- Green Aerobic Oxidation of Thiols to Disulfides by Flavin-Iodine Coupled Organocatalysis
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Coupled catalysis using a riboflavin-derived organocatalyst and molecular iodine successfully promoted the aerobic oxidation of thiols to disulfides under metal-free mild conditions. The activation of molecular oxygen occurred smoothly at room temperature through the transfer of electrons from the iodine catalyst to the biomimetic flavin catalyst, forming the basis for a green oxidative synthesis of disulfides from thiols.
- Iida, Hiroki,Kozako, Ryo,Oka, Marina
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supporting information
p. 1227 - 1230
(2021/06/21)
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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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supporting information
p. 8075 - 8078
(2021/08/20)
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- A novel pathway for the thermolysis of N-nitrosoanthranilates using flash vacuum pyrolysis leading to 7-aminophthalides
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Flash vacuum pyrolysis of methyl N-methyl-N-nitrosoanthranilate leads to elimination of nitric oxide and disproportionation of the formed N-radical to 7-(methylamino)phthalide and methyl N-methylanthranilate. This transformation was found to be a convenient, solvent-free method for the preparation of 7-(methylamino)phthalides. An alternative route through pyrolysis of N-benzyl-N-methyl anthranilates was also investigated. This journal is
- Dallinger, Doris,Kappe, C. Oliver,Zlatkovi?, Dragan
-
supporting information
p. 8371 - 8375
(2020/11/05)
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- Natural gallic acid catalyzed aerobic oxidative coupling with the assistance of MnCO3 for synthesis of disulfanes in water
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The formation of S-S bonds has great significance and value in synthetic chemistry and bioscience. To pursue a sustainable approach for such a synthesis, an aerobic oxidative coupling method for the efficient preparation of organic disulfanes, using a low-toxic natural gallic acid as an organocatalyst, inexpensive MnCO3 as a cocatalyst, O2 as the terminal oxidant and water as the solvent, has been successfully developed. Such metal-organic cooperative catalytic protocol provided an access to various symmetrical and unsymmetrical disulfanes in up to 99% yield. Gram scale synthesis with practical convenience and low loading of catalysts further illustrates the practicability of our method.
- Song, Lijuan,Li, Wenhao,Duan, Wenxue,An, Jichao,Tang, Shanyu,Li, Longjia,Yang, Guanyu
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supporting information
p. 1432 - 1438
(2019/03/26)
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- Synthesis of aryl cyclopropyl sulfides through copper-promoted S-cyclopropylation of thiophenols using cyclopropylboronic acid
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The copper-promoted S-cyclopropylation of thiophenols using cyclopropylboronic acid is reported. The procedure operates under simple conditions to afford the corresponding aryl cyclopropyl sulfides in moderate to excellent yields. The reaction tolerates substitution in ortho-, meta- and para-substitution as well as electron-donating and electron-withdrawing groups. The S-cyclopropylation of a thiophenol was also accomplished using potassium cyclopropyl trifluoroborate.
- Benoit, Emeline,Fnaiche, Ahmed,Gagnon, Alexandre
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p. 1162 - 1171
(2019/06/08)
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- Reusable cobalt-phthalocyanine in water: Efficient catalytic aerobic oxidative coupling of thiols to construct S-N/S-S bonds
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A new aerobic oxidative coupling of thiols in water to construct sulfenamides or disulfides was developed, utilizing cobalt(ii)phthalocyanine-tetra-sodium sulfonate as the catalyst and O2 as the oxidant. The mother liquor could be recycled up to 20 times with negligible loss of activity and only a minor decrease of product yield.
- Dou, Yingchao,Huang, Xin,Wang, Hao,Yang, Liting,Li, Heng,Yuan, Bingxin,Yang, Guanyu
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supporting information
p. 2491 - 2495
(2017/07/17)
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- Synthesis and anti-bacterial activity of a library of 1,2-benzisothiazol-3(2H)-one (BIT) derivatives amenable of crosslinking to polysaccharides
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1,2-Benzisothiazol-3(2H)-one (BIT) is one of the most common chemical biocides in industrial products, with a heterocyclic structure and a wide range of antimicrobial activity. A library of BIT derivatives was synthesized and characterized, from which 18 compounds were selected, tested for anti-bacterial activity relative to the parent molecule and amenable of coupling to plant polysaccharides in general and to galactomannans (GM) in particular, widely used as rheology modifiers, but with limited “biostability”. Four sites on the BIT core were targeted: the nitrogen and the oxygen atoms on the heterocyclic ring, the C5 and the C6 positions on the aromatic ring, where functional groups were introduced. The ultimate aim of this work is to establish whether by covalently linking a biocide to GM polymers, their “biostability” can be improved.
- Viani, Fiorenza,Rossi, Bianca,Panzeri, Walter,Merlini, Luca,Martorana, Alessandra M.,Polissi, Alessandra,Galante, Yves M.
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p. 1745 - 1761
(2017/03/08)
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- Chemoselective synthesis of diaryl disulfides via a visible light-mediated coupling of arenediazonium tetrafluoroborates and CS2
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A highly efficient and chemoselective method for the synthesis of diaryl disulfides is developed via a visible light-promoted coupling of readily accessible arenediazonium tetrafluoroborates and CS2. This practical and convenient protocol provides a direct pathway for the assembly of a series of disulfides in an environmentally friendly manner with good to excellent yields.
- Leng, Jing,Wang, Shi-Meng,Qin, Hua-Li
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supporting information
p. 903 - 909
(2017/06/23)
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- SNAr nucleophilic substitution of 1,9-dihalodipyrrins by S- and N- nucleophiles. Synthesis of new dipyrrins bearing pendant substituents
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5-Aryl-1,9-dichlorodipyrrins react with a series of S- and N- nucleophiles (both alkyl- and aryl- ones). Reagents with mercapto group yield product of double nucleophilic substitution of 5-pheny-1,9-dichlorodipyrrin, i.e. the respective 1,9-bis(alkyl-of arylthio)dipyrrin. On the contrary, 5-(4-nitrophenyl)-1,9-dichlorodipyrrin causes disulfides formation from the S-aliphatic substrates, whereas nucleophilic substitution remains the main path of the reaction for S-aryl ones. The reaction of N-Alkyl nucleophiles proceeds as mono-substitution. UV-Vis spectra feature a batochromic shift for bis-S-substituted products and a hypsochromic shift for mono-N-substituted ones, with respect to the starting dichlrorides.
- Leushina, Evgenia,Tikhomirova, Ksenia,Permyakova, Anastasiya,Ilin, Pavel,Terenina, Maria,Anisimov, Alexander,Khoroshutin, Andrey
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p. 149 - 155
(2016/03/19)
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- Iodide-Catalyzed Synthesis of Secondary Thiocarbamates from Isocyanides and Thiosulfonates
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A new method for the synthesis of secondary thiocarbamates from readily available isocyanides and thiosulfonates with broad functional group tolerance is reported. The reaction proceeds under mild reaction conditions in isopropanol and is catalyzed by inexpensive sodium iodide.
- Mampuys, Pieter,Zhu, Yanping,Sergeyev, Sergey,Ruijter, Eelco,Orru, Romano V. A.,Van Doorslaer, Sabine,Maes, Bert U. W.
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supporting information
p. 2808 - 2811
(2016/07/06)
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- Flavin-catalyzed aerobic oxidation of sulfides and thiols with formic acid/triethylamine
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An efficient and practical catalytic method for the aerobic oxidative transformation of sulfides into sulfoxides, and thiols into disulfides with formic acid/TEA in the presence of a new, readily available, and stable flavin catalyst 5d is described. This journal is the Partner Organisations 2014.
- Murahashi, Shun-Ichi,Zhang, Dazhi,Iida, Hiroki,Miyawaki, Toshio,Uenaka, Masaaki,Murano, Kenji,Meguro, Kanji
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supporting information
p. 10295 - 10298
(2014/08/18)
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- Synthesis and evaluation of novel sulfenamides as novel anti Methicillin-resistant Staphylococcus aureus agents
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A total of 29 novel sulfenamide compounds were synthesized, spectroscopically characterized and evaluated in vitro for antimicrobial activity against various infectious pathogens. Compounds 1b and 2c exhibited potent inhibition against clinical Methicillin-resistant Staphylococcus aureus (MRSA) strains with minimum inhibitory concentration (MIC) values of 1.56 μg/mL.
- Shang, Jian-Li,Guo, Hui,Li, Zai-Shun,Ren, Biao,Li, Zheng-Ming,Dai, Huan-Qin,Zhang, Li-Xin,Wang, Jian-Guo
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supporting information
p. 724 - 727
(2013/02/25)
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- Synthesis and biological evaluation of nonsymmetrical aromatic disulfides as novel inhibitors of acetohydroxyacid synthase
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46 Novel nonsymmetrical aromatic disulfides containing [1,3,4]thiadiazole or [1,3,4]oxadiazole groups were synthesized and their biological activities were evaluated as inhibitors of acetohydroxyacid synthase (AHAS, EC 2.2.1.6). Besides their strong in vitro inhibition against plant AHAS, compounds 3e and 3f also display 80-100% post-emergence herbicidal activities in greenhouse bioassay at 1500 g/ha dosage. The assay of exogenous branched-chain amino acids supplementation on rape root growth of 3e suggests that the herbicidal activity has relationship with AHAS inhibition.
- Li, Zai-Shun,Wang, Wei-Min,Lu, Wei,Niu, Cong-Wei,Li, Yong-Hong,Li, Zheng-Ming,Wang, Jian-Guo
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supporting information
p. 3723 - 3727
(2013/07/25)
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- DBU-Mediated cleavage of aryl- and heteroaryl disulfides
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The capacity of the nitrogen nucleophile, 1,8-diazabicyclo[5.4.0]undec-7- ene (DBU) to reduce aryl- and heteroaryl disulfides to the corresponding mercaptans is demonstrated. While dicarboxylated disulfide analogues afford the mono-DBU disulfide salts, as confirmed by X-ray crystallography, the corresponding methyl esters are cleaved normally. ARKAT-USA, Inc.
- Nyoni, Dubekile,Lobb, Kevin A.,Kaye, Perry T.,Caira, Mino R.
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experimental part
p. 245 - 252
(2012/05/31)
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- Electrosynthesis of fluorinated benzo[ b ]thiophene derivatives
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Anodic fluorination of benzo[b]thiophene derivatives provided a complex mixture of di- and trifluorinated products. On the other hand, anodic fluorination of 3-oxo-2,3-dihydrobenzo[b]thiophene and methyl 3-oxo-2,3-dihydrobenzo[b]thiophene-2-carboxylate gave the corresponding monofluorinated products selectively in moderate yields. Anodic fluorination of methyl α-(2-cyanophenylthio)acetate followed by intramolecular cyclization provided 3-amino-2-fluorobenzo[b]thiophene in excellent yield. Georg Thieme Verlag Stuttgart · New York.
- Yin, Bin,Inagi, Shinsuke,Fuchigami, Toshio
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experimental part
p. 1313 - 1317
(2011/07/08)
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- Oxidation of thiols using K2S2O8 in ionic liquid
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A green, straightforward, and novel method for oxidation of thiols to the corresponding disulfides is reported using K2S2O8 in the ionic liquid 1-butyl-3-methylimidazolium bromide [(bmim)Br] at 65-70C. The corresponding disulfides were obtained in excellent yield and short reaction time.
- Hajipour, Abdol R.,Mostafavi, Majid,Ruoho, Arnold E.
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experimental part
p. 1920 - 1923
(2010/02/28)
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- Carboxy pyridinium bromide perbromide reagents, part I: Selective oxidation of thiols and sulfides
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Efficient and convenient oxidation of aliphatic and aromatic thiols to disulfides and of sulfides to sulfoxides with pyridinium hydrobromide perbromide (PHBP), nicotinic acid hydrobromide perbromide (NAHBP), and 2,6-dicarboxy pyridinium hydrobromide perbromide (DCPHBP) in a solvent or under solvent free conditions and at ambient temperature is introduced. Copyright Taylor & Francis Group, LLC.
- Lakouraj, Moslem M.,Ghodrati, Keivan
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experimental part
p. 1432 - 1439
(2009/05/07)
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- N-(2-Alkoxycarbonylbenzenesulfeny)benzimidazoles as nitrogen-, sulfur-, and carbon-sulfenylation reagents
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N-(2-Alkoxycarbonylbenzenesulfenyl)benzimidazoles reacted with nucleophiles such as amides, imidates, thiols, Grignard reagents, and active methylene compounds to yield the corresponding sulfenylated products: N-acylsulfenamides, N-sulfenylimidates, disulfides, sulfides, and sulfenylated active methylene compounds, respectively.
- Shimizu, Masao,Fukazawa, Hidenori,Inoue, Jun'ichi,Abe, Yoshimoto,Konakahara, Takeo
-
-
- SULPHONIUM SALT INITIATORS
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Compounds of the formula (I), (II), (III), (IV) and wherein, R is hydrogen, C1-C20alkyl; C2-C20alkyl interrupted by one or more O; is -L-X-R2 or - L-R2; R1 has ofr example one of the meanings as given for R; R2 is a monovalent sensitizer or photoinitiator moiety; Ar1 and Ar2 for example independently of one another are phenyl substituted by C1-C20alkyl, halogen or OR3; or are unsubstituted naphthyl, anthryl, phenanthryl or biphenylyl; or are naphthyl, anthryl, phenanthryl or biphenylyl substituted by C1-C20alkyl, OH or OR3; or are -Ar4-A-Ar3; Ar3 is unsubstituted phenyl naphthyl, anthryl, phenanthryl or biphenylyl; or is phenyl, naphthyl, anthryl, phenanthryl or biphenylyl substituted by C1-C20alkyl, OR3 or benzoyl; Ar4 is phenylene, naphthylene, anthrylene or phenanthrylene; A is a direct bond, S, O or C1-C20alkylene; X is CO, C(O)O, OC(O), O, S or NR3 ; L is C1-C20alkylene or C2-C20alkylene interrupted by one or more O; R3 is C1-C20alkyl or C1-C20hydroxyalkyl; and Y is an anion, are suitable as photolatent acid generators.
- -
-
Page/Page column 69; 11
(2008/06/13)
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- Inexpensive, one-pot synthesis of unsymmetrical disulfides using 1-chlorobenzotriazole
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A new synthesis of unsymmetrical disulfides is described. The reaction of a thiol R1SH with 1-chlorobenzotriazole (BtCl) at -78 °C in DCM affords a high-yielding conversion to R1SBt without appreciable formation of the symmetrical disulfide R1SSR1. R1SBt is then reacted with R2SH to form the unsymmetrical disulfide in a one-pot sequence with green character that avoids the use of toxic and harsh oxidizing agents. The methodology has been developed for synthesis of various types of disulfides.
- Hunter, Roger,Caira, Mino,Stellenboom, Nashia
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p. 8268 - 8271
(2007/10/03)
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- Benzo[b]furane and benzo[b]thiophene derivatives
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The present invention relates to benzo[b]furane and benzo[b]thiophene derivatives of the general formula IV as the free base or salts thereof and their use.
- -
-
Page/Page column 18
(2008/06/13)
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- Benzoyloxymethyl p-toluenethiosulfonate: A crystalline, stable synthetic equivalent for+CH2S+
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Benzoyloxymethyl p-toluenethiosulfonate has been developed as a reagent for the one-pot preparation of α-sulfide disulfides and the corresponding symmetrical bissulfide disulfides. The reagent is effective for systems bearing terminal aryl groups. CSIRO 2005.
- Kabir, S. M. Humayun,Langler, Richard F.
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p. 362 - 367
(2007/10/03)
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- 2-(1H-INDOLYLSULFANYL)-BENZYL AMINE DERIVATIVES AS SSRI
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The present invention relates to aniline derivatives of the general formula I and their use as serotonin reuptake inhibitors and preferably also norepinephrine reuptake inhibitors in the treatment of depression, anxiety, affective disorders, pain disorders, attention deficit hyperactivity disorder (ADHD) and stress urinary incontinence.
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Page/Page column 69
(2008/06/13)
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- Oxidation of thiols with 1-butyl-4-aza-1-azoniabicyclo[2.2.2]octane dichromate (BABOD) under non-aqueous conditions
-
The preparation of 1-butyl-4-aza-1-azoniabicyclo[2.2.2]octane dichromate and the use of this reagent for selective oxidation of aromatic and aliphatic thiols to their corresponding disulfides under non-aqueous conditions is reported.
- Hajipoura,Bagheri, Hamid,Ruoho, Arnold E.
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p. 286 - 287
(2007/10/03)
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- Oxidation of thiols to the corresponding symmetric disulfides with benzyltriphenylphosphonium peroxodisulfate (BTPPD) under nonaqueous conditions
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This article describes the preparation of benzyltriphenylphosphonium peroxodisulfate (BTPPD), an efficient and mild reagent for oxidation of a variety of aromatic and aliphatic thiols to the corresponding disulfides in refluxing acetonitrile. The experimental procedure is simple and the products are easily isolated in excellent yields.
- Hajipour, Abdol R.,Ruoho, Arnold E.
-
p. 1277 - 1281
(2007/10/03)
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- Process Development of 1,2-Benzisothiazolin-3(2H)-one by Replacing of the Toxic Materials
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1,2-Benzisothiazolin-3(2H)-one (2) was synthesized by 2,2′- dithiodibenzoic acid (1) with acetamide or urea in high yield via one-pot amidation-cyclization process.
- Jin, Chun Keun,Moon, Jung-Kyen,Lee, Woo Song,Nam, Keun Soo
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p. 1967 - 1968
(2007/10/03)
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- Oxidation of thiols to the corresponding disulfides with tetramethylammonium chlorochromate under non-aqueous conditions
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This paper describes the preparation of tetramethylammonium chlorochromate (TMACC) as an efficient and mild reagent for oxidation in refluxing acetonitrile of a variety of aromatic and aliphatic thiols, giving the corresponding disulfides; the experimental procedure is simple, and the products are easily isolated in excellent yields.
- Hajipour, Abdol R.,Ruoho, Arnold E.
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p. 547 - 549
(2007/10/03)
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- Oxidative coupling of thiols to disulfides by piperazinium dichromate
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Aliphatic and aromatic thiols are oxidized to the corresponding disulfides in the presence of piperazinium dichromate under mild condition.
- Movassagh,Lakouraj,Ghodrati
-
p. 1293 - 1295
(2007/10/03)
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- Oxidative coupling of thiols by pyridinium chlorochromate in solution and solvent free conditions
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Oxidative coupling of aromatic and aliphatic thiols is achieved efficiently by pyridinium chlorochromate in solution and solvent free conditions. Omitting the solvent does not change the reaction time and product yield significantly, while the need of using the solvent is suppressed and workup procedure becomes easier.
- Salehi,Farrokhi,Gholizadeh
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p. 2777 - 2781
(2007/10/03)
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- Silica sulfuric acid/NaNO2 as a novel heterogeneous system for production of thionitrites and disulfides under mild conditions
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Neat chlorosulfonic acid reacts with silica gel to give silica sulfuric acid in which sulfuric acid is immobilized on the surface of silica gel via covalent bond. Thiols can be readily converted to their corresponding thionitrites with a combination of silica sulfuric acid, wet SiO2 and sodium nitrite in dichloromethane at room temperature. Disulfides result from the homolytic cleavage of the sulfur-nitrogen bond of the unstable thionitrites and subsequent coupling of the resultant thiyl radicals.
- Zolfigol, Mohammad Ali
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p. 9509 - 9511
(2007/10/03)
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- A general and highly regio and stereoselective method for the synthesis of (E)-2-(2-arylvinyl)-3,1-benzoxathiin-4-ones through palladium-copper catalysis
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A palladium-copper-catalysed procedure for the synthesis of (E)-2-(2-arylvinyl)-3,1-benzoxathiin-4-ones 5a-5h is developed. 3-[2-(Methoxycarbonyl)phenylthio]propyne 2 reacts with aryl iodides 3a-3h in the presence of bis(triphenylphosphine)palladium(II) dichloride, copper(I) iodide and triethylamine in acetonitrile to furnish the disubstituted alkynes 4a-4h in good yields (70-84%). These on alkaline hydrolysis and subsequent cyclisation of the carboxylic acids formed with copper(I) iodide (20 mol%) and triethylamine in tetrahydrofuran under reflux afford (E)-2-(2-arylvinyl)-3,1-benzoxathiin-4-ones 5a-5h in 61-70% yield rather than the expected benzoxathiepinones 6. The reactions of (E)-2-(2-arylvinyl)-3,1-benzoxathiin-4-ones 5a and 5g with nucleophites and the hydrogenation of compounds 5a, 5b and 5d are also studied.
- Nandi, Bidisha,Kundu, Nitya G.
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p. 1649 - 1655
(2007/10/03)
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- Thiol-dependent DNA cleavage by 3H-1,2-benzodithiol-3-one 1,1-dioxide
-
Hydrodisulfides (RSSH) have previously been implicated as key intermediates in thiol-triggered oxidative DNA damage by the antitumor agent leinamycin. In an effort to better understand DNA damage by RSSH and to expand on the number and type of chemical systems that produce this reactive intermediate, the ability of 3H-1,2-benzodithiol-3-one 1,1-dioxide (11) to serve as a thio-dependent DNA cleaving agent has been investigated. The findings reported here indicate that reaction of 11 with thiols results in release of RSSH and subsequent oxidative DNA strand cleavage. (C) 2000 Elsevier Science Ltd. All rights reserved.
- Breydo, Leonid,Gates, Kent S.
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p. 885 - 889
(2007/10/03)
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- A facile synthesis of 1,2-benzisothiazolin-3-ones from thiosalicylates
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Synthesis of 1,2-benzisothiazolin-3-ones by cyclization of 2- sulfenamoylbenzoates, which were prepared from amination of thiosalicylates by hydroxylamine-O-sulfonic acid, was examined. Although treatment of methyl 2-sulfenamoylbenzoate on heating gave unexpected 2-(2- methoxycarbonylphenylthio)-1,2-benzisothiazolin-3-one, the treatment with base at room temperature afforded 1,2-benzisothiazolin-3-one in a good yield.
- Shimizu, Masao,Kikumoto, Hisashi,Konakahara, Takeo,Gama, Yasuo,Shibuya, Isao
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p. 3005 - 3012
(2007/10/03)
-
- Caro's acid supported on silica gel. Part 1: Oxidative coupling of thiols to disulfides
-
Mild and efficient method for preparation of disulfides from thiols is described using Caro's acid supported on silica gel.
- Movassagh,Lakouraj,Ghodrati
-
p. 3597 - 3603
(2007/10/03)
-
- Novel method for preparation of symmetric disulfides from thiols using enzyme catalysis
-
Mild and efficient method for preparation of variety of symmetric disulfides from oxidation of thiols using horseradish peroxidase or mushroom tyrosinase as catalyst is described.
- Sridhar,Kumara Vadivel,Bhalerao
-
p. 1499 - 1502
(2007/10/03)
-
- A new class of anti-HIV-1 agents targeted toward the nucleocapsid protein NCp7: The 2,2'-dithiobisbenzamides
-
As part of the National Cancer Institute's Drug Screening Program, a new class of antiretrovirals active against the human immunodeficiency virus HIV-1 has been identified, and the HIV-1 nucleocapsid protein NCp7 was proposed as the target of antiviral action. The 2,2'-dithiobis-[4'-(sulfamoyl)benzanilide] (3x) and the 2,2'-dithiobis(5-acetylamino)benzamide (10) represented the prototypic lead structures. A wide variety of 2,2'-dithiobisbenzamides were prepared and tested for anti-HIV-1 activity, cytotoxicity, and their ability to extrude zinc from the zinc fingers for NCp7. The structure-activity relationships demonstrated that the ability to extrude zinc from NCp7 resided in the 2,2'-dithiobisbenzamide core structure. The 3,3' and the 4,4' isomers were inactive. While many analogs based upon the core structure retained the zinc extrusion activity, the best overall anti-HIV-1 activity was only found in a narrow set of derivatives possessing carboxylic acid, carboxamide, or phenylsulfonamide functional groups. These functional groups were more important for reducing cytotoxicity than improving antiviral potency or activity vs NCp7. All of the compounds with antiviral activity also extruded zinc from NCp7. From this study several classes of low μM anti-HIV agents with simple chemical structures were identified as possible chemotherapeutic agents for the treatment of AIDS.
- Domagala, John M.,Bader, John P.,Gogliotti, Rocco D.,Sanchez, Joseph P.,Stier, Michael A.,Song, Yuntao,Vara Prasad,Tummino, Peter J.,Scholten, Jeffrey,Harvey, Patricia,Holler, Tod,Gracheck, Steve,Hupe, Donald,Rice, William G.,Schultz, Robert
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p. 569 - 579
(2007/10/03)
-
- ARYL THIOPYRANO[2,3,4-C,D]INDOLES AS INHIBITORS OF LEUKOTRIENE BIOSYNTHESIS
-
Compounds having the formula I: are inhibitors of 5-lipoxygenase and inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cyto-protective agents. They are also useful in treating angina, cerebral spasm, glomerular nephritis, hepatitis, endotoxemia, psoriasis, uveitis, and allograft rejection and in preventing the formation of atherosclerotic plaques.
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-
-
- Benzothiet-2-ones: Synthesis, Reactions, and Comparison with Benzoxet-2-ones and Benzazetin-2-ones
-
Benzothiet-2-one (5) is obtained as a neat solid, stable below -20 deg C(-45 deg C in solution), by flash vacuum pyrolysis of benzothiophene-2,3-dione (9).Naphthothiet-2-one (21) and naphthothiet-1-one (42) are obtained as stable crystalline solids in near-quantitative yields from the corresponding naphthothiophenediones 20 and 41.Naphthooxet-2-one (31) and naphthoazetin-2-one (36) were generated and observed by IR spectroscopy to be stable below -40 deg C and 0 deg C, respectively.The thietones, oxetones, and azetinones undergo rapid ring-opening reactions with methanol to give the corresponding carboxylic acid esters.They undergo thermal CO elimination with concomitant Wolff-type ring contraction to thioketenes (17, 25, 45), ketenes (30), and nitriles (37), respectively.The di-, oligo-, and polymerization of the thietones has been elucidated.Naphthothiet-1-one (42) reacts with 1-thiocarbonyl-1H-indene (45) to give cycloaddition product 46.Naphthothietones 21 and 42 react with dicyclohexylcarbodiimide to furnish 2-imino-1,3-thiazin-4-one derivatives 47 and 49.
- Wentrup, Curt,Bender, Harald,Gross, Gerhard
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p. 3838 - 3847
(2007/10/02)
-
- Chemistry of Sulfenic Acids. 7. Reason for the High Reactivity of Sulfenic Acids. Stabilization by Intramolecular Hydrogen Bonding and Electronegativity Effects
-
It is proposed that the reason sulfenic acids (RSOH) are so reactive and usually not isolated or even detected is that they form thiosulfinates (RS(O)SR) so readily.This is a consequence of the sulfenic acid hydrogen-bonded dimer, 1, which lowers the energy of activation for thiosulfinate formation.The stability of the few sulfenic acids that have been isolated can be explained in terms of steric, electronic, and intramolecular hydrogen-bonding effects which prevent dimer formation.The importance of these effects on the stability of simple unstable sulfenic acids was demonstrated by flash vacuum pyrolysis (FVP) and the thiosulfinate/vinyl sulfoxide ratio.A novel, high yield, rearrangement of sulfenic acid 19f to 1,3-benzothiazine 26 was observed.
- Davis, Franklin A.,Jenkins, Linda A.,Billmers, Robert L.
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p. 1033 - 1040
(2007/10/02)
-