- Synthesis, characterization and antimicrobial activity of copper(II) complexes with some S-alkyl derivatives of thiosalicylic acid. Crystal structure of the binuclear copper(II) complex with S-methyl derivative of thiosalicylic acid
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The five new copper(II) complexes with some S-alkyl derivatives of thiosalicylic acid (alkyl = benzyl (L1), methyl (L2), ethyl (L3), propyl (L4), butyl (L5)) have been synthesized and characterized by microanalysis and infrared spectra. The spectroscopica
- Nikoli?, Milo? V.,Mijajlovi?, Marina ?.,Jevti?, Verica V.,Ratkovi?, Zoran R.,Radojevi?, Ivana D.,?omi?, Ljiljana R.,Novakovi?, Sladjana B.,Bogdanovi?, Goran A.,Trifunovi?, Sre?ko R.,Radi?, Gordana P.
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- Cytotoxicity of copper(II)-complexes with some S-alkyl derivatives of thiosalicylic acid. Crystal structure of the binuclear copper(II)-complex with S-ethyl derivative of thiosalicylic acid
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The spectroscopically predicted structure of the obtained copper(II)-complex with S-ethyl derivative of thiosalicylic acid was confirmed by X-ray structural study and compared to previously reported crystal structure of the Cu complex with S-methyl deriva
- Nikoli?, Milo? V.,Mijajlovi?, Marina ?.,Jevti?, Verica V.,Ratkovi?, Zoran R.,Novakovi?, Sladjana B.,Bogdanovi?, Goran A.,Milovanovi?, Jelena,Arsenijevi?, Aleksandar,Stojanovi?, Bojana,Trifunovi?, Sre?ko R.,Radi?, Gordana P.
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- DNA binding and antitumor activities of platinum(IV) and zinc(II) complexes with some S-alkyl derivatives of thiosalicylic acid
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A series of complexes of platinum(IV) (C1–C5) and zinc(II) (C6–C10) with S-alkyl derivatives of thiosalicylic acid were prepared and characterized. The interactions of the complexes with calf thymus DNA were analyzed by absorption (UV–Vis) and emission spectral studies (ethidium bromide displacement studies). The cytotoxic activities of complexes C1–C10 were determined against mouse B cell lymphocytic leukemia cells (BCL1), human B-prolymphocytic leukemia (JVM-13), mouse mammary carcinoma cells (4T1), and human mammary carcinoma cells (MDA-MB-468) and compared to the activities of the free ligand precursors and cisplatin. The cytotoxicities of the platinum(IV) and zinc(II) complexes toward mouse tumor cell lines were higher compared with their effects on human tumor cell lines. The zinc(II) complex C9 showed the highest antitumor activity toward the tested human cell lines, while the platinum(IV) complex C4 exhibited the highest antitumor activity toward mouse BCL1 and 4T1 cells. Both C4 and C9 have ligands derived from S-propyl thiosalicylic acid.
- Besser Silconi, Zana,Benazic, Sasa,Milovanovic, Jelena,Jurisevic, Milena,Djordjevic, Dragana,Nikolic, Milos,Mijajlovic, Marina,Ratkovic, Zoran,Radi?, Gordana,Radisavljevic, Snezana,Petrovic, Biljana,Radosavljevic, Gordana,Milovanovic, Marija,Arsenijevic, Nebojsa
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- Sequential C-H activation enabled expedient delivery of polyfunctional arenes
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Modular construction of polyfunctional arenes from abundant feedstocks stands as an unremitting pursue in synthetic chemistry, accelerating the discovery of drugs and materials. Herein, using the multiple C-H activation strategy with versatile imidate esters, the expedient delivery of molecular libraries of densely functionalized sulfur-containing arenes was achieved, which enabled the concise construction of biologically active molecules, such as Bipenamol.
- Cai, Xiaoqing,Chen, Qian,Chen, Xiaojian,Gao, Yang,Huo, Yanping,Li, Xianwei,Ouyang, Wensen,Rao, Jianhang,Wang, Jie
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p. 8075 - 8078
(2021/08/20)
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- METHOD FOR SYNTHESIZING THIOAURONES
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An embodiment of the present invention is a process for producing 2 - benzoic acid compound by reacting a thiosalicylic acid with a strongly basic substance and a benzylhalide. The 2 - methoxy - N N-methyl -2 - benzamides, which are reacted with N - methoxy - N N-methylcarbamoyl chloride to produce N - methoxy-N-methylbenzamides. The N - methoxy - N N-methyl -2 - (benzocyclohexyl) benzamide is treated with arylethynyl salt to prepare 1 - (2- benzocyclohexyl) phenyl -3 - phenyl -2 - profin -1 . The 1 - (2-) phenyl -3 - phenyl -2 - profin -1 - one is treated with an acid material. Provided is a method for preparing a thiouronone compound.
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Paragraph 0146; 0148-0149
(2021/02/12)
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- Design, synthesis and biological activity of selective hCAs inhibitors based on 2-(benzylsulfinyl)benzoic acid scaffold
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A large library of derivatives based on the scaffold of 2-(benzylsulfinyl)benzoic acid were synthesised and tested as atypical inhibitors against four different isoforms of human carbonic anhydrase (hCA I, II, IX and XII, EC 4.2.1.1). The exploration of the chemical space around the main functional groups led to the discovery of selective hCA IX inhibitors in the micromolar/nanomolar range, thus establishing robust structure-activity relationships within this versatile scaffold. HPLC separation of some selected chiral compounds and biological evaluation of the corresponding enantiomers was performed along with molecular modelling studies on the most active derivatives.
- Rotondi, Giulia,Guglielmi, Paolo,Carradori, Simone,Secci, Daniela,De Monte, Celeste,De Filippis, Barbara,Maccallini, Cristina,Amoroso, Rosa,Cirilli, Roberto,Akdemir, Atilla,Angeli, Andrea,Supuran, Claudiu T.
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p. 1400 - 1413
(2019/08/26)
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- Repositioning Salirasib as a new antimalarial agent
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Malaria is a serious tropical disease that kills thousands of people every year, mainly in Africa, due to Plasmodium falciparum infections. Salirasib is a promising cancer drug candidate that interferes with the post-translational modification of Ras. This S-farnesyl thiosalicylate inhibits isoprenylcysteine carboxyl methyltransferase (ICMT), a validated target for cancer drug development. There is a high homology between the human and the parasite enzyme isoforms, in addition to being a druggable target. Looking to repurpose its structure as an antimalarial drug, a collection of S-substituted derivatives of thiosalicylic acid were prepared by introducing 1,2,3-triazole as a diversity entry point or by direct alkylation of the thiol. We further investigated the in vitro toxicity of FTS analogues to Plasmodium falciparum in the asexual stages and in Vero cells. An antiplasmodial activity assay was performed using a simple, high-sensitivity methodology based on nanoluciferase (NLuc)-transfected P. falciparum parasites. The results showed that some of the analogs were active at low micromolar concentration, including Salirasib. The most potent member of the series has S-farnesyl and the 1,2,3-triazole moiety substituted with phytyl. However, the compound substituted with methyl-naphthyl shows promising physicochemical and activity values. The low cytotoxicity in eukaryotic cells of the most active analogs provided good therapeutic indices, being starting-point candidates for future antimalarial drug development.
- Porta, Exequiel O. J.,Bofill Verdaguer, Ignasi,Perez, Consuelo,Banchio, Claudia,Ferreira De Azevedo, Mauro,Katzin, Alejandro M.,Labadie, Guillermo R.
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supporting information
p. 1599 - 1605
(2019/09/30)
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- Cyclic analogue of S-benzylisothiourea that suppresses kynurenine production without inhibiting indoleamine 2,3-dioxygenase activity
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Kynurenine is biosynthesised from tryptophan catalysed by indoleamine 2,3-dioxygenase (IDO). The abrogation of kynurenine production is considered a promising therapeutic target for immunological cancer treatment. In the course of our IDO inhibitor programme, formal cyclisation of the isothiourea moiety of the IDO inhibitor 1 afforded the 5-Cl-benzimidazole derivative 2b-6, which inhibited both recombinant human IDO (rhIDO) activity and cellular kynurenine production. Further derivatisation of 2b-6 provided the potent inhibitor of cellular kynurenine production 2i (IC50 = 0.34 μM), which unexpectedly exerted little effect on the enzymatic activity of rhIDO. Elucidation of the mechanism of action revealed that compound 2i suppresses IDO expression at the protein level by inhibiting STAT1 expression in IFN-γ-treated A431 cells. The kynurenine-production inhibitor 2i is expected to be a promising starting point for a novel approach to immunological cancer treatment.
- Fukuda, Miwa,Sasaki, Tomomi,Hashimoto, Tomoko,Miyachi, Hiroyuki,Waki, Minoru,Asai, Akira,Takikawa, Osamu,Ohno, Osamu,Matsuno, Kenji
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supporting information
p. 2846 - 2849
(2018/07/30)
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- Synthesis and Crystal Structures of Diaryl Thioethers and Aryl Benzyl Thioethers Derived from Thiosalicylic Acid
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Abstract: Reaction of thiosalicylic acid and iodobenzene or 1-fluoro-2-nitrobenzene in the presence of two equiv. of K2CO3 in acetone–water afforded the according diaryl thioethers 1 and 2 bearing carboxyl groups. Treatment of thiosalicylic acid with benzyl bromide-type compounds under similar reaction conditions gave aryl benzyl thioethers 3–8 in excellent yields. Moreover, reactions of thiosalicylic acid and benzyl bromide in the presence of excess K2CO3 led to isolation of compound 9 (Leka et al. in Acta Cryst E69:o285–0286, 2013) through further esterification of the carboxyl group. Crystal structures of 2, 5–7 and 9 (Leka et al. in Acta Cryst E69:o285–0286, 2013), along with their spectroscopic properties are reported. Weak hydrogen-bonding interactions exist in compound 2 and isomers 5–7. Compounds 2 and 7 crystallize in the monoclinic space group P21/n and C2/c, respectively, with a = 12.04(3), b = 7.311(19), C=14.22(4) ?, β = 93.94(3)°, and Z = 4 for 2, and a = 14.934(13), b = 5.116(5), C=33.76(3) ?, β = 91.523(12)°, and Z = 8 for 7. The unit cell of 5 has triclinic P-1 symmetry with the cell parameters a = 5.4334(14), b = 7.7787(19), C=16.488(4) ?, α = 76.601(3)°, β = 86.078(3)°, γ = 70.772(3)°, and Z = 2 for 5. Compound 6 crystallizes in the orthorhombic space group Pbca with a = 15.1881(12), b = 7.3288(6), C=23.7366(19) ?, and Z = 8. Graphical Abstract: Reactions of thiosalicylic acid and a series of aryl- or benzyl halides in the presence of K2CO3 in acetone–water resulted in the formation of according diaryl thioethers and aryl benzyl thioethers in excellent yields.
- Liu, Dan,Chen, Min,Fang, Duowen,Jia, Ai-Quan,Zhang, Qian-Feng
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- Cytotoxicity of palladium(II) complexes with some alkyl derivates of thiosalicylic acid. Crystal structure of the bis(S-butyl-thiosalicylate)palladium(II) complex, [Pd(S-bu-thiosal)2]
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The spectroscopically predicted structure of the obtained bis(S-butyl-thiosalicylate)palladium(II) complex, [Pd(S-bu-thiosal)2], was confirmed by an X-ray structural study. The asymmetric unit of [Pd(S-bu-thiosal)2] consists of neutr
- Mijajlovi?, Marina ?.,Nikoli?, Milo? V.,Jevti?, Verica V.,Ratkovi?, Zoran R.,Markovi?, Bojana Simovi?,Volarevi?, Vladislav,Arsenijevi?, Neboj?a N.,Novakovi?, Sladjana B.,Bogdanovi?, Goran A.,Trifunovi?, Sre?ko R.,Radi?, Gordana P.
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- Cu(II)-mediated C-S/N-S bond formation via C-H activation: Access to benzoisothiazolones using elemental sulfur
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A copper-mediated C-S/N-S bond-forming reaction via C-H activation that uses elemental sulfur has been developed. The addition of TBAI was found to be crucial for the success of this transformation. The method is scalable, shows excellent functional group tolerance, and is compatible with heterocycle substrates, providing efficient and practical access to benzoisothiazolones. The direct diversification of the benzoisothiazolone products into a variety of sulfur-containing compounds is also demonstrated.
- Chen, Fa-Jie,Liao, Gang,Li, Xin,Wu, Jun,Shi, Bing-Feng
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p. 5644 - 5647
(2015/02/19)
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- Mercaptobenzoic acid-palladium(0) complexes as active catalysts for S-benzylation with benzylic alcohols via (η3-benzyl)palladium(II) cations in water
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Mercaptobenzoic acid-palladium(0) complexes show high catalytic activity for S-benzylation with benzylic alcohols via the (η3-benzyl) palladium(ii) cation in water. Notably, these palladium(0) complexes could play an important role in formation
- Hikawa, Hidemasa,Azumaya, Isao
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p. 5964 - 5972
(2014/08/05)
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- Palladium-catalyzed S-benzylation of unprotected mercaptobenzoic acid with benzyl alcohols in water
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Palladium-catalyzed S-benzylation of unprotected mercaptobenzoic acids with benzyl alcohols gave only S-benzylated mercaptobenzoic acids in good yields. Water may play an important role for the smooth generation of the (η3-benzyl)palladium spec
- Hikawa, Hidemasa,Yokoyama, Yuusaku
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supporting information; experimental part
p. 2942 - 2945
(2012/05/05)
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- Synthesis, characterization and antimicrobial activity of palladium(II) complexes with some alkyl derivates of thiosalicylic acids: Crystal structure of the bis(S-benzyl-thiosalicylate)-palladium(II) complex, [Pd(S-bz-thiosal) 2]
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S-Alkyl (R = benzyl, methyl, ethyl, propyl and butyl) derivatives of thiosalicylic acid and the corresponding palladium(II) complexes were prepared and their structures were proposed on the basis of infrared, 1H and 13C NMR spectrosc
- Radic, Gordana P.,Gloovic, Verica V.,Radojevic, Ivana D.,Stefanovic, Olgica D.,Comic, Ljiljana R.,Ratkovic, Zoran R.,Valkonen, Arto,Rissanen, Kari,Trifunovic, Srecko R.
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experimental part
p. 69 - 76
(2012/03/13)
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- An umpolung sulfoxide reagent for use as a functionalized benzyl carbanion equivalent
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N-Methyl ortho-carbamoylaryl benzyl sulfoxides can be used as synthetic equivalents for α-hydroxy, α-chloro, and α-acetammido benzyl carbanions by means of a two-step sequence involving highly diastereoselective α-C-alkylation with alkyl halides followed by displacement of the sulfinyl residue (which can be recovered and recycled) by a hydroxyl, a chlorine or an acetamido, respectively, under non-oxidative Pummerer conditions. The scope and limits of the method, including a stereoselective version of the reaction, as well as the mechanism of the process are discussed in detail.
- Pinna, Giovanni,Bellucci, Maria Cristina,Malpezzi, Luciana,Pisani, Laura,Superchi, Stefano,Volonterio, Alessandro,Zanda, Matteo
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experimental part
p. 5268 - 5281
(2011/08/06)
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- Synthesis, spectral characterization and electrochemical properties of (2-alkylthiobenzoyl)ferrocenes. Crystal structures of 2-methylthio, 2-ethylthio and 2-isopropylthio derivatives
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The one-pot synthesis of seven new (2-alkylthiobenzoyl)ferrocenes has been achieved by Friedel-Crafts acylation of ferrocene with acid chlorides generated in situ from the corresponding carboxylic acids and phosphorous trichloride. The obtained compounds
- Ratkovi?, Zoran,Novakovi?, Sladana B.,Bogdanovi?, Goran A.,?egan, Dejan,Vuki?evi?, Rastko D.
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scheme or table
p. 2311 - 2317
(2010/09/06)
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- Excited state distortion in photochromic ruthenium sulfoxide complexes
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A series of photochromic ruthenium sulfoxide complexes of the form [Ru(bpy)2(OSOR)]+, where bpy is 2,2-bipyridine and OSOR is 2-(benzylsulfinyl)benzoate (OSOBn), 2-(napthalen-2-yl-methylsulfinyl)-benzoate (OSONap), or 2-(pentafluorophenylmethanesulfinyl)benzoate (OSOBnF5), have been synthesized and characterized. In aggregate, the data are consistent with phototriggered isomerization of the sulfoxide from S-bonded to O-bonded. The S-bonded complexes feature 3MLCT absorption maxima at 388 nm (R = BnF5), 396 nm (R = Bn), and 400 nm (R = Nap). Upon charge transfer excitation the S-bonded peak diminishes concomitant with new peaks growing in at ～350 and ～495 nm. Spectroscopic and electrochemical data suggest that the electronic character of the substituent on the sulfur affects the properties of the S-bonded complexes, but not the O-bonded complexes. The isomerization is reversible in methanol solutions and, in the absence of light, thermally reverts to the S-bonded isomer with biexponential kinetics. The quantum yields of isomerization (φs→o) were found to be 0.32, 0.22, and 0.16 for the R = BnF5, Bn, and Nap complexes, respectively. Kinetic analyses of femtosecond transient absorption data were consistent with a nonadiabatic mechanism in which isomerization occurs from a thermally relaxed 3MLCT state of S-bonded (or n2-sulfoxide) character directly to the singlet O-bonded ground state. The time constants of isomerization (τs→o) were found to be 84, 291, and 427 ps for the R = BnF5, Bn, and Nap complexes, respectively. Analysis of room temperature absorption and 77 K emission spectra reveal significant distortion between the S-bonded ground state (1GSS) and singlet metal-to-ligand charge transfer state (1MLCTS) and thermally relaxed 3MLCT, respectively. The distortion is primarily attributed to low frequency metal-ligand and S=O vibrational modes, which are intrinsically involved in the isomerization pathway.
- McClure, Beth Anne,Abrams, Eric R.,Rack, Jeffrey J.
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experimental part
p. 5428 - 5436
(2010/07/04)
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- Regioselective copper-catalyzed C-N and C-S bond formation using amines, thiols and halobenzoic acids
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A regioselective method for highly efficient C-N and C-S bond formation with 2-halobenzoic acids is described. The Cu/Cu2O-catalyzed reaction is carried out in 2-ethoxyethanol or ethylene glycol diethyl ether and does not require the use of strong base or other additives. This procedure eliminates the need for acid protection, tolerates a wide range of functional groups and provides aromatic and aliphatic amines and sulfides in 81-99% yield. Georg Thieme Verlag Stuttgart.
- Liu, Shuanglong,Pestano, John Paul C.,Wolf, Christian
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p. 3519 - 3527
(2008/09/19)
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- A simple one-pot synthesis of hydroxylated and carboxylated aryl alkyl sulfides from various bromobenzenes
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A simple one-pot synthesis of aryl alkyl sulfides from various bromobenzenes containing a hydroxy, hydroxymethyl, hydroxyethyl, and carboxylic acid group at -o, -m, and -p positions is reported here. The reaction proceeds through, in sequence, in situ pro
- Ko, Jaeyoung,Ham, Jungyeob,Yang, Inho,Chin, Jungwook,Nam, Sang-Jip,Kang, Heonjoong
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p. 7101 - 7106
(2007/10/03)
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- Design and synthesis of new 2-substituted-5-(2-benzylthiophenyl)-1,3,4- oxadiazoles as benzodiazepine receptor agonists
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A series of new 2-substituted-5-(2-benzylthiophenyl)-1,3,4-oxadiazoles was designed and synthesized as anticonvulsant agents. Conformational analysis and superimposition of energy minima conformers of the designed molecules on estazolam, a known benzodiazepine receptor agonist, revealed that the main proposed benzodiazepine pharmacophores were well matched. Electroshock and pentylenetetrazole-induced lethal convulsion tests showed that the introduction of an amino group in position 2 of 1,3,4-oxadiazole ring and a fluoro substituent at para position of benzylthio moiety had the best anticonvulsant activity. It seems this effect is mediated through benzodiazepine receptors mechanism.
- Zarghi, Afshin,Faizi, Mehrdad,Shafaghi, Bijan,Ahadian, Avideh,Khojastehpoor, Hamid R.,Zanganeh, Vahideh,Tabatabai, Sayyed A.,Shafiee, Abbas
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p. 3126 - 3129
(2007/10/03)
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- Synthesis of 1-aryl-tetralins and 4-aryl-benzopyrans by sulfoxide-mediated benzylic carbocation cyclizations
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An alkylation/cyclization sequence, with both steps mediated by the ortho-N-methylformamido-phenylsulfinyl function, provided two new C-C bonds and an efficient entry to 1-aryl-tetralins and 4-aryl-benzopyrans. Scope and limits of the process have been studied in detail.
- Volonterio, Alessandro,Zanda, Matteo
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p. 8723 - 8726
(2007/10/03)
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- Amide inhibitors of microsomal triglyceride transfer protein
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The present invention provides compounds having the Formula I The present invention also provides pharmaceutical compositions comprising a compound of Formula I and methods of treatment of atherosclerosis, obesity, restenosis, coronary heart disease, hype
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- Arylsulfanyl and heteroarylsulfanyl derivatives for treating pain
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According to the invention there is provided a compound the formula I; wherein A, X, B, R1, R2, R3 and R4 are as defined in the specification.
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- Amide inhibitors of microsomal triglyceride transfer protein
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The present invention provides compounds having the Formula I The present invention also provides pharmaceutical compositions comprising a compound of Formula I and methods of treatment of atherosclerosis, obesity, restenosis, coronary heart disease, hype
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- An umpolung sulfoxide reagent as α-hydroxy and α-chloro benzyl carbanion equivalents
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ortho-[(N-Methyl)carbamoyl]phenyl benzyl sulfoxide is used as a synthetic equivalent of α-hydroxy and α-chloro benzyl carbanions by means of a two-step sequence involving (1) highly stereoselective α-C-alkylation with alkyl bromides, and (2) displacement of the sulfinyl group by an OH or a Cl under Pummerer or chloro-Pummerer conditions, respectively. The sulfinyl auxiliary can be effectively regenerated and recycled.
- Volonterio, Alessandro,Bravo, Pierfrancesco,Zanda, Matteo
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p. 6537 - 6540
(2007/10/03)
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- Arginine-Vasopressin Analogs with Thiosalicylic Acid in Position 1
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Three analogs of arginine-vasopressin were synthesized in which the cysteine residue in position 1 was substituted by thiosalicylic acid residue.Their pressor and antidiuretic activities were severely depressed and were devoid of antagonistic potencies.The binding affinities of these analogs to V1 and V2 receptors were also sharply decreased.This is due to large conformational changes of the N-terminal hexapeptide ring, caused by rigid thiosalicylic acid residue.
- Lankiewicz, Leszek,Kasprzykowski, Franciszek,Grzonka, Zbigniew,Melin, Per,Boer, Reiner,Fahrenholz, Falk
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p. 375 - 383
(2007/10/02)
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- Cyclic Sulfenylcarboxylates from 4H-3,1-Benzoxathiin-4-one 1-Oxides. A New Ring Contraction Reaction
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4H-3,1-Benzoxathiin-4-one 1-oxides 4 eliminate aldehydes on heating.Corresponding to the substituent in 8-position, ring contraction occurs to give 3H-2,1-benzoxathiol-3-ones 2 or 3H-1,2-benzisothiazol-3-ones 8.The dependance on the substituents and the mechanism of the reaction are discussed.
- Krische, Bernd,Walter, Wolfgang
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p. 1708 - 1727
(2007/10/02)
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