15867-06-8Relevant academic research and scientific papers
One-pot three-component route for the synthesis of S-trifluoromethyl dithiocarbamates using Togni's reagent
Halimehjani, Azim Ziyaei,Dra?ínsky, Martin,Beier, Petr
, p. 2502 - 2508 (2017)
A one-pot three-component route for the synthesis of S-trifluoromethyl dithiocarbamates by the reaction of secondary amines, carbon disulfide and Togni's reagent is described. The reactions proceed in moderate to good yields. A similar reaction using a primary aliphatic amine afforded the corresponding isothiocyanate in high yield. A variable temperature NMR study revealed a rotational barrier of 14.6, 18.8, and 15.9 kcal/mol for the C-N bond in the dithiocarbamate moiety of piperidine, pyrrolidine, and diethylamine adducts, respectively. In addition, the calculated barriers of rotation are in reasonable agreement with the experiments.
Synthesis, in-vitro antiprotozoal activity and molecular docking study of isothiocyanate derivatives
Al-Harrasi, Ahmed,Babanezhad Harikandei, Kosar,Bararjanian, Morteza,Ebrahimi, Samad Nejad,Kaiser, Marcel,Salehi, Peyman
, (2019/12/09)
Novel isothiocyanate derivatives were synthesized starting from noscapine, bile acids, amino acids, and some aromatic compounds. Antiparasitic activities of the synthesized derivatives were tested against four unicellular protozoa, i.e., Trypanosoma brucei rhodesiense, T. cruzi, Leishmania donovani, and Plasmodium falciparum. Interestingly, seven isothiocyanate analogues displayed promising antiparasitic activity against Leishmania donovani with IC50 values between 0.4 and 1.0 μM and selectivity index (SI) ranged from 7.8 to 18.4, comparable to the standard drug miltefosine (IC50 = 0.7 μM). Compound 7h demonstrated the best antileishmanial activity with an IC50 value of 0.4 μM. Seven products exhibited inhibition activity against T. brucei rhodesiense with IC50s below 2.0 μM and SI between 2.7 and 29.3. Four primary amine derivatives of noscapine and five isothiocyanate derivatives exhibited antiplasmodial activity with IC50s in the range of 1.1–2.7 μM and SI values between 1.1 and 14.5. The isothiocyanate derivative 7c showed against T. cruzi with an IC50 value of 1.9 μM and SI 4. Molecular docking and ADMET studies were performed to investigate the interaction between active ligands and T. brucei trypanothione reductase active site. The docking studies showed significant binding affinity of noscapine derivatives to enzyme active site and good compatibility with experimental data.
Synthesis of novel dithiocarbamates and xanthates using dialkyl azodicarboxylates: S–N bond formation
Ziyaei Halimehjani, Azim,Klepetá?ová, Blanka,Beier, Petr
, p. 1850 - 1858 (2018/03/06)
A one?pot three?component route for the synthesis of a novel category of dithiocarbamates or xanthates is developed by a reaction of in-situ generated dithiocarbamic acids or xanthates with dialkyl azodicarboxylates under mild and catalyst-free conditions. The reaction is characterized by a wide scope, high efficiency and straightforward isolation protocol. The synthetic utility of the dithiocarbamates and xanthates was demonstrated on the preparation of symmetrical and unsymmetrical thioureas, isothiocyanates, and thiocarbamates.
Cobalt mediated by desulfurization toward the synthesis of isothiocyanates
Seelam, Mohan,Shaik, Bajivali,Kammela, Prasada Rao
supporting information, p. 1759 - 1765 (2016/10/31)
A highly efficient and simple protocol for the construction of aromatic and aliphatic isothiocyanates from their respective amines in the presence of cheap, readily available, and air-stable cobalt catalyst is described. All reactions were carried out under optimized reaction conditions and gave target products in good to excellent yields within shorter reaction time.
Application of the β-cyclodextrin supramolecules as a green accelerator hosts in one-step preparation of highly functionalised rhodanine scaffolds
Rostamnia, Sadegh,Doustkhah, Esmail,Hassankhani, Asadollah
, p. 1 - 3 (2015/08/18)
β-Cyclodextrin (β-CD) supramolecule was found to be a convenient, green and economical tool in one-pot synthesis of rhodanine scaffolds as a highly efficient mediating agent in aqueous media in which the reaction accelerated to complete in 15 min and room
Synthesis, antifungal activities and molecular docking studies of novel 2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl dithiocarbamates
Zou, Yan,Yu, Shichong,Li, Renwu,Zhao, Qingjie,Li, Xiang,Wu, Maocheng,Huang, Ting,Chai, Xiaoxun,Hu, Honggang,Wu, Qiuye
, p. 366 - 374 (2014/02/14)
A series of 2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl) propyl dithiocarbamates as new analogs of fluconazole were synthesized and their antifungal activities were evaluated. Among these compounds, 2a-f and 3a-q exhibited higher activities than fluconazole against nearly all fungi tested except Aspergillus fumigatus. Noticeably, the in vitro biological activities of 2b, 3a, 3c, 3h-k, and 3o-q against Candida species were much better than those of fluconazole and ketoconazole. Also, 2a-d, 3a-d, 3e-f, 3h-k, 3p and 3q showed higher activities against A. fumi than fluconazole. Computational docking experiments indicated that the inhibition of CYP51 involved a coordination bond with iron of the heme group, the hydrophilic H-bonding region, the hydrophobic region, and the narrow hydrophobic cleft.
Efficient one-pot synthesis of alkyl 3-(alkyl)-4-methyl-2-thioxo-2,3- dihydrothiazole-5-carboxylates in a multi component reaction
Iravani, Nasir,Albadi, Jalal,Varnaseri, Somaieh,Jaberi, Zahra,Karami, Nahid,Khadamati, Marzieh
, p. 1567 - 1570 (2013/03/28)
A simple and efficient one-pot synthesis of alkyl 2-(alkyl)-4-methyl-2- thioxo-2,3-dihydrothiazole-5-carboxylates from the reaction of primary alkylamines and carbon disulfide in the presence of 2-chloro-1,3-dicarbonyl compounds is described. This new pro
A novel, one-pot four-component route to 2′-thioxo-2′,3′- dihydrospiro[indole-3,6′-[1,3]thiazin]-2-one derivatives
Alizadeh, Abdolali,Mokhtari, Javad
experimental part, p. 1315 - 1319 (2011/09/14)
An efficient route to 2′,3′-dihydro-2′- thioxospiro[indole-3,6′-[1,3]thiazin]-2(1H)-one derivatives is described. It involves the reaction of isatine, 1-phenyl-2-(1,1,1-triphenyl- λ5-phosphanylidene)ethan-1-one, and different amines in the presence of CS2 in dry MeOH at reflux (Scheme 1). The alkyl carbamodithioate, which results from the addition of the amine to CS 2, is added to the α,β-unsaturated ketone, resulting from the reaction between 1-phenyl-2-(1,1,1-triphenyl-λ5- phosphanylidene)ethan-1-one and isatine, to produce the 3′-alkyl-2′, 3′-dihydro-4′-phenyl-2′-thioxospiro[indole-3,6′-[1,3] thiazin]-2(1H)-one derivatives in excellent yields (Scheme 2). Their structures were corroborated spectroscopically (IR, 1H- and 13C-NMR, and EI-MS) and by elemental analyses. Copyright
