- Efficient synthesis of 2-imino-1,2-dihydroquinolines and 2-imino-thiochromenes via copper-catalyzed domino reaction
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A domino approach to 2-imino-1,2-dihydroquinolines and 2-imino-thiochromenes from sulfonyl azides, alkynes, and 2-acyl anilines or the potassium salt of 2-mercapto-benzaldehyde has been developed. This one-pot method is efficient and versatile.
- Cui, Sun-Liang,Wang, Jing,Wang, Yan-Guang
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Read Online
- DEPALMITOYLATING COMPOSITIONS AND THE USE THEREOF
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Disclosed herein, inter alia, are depalmitoylating compounds, compositions, and methods of use thereof.
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- A cascade deprotonation/intramolecular aldol reaction of α-carbonyl sulfonium ylides with 2-mercaptoindole-3-carbaldehydes and 2-mercaptobenzaldehydes to access thieno[2,3-b]indoles and benzothiophenes
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The first catalyst-free cascade deprotonation/intramolecular aldol reaction of α-carbonyl sulfonium ylides with 2-mercaptoindole-3-carbaldehydes and 2-mercaptobenzaldehydes was developed. A series of thieno[2,3-b]indoles and benzothiophenes were smoothly obtained in high to excellent yields. The salient features of the protocol include catalyst-free conditions, an environment-friendly solvent, broad substrate scope, and large-scale synthesis.
- Yang, Lei,Zhou, Shun,Zhao, Jian-Qiang,You, Yong,Wang, Zhen-Hua,Zhou, Ming-Qiang,Yuan, Wei-Cheng
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p. 3678 - 3686
(2021/05/05)
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- Visible-light induced photo-click and release strategy between monoarylsydnone and phenoxylfumarate
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We report a visible-light induced photo-click and release platform between monoarylsydnone (MASyd) and phenoxylfumarates. The pyrazoline produced by the cycloaddition undergoes a photo-aromatization to form a fluorescent pyrazole. Meanwhile, the photo-aro
- Li, Baolin,Liu, Hui,Shen, Xin,Xie, Xinyu,Yu, Zhipeng,Zhao, Xiaohu,Zheng, Tingting,Zheng, Yuanqin
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p. 8135 - 8138
(2021/08/23)
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- Synthesis and evaluation of antileishmanial and cytotoxic activity of benzothiopyrane derivatives
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In continuation of our efforts to identify promising antileishmanial agents based on the chroman scaffold, we synthesized several substituted 2H-thiochroman derivatives, including thiochromenes, thichromanones and hydrazones substituted in C-2 or C-3 with carbonyl or carboxyl groups. Thirty-two compounds were thus obtained, characterized, and evaluated against intracellular amastigotes of Leishmania (V) panamensis. Twelve compounds were active, with EC50 values lower than 40 μM, but only four compounds displayed the highest antileishmanial activity, with EC50 values below 10 μM; these all compounds possess a good Selectivity Index > 2.6. Although two active compounds were thiochromenes, a clear structure-activity relationship was not detected since each active compound has a different substitution pattern.
- Ortiz, Cristian,Echeverri, Fernando,Robledo, Sara,Lanari, Daniela,Curini, Massimo,Qui?ones, Wiston,Vargas, Esteban
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- INHIBITORS OF GLUCOSE TRANSPORTERS (GLUTS)
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The present invention relates to 2,6-methanobenzo[g][1]oxacin-4-onecompounds and their analog compounds and pharmaceutically acceptable salts thereof as selective inhibitor of glucose transporters 1 and 3 (GLUTs 1 and 3), to methods of preparing said compounds, and to the use thereof as pharmaceutically active agents, especially for the prophylaxis and/or treatment of metabolic diseases, immunological diseases, autoimmune diseases, inflammation, graft versus host disease, cancer, and metastasis thereof. Furthermore, the present invention is directed to pharmaceutical composition comprising at least one of 2,6-methanobenzo[g][1]oxacin-4-one compounds and their analog compounds.
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Page/Page column 62
(2020/03/29)
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- Silver-Mediated Oxidative Decarboxylative Trifluoromethylthiolation of Coumarin-3-carboxylic Acids
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The introduction of trifluoromethylthio groups into organic compounds, in particular heterocycles, is important because of the prevalence of these structures in medicinally and agriculturally relevant molecules. Herein, the silver-mediated oxidative decarboxylative trifluoromethylthiolation of coumarin-3-carboxylic acids is reported. This methodology utilizes existing carboxylic acid functionalities for the direct conversion to CF3S groups and results in a broad scope of 3-trifluoromethylthiolated coumarins, including analogues of natural products, in moderate to excellent yields.
- Li, Minghao,Petersen, Jeffrey L.,Hoover, Jessica M.
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p. 638 - 641
(2017/02/10)
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- ALDEHYDE CAPTURE LIGATION TECHNOLOGY FOR SYNTHESIS OF AMIDE BONDS
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The present invention relates to ligation agents and their use in making an amide ligation product. Methods of making the ligation agents are also disclosed.
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Paragraph 0233; 0234
(2017/09/13)
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- Efficient synthesis of benzothiophenes by [4+1] cycloaddition of 2-mercaptobenzaldehyde derivatives with isocyanides
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We developed a [4+1] cycloaddition reaction of isocyanides with 2-mercaptobenzaldehydes and/or their disulfide derivatives, promoted by LiI·2H2O, to afford benzothiophene derivatives in moderate to good yields. Isocyanides, 2-mercaptobenzaldehydes and disulfide derivatives of various types were used successfully in the reaction.
- Soeta, Takahiro,Shitaya, Saori,Okuno, Takumi,Fujinami, Shuhei,Ukaji, Yutaka
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p. 7901 - 7905
(2016/11/18)
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- Three-component 2-aryl substituted benzothiophene formation under transition-metal free conditions
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A base-mediated 2-aryl substituted benzothiophene formation from 2-bromobenzene aldehydes, benzylic esters and elemental sulfur under transition-metal-free conditions is described. Various 2-aryl substituted benzothiophene were efficiently obtained under mild conditions.
- Jiang, Pengcheng,Che, Xingzong,Liao, Yunfeng,Huang, Huawen,Deng, Guo-Jun
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p. 41751 - 41754
(2016/05/24)
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- Aldehyde capture ligation for synthesis of native peptide bonds
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Chemoselective reactions for amide bond formation have transformed the ability to access synthetic proteins and other bioconjugates through ligation of fragments. In these ligations, amide bond formation is accelerated by transient enforcement of an intramolecular reaction between the carboxyl and the amine termini of two fragments. Building on this principle, we introduce an aldehyde capture ligation that parlays the high chemoselective reactivity of aldehydes and amines to enforce amide bond formation between amino acid residues and peptides that are difficult to ligate by existing technologies.
- Raj, Monika,Wu, Huabin,Blosser, Sarah L.,Vittoria, Marc A.,Arora, Paramjit S.
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supporting information
p. 6932 - 6940
(2015/06/16)
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- ALDEHYDE CAPTURE LIGATION TECHNOLOGY FOR SYNTHESIS OF AMIDE BONDS
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The present invention relates to ligation agents and their use in making an amide ligation product. Methods of making the ligation agents are also disclosed.
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- Peptide 2-formylthiophenol esters do not proceed through a Ser/Thr ligation pathway, but participate in a peptide aminolysis to enable peptide condensation and cyclization
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Peptide thiol salicylaldehyde (SAL) esters unexpectedly do not follow a Ser/Thr ligation pathway to react with peptides containing N-terminal Ser/Thr, but proceed towards a peptide aminolysis in DMSO. The reaction takes place even at a low substrate concentration (1 mM). The method has been successfully used to synthesize several natural cyclic peptides, with a high ratio of monocyclic to dimeric products.
- Tung, Chun Ling,Wong, Clarence T. T.,Li, Xuechen
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supporting information
p. 6922 - 6926
(2015/06/25)
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- Ascorbate mediated copper catalyzed reductive cross-coupling of disulfides with aryl iodides
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The concept of using ascorbic acid as a mediator/ reducing agent in a Cu(i) catalyzed process is introduced and further demonstrated on a cross-coupling reaction of aryl iodides with disulfides.
- Martinek, Marek,Korf, Michal,Srogl, Jiri
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supporting information; experimental part
p. 4387 - 4389
(2010/08/06)
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- Efficient method for synthesis of 2-acetylbenzo(b)thiophene and its derivatives, the key synthons for 5-lipoxygenase inhibitors
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An efficient method was developed for synthesis of 2-acetylbenzo(b) thiophene (2a), the key intermediate for zileuton (1). Synthesis involves treatment of 2-chlorobenzaldehyde (5a) with tert-butylmercaptan (6) to form 2-(tert-butylthio)benzaldehyde (7a), which upon treatment with HBr in water gave the disulfide derivative 2,2'-disulfanediyldibenzaldehyde (8a) in 97% yield. Finally, the reaction of 8a with acetylacetone (9) and 1-chloroacetone (10) gave 2-acetylbenzo(b)thiophene (2a) in 94% yield. The methodology is general and suitable for the preparation of its derivatives, 2b-d. Copyright
- Chemburkar, Sanjay R.,Anderson, David G.,Reddy, Rajarathnam E.
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experimental part
p. 1887 - 1894
(2010/09/07)
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- NOVEL CHROMENE AND THIOCHROMENE CARBOXAMIDE DERIVATIVES, METHODS FOR PREPARING SAME AND THERAPEUTIC APPLICATIONS OF SAME
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The present invention relates to novel chromene or thiochromene carboxamide derivatives, the preparation of same, pharmaceutical compositions of same and the use of same as dopamine D3 ligands as a medicament for central nervous system disorders.
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Page/Page column 41
(2008/06/13)
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- Synthesis and biological evaluation of sulfur-containing cinnamate and salicylate derivatives
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UV irradiation induced formation of reactive oxygen radical species and matrix metalloproteinases (MMPs) are thought to be involved in photo-damage to the skin. MMP-1 is the major collagenolytic enzyme responsible for collagen destruction in skin tissue. To develop new anti-photoaging agents, a series of 2,2′-dithiocinnamate derivatives and 2,2′-dithio or 2-thiobenzoate derivatives were designed and synthesized. The biological activities of the synthesized compounds were assayed for ABTS [2,2′-azinobis-(3-ethyl-benzo- thiazoline-6-sulfonic acid)] radical scavenging activity, MMP-1 inhibitory activity, and cytotoxicity to human dermal fibroblast cells. Compounds with potential of resistance to UV irradiation were identified. These compounds are expected to be useful for preventing photo-damage to the skin.
- Chiang, Chih-Chia,Chang, Tsu-Chung,Tsai, Hou-Jen,Hsu, Ling-Yih
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p. 369 - 373
(2008/09/20)
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- Dialkyl 2H-1-benzothiopyran-2,3-dicarboxylates via intramolecular Wittig reaction
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Reaction of 3-mercaptobenzaldehyde (1) with dialkyl acetylenedicarboxylate in the presence of triphenylphosphine leads to the corresponding 2H-1-benzothiopyran 2,3-diesters.
- Hekmatshoar, Rahim,Javanshir, Shahrzad,Heravi, Majid M.
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- Synthesis and electrochemical characterization of CoII, Ni II, and CuII complexes with organic N2S 2-type ligands derived from 2-thio-substituted benzaldehydes and aromatic amines
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Transition metal complexes (NiII, CoII, and Cu II) with tetradentate N2S2-type ligands (L), which are reaction products of 2-thio-substituted benzaldehydes with aromatic amines (3-aminopyridine or 2-a
- Beloglazkina,Shimorsky,Majouga,Moiseeva,Zyk
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p. 2189 - 2199
(2008/09/18)
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- Oxidation of thiols to bisulfides using silica chloride as a heterogeneous catalyst
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Silica chloride is used as a selective and effective heterogeneous catalyst for the rapid conversion of thiols to disulfides with quantitative yields in a very short period of time. Copyright
- Sathe, Manisha,Ghorpade, Ramarao,Kaushik, Mahabir Parshad
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p. 1048 - 1049
(2007/10/03)
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- Synthesis of substituted dihydrobenzothiopyrans and dihydrobenzopyrans by cation-mediated cyclisation reactions
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Treatment with acid of thiosalicylaldehyde- and salicylaldehyde-derived phenyl 3-phenyl-2-propenyl thioethers and ethers possessing latent oxonium ion functionality triggers simple or tandem cyclisation to give substituted dihydrobenzothiopyrans and dihyd
- Bonfanti, Jean-Fran?ois,Craig, Donald
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p. 3719 - 3723
(2007/10/03)
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- Titanium reagents for the synthesis of 2-substituted benzo[b]thiophenes on the solid phase
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Titanium(IV) benzylidenes (Schrock carbenes) bearing a masked sulfur nucleophile in the ortho position were generated from thioacetals with use of low-valent titanocene complex Cp2Ti[P(OEt)3]2 and alkylidenated Merrifield resin-bound esters to give enol ethers. Treatment of the resin-bound enol ethers with a 5:5:90 mixture of TFA, TFAA, and dichloromethane led to cleavage from resin, removal of the tert- butyldimethylsilyl (TBDMS) protecting group, and concomitant cyclization to complete the traceless solid-phase synthesis (SPS) of benzothiophenes. Switching the nature of the linker from acid-stable to acid-sensitive ensured good purity.
- Roberts, Christine F.,Hartley, Richard C.
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p. 6145 - 6148
(2007/10/03)
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- Synthesis and biological activity of sulfur-containing aryl-aldehyde Schiff bases.
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A series of chemically modified aryl-aldehyde Schiff bases has been synthesized and tested for their antioxidant activity and radiation protection. We observed that disulfide-containing aryl-aldehyde Schiff base 6c exhibited potent free radical scavenging
- Jiang, Jyh-Jia,Chang, Tsu-Chung,Hsu, Wen-Lin,Hwang, Jing-Min,Hsu, Ling-Yih
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p. 1307 - 1310
(2007/10/03)
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- Simple and selective oxidation of thiols to disulfides with dimethylsulfoxide catalyzed by dichlorodioxomolybdenum(VI)
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Selective and quantitative conversion of thiols to disulfides was effected by dimethyl sulfoxide under mild conditions catalyzed by dichlorodioxomolybdenum(VI).
- Sanz, Roberto,Aguado, Rafael,Pedrosa, María R.,Arnáiz, Francisco J.
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p. 856 - 858
(2007/10/03)
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- Asymmetric copper complexes of stable mono-tert-butyl monobenzyl dithioether N2S2 ligands
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Attempts to form copper complexes of new N2S2 compounds, in which one sulfur donor is a thiolate and the other a thioether, have been made by protecting the potential thiolate through tert-butylation and benzylating the other. Wherea
- Nation, David A.,Taylor, Max R.,Wainwright, Kevin P.
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p. 3001 - 3009
(2007/10/03)
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- Oxidative cleavage of aryl or alkyl tert-butyl sulfides with dimethyl sulfoxide/hydrobromic acid to form symmetrical aryl or alkyl disulfides
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The use of dimethyl sulfoxide and hydrobromic acid as a reagent to oxidatively cleave (tert-butylthio)benzaldehydes, aryl or alkyl tert-butyl sulfides to their corresponding symmetrical disulfides is discussed. A brief mechanistic rationale is given based upon several control experiments.
- Dickman,Chemburkar,Konopacki,Elisseou
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p. 573 - 574
(2007/10/02)
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- Process for the production of 2-acetylbenzo [β]thiophenes
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A process for the production in high yield of 2-acetylbenzo[β]thiophene and its alkyl and alkoxy substituted derivatives by converting a 2-halobenzaldehyde to a 2,2'-dithiobis(benzaldehyde) intermediate and reacting that intermediate successively with 2,4-pentanedione and chloroacetone in the presence of base.
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- An Efficient and Convenient Synthesis of 2-Mercaptobenzaldehyde
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An efficient and convenient synthesis of 2-mercaptobenzaldehyde (1) is described.
- Kasmai, Hamid S.,Mischke, Steven G.
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p. 763 - 765
(2007/10/02)
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- Chemistry of Sulfenic Acids. 7. Reason for the High Reactivity of Sulfenic Acids. Stabilization by Intramolecular Hydrogen Bonding and Electronegativity Effects
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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)
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- Iron Complexes of N-Substituted Thiosalicylideneimines. Part 1. Synthesis and Reactions with Oxygen and Carbon Monoxide
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Iron(II) complexes with N-substituted bidentate and tetradentate thiosalicylideneimines can be prepared by the reaction of bis(thiosalicylaldehydato)iron(II) with appropriate primary amines.The bidentate compounds show S = 2 spin states while a number of the tetradentate compounds have the unusual S = 1 state.The tetradentate complexes react with CO to form monocarbonyl complexes and with O2 to form FeIII μ-oxo-bridged derivatives.Some evidence is presented to support the preliminary formation at low temperatures of a dinuclear iron(III) peroxo-species as the precursor of the μ-oxo-compounds.Several spin-paired FeIII compounds containing SN2-bonded tridentate ligands are also reported.
- Marini, Peter J.,Murray, Keith S.,West, Bruce O.
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p. 143 - 152
(2007/10/02)
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