- Reactions of 2-lithiated indoles with elemental sulfur. Formation of pentathiepino[6,7-b]indoles and indoline-2-thiones
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The reactions of 2-lithiated indole and 1-methylindole with elemental sulfur have been studied, leading e.g. to a rational approach to pentathiepino[6,7-b]indoles 5 and 10. Notable amounts of the previously known tetrathiocino[5,6-b:8,7-b′]diindole 11 could be observed as a side reaction in the preparation of 10. Treatment of the anions of indoline-2-thiones 6 or 7 with sulfur also gave the pentathiepins 5 or 10, respectively. In addition, a convenient and clean lithiation route to indoline-2-thione (6) has been developed.
- Rewcastle, Gordon W,Janosik, Tomasz,Bergman, Jan
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- Preparation of Benzothiopyrano[2,3-b]indoles by thereaction of 1,3-dihydroindole-2-thiones with certain dienophiles
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Benzothiopyrano[2,3-b]indoles were prepared by the cyclization of 1,3-dihydroindole-2-thiones with varions dienophiles. The 1,3-dihydroindole-2- thiones were readily synthesized by the reaction of oxindole with P2S5 followed by a piperidine-mediated condensation of the resulting thioindole with a suitable aromatic aldehyde.
- Kamila, Sukanta,Biehl, Ed
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- Synthesis of thieno[2,3-b]indole-2,3-diones and their ring expansions induced by diazomethane
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Indole-2-thione 3 reacted quickly with oxalyl chloride to yield thieno[2,3-b]indole-2,3-dione 4 together with the isomer thiazolo[3,2-a]indole-2,3-dione 5. These thieno[2,3-b]indole-2,3diones underwent ring expansions when treated with diazomethane and e.g. thieno[2,3-b]indole-2,3-dione 4 gave the thiopyrano derivative 16, after two insertions.
- Berg, Robert,Bergman, Jan
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- Synthesis of 2-(Arylthio)indolenines via Chemoselective Arylation of Thio-Oxindoles with Arynes
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A chemoselective S-arylation reaction of thio-oxindoles with arynes is presented. The reaction was performed under mild conditions and provided a straightforward synthesis of 2-(arylthio)indolenines in good to excellent yields. Besides, this simple operat
- Saputra, Adi,Fan, Rong,Yao, Tuanli,Chen, Jian,Tan, Jiajing
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supporting information
p. 2683 - 2688
(2020/05/18)
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- Indolylthio glycosides as effective building blocks for chemical glycosylation
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The S-indolyl (SIn) anomeric moiety was investigated as a new leaving group that can be activated for chemical glycosylation under a variety of conditions including thiophilic and metal-assisted pathways. Understanding of the reaction pathways for the SIn moiety activation was achieved via the extended mechanistic study. Also reported is how the new SIn donors fit into selective activation strategies for oligosaccharide synthesis.
- Demchenko, Alexei V.,Shrestha, Ganesh,Panza, Matteo,Singh, Yashapal,Rath, Nigam P.
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p. 15885 - 15894
(2021/01/19)
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- Nickel(ii)-catalyzed asymmetric thio-Claisen rearrangement of α-diazo pyrazoleamides with thioindoles
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A nickel(ii) catalyzed enantioselective thio-Claisen rearrangement of α-diazo pyrazoleamides with thioindoles was realized with modified chiral N,N′-dioxide ligands, affording a variety of C3-substituted indole derivatives in high yields (up to 95%) with excellent enantioselectivities (up to 96% ee) under mild reaction conditions. A possible transition state model was proposed based on previous reports and the X-ray crystal structure of the catalyst.
- Yang, Wei,Lin, Xiaobin,Zhang, Yongyan,Cao, Weidi,Liu, Xiaohua,Feng, Xiaoming
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supporting information
p. 10002 - 10005
(2020/09/15)
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- Tandem Double-Cross-Coupling/Hydrothiolation Reaction of 2-Sulfenyl Benzimidazoles with Boronic Acids
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A new tandem palladium-catalyzed reaction involving a Suzuki-Miyaura coupling, a desulfenylative coupling, and a hydrothiolation of a triple bond is reported. Notably, the desulfenylative coupling occurs without copper(I) assistance and the hydrothiolatio
- Lopes, Alexandra Basilio,Choury, Mickael,Wagner, Patrick,Gulea, Mihaela
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supporting information
p. 5943 - 5947
(2019/08/26)
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- One-pot mild and efficient synthesis of [1,3]thiazino[3,2-: A] indol-4-ones and their anti-proliferative activity
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A base mediated environmentally benign one-pot efficient methodology has been developed for the synthesis of [1,3]thiazino[3,2-a]indol-4-ones using indoline-2-thiones and propiolate esters in aqueous medium. The conjugate addition of thiones first results in ethyl (3-(indol-2-yl)thio)acrylates in situ, which subsequently undergoes intramolecular cyclization to produce indole-fused thiazin-4-ones in good to excellent yields. The cytotoxic screening of the synthesized compounds using MTT assay revealed the anti-proliferative nature of these frameworks against triple negative breast cancer cell lines with the highest activity emanating from 4H-[1,3]thiazino[3,2-a]indol-4-one and 8-methyl-2-propyl-4H-[1,3]thiazino[3,2-a]indol-4-one compounds.
- Rhodes, Steven,Short, Spencer,Sharma, Sidhika,Kaur, Ramneet,Jha, Mukund
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supporting information
p. 3914 - 3920
(2019/04/30)
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- Metal-free hydroamination of alkynes: A mild and concise synthesis of thiazolo[3,2- a ]indoles and their cytotoxic activity
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A metal-free, mild and efficient method for the synthesis of thiazolo[3,2- a ]indoles has been developed starting from indoline-2-thiones. The reaction methodology involves first the formation of thermally labile 2-(prop-2-ynylthio)-1 H -indole intermedia
- Bhave, Vishakha S.,Hojo, Ryoga,Jha, Mukund,Rhodes, Steven,Short, Spencer
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supporting information
p. 4263 - 4270
(2019/11/13)
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- A THIONATION PROCESS AND A THIONATING AGENT
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A process for transforming a group >C=O (I) in a compound into a group >C=S (II) or into a tautomeric form of group (II) in a reaction giving a thionated reaction product, by use of crystalline P2S5·2 C5H5N as a thionating agent. A thionating agent which is crystalline P2S5·2 C5H5N
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Page/Page column 10
(2012/08/27)
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- A thionation process and a thionating agent
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A process for transforming a group >C=O (I) in a compound into a group >C=S (II) or into a tautomeric form of group (II) in a reaction giving a thionated reaction product, by use of crystalline P2S5·2 C5H5N as a thionating agent. A thionating agent which is crystalline P2S5·2 C5H5N.
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Page/Page column 14
(2012/08/14)
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- Thionations using a P4S10-pyridine complex in solvents such as acetonitrile and dimethyl sulfone
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Tetraphosphorus decasulfide (P4S10) in pyridine has been used as a thionating agent for a long period of time. The moisture-sensitive reagent has now been isolated in crystalline form, and the detailed structure has been determined by X-ray crystallography. The thionating power of this storable reagent has been studied and transferred to solvents such as acetonitrile in which it has proven to be synthetically useful and exceptionally selective. Its properties have been compared with the so-called Lawesson reagent (LR). Particularly interesting are the results from thionations at relatively high temperatures (165 °C) in dimethyl sulfone as solvent. Under these conditions, for instance, acridone and 3-acetylindole could quickly be transformed to the corresponding thionated derivatives. Glycylglycine similarly gave piperazinedithione. At these temperatures, LR is inefficient due to rapid decomposition. The thionated products are generally cleaner and more easy to obtain because in the crystalline reagent, impurities which invariably are present in the conventional reagents, P4S 10 in pyridine or LR, have been removed. 2011 American Chemical Society.
- Bergman, Jan,Pettersson, Birgitta,Hasimbegovic, Vedran,Svensson, Per H.
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experimental part
p. 1546 - 1553
(2011/06/11)
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- Identification of indoline-2-thione analogs as novel potent inhibitors of α-melanocyte stimulating hormone induced melanogenesis
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Based on the hits, 3,4-dihydroquinazoline-2-thione (1) and benzimidazole-2-thione (2), a series of indole-2-thione (3) and indole-2-thiol inhibitors (4) of melanogenesis were designed, synthesized and evaluated in melanoma B16 cells under the stimulant of α-melanocyte stimulating hormone (α-MSH). The indole-2-thione compounds (3a-g) exhibited an effective inhibitory activity on melanin synthesis. The Structure-Activity Relationship (SAR) studies of 2 have revealed that in potent inhibitor 3a (>100% inhibition at 30μM, IC50=1.40μM) the role of nitrogen (3-N) at 3-position is insignificance. In addition, the hydrophobic substituents of 3 were better than the hydrophilic one. However, conversion of thione (-C=S, 3) to thiol (-C-SH, 4) led to decrease in the potency.
- Thanigaimalai, Pillaiyar,Lee, Ki-Cheul,Sharma, Vinay Kumar,Sharma, Niti,Roh, Eunmiri,Kim, Youngsoo,Jung, Sang-Hun
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experimental part
p. 1285 - 1288
(2011/11/12)
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- Highly efficient synthesis of thieno[2,3-b]indole derivatives
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Thieno[2,3-b]indole derivatives were efficiently prepared via the reaction of 1,3-dihydro-2H-indole-2-thiones with α-bromo-substituted ketones or aldehydes and in the presence of Et3N (Scheme 2 and Table). The reaction took place under very mil
- Boeini, Hassan Zali
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experimental part
p. 1268 - 1272
(2009/10/16)
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- Synthesis and biological evaluation of 3-(substituted-benzylidene)-1,3- dihydro-indolin derivatives as human protein kinase CK2 and p60c-Src tyrosine kinase inhibitors
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Human protein kinase CK2 is an ubiquitous serine/threonine kinase that is typically found in tetrameric complexes consisting of two catalytic (α and/or α′) and two regulatory β subunits. Although there is growing evidence that besides the participation of CK2 in a complex series of cellular functions, this protein kinase is involved in cell viability, cell proliferation, and neoplastic transformation. In the present study, a series of 3-(substituted-benzylidene)-1,3-dihydro-indolin-2-thione derivatives and the corresponding indolin-2-one congeners were tested for their inhibition of human recombinant protein kinase CK2 in vitro. The efficacy of these compounds was compared with their inhibitory results of p60c-Src tyrosine kinase. It was found that 3-(substituted-benzylidene)-1,3-dihydro-indolin-2-thione derivatives are more effective than indolin-2-one congeners for the inhibition of CK2 and p60c-Src tyrosine kinase.
- Oelgen, Suereyya,Goetz, Claudia,Jose, Joachim
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p. 715 - 718
(2008/01/27)
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- Concise syntheses of the cruciferous phytoalexins brassilexin, sinalexin, wasalexins, and analogues: Expanding the scope of the Vilsmeier formylation
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(Chemical Equation Presented) Efficient syntheses of the phytoalexins brassilexin, sinalexin, and analogues are demonstrated through the application of the Vilsmeier formylation to indoline-2-thiones followed by a new aqueous ammonia workup procedure. Similarly, a very concise two-pot synthesis of the phytoalexins wasalexins using sequential formylation-amination of indolin-2-ones is described. Remarkably, this novel aqueous ammonia workup allows the sequential one-pot formylation-amination, expanding substantially the scope of the Vilsmeier formylation of both indoline-2-thiones and indolin-2-ones. The examination of the formylation-amination reaction and optimization of conditions, as well as the syntheses and antifungal activities of several brassilexin analogues, are reported.
- Pedras, M. Soledade C.,Jha, Mukund
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p. 1828 - 1834
(2007/10/03)
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- Synthesis and anti-tyrosine kinase activity of 3-(substituted-benzylidene)- 1, 3-dihydro-indolin derivatives: Investigation of their role against p60 c-Src receptor tyrosine kinase with the application of receptor docking studies
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A series of 3-(substituted-benzylidene)-1, 3-dihydro-indolin-2-thione derivatives were synthesized as modified congeners of 3-(substituted- benzylidene)-1, 3-dihydro-indolin-2-one series. All the synthesized compounds were examined for their in vitro anti-tyrosine kinase activity against p60 c-Src. The activity results revealed that compounds (Z)-3-(4′-Dimethylamino-benzylidene)-1, 3-dihydro-indolin-2-thione (12) (E)-3-(2′, 6′-Dichloro-benzylidene)-1, 3-dihydro-indolin-2-thione (13) and (E)-3-(3′-Hydroxy-4′-methoxy-benzylidene)-1, 3-dihydro-indolin-2-thione (19) exhibited anti-tyrosine kinase activity with IC50 value of 21.91, 21.20 and 30.92 μM, respectively. These results are comparable to PP1 [1-tert-Butyl-3-p-tolyl-1H-pyrazolo[3, 4-d]pyrimidine-4-yl-amine] (IC50 = 0.17 μM), which is reported as a potent and selective p60c-Src tyrosine kinase inhibitor. Some thio congeners are found to be more potent than oxo derivatives; however, no significant correlation was observed between the activity profiles of these two series. Docking program was used to investigate the docking mode of each compound at the active site. Among all of the compounds, only (Z)-3-(2′-Chloro-benzylidene)-1, 3-dihydro-indolin-2-one (8) and (E)-3-(3′-Nitro-benzylidene)-1, 3-dihydro-indolin-2-thione (16) were docked at the active site where the PP1 was embedded.
- Olgen, Sureyya,Akaho, Eiichi,Nebioglu, Dogu
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p. 497 - 506
(2007/10/03)
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- Conversion of indoline-2-thione and oxindole to isatin - Some new observations
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Indoline-2-thione (1) and oxindole, when treated separately with ceric ammonium nitrate adsorbed on silica gel (CAN-SiO2) in acetonitrile, furnished isatin (2) as the sole product, whereas Montmorillonite K10 clay alone converted oxindole to isatin in a dry reaction.
- Banerjee, Satarupa,Sarkar, Sandipan,Basak, Ramkrishna,Chakrabarty, Manas
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p. 169 - 170
(2007/10/03)
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- Heterocyclic compounds, their preparation and their therapeutic use
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A compound of formula (I): STR1 wherein Y1, Y2, Y3 and Y4 are each hydrogen, halogen, nitro, cyano, hydroxyl, thiol, amino, alkyl, haloalkyl, alkylthio, a protected or unprotected carboxyl, a protected or unprotected sulfonamide, or tetrazol; one of R1 and R2 is hydrogen, alkyl, aryl, aralkyl, oxazolyl, or a protected or unprotected carboxyl and the other of R1 and R2 is hydrogen, alkyl, aryl or aralkyl; and R3 is hydrogen or an amino protecting group, and pharmaceutically acceptable salts or esters thereof. The compounds are effective for treating dementia, Alzheimer's disease and delirium and are effective as sedatives.
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- Biotransformation of the Brassica Phytoalexin Brassicanal A by the Blackleg Fungus
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The biotransformation of the brassica phytoalexin brassicanal A by the blackleg fungus [Leptosphaeria maculans (Desm.) Ces. et de Not., asexual stage Phoma lingam (Tode ex Fr.) Desm] was investigated. Three main biotransformation products were detected and isolated; their chemical structures were determined by spectroscopic methods and concomitant synthesis. Additionally, the antifungal activities of brassicanal A and its biotransformation products were compared. Overall, the biotransformation pathway suggests that the blackleg fungus has enzymes to carry out this biotransformation different from those involved in the biotransformation of the brassica phytoalexin brassinin.
- Pedras, M. Soledade C.,Khan, Abdul Q.
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p. 3403 - 3407
(2007/10/03)
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- Heterocyclic Aromatic Anions with 4n + 2 ?-Electrons
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Equilibrium acidities in DMSO for several cyclic carboxamides, thiocarboxamides, esters, and sulfones that form anions possessing 4n + 2 electrons have been measured.Aromatic stabilization energies (ASEs) for these anions have been estimated by comparing
- Bordwell, Frederick G.,Fried, Herbert E.
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p. 4218 - 4223
(2007/10/02)
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- INDOLE- AND PYRROLE-SULFONIUM YLIDES
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Electrophilic substitution of indole and pyrrole with sulfoxides and acid anhydrides leads to the formation of indole-3-sulfonium salts and pyrrole-2-sulfonium salts.These are deprotonated with potassium carbonate to give indole-3-sulfonium ylides and pyr
- Hartke, Klaus,Teuber, Dorothee,Gerber, Hans-Dieter
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p. 3261 - 3270
(2007/10/02)
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- A NEW PREPARATION OF N-ARYL-1-ALKYNESULPHENAMIDES AND THEIR THERMAL REARRANGEMENTS INTO INDOLINE-2-THIONES
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Reaction of 1-alkynyl-lithio derivatives with N,N-dialkylaminosulphenyl chlorides 3a,b affords the N,N-dialkyl-1-alkynesulphenamides 4.When treated with stoichiometric amounts of a substituted benzenamine and methanesulfonic (or trifluoroacetic) acid, the sulphenamides 4, are converted into N-aryl-1-alkynesulphenamides 6-20.On heating in benzene, many of these sulphenamides 6-20 undergo -sigmatropic rearrangements followed by cyclisation of the intermediate thioketenes yielding the substituted indoline-2-thiones 21-30.
- Baudin, Jean-Bernard,Julia, Sylvestre A.,Lorne, Robert
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p. 181 - 188
(2007/10/02)
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- Tetrahydrothiopyrano[2,3-b]indole derivatives
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Tetrahydrothiopyrano[2,3-b]indole derivative represented by the formula I: STR1 wherein R1 is hydrogen, alkyl, hydroxyalkyl, alkenyl, aralkyl, aryl, --COR5 (wherein R5 is alkyl, alkenyl, aryl or alkoxy) or STR2 (wherein Y is alkylene, oxoalkylene, hydroxyalkylene and R6 and R7 are each hydrogen or alkyl): R2 is hydrogen or alkyl; R3 is hydrogen, alkyl, hydroxyalkyl, alkenyl, aralkyl, aryl or dialkylaminoalkyl or STR3 is pyrrolidino, piperidino, piperazino, 4-alkylpiperazino, 4-arylpiperazino or morpholino; R4 is hydrogen or alkyl; A is methylene, alkylmethylene, ethylene, alkylethylene; X is hydrogen or one or two groups selected from the group consisting of halogen, alkyl, alkoxy, hydroxy and halogenoalkyl; and n is an integer of 0 to 2 and its pharmaceutically acceptacle salts; synthesized from 2-propargylthioindole or 2-(4-hydroxy-2-butynylthio)-indole; useful as analgesic and anti-inflammatory agent.
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- Substituted indoles
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Substituted thioindoles and their sulfoxide and sulfone derivatives, useful as cardiac rate lowering agents and for other pharmacological properties, and precursors therefor.
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