- New class of benzothiophene morpholine analogues with high selectivity and affinity were designed and evaluated for anti-drug addiction
-
To probe the mechanism of dopamine receptors in drug addiction and look for potential new methods for treating this disease, we have designed and synthesized benzothiophene morpholine analogues that were considered as dopamine D3 receptor-selective ligands. Radioligand binding assay was used to determine the binding affinity of target compounds. Members of this class have great selectivity and binding affinity in D3 receptor. In addition, the ability of these compounds to mitigate the symptoms of addiction from opioids was investigated in animal behavior patterns, and we have found that two compounds (18a and 18d) have good affinity in the D3R and exhibit the efficacy of anti-drug addiction in morphine-dependent mice induced by naloxone.
- Cai, Jin,Wang, Yuhong,Chen, Xixi,Ji, Min
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p. 634 - 649
(2022/03/01)
-
- Fragment-based drug design targeting syntenin PDZ2 domain involved in exosomal release and tumour spread
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Syntenin stimulates exosome production and its expression is upregulated in many cancers and implicated in the spread of metastatic tumor. These effects are supported by syntenin PDZ domains interacting with syndecans. We therefore aimed to develop, throu
- Barral, Karine,Benmansour, Fatiha,Derviaux, Carine,Egea-Jimenez, Antonio Luis,Feracci, Mikael,Garcia, Manon,Hoffer, Laurent,Morelli, Xavier,Roche, Philippe,Zimmermann, Pascale,Leblanc, Rapha?l
-
-
- Synthesis of benzothiazonine by rhodium-catalyzed denitrogenative transannulation of 1-sulfonyl-1,2,3-triazole and thiochromone
-
A facile synthesis of multi-functionalized benzothiazonine was achieved by the rhodium-catalyzed denitrogenative annulation of 1-sulfonyl-1,2,3-triazole and thiochromone. In view of the excellent atom economy, broad substrate scope and easy availability of starting materials, the protocol provided an efficient strategy for the construction of mediumN,S-heterocycles.
- Duan, Shengguo,Jablasone, Saygbechi T.,Li, Chuan-Ying,Xu, Ze-Feng,Ye, Zihang
-
supporting information
p. 5758 - 5761
(2021/07/12)
-
- Biocatalytic Oxidation of Sulfides to Sulfones
-
This paper describes a method for the biocatalytic oxidation of sulfides. During the screening of microorganisms using pure cultures of bacteria and fungi for the oxidation of sulfides, it was observed that a number of strains of microorganisms, were able to oxidize various sulfides (1-4), but the desired sulfoxide was either not obtained or obtained only as a minor product. A close observation of the reaction showed complete oxidation and thus sulfone (5-8) formation had occurred in these cases. Sulfones are used to stabilize intermediates like α-radicals, α-anions etc. and also used as cationic synthons in many known reactions. This prompted us to explore the sulfone synthesis by biocatalytic route. Approximately 20% of the strains tested (400 bacterial and 200 fungal) showed the formation of sulfone with conversion rate varying from 3 to 100% based on TLC analysis. There were two strains of fungi, Aspergillus ochraceus MTCC 5245 and Penicillium Funiculosum MTCC 5246 which showed excellent biocatalytic activity for oxidation sulfides to corresponding sulfones in high yield. In all these strains, the product was different from corresponding standard sulfoxide prepared by oxidation with m-chloroperbenzoic acid but well corresponded with the standard sample of sulfone prepared by oxidation of the corresponding sulfides with oxone. The identity of sulfones in all cases was confirmed by 1H NMR. Published by Oriental Scientific Publishing Company
- Dhiman, Shefali
-
p. 250 - 255
(2021/03/29)
-
- Synthesis and anti cervical cancer activity of novel 5H-thiochromeno [4,3-d]pyrimidines
-
A series of novel 5H-Thiochromeno[4,3-d]pyrimidine derivatives were synthesized, purified and characterized by different spectroscopy techniques such as1H NMR,13C NMR, Mass and Elemental Analysis. The new compounds were evaluated for their anti-cervical cancer activity on Human Cervical Cell Line HeLa. They were found to be potent anti-cervical cancer agents with GI50 values less than 10 μg/mL with respect to positive control drug Adriamycin.
- Naliapara, Yogesh,Pandya, Dhananjay
-
p. 294 - 302
(2020/04/21)
-
- Cu(I)-Catalyzed Enantioselective Alkynylation of Thiochromones
-
A highly efficient asymmetric synthesis of chiral thiochromanones is developed via Cu(I)/phosphoramidite catalyzed asymmetric alkynylation of thiochromones under mild reaction conditions. The catalyst system is tolerant of various thiochromone precursors and terminal alkynes. The established asymmetric transformation provides different enatiomeric-enriched thiochromanones with more molecular complexity and enables access to chiral thioflavanones, a subgroup of flavonoid by further functionalization.
- Chang, Xiaoyong,Lin, Zhenyang,Meng, Ling,Ngai, Ka Yan,Wang, Jun
-
supporting information
p. 1155 - 1159
(2020/02/26)
-
- Synthesis method of 2,3-dihydrothiochromene-4-one and derivative thereof
-
The invention discloses a synthesis method of 2,3-dihydrothiochromene-4-one and a derivative thereof. The synthesis method is characterized in that a substituted and unsubstituted aromatic thiophenolcompound is used as a raw material, and reacts with acrylic acid to generate corresponding aromatic thiopropionic acid, and cyclizing is performed under the action of concentrated sulfuric acid to obtain the corresponding 2,3-dihydrothiochromene-4-one and the derivative thereof. According to the invention, the raw materials use acrylic acid and concentrated sulfuric acid, so that the raw materialsare easy to obtain, the cost is low, and the feeding is easy; and the post-treatment only needs acidification, extraction, washing and solvent evaporation, so that the method is simple in post-treatment, high in yield, low in cost and suitable for industrial production.
- -
-
Paragraph 0020-0022
(2020/02/14)
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- 2-Sulfonylpyrimidines Target the Kinesin HSET via Cysteine Alkylation
-
Supernumerary centrosomes are a source of aneuploidy, and cells have adopted different mechanisms to avoid multipolar mitoses. The kinesin HSET is required for pseudo-bipolar mitoses in cancer cells with amplified centrosomes and suppression of HSET activ
- F?rster, Tim,Shang, Erchang,Shimizu, Kenshiro,Sanada, Emiko,Sch?lermann, Beate,Huebecker, Mylene,Hahne, Gernot,López-Alberca, Maria Pascual,Janning, Petra,Watanabe, Nobumoto,Sievers, Sonja,Giordanetto, Fabrizio,Shimizu, Takeshi,Ziegler, Slava,Osada, Hiroyuki,Waldmann, Herbert
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supporting information
p. 5486 - 5496
(2019/06/24)
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- Synthesis of Novel Pterocarpen Analogues via [3?+?2] Coupling-Elimination Cascade of α,α-Dicyanoolefins with Quinone Monoimines
-
By employing triethylamine as a catalyst, [3?+?2] coupling-elimination cascade of α,α-dicyanoolefins with quinone monoimines was realized. The reactions afforded various novel pterocarpen analogues with generally moderate yields (up to 75%). In addition, a plausible reaction mechanism was proposed.
- Chen, Hui,Zhao, Sihan,Cheng, Shaobing,Dai, Xingjie,Xu, Xiaoying,Yuan, Weicheng,Zhang, Xiaomei
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p. 1672 - 1683
(2019/04/08)
-
- Chroman-4-one hydrazones derivatives: synthesis, characterization, and in vitro and in vivo antileishmanial effects
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In searching for better therapeutic alternatives to treat cutaneous leishmaniasis (CL), this study aimed to obtain and evaluate the efficacy and toxicity of new chroman-4-one hydrazones derivatives. Compounds were prepared and characterized, and then transformed into hydrazonas for molecular optimization. Their cytotoxicity was tested in different cell types using an in vitro MTT assay and the efficacy was evaluated using an in vitro macrophage intracellular amastigotes of Leishmania (Viannia) panamensis and L. (V) braziliensis by flow cytometry. The therapeutic effect of two formulations of chroman-4-one hydrazones on the CL induced by L. (V) braziliensis in golden hamsters was determined according to the size of lesions after treatment. The effect of these compounds in the production of inflammatory mediators and cell migration was also determined by in vitro assays using human fibroblasts models. Neither cytotoxicity nor genotoxicity was observed. The benzoic acid hydrazone derivative 2-(2,3-dihydro-4H-1-benzopyran-4-ylidene) hydrazide (4), produced a higher percentage of clinical cures, followed by benzoic acid, 2-(2,3-dihydro-4H-1-benzothiopyran-4-ylidene) hydrazide (3), while benzoic acid, 2-(2,3-dihydro-1,1-dioxide-4H-1-benzothiopyran-4-ylidene) hydrazide (5) and 4-pyridinecarboxylic acid, 2-(4H-1-benzopyran-4-ylidene) hydrazide (6) caused a poor therapeutic response. The compound 4 also showed an effect in the inflammatory and fibroblast migration processes. In conclusion, this is the first report of antileishmanial activity combined with inflammatory and wound healing properties. Results obtained here suggest that this strategy could be a good alternative for development of new drugs for the treatment of CL.
- Upegui, Yulieth,Rios, Karina,Qui?ones, Wiston,Echeverri, Fernando,Archbold, Rosendo,Murillo, Javier D.,Torres, Fernando,Escobar, Gustavo,Vélez, Iván D.,Robledo, Sara M.
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p. 2184 - 2199
(2019/11/03)
-
- Development of conjugate addition of lithium dialkylcuprates to thiochromones: Synthesis of 2-alkylthiochroman-4-ones and additional synthetic applications
-
Lithium dialkylcuprates undergo conjugate addition to thiochromones to afford 2-alkylthiochroman-4-ones in good yields. This approach provide an efficient and general synthetic approach to privileged sulfur-containing structural motifs and valuable precursors for many pharmaceuticals, starting from common substrates-thiochromones. Good yields of 2-alkyl-substituted thiochroman-4-ones are attained with lithium dialkylcuprates, lithium alkylcyanocuprates or substoichiometric amount of copper salts. The use of commercially available inexpensive alkyllithium reagents will expedite the synthesis of a large library of 2-alkyl substituted thiochroman-4-ones for additional synthetic applications.
- Bass, Shekinah A.,Parker, Dynasty M.,Bellinger, Tania J.,Eaton, Aireal S.,Dibble, Angelica S.,Koroma, Kaata L.,Sekyi, Sylvia A.,Pollard, David A.,Guo, Fenghai
-
supporting information
(2018/08/21)
-
- Cu-Catalyzed Conjugate Addition of Grignard Reagents to Thiochromones: An Enantioselective Pathway for Accessing 2-Alkylthiochromanones
-
The enantioselective incorporation of alkyl groups in thiochromones was realized for the first time by a Cu/(R, S)-PPF-P t Bu 2 -catalyzed conjugate addition of Grignard reagents to thiochromones. With this method, a series of 2-methylthiochromanones were obtained in good yields (up to 96% yield) with moderate-to-good ee values (up to 87% ee). The established method expedites the synthesis of a large library of chiral thiochromanones for further synthetic applications and biological studies.
- Luo, Shihui,Meng, Ling,Yang, Qingxiong,Wang, Jun
-
supporting information
p. 2071 - 2075
(2018/09/18)
-
- Hydrazone derivatives enhance antileishmanial activity of thiochroman-4-ones
-
Cutaneous leishmaniasis (CL) is a neglected tropical disease, which causes severe skin lesions. Due to the lack of effective vaccines, and toxicity or reduced effectiveness of available drugs in addition to complex and prolonged treatments, there is an urgent need to develop alternatives for the treatment for CL with different mechanisms of action. In our effort to search for new promising hits against Leishmania parasites we prepared 18 acyl hydrazone derivatives of thiochroman-4-ones. Compounds were evaluated for their in vitro antileishmanial activity against the intracellular amastigote form of Leishmania panamensis and cytotoxic activity against human monocytes (U-937 ATCC CRL-1593.2). Our results show that derivatization of the thiochroman-4-ones with acyl hydrazones significantly enhances the antileishmanial activity. Among the compounds tested semicarbazone and thiosemicarbazone derivatives of thioflavanone 19 and 20 displayed the highest antileishmanial activities, with EC50 values of 5.4 and 5.1 μM and low cytotoxicities (100.2 and 50.1 μM respectively), resulting in higher indexes of selectivity (IS).
- Vargas, Esteban,Echeverri, Fernando,Upegui, Yulieth A.,Robledo, Sara M.,Qui?ones, Wiston
-
-
- Rh-Catalyzed Conjugate Addition of Arylzinc Chlorides to Thiochromones: A Highly Enantioselective Pathway for Accessing Chiral Thioflavanones
-
A highly efficient asymmetric synthesis of chiral thioflavanones is developed via conjugate addition of arylzinc reagents to thiochromones using Rh(COD)Cl2/(R)-3,4,5-MeO-MeOBIPHEP catalyst. This method overcomes catalyst poisoning and substrate inertness and affords a series of chiral thioflavanones (2-arylthiochroman-4-ones) in good yields (up to 91% yield) with excellent ee values (up to 97% ee). The established asymmetric synthesis paves the way for further pharmaceutical studies.
- Meng, Ling,Jin, Ming Yu,Wang, Jun
-
p. 4986 - 4989
(2016/10/14)
-
- Synthesis, characterization and anti-cancer activity of hydrazide derivatives incorporating a quinoline moiety
-
Identification of the novel (E)-N1-((2-chloro-7-methoxyquinolin-3-yl)methylene)-3-(phenylthio) propanehydrazide scaffold 18 has led to the development of a new series of biologically active hydrazide compounds. The parent compound 18 and new quinoline derivatives 19-26 were prepared from the corresponding quinoline hydrazones and substituted carboxylic acids using EDC-mediated peptide coupling reactions. Further modification of the parent compound 18 was achieved by replacement of the quinoline moiety with other aromatic systems. All the newly synthesized compounds were evaluated for their anti-cancer activity against the SH-SY5Y and Kelly neuroblastoma cell lines, as well as the MDA-MB-231 and MCF-7 breast adenocarcinoma cell lines. Analogues 19 and 22 significantly reduced the cell viability of neuroblastoma cancer cells with micromolar potency and significant selectivity over normal cells. The quinoline hydrazide 22 also induced G1 cell cycle arrest, as well as upregulation of the p27kip1 cell cycle regulating protein.
- Bingul, Murat,Tan, Owen,Gardner, Christopher R.,Sutton, Selina K.,Arndt, Greg M.,Marshall, Glenn M.,Cheung, Belamy B.,Kumar, Naresh,Black, David StC.
-
-
- Borontribromide-mediated C-C bond formation in cyclic ketones: A transition metal free approach
-
Borontribromide (BBr3) is a well-known demethylating agent. The current investigation was focused on a new application of borontribromide as a C-C bond forming agent in cyclic ketones. In this study, borontribromide mediated C-C bond formation reactions of tetralones, chromenone, thiochromenone and indanones were explored. A methoxy group containing ketones showed selective C-C bond formation reaction instead of demethylation of the methoxy group. MM2 steric energy calculations for the final products showed that the reaction favored the formation of exo- or endo-cyclic double bond containing products, depending upon their low MM2 steric energy in a specific frame structure, as observed in X-ray crystallography. A comprehensive crystallographic and pi-stacking analysis of product 10a demonstrated the formation of 10a as an enantiomeric mixture, and its centre of inversion was stabilized by a set of three unique pi-pi interactions.
- Ahmad, Imran,Pathak, Vinay,Vasudev, Prema G.,Maurya, Hardesh K.,Gupta, Atul
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p. 24619 - 24634
(2014/07/07)
-
- Direct Michael addition to electron-deficient alkenes using diorganyl dichalcogenides (Te/S) and NaBH4/PEG-400
-
Nucleophilic species of tellurium and sulfur were generated in situ from the reaction of the respective diorganyl dichalcogenides with NaBH4in PEG-400 as solvent and selectively added to electron-deficient alkenes. Chalcogenolate anions were directly added at mild conditions by this simple procedure and in all cases furnished the respective Michael adducts in short reaction times and good yields.
- Perin, Gelson,Borges, Elton L.,Peglow, Thiago J.,Lenard?o, Eder J.
-
supporting information
p. 5652 - 5655
(2014/12/11)
-
- Inhibition of monoamine oxidase by 8-phenoxymethylcaffeine derivatives
-
A recent study has reported that a series of 8-benzyloxycaffeines are potent and reversible inhibitors of both human monoamine oxidase (MAO) isoforms, MAO-A and -B. In an attempt to discover additional caffeine derivatives with potent MAO inhibitory activities, and to contribute to the known structure-activity relationships of MAO inhibition by caffeine derived compounds, the present study investigates the MAO inhibitory potencies of series of 8-phenoxymethylcaffeine and 8-[(phenylsulfanyl)methyl]caffeine derivatives. The results document that the 8-phenoxymethylcaffeine derivatives act as potent reversible inhibitors of MAO-B, with IC50 values ranging from 0.148 to 5.78 μM. In contrast, the 8-[(phenylsulfanyl)methyl]caffeine derivatives were found to be weak inhibitors of MAO-B, with IC50 values ranging from 4.05 to 124 μM. Neither the 8-phenoxymethylcaffeine nor the 8-[(phenylsulfanyl)methyl]caffeine derivatives exhibited high binding affinities for MAO-A. While less potent than the 8-benzyloxycaffeines as MAO-B inhibitors, this study concludes that 8-phenoxymethylcaffeines may act as useful leads for the design of MAO-B selective inhibitors. Such compounds may find application in the therapy of neurodegenerative disorders such as Parkinson's disease. Using molecular docking experiments, this study also proposes possible binding orientations of selected caffeine derivatives in the active sites of MAO-A and -B.
- Okaecwe, Thokozile,Swanepoel, Abraham J.,Petzer, Anél,Bergh, Jacobus J.,Petzer, Jacobus P.
-
experimental part
p. 4336 - 4347
(2012/08/28)
-
- Synthesis and in vitro anti-hepatitis B virus activity of 6H-[1]benzothiopyrano[4,3-b]quinolin-9-ols
-
A series of novel 6H-[1]benzothiopyrano[4,3-b]quinoline derivatives were prepared and evaluated for their anti-hepatitis B virus (HBV) activity and cytotoxicity in human hepatoblastoma-derived liver Hep-G2 cells. Compounds 10g, 10h, 10j, 10l and 10o were found to be potent anti-HBV compounds with IC50 values less than 50 μM. The most promising compound was 10l, with an IC50 value of 14.7 μM and a SI value of 12.4. This is the first report of the anti-HBV effects of 6H-[1]benzothiopyrano[4,3-b] quinolin-9-ols. Crown Copyright
- Jia, Wei,Liu, Yajing,Li, Wei,Liu, Yan,Zhang, Dajun,Zhang, Peng,Gong, Ping
-
experimental part
p. 4569 - 4574
(2009/10/17)
-
- Borax-catalyzed and pH-Controlled selective oxidation of organic sulfides by H2O2: An environmentally clean protocol
-
The selective oxidation of sulfides to sulfoxides and sulfones was achieved in high yields at: room temperature with borax as a recyclable catalyst and H2O2 as the terminal oxidant by varying the pH of the reaction medium. The borax/H2O2 system can chemoselectively oxidize alkyl and aryl sulfides in the presence of oxidation-prone functional, groups such as C=C, -CN, and -OH.
- Hussain, Sahid,Bharadwaj, Saitanya K.,Pandey, Ravindra,Chaudhuri, Mihir K.
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experimental part
p. 3319 - 3322
(2011/03/17)
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- Fluoride ion-catalyzed conjugate addition for easy synthesis of 3-sulfanylpropionic acid from thiol and α,β-unsaturated carboxylic acid
-
3-Sulfanylpropionic acids are obtained in excellent yields by proceeding through a simple, mild, and efficient procedure utilizing tetrabutylammonium fluoride (TBAF) as catalyst.
- Gao, Shijay,Tseng, Chi,Tsai, Cheng Hsuan,Yao, Ching-Fa
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p. 1955 - 1961
(2008/09/17)
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- Fluoroboric acid adsorbed on silica-gel (HBF4-SiO2) as a new, highly efficient and reusable heterogeneous catalyst for thia-Michael addition to α,β-unsaturated carbonyl compounds
-
Fluoroboric acid adsorbed on silica-gel (HBF4-SiO2) has been found to be a new and highly efficient heterogeneous catalyst for thia-Michael addition to α,β-unsaturated carbonyl compounds under solvent-free conditions. In the case of
- Sharma, Gaurav,Kumar, Raj,Chakraborti, Asit K.
-
p. 4272 - 4275
(2008/09/21)
-
- Design of potent inhibitors of human β-secretase. Part 1
-
We describe a novel series of potent inhibitors of human β-secretase. These compounds possess the hydroxyethyl amine transition state isostere. A 2.5 A crystal structure of inhibitor 32 bound to BACE is provided.
- Freskos, John N.,Fobian, Yvette M.,Benson, Timothy E.,Bienkowski, Michael J.,Brown, David L.,Emmons, Thomas L.,Heintz, Robert,Laborde, Alice,McDonald, Joseph J.,Mischke, Brent V.,Molyneaux, John M.,Moon, Joseph B.,Mullins, Patrick B.,Bryan Prince,Paddock, Donna J.,Tomasselli, Alfredo G.,Winterrowd, Gregory
-
-
- Solvent-free conjugated addition of thiols to citral using KF/alumina: preparation of 3-thioorganylcitronellals, potential antimicrobial agents
-
A general, clean and easy method for the conjugated addition of thiols to citral promoted by KF/Al2O3 under solvent-free conditions at room temperature or under MW irradiation is described. It was found that the same protocol is appl
- Lenard?o, Eder J.,Ferreira, Patrícia C.,Jacob, Raquel G.,Perin, Gelson,Leite, Fábio P.L.
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p. 6763 - 6766
(2008/02/13)
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- Iodine catalyzed conjugate addition of mercaptans to α,β- unsaturated carboxylic acids under solvent-free condition
-
We have described herein molecular iodine catalyzed Michael addition of thiol to α,β-unsaturated carboxylic acids. This environmentally benign catalytic system (iodine) used under mild and solvent-free conditions to achieve the corresponding adducts in excellent yield.
- Gao, Shijay,Tzeng, Tingkai,Sastry,Chu, Cheng-Ming,Liu, Ju-Tsung,Lin, Chunchi,Yao, Ching-Fa
-
p. 1889 - 1893
(2007/10/03)
-
- SUBSTITUTED BENZO-CONDENSED CYCLOHEXANONE DERIVATIVES AND THE USE THEREOF FOR MEDICAMENT PRODUCTION
-
The invention relates to substituted benzo-condensed cyclohexanone derivatives, to a method for the production thereof, to medicaments containing said derivatives and to the use of the inventive compounds for producing medicaments.
- -
-
Page/Page column 61
(2008/06/13)
-
- SUBSTITUTED ACETOPHENOME AS MS REAGENTS
-
The invention provides reagents and kits for introducing a fixed charge to the side-chain of methionine, and peptides and proteins containing methionine, for selective identification by tandem mass spectrometry. The reagents are based on substituted aceto
- -
-
Page/Page column 15
(2010/02/14)
-
- Kinetics and mechanism of thermal gas-phase elimination of β-substituted carboxylic acids
-
3-Phenoxypropanoic acid (1), 3-(phenylthio)propanoic acid (2), and 4-phenylbutanoic acid (3) were pyrolysed between 520 and 682 K. Analysis of the pyrolysates showed the elimination products to be acrylic acid and the corresponding arene. Pyrolysis of ethyl 3-phenoxypropanoate (4) and its methyl analogue (5), ethyl 3-(phenylthio)propanoate (6) and its methyl counterpart (7), and 3-phenoxypropane nitrile (8) were also investigated between 617 and 737 K. The thermal gas-phase elimination kinetics and product analysis are compatible with a thermal retro-Michael reaction pathway involving a four-membered cyclic transition state.
- Al-Awadi,Abdallah,Dib,Ibrahim,Al-Awadi,El-Dusouqui
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p. 5769 - 5777
(2007/10/03)
-
- A structure-taste study of arylsulfonyl(cyclo)alkanecarboxylic acids
-
A number of sweeteners contain a sulfonyl group. In our current search for new glucophores several new compounds containing such group were obtained. A series of novel 1-phenylsulfonylcyklohexanecarboxylic acids and 2-arylsulfonylalkanecarboxylic acids was obtained and evaluated for their sweet taste quality. It has been found that methyl substituents are of the key importance for the activity of these compounds.
- Lysiak, Violetta,Ratajczak, Aleksander,Mencel, Agnieszka,Jarzembek, Krystyna,Polanski, Jaroslaw
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p. 671 - 675
(2007/10/03)
-
- Nickel chloride catalyzed arylation of 3-mercaptopropionic acid: A facile one step route to 3-aryl mercaptopropionic acids from unactivated aryl halides and arenes
-
Nickel chloride catalyzed arylation of 3-mercaptopropionic acid by (i) unactivated aryl halides (path a) and (ii) diphenyliodonium bromide (path b) gave 3-aryl mercaptopropionic acid (3) in good yield.
- Gogia, Santosh,Sirohi, Reenu,Gupta, Suman,Kishore,Joshi
-
p. 515 - 517
(2007/10/03)
-
- A rapid and efficient synthesis of thiochroman-4-ones under microwave irradiation
-
Thiochroman-4-ones were synthesised by the cyclization of β-arylthiopropionic acids which were prepared by the condensation of the arylthiols with chloropropionic acid under microwave irriadiation within 4min.
- Li, Ji-Tai,Li, Hong-Ya,Li, Hui-Zhang,Xiao, Li-Wei
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p. 394 - 395
(2007/10/03)
-
- Nickel chloride hexahydrate: A novel reagent for Michael addition on α,β-unsaturated acids - A facile one-step route to 3-arylmercaptopropionic acids from thiophenols and α,β-unsaturated acids
-
Michael additions have been successfully carried out in presence of a base, but when an α,β00-unsaturated acid is a substrate, it would be most unlikely for a carboxylate ion bearing α,β-unsaturated site to undergo a Michael addition. This problem has been circumvented in the present paper by carrying out a nickel chloride hexahydrate mediated Michael addition of thiophenols 1a-k on acrylic acid and on cinnamic acid to give 3-aryl mercaptopropionic acids 3a-k in excellent yield.
- Gogia, Santosh,Sirohi, Reenu,Gupta, Suman,Kishore,Joshi
-
p. 1008 - 1011
(2007/10/03)
-
- Chalcogeno Morita-Baylis-Hillman Reaction of 2-(Methylchalcogeno)phenyl Vinyl Ketones with Aldehydes, Ketones, and α-Dicarbonyl Compounds
-
Reactions of 2-(methylchalcogeno)phenyl vinyl ketones 1 and 4 with aldehydes 5 were conducted in the presence of BF3·Et 2O. The reaction was quenched by addition of Et3N and gave the Morita-Baylis-Hillman adducts 6-7 in good yields. When the reaction mixture of 1 with 5a was worked up with saturated aqueous NaHCO3, the sulfonium salt 8a was obtained together with 6. Ketones 10, α-diketones, and α-oxo esters 13, which hardly react in the traditional Morita-Baylis-Hillman reaction, similarly reacted with 2-(methylchalcogeno)phenyl vinyl ketones 1 and 4 to give the Morita-Baylis-Hillman adducts 11-12 and 14-15. Selenochromanones 9 and 16 were obtained together with 7 and 15 from reactions of seleno derivative 4, with 5 and 13 as by-products. The formation mechanism for the sulfonium salt syn-trans-8a is discussed. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
- Kinoshita, Hironori,Kinoshita, Sayaka,Munechika, Yukari,Iwamura, Tatsunori,Watanabe, Shin-Ichi,Kataoka, Tadashi
-
p. 4852 - 4861
(2007/10/03)
-
- Preparation of 1-phenylcyclohexa-2,5-diene-1-carboxylates and their use in free-radical mediated syntheses
-
Synthetic routes to pure 1-phenylcyclohexa-2,5-diene-1-carboxylic acid and derived esters were developed. Esters containing appropriately unsaturated side chains generated the corresponding alkenyl radicals and hence gave good yields of 5-exo ring closure products in organotin-free reactions. Extrusion of phenyl radicals from the intermediate cyclohexadienyl type radicals was not observed, and this alternative β-scission did not compete under any conditions. Yields from alkylations of olefins in analogous intermolecular processes were, however, poor. As a spin-off from the research, it was found that 1-phenylcyclohexa-2,5-diene-1-carboxylic acid (6) was a useful source of hydroxyformyl (formate) radicals in organic solvents.
- Baguley, Paul A.,Jackson, Leon V.,Walton, John C.
-
p. 304 - 309
(2007/10/03)
-
- Synthesis of methoxy-2-quinolones via Pummerer-type cyclization of N-aryl-N-methyl-3-(phenylsulfinyl)propionamides
-
The thionium ions 10 generated by Pummerer reaction of N-aryl-N-methyl-3-(phenylsulfinyl)propionamides 4 caused not only an electrophilic cyclization reaction producing 2-quinolones 8, but also the formation of the vinyl sulfides 5 and 6 in favor of the l
- Toda,Sakagami,Goan,Simakata,Saitoh,Horiguchi,Sano
-
p. 1854 - 1861
(2007/10/03)
-
- Alkyl- and Arylthiodediazoniations of Dry Arenediazonium o-Benzenedisulfonimides. Efficient and Safe Modifications of the Stadler and Ziegler Reactions to Prepare Alkyl Aryl and Diaryl Sulfides
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The reaction between dry arenediazonium o-benzenedisulfonimides 1 and sodium thiolates in anhydrous methanol represents an efficient and safe procedure, of general validity, for the preparation of unfunctionalized or variously functionalized alkyl aryl and diaryl sulfides. As a rule, the reaction temperature was maintained at 0-5°C for the alkylthiodediazoniations and at room temperature (20-25°C) for the arylthiodediazoniations. The sulfide yields are generally high; of the 63 considered examples, 43 gave yields greater than 80% and 13 were between 70% and 80%. Lower yields were obtained only when sterically hindered diazonium salts or thiols were used. A good amount of the o-benzenedisulfonimide (8) was always recovered from the reactions and could be reused to prepare salts 1. The copious experimental data collected in homogeneous conditions have offered several starting points for the study of the mechanism of these reactions.
- Barbero, Margherita,Degani, Iacopo,Diulgheroff, Nicola,Dughera, Stefano,Fochi, Rita,Migliaccio, Mara
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p. 5600 - 5608
(2007/10/03)
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- A general diastereoselective synthesis of spiroacetals related to those in ionophores via the reaction of lactones with cerium(III) γ-cerioalkoxide. MAD reverses the diastereoselectivity of the addition of methylmetallics to a β-keto ether
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The following steps constitute a fairly general and stereoselective synthesis of spiroacetals. 1. Thiophenol is added to acrylic acid. 2. The latter is treated consecutively with butyllithium, CeCl3, and an organolithium compound. 3. The resulting 3-(phenylthio) ketone is either reduced in the presence of zinc ion to yield mainly one diastereomer or treated with methyllithium or methylmagnesium chloride in the presence or absence of methylaluminum bis(2,6-di-tert-butyl-4-methylphenoxide) (MAD, 25) to yield selectively either of two diastereomeric 3-(phenylthio) alcohols. 4. The alcohol is treated with butyllithium, lithium 4,4'-di-tert-butylbiphenylide (LDBB), and CeCl3, to yield a cerium(III) γ-cerioalkoxide, which is added to a lactone, the reaction being quenched with acid. In the addition to the keto ether in the absence of MAD, methyllithium or methylmagnesium chloride give very predominantly the erythro alcohol, presumably via Cram's chelate model, while in the presence of excess MAD, the threo product is very predominant, possibly because each oxygen atom is complexed with the bulky aluminum reagent. The methodology is demonstrated by the preparation of diastereomeric spiroacetals related to those found in a number of natural ionophores by using as the reaction partner of the carboxylate salt, α-lithio tetrahydrofuran or tetrahydropyran, readily generated by reductive lithiation of the corresponding α-(phenylthio) heterocycle with LDBB, and by employing methylmetallics rather than reducing agents for the reaction with the ketone.
- Ahn,Cohen
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p. 3142 - 3150
(2007/10/02)
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- Chemistry of O-silylated ketene acetals: A mild and convenient synthesis of β-lactam antibiotics
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β-Amido sulfoxides (1) reacted with O-silylated ketene acetal (16) in dry acetonitrile in the presence of a catalytic amount of zinc iodide to give the 4-phenylthioazetidin-2-ones (17). Oxidation of 17 with m-chloroperbenzoic acid gave the corresponding s
- Kita,Shibata,Tamura,Miki
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p. 2225 - 2232
(2007/10/02)
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- The Preparation of Some β-Sulfonylacrylate Thioesters and β-Sulfonylvinyl Ketones
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β-Sulfonylacrylate phenyl and t-butyl thioesters, and β-sulfonylvinyl ketones have been prepared by oxidation of the corresponding β-aryl- and β-alkyl-thio compounds.In one case the β-sulfonylvinyl ketone was obtained from an epoxy sulfone.The β-aryl- and β-alkyl-thio compounds were obtained by chlorination-dehydrochlorination of saturated precursors.The reactions of 3-(phenylthio)propionyl chloride with organocadmium and Grignard reagents were used to prepare some of the saturated precursors of the β-sulfonylvinyl ketones.
- Haynes, Richard K.,Vonwiller, Simone C.,Stokes, John P.,Merlino, Louisa M.
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p. 881 - 895
(2007/10/02)
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- Bicycloheptane substituted diamide and its congener prostaglandin analogs
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Bicycloheptane substituted amide prostaglandin analogs are provided having the structural formula STR1 wherein m is 0 to 4; A is --CH=CH-- or --CH2 --CH2 --; n is 1 to 5; Q is --CH=CH--, --CH2 --, STR2 or a single bond; R is CO2 H, CO2 alkyl, CO2 alkali metal, CO2 polyhydroxyamine salt, --CH2 OH, STR3 wherein R4 and R5 are the same or different and are H, lower alkyl, hydroxy, lower alkoxy or aryl, at least one of R4 and R5 being other than hydroxy and lower alkoxy; p is 1 to 4; R1 is H or lower alkyl; q is 1 to 12; R2 is H or lower alkyl; and R3 is H, lower alkyl, lower alkenyl, lower alkynyl, aryl, arylalkyl, lower alkoxy, aryloxy, arylalkyloxy, amino, alkylamino arylamino, arylalkylamino, lower alkyl-S-, aryl-S-, arylalkyl-S-, STR4 (wherein n' is 0, 1 or 2), alkylaminoalkyl, arylaminoalkyl, arylalkylaminoalkyl, alkoxyalkyl, aryloxyalkyl or arylalkoxyalkyl. The compounds are cardiovascular agents useful, for example, in the treatment of thrombotic disease.
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- Bisthioamide-7-oxabicycloheptane prostaglandin analogs
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Bisthioamide-7-oxabicycloheptane prostaglandin analogs are provided having the structural formula STR1 wherein A is --CH=CH-- or --CH2 --CH2 --; n is 1 to 5; R is CO2 H, CO2 lower alkyl or STR2 q is 1 to 12; and R1 is H, lower alkyl, lower alkenyl, lower alkynyl, aryl, arylalkyl, lower alkoxy, aryloxy, arylalkyloxy, amino, alkylamino arylamino, arylalkylamino, lower alkyl-S-aryl-S-, arylalkyl-S-, STR3 (wherein n' is 0, 1 or 2), alkylaminoalkyl, arylaminoalkyl, arylalkylaminoalkyl, alkoxyalkyl, aryloxyalkyl or arylalkoxyalkyl. The compounds are cardiovascular agents useful, for example, in the treatment of thrombotic disease.
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- 7-oxabicycloheptane substituted hydroxamic acid prostaglandin analogs
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7-Oxabicycloheptane substituted hydroxamic acid prostaglandin analogs are provided having the structural formula STR1 wherein A is --CH=CH-- or --CH2 -CH2 --; n is 1 to 5; R is CO2 H, CO2 alkyl, CO2 a
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- 5,6-epoxy-7-oxabicycloheptane substituted diamide prostaglandin analogs
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5,6-Epoxy-7-oxabicycloheptane substituted diamide prostaglandin analogs are provided having the structural formula STR1 wherein A is --CH=CH-- or --CH2 --CH2 --; n is 1 to 5; R is CO2 H, CO2 alkyl, CO2 alkali metal, CO2 polyhydroxyamine salt or STR2 q is 1 to 12; and R1 is H, lower alkyl, lower alkenyl, lower alkynyl, aryl, arylalkyl, lower alkoxy, aryloxy, arylalkyloxy, amino, alkylamino arylamino, arylalkylamino, STR3 (wherein n' is 0, 1 or 2), alkylaminoalkyl, arylaminoalkyl, arylalkylaminoalkyl, alkoxyalkyl, aryloxyalkyl or arylalkoxyalkyl. The compounds are cardiovascular agents useful, for example, in the treatment of thrombotic disease.
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- 7-thiabicycloheptane substituted diamide and its congener prostaglandin analogs
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7-Thiabicycloheptane substituted diamide and congener prostaglandin analogs are provided having the structural formula STR1 wherein m is 1 to 4; A is --CH=CH-- or --CH2 --CH2 --; n is 1 to 5; R is CO2 H, CO2 alkyl, CO2 alkali metal, CO2 polyhydroxyamine salt, --CH2 OH, STR2 wherein R3 and R4 are the same or different and are H, lower alkyl, hydroxy, lower alkoxy or aryl, at least one of R3 and R4 being other than hydroxy and lower alkoxy; p is 1 to 4; Z is STR3 q is 1 to 12; R1 is H or lower alkyl; and R3 is H, lower alkyl, lower alkenyl, lower alkynyl, aryl, arylalkyl, lower alkoxy, aryloxy, arylalkyloxy, amino, alkylamino arylamino, arylalkylamino, STR4 (wherein n' is 0, 1 or 2), alkylaminoalkyl, arylaminoalkyl, arylalkylaminoalkyl, alkoxyalkyl, aryloxyalkyl or arylalkoxyalkyl. The compounds are cardiovascular agents useful, for example, in the treatment of thrombotic disease.
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- 7-OXABICYCLOHEPTANE SUBSTITUTED DIAMIDE AND ITS CONGENER PROSTAGLANDIN ANALOGS USEFUL IN THE TREATMENT OF THROMBOTIC DISEASE
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7-Oxabicycloheptane substituted amide prostaglandin analogs are provided having the structural formula STR1 wherein m is 0 to 4; A is--CH=CH--or--CH 2--CH 2--; n is 1 to 5; Q is--CH=CH--,--CH 2--, STR2 or a single bond; R is CO 2 H, CO 2 alkyl, CO 2 alkali metal, CO 2 polyhydroxyamine salt,--CH 2 OH, STR3 wherein R. sup.4 and R 5 are the same or different and are H, lower alkyl, hydroxy, lower alkoxy or aryl, at least one of R 4 and R 5 being other than hydroxy and lower alkoxy; p is 1 to 4; R. sup.1 is H or lower alkyl; q is 1 to 12; R 2 is H or lower alkyl; and R 3 is H, lower alkyl, lower alkenyl, lower alkynyl, aryl, arylalkyl, lower alkoxy, aryloxy, arylalkyloxy, amino, alkylamino arylamino, arylalkylamino, STR4 (wherein n' is 0, 1 or 2), alkylaminoalkyl, arylaminoalkyl, arylalkylaminoalkyl, alkoxyalkyl, aryloxyalkyl or arylalkoxyalkyl.The compounds are cardiovascular agents useful, for example, in the treatment of thrombotic disease.
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- Formation of β-lactams from 3-phenylthiopropionamide derivatives. A possible model for penicillin biosynthesis
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The Cu-catalysed reaction of the substituted 3-phenylthiopropianamide with di-t-butyl peroxide gives the β-lactam via oxidative cyclisation of the α-thioalkyl radical. Similar reactions of the propionamides with t-butyl perbenzoate give benzoates which can be readily converted into the β-lactams, but neither β-lactams nor benzoates can be obtained from the thiazepines. Dimethyl disulfide is benzoyloxylated on treatment with t-butyl perbenzoate. The relevance of these results to penicillin biosynthesis is discussed.
- Beckwith,Easton
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p. 3995 - 4001
(2007/10/02)
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- Hard Acid and Soft Nucleophile Systems. 5. Ring-Opening Reaction of Lactones to ω-Alkylthio or ω-Arylthio Carboxylic Acids with Aluminum Halide and Thiol
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Lactones were converted into ω-alkylthio carboxylic acids in high yields through ω-carbon-oxygen bond cleavage when they were treated with aluminun halide and alkanethiol.The aluminum halide and arenethiol system has also been found to be useful for the preparation of the synthetically valuable ω-arylthio carboxylic acids from lactones.
- Node, Manabu,Nishide, Kiyoharu,Ochiai, Masahito,Fuji, Kaoru,Fujita, Eiichi
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p. 5163 - 5166
(2007/10/02)
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- Action d'organolithiens et organomagnesiens sur la propiolactone en presence de sel cuivreux Synthese d'acides carboxyliques
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Organocuprate reagents, as well as Grignard reagents under the catalytic action of copper bromide, react with propiolactone to give the corresponding homologous acid with three more carbon atoms in good yields.
- Normant, J. F.,Alexakis, A.,Cahiez, G.
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p. 935 - 938
(2007/10/02)
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- 1,4-Dihydro-4-oxo-benzothiopyrano (4,3-b)pyridine-2-carboxylates and derivatives
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Compounds of formula 1 STR1 in which R1, R2, R3 and R4 are the same or different selected from the group consisting of hydrogen, halogen, nitro, trifluoromethyl, lower alkyl and lower alkoxy, or R1 and R2, R2 and R3, or R3 and R4 together form a CH2 CH2 CH2 CH2 chain and R3 and R4, R1 and R4 and R1 and R2, respectively, are as defined above, R5 is hydrogen, lower alkyl or a radical of formula -Alk-OR6 wherein Alk is an alkylene selected from the group consisting of CR7 R8, CR7 R8 CR9 R10, CR7 R8 CR9 R10 CR11 R12 and CR7 R8 CR9 R10 CR11 R12 CR13 R14 wherein each of R7, R8, R9, R10, R11, R12, R13 and R14 is hydrogen or lower alkyl and R6 is hydrogen or lower alkyl; R15 is hydrogen or lower alkyl; X is O, S, SO or SO2 ; and Y is O or NR16 wherein R16 is hydrogen or lower alkyl, are disclosed. The compounds of formula 1 are useful for treating allergic conditions and for treating microbial infections. Methods for the preparation and use of said compounds are disclosed.
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