147091-08-5Relevant articles and documents
New mild and simple approach to isothiocyanates: A class of potent anticancer agents
Luo, Bingling,Wang, Jiankang,Li, Xiaobing,Lu, Wenhua,Yang, Jing,Hu, Yumin,Huang, Peng,Wen, Shijun
, (2017)
In our current work, acetyl chloride-mediated synthesis of phenethyl isothiocyanate (PEITC) derivatives proves to be convenient and provides the expected products at good to excellent yields. Biological evaluation and structure-activity relationship analysis found that the novel compound 7 showed the best anticancer activity against human cancer cell line Panc1 and HGC27 compared with PEITC. Compounds 6 and 7 induced more apoptosis in pancreatic cancer cells but less toxicity in non-cancer cells. Further biological study demonstrated that 7 substantially increased intracellular reactive oxygen species (ROS) and depleted glutathione (GSH), leading to an oxidative stress to kill cancer cell.
Thiourea-based non-nucleoside inhibitors of HIV reverse transcriptase as bifunctional organocatalysts in the asymmetric Strecker synthesis
Tsogoeva, Svetlana B.,Hateley, Martin J.,Yalalov, Denis A.,Meindl, Kathrin,Weckbecker, Christoph,Huthmacher, Klaus
, p. 5680 - 5685 (2005)
The potential of novel and known pyridyl thiourea derivatives (non-nucleoside inhibitors (NNI) of HIV reverse transcriptase) as bifunctional organic catalysts in the asymmetric Strecker synthesis was investigated. It was shown that incorporation of the im
A more sustainable isothiocyanate synthesis by amine catalyzed sulfurization of isocyanides with elemental sulfur
Nickisch,Conen,Gabrielsen,Meier
, p. 3134 - 3142 (2021/01/28)
Isothiocyanates (ITCs) are typically prepared using amines and highly toxic reagents such as thiophosgene, its derivatives, or CS2. In this work, an investigation of a multicomponent reaction (MCR) using isocyanides, elemental sulfur and amines revealed that isocyanides can be converted to isothiocyanates using sulfur and catalytic amounts of amine bases, especially DBU (down to 2 mol%). This new catalytic reaction was optimized in terms of sustainability, especially considering benign solvents such as Cyrene or γ-butyrolactone (GBL) under moderate heating (40 °C). Purification by column chromatography was further optimized to generate less waste by maintaining high purity of the product. Thus, E-factors as low as 0.989 were achieved and the versatility of this straightforward procedure was shown by converting 20 different isocyanides under catalytic conditions, while obtaining moderate to high yields (34-95%). This journal is
Synthesis of isothiocyanates using DMT/NMM/TsO? as a new desulfurization reagent
Janczewski, ?ukasz,Kolesińska, Beata,Kr?giel, Dorota
, (2021/05/29)
Thirty-three alkyl and aryl isothiocyanates, as well as isothiocyanate derivatives from esters of coded amino acids and from esters of unnatural amino acids (6-aminocaproic, 4-(aminomethyl)benzoic, and tranexamic acids), were synthesized with satisfactory or very good yields (25–97%). Synthesis was performed in a “one-pot”, two-step procedure, in the presence of organic base (Et3 N, DBU or NMM), and carbon disulfide via dithiocarbamates, with 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium toluene-4-sulfonate (DMT/NMM/TsO? ) as a desulfurization reagent. For the synthesis of aliphatic and aromatic isothiocyanates, reactions were carried out in a microwave reactor, and selected alkyl isothiocyanates were also synthesized in aqueous medium with high yields (72–96%). Isothiocyanate derivatives of L-and D-amino acid methyl esters were synthesized, under conditions without microwave radiation assistance, with low racemization (er 99 > 1), and their absolute configuration was confirmed by circular dichroism. Isothiocyanate derivatives of natural and unnatural amino acids were evaluated for antibacterial activity on E. coli and S. aureus bacterial strains, where the most active was ITC 9e.
Synthesis, biological activity and in silico pharmacokinetic prediction of a new 2-thioxo-imidazoldidin-4-one of primaquine
Pereira, Mariana,Caljon, Guy,Gouveia, Maria Jo?o,Maes, Louis,Vale, Nuno
, p. 1 - 11 (2021/03/16)
The discovery of novel antiparasitic drugs for neglected tropical diseases (NTDs) constitutes a global urgency and requires a range of innovative strategies to ensure a sustainable pipeline of lead compounds. Thus far, primaquine (PQ) is the only transmis
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.
Na2S2O8-mediated efficient synthesis of isothiocyanates from primary amines in water
Fu, Zhicheng,Yuan, Wenhao,Chen, Ning,Yang, Zhanhui,Xu, Jiaxi
supporting information, p. 4484 - 4491 (2018/10/17)
We have developed two green, practical, and efficient procedures, including a one-pot one, to synthesize isothiocyanates from amines and carbon disulfide via desulfurization with sodium persulfate. Water is used as the solvent. Basic conditions are necessary for good chemoselectivity for isothiocyanates. Structurally diverse linear and branched alkyl amines and aryl amines are readily converted to isothiocyanates by the two procedures in satisfactory yields. Halogens, benzylic C-H bonds, methylthio, nitro, ester, alkenyl, electron-rich or -deficient (hetero)aryls, acetylenyl, and even phenolic and alcoholic hydroxyls are well tolerated. The one-pot procedure in water can also be used to realize the preparation of chiral isothiocyanates from chiral amines, and the modification of bioactive structures with free amino groups. In large-scale preparation, simple and practical purification procedures independent of column chromatography are developed.
T3P - A Benign Desulfurating Reagent in the Synthesis of Isothiocyanates
Janczewski, ?ukasz,Gajda, Anna,Frankowski, Sebastian,Goszczyński, Tomasz M.,Gajda, Tadeusz
, p. 1141 - 1151 (2017/12/06)
A number of alkyl, aryl and bifunctional isothiocyanates are obtained in moderate to high yields (41-94%) in a two-step, one-pot reaction of the parent primary amines or their salts with carbon disulfide, followed by reaction of the thus formed dithiocarbamates with T3P (propane phosphonic acid anhydride) as a new and efficient desulfurating agent.
Chiral recognition of carboxylates by a static library of thiourea receptors with amino acid arms
Ulatowski, Filip,Jurczak, Janusz
, p. 4235 - 4243 (2015/05/13)
Chiral recognition is based on a large network of very subtle interactions whose outcome is difficult to predict. A combinatorial approach is therefore the most suitable to search for the most efficient receptor and obtain a structure-enantioselectivity correlation. We synthesized a set of 12 receptors constructed with 1,9-diaminoantracene and α-amino acid esters, linked via thiourea groups. The association constants and enantioselectivities for the complexes with mandelate and N-acetylphenylalanine were determined by competitive NMR titrations. Association constants quite regularly depend on the substituents in the receptor structure, but the distribution of enantioselectivities across the library could not easily be rationalized.
A facile one-pot synthesis of selenoureidopeptides employing lialhseh through staudinger aza-wittig-type reaction
Sharanabai, Kupendra M.,Prabhu, Girish,Panduranga, Veladi,Sureshbabu, Vommina V.
, p. 801 - 806 (2015/03/14)
A one-pot protocol for the synthesis of selenoureidopeptides employing lithium aluminum hydride hydroselenide (LiAlHSeH) as a selenating agent via a Staudinger aza-Wittig-type reaction is reported. The protocol involves the use of Nα-protected aminoalkyl azides and isothicyanato esters to afford the desired products in good yields. This protocol is a direct approach to the synthesis of selenourea compounds that avoids the synthesis of isoselenocyanates and does not require multistep synthesis.
