthesis of aliphatic isothiocyanates and thioureas on solid phase using peptide coupling reagents [J].
Boas, U ;
Gertz, H ;
Christensen, JB ;
Heegaard, PMH .
TETRAHEDRON LETTERS, 2004, 45 (02) :269-272
[6]   Biological in Vitro and in Vivo Studies of a Series of New Asymmetrical Cationic [99mTc(N)(DTC-Ln)(PNP)]+ Complex (DTC-Ln = Alicyclic Dithiocarbamate and PNP = Diphosphinoamine) [J].
Bolzati, Cristina ;
Cavazza-Ceccato, Mario ;
Agostini, Stefania ;
Refosco, Fiorenzo ;
Yamamichi, Yoshihiro ;
Tokunaga, Shinji ;
Carta, Davide ;
Salvarese, Nicola ;
Bernardini, Daniele ;
Bandoli, Giuliano .
BIOCONJUGATE CHEMISTRY, 2010, 21 (05) :928-939
[7]   Exploring the Structural Requirements for Inhibition of the Ubiquitin E3 Ligase Breast Cancer Associated Protein 2 (BCA2) as a Treatment for Breast Cancer [J].
Brahemi, Ghali ;
Kona, Fathima R. ;
Fiasella, Annalisa ;
Buac, Daniela ;
Soukupova, Jitka ;
Brancale, Andrea ;
Burger, Angelika M. ;
Westwell, Andrew D. .
JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (07) :2757-2765
[8]   Synthesis and antiproliferative activity of 4-substituted-piperazine-1-carbodithioate derivatives of 2,4-diaminoquinazoline [J].
Cao, Sheng-Li ;
Han, Ying ;
Yuan, Chong-Zhen ;
Wang, Yao ;
Xiahou, Zhi-Kai ;
Liao, Ji ;
Gao, Rui-Ting ;
Mao, Bei-Bei ;
Zhao, Bao-Li ;
Li, Zhong-Feng ;
Xu, Xingzhi .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 64 :401-409
[9]   Synthesis and in vitro antitumor activity of 4(3H)-quinazolinone derivatives with dithiocarbamate side chains [J].
Cao, SL ;
Feng, YP ;
Jiang, YY ;
Liu, SY ;
Ding, GY ;
Li, RT .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (07) :1915-1917
[10]   Dithiocarbamates Strongly Inhibit Carbonic Anhydrases and Show Antiglaucoma Action in Vivo [J].
Carta, Fabrizio ;
Aggarwal, Mayank ;
Maresca, Alfonso ;
Scozzafava, Andrea ;
McKenna, Robert ;
Masin, Emanuela ;
Supuran, Claudiu T. .
JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (04) :1721-1730