- N-Thiocyanato-2,10-camphorsultam Derivatives: Design and Applications of Original Electrophilic Thiocyanating Reagents
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The synthesis of bench-stable electrophilic thiocyanating reagents was depicted in two steps from readily available starting materials in good yields. These newly designed electrophilic reagents were successfully applied for the thiocyanation of different
- Gao, Mélissa,Vuagnat, Martin,Jubault, Philippe,Besset, Tatiana
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supporting information
(2021/11/30)
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- N-doped ZnO as an efficient photocatalyst for thiocyanation of indoles and phenols under visible-light
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In this study, nitrogen-doped ZnO nanorods (N–ZnO NRs) were synthesized via a very simple hydrothermal process, fully characterized, and this photocatalyst was successfully exploited in thiocyanation reactions of indoles and phenols at room temperature under visible light irradiation. Two important classes of aromatic compounds indoles, and phenols using N–ZnO NRs as photocatalyst treated with ammonium thiocyanate as thiocyanation agent formed the corresponding thiocyano compounds in good yields. Nitrogen is one of the most appropriate p-type dopants that is nontoxic, similar to the atomic radius to oxygen, and lower electronegativity and ionization energy than the O atom. Therefore, the N doping converts ZnO into the p-type ZnO semiconductor structure. This potent, simple, and versatile protocol afforded thiocyanation reactions of indole and phenols under visible light. The reactions proceeded through a radical pathway by applying air molecular oxygen as a low cost and environmentally friendly terminal oxidant. The proposed mechanism based on control experiments was thoroughly described. Graphic abstract: [Figure not available: see fulltext.]
- Hosseini-Sarvari, Mona,Sarvestani, Abdollah Masoudi
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p. 903 - 911
(2021/07/17)
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- ARS-TiO2 photocatalyzed direct functionalization of sp2 C-H bonds toward thiocyanation and cyclization reactions under visible light
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An ARS-TiO2 photocatalyst has been prepared, by a simple method through stirring a mixture of ARS and TiO2 at room temperature in the dark, to extend the photocatalytic response of titanium dioxide toward the visible light spectrum. The synergic effect of ARS and TiO2 in the photocatalyst system has catalyzed direct C-H functionalization of sp2 C-H bonds toward thiocyanation and cyclization reactions. Several aromatic and heteroaromatic scaffolds (2-phenylamino-thiazole, phenol, aniline, indole and pyrrole derivatives) were treated with the thiocyanate anion at room temperature. Herein, the first report on thiocyanation of phenol and synthesis of 2-aminobenzothiazole derivatives under visible light is presented.
- Hosseini-Sarvari, Mona,Hosseinpour, Zeinab,Koohgard, Mehdi,Sarvestani, Abdollah Masoudi
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p. 1401 - 1407
(2020/03/26)
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- Visible-light-enabled regioselective aerobic oxidative C(sp2)-H thiocyanation of aromatic compounds by Eosin-Y photocatalyst
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Herein, visible-light-enabled regioselective aerobic oxidative C(sp2)-H thiocyanation of aromatic compounds has been developed by employing eosin-Y as effective photocatalyst and oxygen as the green terminal oxidant. This process featured green, efficient and operationally simple. Furthermore, the practicality and utility of this protocol was demonstrated by the gram scale synthesis. Mechanistic studies suggested that this reaction was realized via a photoredox radical pathway.
- Yi, Bing,Wen, Xiaoyong,Yi, Ziqi,Xie, Yanjun,Wang, Qiang,Tan, Jian-Ping
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supporting information
(2020/11/19)
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- Selectfluor-initiated cyanation of disulfides to thiocyanates
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A Selectfluor-initiated cyanation of disulfides to thiocyanates has been developed. In this process, Selectfluor was employed as the oxidant and trimethylsilyl cyanide was used as the cyanation reagent. It provides an eco-friendly and simple way to synthesize the thiocyanates.
- Zhou, Pengpeng,Chen, Chuan,Li, Shubai
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p. 376 - 380
(2020/02/13)
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- An electrochemical method for deborylative seleno/thiocyanation of arylboronic acids under catalyst- And oxidant-free conditions
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An electrochemical deborylative seleno/thiocyanation of arylboronic acids has been well established to synthesize the corresponding aryl seleno/thiocyanates with good functional group tolerance under ambient conditions. A gram-scale reaction has been performed to highlight the advantages of the protocol. Preliminary mechanistic studies indicate that the oxidation of the seleno/thiocyanate anion occurs prior to that of the arylboronic acid substrate in galvanostatic mode, and that free radicals are involved in the process.
- He, Dongdong,Yao, Jiaojiao,Ma, Boling,Wei, Jinghao,Hao, Guangguo,Tuo, Xun,Guo, Shengmei,Fu, Zhengjiang,Cai, Hu
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supporting information
p. 1559 - 1564
(2020/03/26)
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- Thiocyanation of aromatic and heteroaromatic compounds with 1-Chloro-1,2-benziodoxol-3-(1H)-one and (Trimethylsilyl)isothiocyanate
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Thiocyanation of aromatic compounds has been investigated using the combination of 1-chloro-1,2-benziodoxol-3-(1H)-one (1) and (trimethylsilyl)isothiocyanate (TMSNCS). The reaction with electron rich aromatic compounds proceeded smoothly to provide the th
- Ito, Yuta,Touyama, Akihiro,Uku, Minako,Egami, Hiromichi,Hamashima, Yoshitaka
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p. 1015 - 1018
(2019/09/12)
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- N -Thiocyanato-dibenzenesulfonimide: A new electrophilic thiocyanating reagent with enhanced reactivity
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A novel electrophilic thiocyanating reagent, N-thiocyanato-dibenzenesulfonimide, was prepared and exhibited enhanced electrophilicity with a wide scope of substrates. Thus, it reacted with activated aromatics such as phenols, indoles, anilines and anisoles without a catalyst giving the corresponding thicyanate derivatives in high yields, while TfOH for unactivated arenes and hetero aromatics and Zn(OTf)2 for ketones was used as the catalyst, respectively. It is noteworthy that internal alkenes and styrenes were bifunctionalized giving 1,2-amino thiocyanates in high yields.
- Li, Chengqiu,Long, Pingliang,Wu, Haopeng,Yin, Hongquan,Chen, Fu-Xue
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supporting information
p. 7131 - 7134
(2019/08/07)
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- Rapid and efficient thiocyanation of phenols, indoles, and anilines in 1,1,1,3,3,3-hexafluoro-2-propanol under ultrasound irradiation
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An efficient ultrasound-promoted thiocyanation of phenols, indoles, and anilines in the presence of N-chlorosuccinimide and NH4SCN using 1,1,1,3,3,3-hexafluoro-2-propanol as the solvent has been developed. The major features of the present protocol include the mild reaction conditions, short reaction times, good to excellent yields, and broad substrate scope. Moreover, scale-up synthesis can be achieved and the solvent can be easily recovered and reused.
- Wang, Zhonghao,Wang, Liang,Chen, Qun,He, Ming-yang
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supporting information
p. 76 - 84
(2017/12/28)
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- Preparation and structure of phenolic aryliodonium salts
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Phenol based aryliodonium salts were prepared by the reaction of [hydroxy(tosyloxy)iodo]arenes with aryl silyl ethers in the presence of trifluoromethanesulfonic acid. Structures of several aryliodonium salts with the hydroxy group in the para-position of the phenyl ring were established by single crystal X-ray crystallography. Under basic conditions, 4-hydroxyphenyl(phenyl)iodonium salts form a dimeric hypervalent iodine(iii) complex, oxyphenyl(phenyl)iodonium ylidic salt, the solid structure of which was confirmed by X-ray crystallography. Phenolic iodonium salts are potentially useful phenol transfer reagents in reactions with various anionic nucleophiles.
- Yoshimura, Akira,Shea, Michael T.,Guselnikova, Olga,Postnikov, Pavel S.,Rohde, Gregory T.,Saito, Akio,Yusubov, Mekhman S.,Nemykin, Victor N.,Zhdankin, Viktor V.
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p. 10363 - 10366
(2018/09/21)
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- Direct Photocatalytic S-H Bond Cyanation with Green cN Source
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Herein we report a novel C-S bond cleavage and reconstruction strategy for the synthesis of thiocyanates through direct photocatalytic S-H bond cyanation from thiols and inorganic thiocyanate salts. In our strategy, the unprecedented example of cutting off C-S bond of SCN- to deliver the green CN sources is demonstrated. This transformation features nontoxic and inexpensive CN sources, available starting materials, metal-/base-/ligand-/peroxide-free, high step economy and mild conditions. It leads to the construction of various thiocyanates and some medicinally and biologically active thiocyanate-containing molecules.
- Guo, Wei,Tan, Wen,Zhao, Mingming,Zheng, Lvyin,Tao, Kailiang,Chen, Deliang,Fan, Xiaolin
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supporting information
p. 6580 - 6588
(2018/05/29)
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- Preparation method for thiocyanide compound
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The invention discloses a preparation method for a thiocyanide compound. The preparation method comprises the following steps: taking a sulfhydryl compound, thiocyanate as raw materials, taking rose-bengal, eosine Y or eosin B as a catalyst, performing illumination, generating a thiocyanide compound after the illumination reaction. According to the preparation method provided by the invention, thiocyanide is decomposed into thiocyanate ions; the sulfhydryl compound generates sulfhydryl radical under the action of light and the catalyst, and the sulfhydryl radical is used for attacking carbon atoms in thiocyanate ions to obtain a intermediate; sulfide is removed from the intermediate to obtain the thiocyanide compound. The rose-bengal, the eosine Y or the eosin B used by the method containno heavy metal ion, and the adverse effect on the performance of the thiocyanide compound by the heavy metal ion residue is avoided; in addition, the catalyst is easily removed, so that a favorable condition is provided for the preparation of the thiocyanide compound with higher purity.
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Paragraph 0098; 0099; 0104; 0105
(2018/06/16)
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- N-Thiocyanatosaccharin: A "sweet" Electrophilic Thiocyanation Reagent and the Synthetic Applications
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N-Thiocyanatosaccharin (R1) was readily prepared from the sweet additive Saccharin in two steps with a 71% overall yield. By applying this new reagent to diverse nucleophiles such as benzothiophenes, indoles, oxindoles, aromatic amines, phenols, β-keto carbonyl compounds, and aromatic ketones, a novel electrophilic thiocyanation reaction was achieved with high yields (up to 99%). The potential recycling of Saccharin, the wide scope of substrates, and the mild reaction conditions made this protocol much more practical.
- Wu, Di,Qiu, Jiashen,Karmaker, Pran Gopal,Yin, Hongquan,Chen, Fu-Xue
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supporting information
p. 1576 - 1583
(2018/02/09)
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- Transition-metal-free regioselective thiocyanation of phenols, anilines and heterocycles
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An expedient direct and regioselective thiocyanation of phenols, anilines and heterocycles is described. Transformation is realized via the direct C[sbnd]H functionalization under transition metal free conditions at ambient temperature in excellent yields. Method proved to be monoselective and variety of functional groups tolerated the reaction conditions. The practicality of the protocol is demonstrated in gram scale synthesis of a precursor of PPAR δ agonist in excellent yield.
- Mete, Trimbak B.,Khopade, Tushar M.,Bhat, Ramakrishna G.
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supporting information
p. 415 - 418
(2017/01/10)
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- Synthesis of perfluoroalkyl thioethers from aromatic thiocyanates by iron-catalysed decarboxylative perfluoroalkylation
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Easily available aryl and heteroaryl thiocyanates were converted into the corresponding perfluoroalkyl thioethers via decarboxylation of potassium perfluoroalkylcarboxylates, catalysed by the inexpensive and environmentally benign iron(III) chloride.
- Exner, Benjamin,Bayarmagnai, Bilguun,Matheis, Christian,Goossen, Lukas J.
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supporting information
p. 89 - 93
(2017/06/23)
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- Graphene oxide: A promising carbocatalyst for the regioselective thiocyanation of aromatic amines, phenols, anisols and enolizable ketones by hydrogen peroxide/KSCN in water
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Graphene oxide (GO), as a heterogeneous carbocatalyst, catalyzes the direct thiocyanation of a variety of arenes including aromatic amines, phenols, anisols and carbonyl compounds that possessing α-hydrogen in the presence of hydrogen peroxide and KSCN in water as a green media. This procedure is chemoselective, avoids the use of precious metals and toxic solvents and has a broad substrate scope. Easy removal from the reaction mixture and recyclability with no loss of activity are the key features of graphene oxide in this catalytic system.
- Khalili, Dariush
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p. 2547 - 2553
(2016/03/19)
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- Oxidant-free thiocyanation of phenols and carbonyl compounds under solvent-free conditions by AlCl 3/NH 4SCN
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A simple, efficient, solvent-free, and mild method for thiocyanation of phenols by ammonium thiocyanate (NH4SCN) in the presence of AlCl3 has been developed. This new methodology was used to prepare para-thiocyanated products in good to excellent yields at 70°C. In addition, the successful α-thiocyanation of various ketones has also been described. Finally, a plausible mechanism of thiocyanation has been suggested.
- Nikoofar, Kobra,Gorji, Samareh
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- Synthesis of Aryl Tri- and Difluoromethyl Thioethers via a C H-Thiocyanation/Fluoroalkylation Cascade
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An AlCl3-catalyzed C H thiocyanation was discovered and combined with a Langlois-type trifluoromethylation to afford aryl trifluoromethyl thioethers directly from arenes, N-thiocyanatosuccinimide (NTS) and Ruppert-Prakash reagent. An analogous combination with a copper-mediated difluoromethylation gives access to aryl difluoromethyl thioethers. Both processes proceed with exceptional regioselectivity for the most electron-rich, sterically least hindered position of the arene. The sulfur and fluoroalkyl groups originate from different sources, so that the use of expensive, preformed fluoroalkylthiolation reagents is avoided. Perfectly formed: An AlCl3-catalyzed C H thiocyanation was combined with a Langlois-type trifluoromethylation to afford aryl trifluoromethyl thioethers directly from arenes, N-thiocyanatosuccinimide, and TMS-CF3 (see scheme). An analogous combination of the thiocyanation with a copper-mediated difluoromethylation gives access to aryl difluoromethyl thioethers. The sulfur and fluoroalkyl groups originate from different sources, so that preformed fluoroalkylthiolation reagents are avoided.
- Jouvin, Kévin,Matheis, Christian,Goossen, Lukas J.
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supporting information
p. 14324 - 14327
(2015/10/05)
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- Iron-Catalyzed Decarboxylation of Trifluoroacetate and Its Application to the Synthesis of Trifluoromethyl Thioethers
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Nucleophilic CF3 has been generated by decarboxylation of potassium trifluoroacetate, arguably the most easy-to-handle, inexpensive, and sustainable source of trifluoromethyl groups. Simple iron(II) chloride catalyzes the decarboxylation as well as a subsequent trifluoromethylation of organothiocyanates, resulting in a straightforward synthesis of trifluoromethyl thioethers. The KCN byproduct is absorbed by iron(II) with formation of nontoxic potassium hexacyanoferrate. An analogous trifluoromethylation of aldehydes with trifluoroacetate underlines the synthetic potential of such iron-catalyzed decarboxylative trifluoromethylations.
- Exner, Benjamin,Bayarmagnai, Bilguun,Jia, Fan,Goossen, Lukas J.
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supporting information
p. 17220 - 17223
(2016/01/25)
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- Nitromethane as a cyanating reagent for the synthesis of thiocyanates
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Nitromethane has been developed to be an effective cyanating reagent for the synthesis of thiocyanates. In the presence of iodine and base, a wide range of disulfides were reacted with nitromethane smoothly to give diverse thiocyanates in moderate to good yields.
- Wang, Zuo-Hui,Ji, Xiao-Ming,Hu, Mao-Lin,Tang, Ri-Yuan
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supporting information
p. 5067 - 5070
(2015/08/06)
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- Practical access to aromatic thiocyanates by CuCN-mediated direct aerobic oxidative cyanation of thiophenols and diaryl disulfides
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The practical and mild aerobic oxidative CuCN-mediated cyanation of thiophenols and diaryl disulfides was investigated. The reaction was performed in air at room temperature and reached aromatic thiocyanates in moderate to good yields starting from a broad range of diversely functionalized substrates.
- Castanheiro, Thomas,Gulea, Mihaela,Donnard, Morgan,Suffert, Jean
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supporting information
p. 7814 - 7817
(2015/02/19)
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- Facile method for thiocyanation of activated arenes using iodic acid in combination with ammonium thiocyanate
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A facile method for direct thiocyanation of activated arenes using iodic acid in combination with ammonium thiocyanate is described.
- Mahajan, Ulhas S.,Akamanchi, Krishnacharya G.
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experimental part
p. 2674 - 2682
(2009/12/04)
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- Synthesis of aryl thiocyanates using Al2O3/MeSO 3H (AMA) as a novel heterogeneous system
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Indoles and various aromatic and heteroaromatic compounds undergo smooth thiocyanation with ammonium thiocyanate in the presence of a mixture of Al 2O3, MeSO3H (AMA) under mild conditions without use of any organic solvent
- Hosseini-Sarvari, Mona,Tavakolian, Mina
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experimental part
p. 318 - 321
(2009/04/16)
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- Efficient and novel method for thiocyanation of aromatic and heteroaromatic compounds using bromodimethylsulfonium bromide and ammonium thiocyanate
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Various aromatic and heteroaromatic compounds have been efficiently thiocyanated by using a novel combination of bromodimethylsulfonium bromide (BDMS) and ammonium thiocyanate. Georg Thieme Verlag Stuttgart.
- Bhalerao, Dinesh S.,Akamanchi, Krishnacharya G.
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p. 2952 - 2956
(2008/03/12)
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- 2-Cyanopyridazin-3(2H)-ones: Effective and chemoselective electrophilic cyanating agents
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2-Cyanopyridazin-3(2H)-ones are novel, effective, selective and electrophilic cyanating agents. A variety of amino, thiol and carbon nucleophiles are chemoselectively N-, S- or C-cyanated in excellent yield using 2-cyanopyridanzin-3(2H)-ones in water or tetrahydrofuran.
- Kim, Jeum-Jong,Kweon, Deok-Heon,Cho, Su-Dong,Kim, Ho-Kyun,Jung, Eun-Young,Lee, Sang-Gyeong,Falck,Yoon, Yong-Jin
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p. 5889 - 5894
(2007/10/03)
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- Compounds that modulate PPAR activity and methods of preparation
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This invention relates to compounds that alter PPAR activity. The invention also relates to pharmaceutically acceptable salts of the compounds, pharmaceutically acceptable compositions comprising the compounds or their salts, and methods of using them as therapeutic agents for treating or preventing dyslipidemia, hypercholesterolemia, obesity, hyperglycemia, atherosclerosis, hypertriglyceridemia and hyperinsulinemia in a mammal. The present invention also relates to methods for making the disclosed compounds.
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- An Improved Iodine(III) Mediated Method for Thiocyanation of 2-Arylindan-1,3-diones, Phenols, and Anilines
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An improved method for thiocyanation of 2-arylindan- 1,3-diones, phenols, and anilines using a reagent combination of (dichloroido)-benzene and potassium thiocyanate in dry dichloromethane is described.
- Prakash, Om,Kaur, Harpreet,Pundeer, Rashmi,Dhillon,Singh, Shiv P.
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p. 4037 - 4042
(2007/10/03)
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- Compounds that modulate PPAR activity and methods for their preparation
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This invention discloses compounds that alter PPAR activity. The invention also discloses pharmaceutically acceptable salts of the compounds, pharmaceutically acceptable compositions comprising the compounds or their salts, and methods of using them as therapeutic agents for treating or preventing disipidemia, hypercholesteremia, obesity, eating disorders, hyperglycemia, atherosclerosis, hypertriglyceridemia, hyperinsulinemia and diabetes in a mammal as well as methods of supressing appetite and modulating leptin levels in a mammal. The present invention also discloses methods for making the disclosed compounds.
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- Novel process for generating useful electrophiles from common anions using Selectfluor fluorination agent
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In the present work, the electrophile equivalents C1+, Br+, SCN+, and NO2+ are generated from their respective sodium, potassium, and in some cases ammonium salts (M+X-) by reaction with Selectfluor electrophilic fluorination agent in acetonitrile solution at room temperature. These generated electrophilic species subsequently react in situ with a variety of aromatic substrates containing one or more substituent groups including H, F, C1, CH3, COOH, C(O)CH3, NO2, and OR′ and NR′R″ where R′ and R″ are H or CH3. The resulting substitution products are, in most cases, isolable as pure compounds in high yield. Variations in the process include the use of other anions, electrophilic fluorination agents, and solvents.
- Syvret, Robert G.,Butt, Kathleen M.,Nguyen, Tung P.,Bulleck, Victoria L.,Rieth, Ryan D.
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p. 4487 - 4493
(2007/10/03)
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- A facile synthesis of aryl thiocyanates using sodium perborate
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A simple and convenient synthesis of aryl thiocyanates in high yields using sodium perborate is described.
- Jadhav,Pal,Wadgaonkar,Salunkhe
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p. 3041 - 3045
(2007/10/03)
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- Process for generating electrophiles from anions by reaction with electrophilic fluorinating agent
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A process includes substituting a substituent on a substrate. The process includes reacting a salt of an anionic form of the substituent with an electrophilic fluorination agent to provide an electrophile containing a cationic form of the substituent. The electrophile is then electrophilically substituted on the substrate. In some aspects of the process, the substrate can be an aromatic or a non-aromatic. The process can be used for a variety of reactions having electrophilic mechanisms, including halogenation, thiocyanation and nitration.
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- An efficient p-thiocyanation of phenols and naphthols using a reagent combination of phenyliodine dichloride and lead(II) thiocyanate
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A combination of PhICl2 and Pb(SCN)2 is effective for the p-selective thiocyanation of various types of p-unsubstituted phenols and naphthols 1 to give p-thiocyanatophenols and naphthols 3. The reaction proceeded at 0 °C to room temperature in good to quantitative yields. Twenty-five examples are given, in which various functional groups, such as chloro, allyl, carbonyl, ester, amide, and primary hydroxyl groups are shown to be compatible with this reaction.
- Kita, Yasuyuki,Takeda, Yoshifumi,Okuno, Takayuki,Egi, Masahiro,Iio, Kiyosei,Kawaguchi, Ken-Ichi,Akai, Shuji
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p. 1887 - 1890
(2007/10/03)
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- A two phase electrochemical method for thiocyanation
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A two phase electrochemical method for thiocyanation has been described. Thiocyano derivatives of aromatic amines and phenols and isothiocyano derivatives of substituted amines were obtained in 50-80% yield.
- Krishnan,Gurjar
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p. 2741 - 2744
(2007/10/02)
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- Novel phenolic thioethers as inhibitors of 5-lipoxygenase
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The compounds of the present invention comprise substituted phenolic thioethers represented by the formula: STR1 wherein: R1 and R2 are the same or different and independently represent tert-alkyl or phenyl; A represents methylene or methylene substituted by alkyl, dialkyl or hydroxy, provided that when A includes hydroxymethylene, the hydroxymethylene group is not adjacent to a heteroatom; B represents sulfur, sulfoxide, sulfone, oxygen, --NH-- or nitrogen substituted by alkyl, phenyl, benzyl, substituted phenyl or substituted benzyl; C represents methylene or methylene substituted by alkyl; R3 represents CO2 H, CO2 -alkyl or a tetrazole group; m is 0 or 1, n is 2, 3 or 4 and p is 1, 2 or 3; and the pharmaceutically acceptable salts thereof. The compounds of the present invention are specific inhibitors of 5-lipoxygenase and, therefore, are useful in the treatment of local and systemic inflammation, allergy and hypersensitivity reactions and other disorders in which agents formed in the 5-lipoxygenase metabolic pathway are involved.
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- Phenolic thioethers as inhibitors of 5-lipoxygenase
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The compounds of the present invention comprise substituted phenolic thioethers represented by the formula: STR1 wherein: R1 and R2 are the same or different and independently represent tert-alkyl or phenyl; A represents methylene or methylene substituted by alkyl, dialkyl or hydroxy, provided that when A includes hydroxymethylene, the hydroxymethylene group is not adjacent to a heteroatom; B represents sulfur, sulfoxide, sulfone, oxygen, --NH-- or nitrogen substituted by alkyl, phenyl, benzyl, substituted phenyl or substituted benzyl; C represents methylene or methylene substituted by alkyl; R3 represents CO2 H, CO2 -alkyl or a tetrazole group; m is 0 or 1, n is 2, 3 or 4 and p is 1, 2 or 3; amd the pharmaceutically acceptable salts thereof. The compounds of the present invention are specific inhibitors of 5-lipoxygenase and, therefore, are useful in the treatment of local and systemic inflammation, allergy and hypersensitivity reactions and other disorders in which agents formed in the 5-lipoxygenase metabolic pathway are involved.
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