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Unexpected ritter reaction during acid-promoted 1,3-dithiol-2-one formation
A series of aryl-substituted 1,3-dithiol-2-ones was prepared by the Bhattacharya-Hortmann cyclization method. Unexpectedly, a Ritter reaction occurred during the acid-catalyzed cyclization at the cyano group of the aryl substituents and 1,3-dithiol-2-ones bearing a carboxy or a carboxamide group could be selectively obtained (see 1 and 2a in Scheme 1). The formation of the acid or the amide functionality was temperature-dependent so that the one or the other group could be introduced selectively by modifying the reaction temperature. Copyright
Dumur, Frederic,Mayer, Cedric R.
p. 889 - 896
(2013)
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Electroselective α-bromination of acetophenone using: In situ bromonium ions from ammonium bromide
A greener and expeditious method for the side chain bromination of acetophenone using in situ generated bromonium ions from NH4Br and a catalytic amount of H2SO4 as a supporting electrolyte in a H2O:CH3CN medium at ambient temperature has been developed in an undivided cell equipped with a Pt/Pt electrode. This method results in a good yield (80%) of α-bromo acetophenone with high selectivity when only 2F of electricity was passed. Optimization studies such as variation of the current density, charge passed, solvent, solvent/water ratio, acid, acid strength, bromide salt, bromide salt concentration, etc., are carried out and reported.
Jagatheesan,Joseph Santhana Raj,Lawrence,Christopher
p. 35602 - 35608
(2016)
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High Chemo-/Stereoselectivity for Synthesis of Polysubstituted Monofluorinated Pyrimidyl Enol Ether Derivatives
A novel intramolecular Smiles rearrangement of α-fluoro-β-keto-pyrimidylsulfones (usually used as a carbon nucleophile) was developed, providing a versatile avenue for synthesis of tri/tetra-substituted monofluorinated pyrimidyl enol ethers. Among these, diverse (Z)-monofluorovinylsulfones and sulfinates were efficiently assembled by adding extra electrophile and fine-tuning reaction conditions. The process is triggered by a keto-enol tautomerism from enol oxyanion to pyrimidine 2-carbon, completely different from the classical carbon nucleophilic addition reaction approach.
Kang, Lei,Wang, Fang,Zhang, Jinlong,Yang, Huameng,Xia, Chungu,Qian, Jinlong,Jiang, Gaoxi
supporting information
p. 1669 - 1674
(2021/03/08)

Base-Catalyzed Intramolecular Defluorination/O-Arylation Reaction for the Synthesis of 3-Fluoro-1,4-oxathiine 4,4-Dioxide
A novel process involving base-catalyzed intramolecular defluorination/O-arylation of readily available α-fluoro-β-one-sulfones was realized and provided a series of 3-fluoro-1,4-oxathiine 4,4-dioxide derivatives in good to excellent yields. Unlike traditional defluorination reactions with stoichiometric base as the deacid reagent, this process is triggered by a catalytic amount of base (TMG: tetramethylguanidine) and molecular sieves serve as both an adsorbent to remove HF acid and an activator to assist C-F bond cleavage.
Kang, Lei,Zhang, Jinlong,Yang, Huameng,Qian, Jinlong,Jiang, Gaoxi
supporting information
p. 785 - 789
(2021/04/09)

An umpolung oxa-[2,3] sigmatropic rearrangement employing arynes for the synthesis of functionalized enol ethers
An oxa-[2,3] sigmatropic rearrangement involving arynes is reported featuring the umpolung of ketones, where the C=O bond polarity is reversed. The in situ-generated sulfur ylides from β-keto thioethers and arynes undergo efficient rearrangement allowing the facile and robust synthesis of functionalized enol ethers in high yields and excellent functional group compatibility. Preliminary mechanistic studies rule out the possibility of Pummerer-type rearrangement operating in this case.
Gaykar, Rahul N.,George, Malini,Guin, Avishek,Bhattacharjee, Subrata,Biju, Akkattu T.
supporting information
p. 3447 - 3452
(2021/05/04)

Flexible on-site halogenation paired with hydrogenation using halide electrolysis
Direct electrochemical halogenation has appeared as an appealing approach in synthesizing organic halides in which inexpensive inorganic halide sources are employed and electrical power is the sole driving force. However, the intrinsic characteristics of direct electrochemical halogenation limit its reaction scope. Herein, we report an on-site halogenation strategy utilizing halogen gas produced from halide electrolysis while the halogenation reaction takes place in a reactor spatially isolated from the electrochemical cell. Such a flexible approach is able to successfully halogenate substrates bearing oxidatively labile functionalities, which are challenging for direct electrochemical halogenation. In addition, low-polar organic solvents, redox-active metal catalysts, and variable temperature conditions, inconvenient for direct electrochemical reactions, could be readily employed for our on-site halogenation. Hence, a wide range of substrates including arenes, heteroarenes, alkenes, alkynes, and ketones all exhibit excellent halogenation yields. Moreover, the simultaneously generated H2at the cathode during halide electrolysis can also be utilized for on-site hydrogenation. Such a strategy of paired halogenation/hydrogenation maximizes the atom economy and energy efficiency of halide electrolysis. Taking advantage of the on-site production of halogen and H2gases using portable halide electrolysis but not being suffered from electrolyte separation and restricted reaction conditions, our approach of flexible halogenation coupled with hydrogenation enables green and scalable synthesis of organic halides and value-added products.
Shang, Xiao,Liu, Xuan,Sun, Yujie
supporting information
p. 2037 - 2043
(2021/03/26)

Oxidation Potential-Guided Electrochemical Radical-Radical Cross-Coupling Approaches to 3-Sulfonylated Imidazopyridines and Indolizines
Oxidation potential-guided electrochemical radical-radical cross-coupling reactions between N-heteroarenes and sodium sulfinates have been established. Thus, simple cyclic voltammetry measurement of substrates predicts the likelihood of successful radical-radical coupling reactions, allowing the simple and direct synthetic access to 3-sulfonylated imidazopyridines and indolizines. The developed electrochemical radical-radical cross-coupling reactions to sulfonylated N-heteroarenes boast the green synthetic nature of the reactions that are oxidant- and metal-free.
Kim, Wansoo,Kim, Hun Young,Oh, Kyungsoo
p. 15973 - 15991
(2021/07/26)

Ground-State Electron Transfer as an Initiation Mechanism for Biocatalytic C-C Bond Forming Reactions
The development of non-natural reaction mechanisms is an attractive strategy for expanding the synthetic capabilities of substrate promiscuous enzymes. Here, we report an "ene"-reductase catalyzed asymmetric hydroalkylation of olefins using α-bromoketones as radical precursors. Radical initiation occurs via ground-state electron transfer from the flavin cofactor located within the enzyme active site, an underrepresented mechanism in flavin biocatalysis. Four rounds of site saturation mutagenesis were used to access a variant of the "ene"-reductase nicotinamide-dependent cyclohexanone reductase (NCR) from Zymomonas mobiles capable of catalyzing a cyclization to furnish β-chiral cyclopentanones with high levels of enantioselectivity. Additionally, wild-type NCR can catalyze intermolecular couplings with precise stereochemical control over the radical termination step. This report highlights the utility for ground-state electron transfers to enable non-natural biocatalytic C-C bond forming reactions.
Fu, Haigen,Lam, Heather,Emmanuel, Megan A.,Kim, Ji Hye,Sandoval, Braddock A.,Hyster, Todd K.
supporting information
p. 9622 - 9629
(2021/07/01)

Rhodium-Catalyzed Annulation of Phenacyl Ammonium Salts with Propargylic Alcohols via a Sequential Dual C-H and a C-C Bond Activation: Modular Entry to Diverse Isochromenones
Given their omnipresence in natural products and pharmaceuticals, isochromenone congeners are one of the most privileged scaffolds to synthetic chemists. Disclosed herein is a dual (ortho/meta) C-H and C-C activation of phenacyl ammonium salts (acylammonium as traceless directing group) toward annulation with propargylic alcohols to accomplish rapid access for novel isochromenones by means of rhodium catalysis from readily available starting materials. This operationally simple protocol features broad substrate scope and wide functional group tolerance. Importantly, the protocol circumvents the need of any stoichiometric metal oxidants and proceeds under aerobic conditions.
Nanubolu, Jagadeesh Babu,Reddy Singam, Maneesh Kumar,Sridhar Reddy, Maddi,Suresh, Vavilapalli,Suri Babu, Undamatla
supporting information
p. 7888 - 7893
(2021/10/25)

Usnic Acid Enaminone-Coupled 1,2,3-Triazoles as Antibacterial and Antitubercular Agents
(+)-Usnic acid, a product of secondary metabolism in lichens, has displayed a broad range of biological properties such as antitumor, antimicrobial, antiviral, anti-inflammatory, and insecticidal activities. Interested by these pharmacological activities and to tap into its potential, we herein present the synthesis and biological evaluation of new usnic acid enaminone-conjugated 1,2,3-triazoles 10-44 as antimycobacterial agents. (+)-Usnic acid was condensed with propargyl amine to give usnic acid enaminone 8 with a terminal ethynyl moiety. It was further reacted with various azides A1-A35 under copper catalysis to give triazoles 10-44 in good yields. Among the synthesized compounds, saccharin derivative 36 proved to be the most active analogue, inhibiting Mycobacterium tuberculosis (Mtb) at an MIC value of 2.5 μM. Analogues 16 and 27, with 3,4-difluorophenacyl and 2-acylnaphthalene units, respectively, inhibited Mtb at MIC values of 5.4 and 5.3 μM, respectively. Among the tested Gram-positive and Gram-negative bacteria, the new derivatives were active on Bacillus subtilis, with compounds 18 [3-(trifluoromethyl)phenacyl] and 29 (N-acylmorpholinyl) showing inhibitory concentrations of 41 and 90.7 μM, respectively, while they were inactive on the other tested bacterial strains. Overall, the study presented here is useful for converting natural (+)-usnic acid into antitubercular and antibacterial agents via incorporation of enaminone and 1,2,3-triazole functionalities.
Bangalore, Pavan K.,Vagolu, Siva K.,Bollikanda, Rakesh K.,Veeragoni, Dileep K.,Choudante, Pallavi C.,Misra, Sunil,Sriram, Dharmarajan,Sridhar, Balasubramanian,Kantevari, Srinivas
supporting information
p. 26 - 35
(2020/01/03)

Pd-Catalyzed Decarboxylative Olefination: Stereoselective Synthesis of Polysubstituted Butadienes and Macrocyclic P-glycoprotein Inhibitors
The efficient and stereoselective synthesis of polysubstituted butadienes, especially the multifunctional butadienes, represents a great challenge in organic synthesis. Herein, we wish to report a distinctive Pd(0) carbene-initiated decarboxylative olefination approach that enables the direct coupling of diazo esters with vinylethylene carbonates (VECs), vinyl oxazolidinones, or vinyl benzoxazinones to afford alcohol-, amine-, or aniline-containing 1,3-dienes in moderate to high yields and with excellent stereoselectivity. This protocol features operational simplicity, mild reaction conditions, a broad substrate scope, and gram-scalability. Notably, a structurally unique allylic Pd(II) intermediate was isolated and characterized. DFT calculation and control experiments demonstrated that a rare Pd(0) carbene intermediate could be involved in this reaction. Moreover, the polysubstituted butadienes as novel building blocks were unprecedentedly assembled into macrocycles, which efficiently inhibited the P-glycoprotein and dramatically reversed multidrug resistance in cancer cells by 190-fold.
Chen, Xiangyang,Hao, Jiping,Houk, K. N.,Li, Yingzi,Lou, Liguang,Quan, Haitian,Song, Bichao,Wang, Lu,Xia, Yuanzhi,Xie, Peipei,Xu, Zhongliang,Yang, Weibo
supporting information
p. 9982 - 9992
(2020/06/27)

Synthesis and Structure-Activity Relationship of Dual-Stage Antimalarial Pyrazolo[3,4- b]pyridines
Malaria remains one of the most deadly infectious diseases, causing hundreds of thousands of deaths each year, primarily in young children and pregnant mothers. Here, we report the discovery and derivatization of a series of pyrazolo[3,4-b]pyridines targeting Plasmodium falciparum, the deadliest species of the malaria parasite. Hit compounds in this series display sub-micromolar in vitro activity against the intraerythrocytic stage of the parasite as well as little to no toxicity against the human fibroblast BJ and liver HepG2 cell lines. In addition, our hit compounds show good activity against the liver stage of the parasite but little activity against the gametocyte stage. Parasitological profiles, including rate of killing, docking, and molecular dynamics studies, suggest that our compounds may target the Qo binding site of cytochrome bc1.
Eagon, Scott,Hammill, Jared T.,Sigal, Martina,Ahn, Kevin J.,Tryhorn, Julia E.,Koch, Grant,Belanger, Briana,Chaplan, Cory A.,Loop, Lauren,Kashtanova, Anna S.,Yniguez, Kenya,Lazaro, Horacio,Wilkinson, Steven P.,Rice, Amy L.,Falade, Mofolusho O.,Takahashi, Rei,Kim, Katie,Cheung, Ashley,Dibernardo, Celine,Kimball, Joshua J.,Winzeler, Elizabeth A.,Eribez, Korina,Mittal, Nimisha,Gamo, Francisco-Javier,Crespo, Benigno,Churchyard, Alisje,García-Barbazán, Irene,Baum, Jake,Anderson, Marc O.,Laleu, Beno?t,Guy, R. Kiplin
p. 11902 - 11919
(2020/11/26)

Selective Debromination of α,α,α-Tribromomethylketones with HBr–H2O Reductive Catalytic System
A debromination of α,α,α-tribromomethylketones is developed for chemoselective synthesis of α-mono- and α,α-dibromomethylketones with high selectivity under H2O–HBr reductive conditions. This method offers an efficient and direct way to synthesize α-mono or α,α-dibromomethylketone compounds in high to excellent yields through the process of HBr self-circulation in water.
Cheng, Zhao,Guo, Hongmei,Huang, Guozheng,Rexit, Abulikemu Abudu,Wang, Hui,Zheng, Meng-Xia
p. 6455 - 6458
(2020/10/21)

Facile Synthesis of α-Haloketones by Aerobic Oxidation of Olefins Using KX as Nonhazardous Halogen Source
An operationally simple and safe synthesis of α-haloketones using KBr and KCl as nonhazardous halogen sources is reported. It involves an iron-catalysed reaction of alkenes with KBr/KCl using O2 as terminal oxidant under the irradiation of visible-light. This strategy avoids the risks associated with handling halo-contained electrophiles (Cl2, Br2, NCS, NBS). The process is tolerant to several functional groups, and extended to a range of substituted styrenes in up to 89% yield. A radical reaction pathway is proposed based on control experiments and spectroscopy studies.
Luo, Zhibin,Meng, Yunge,Gong, Xinchi,Wu, Jie,Zhang, Yulan,Ye, Long-Wu,Zhu, Chunyin
supporting information
p. 173 - 177
(2020/01/02)

Organocatalyzed Enantioselective Michael Addition of 2-Hydroxypyridines and α,β-Unsaturated 1,4-Dicarbonyl Compounds
The framework of 2-pyridones is prevalent in biologically and medicinally important molecules. Here we report that chiral N-substituted 2-pyridones were prepared by enantioselective, organocatalytic aza-Michael additions of halogenated 2-hydroxypyridines (pyridin-2(1H)-ones) to α,β-unsaturated-1,4-dketones or 1,4-ketoesters. The reactions were optimized by the choice of solvents and systematic screening of Cinchona alkaloid-based bifunctional catalysts to achieve excellent yields and enantioselectivities (up to 98% yield and >99% ee). Density functional theory calculations provided rationales for the observed enantioselectivity. Formal synthesis of a human rhinovirus protease inhibitor was achieved using the chiral Michael adduct generated by this method. (Figure presented.).
Wu, Yu-Chun,Jhong, Yi,Lin, Hui-Jie,Swain, Sharada Prasanna,Tsai, Hui-Hsu Gavin,Hou, Duen-Ren
p. 4966 - 4982
(2019/11/03)

2-Amino-4-arylthiazoles through One-Pot Transformation of Alkylarenes with NBS and Thioureas
Treatment of alkylarenes with N-bromosuccinimide in a mixture of ethyl acetate and water at 60 °C, a mixture of acetonitrile and water at 80 °C, or a mixture of diethyl carbonate and water under irradiation with a tungsten lamp, followed by a reaction with thioureas or arenethioamides provided the corresponding 2-amino- 4-arylthiazoles or 2,4-diarylthiazoles in good to moderate yields, respectively, in one pot. The present reaction is an efficient one-pot transformation method of alkylarenes into 2-amino-4-arylthiazoles and 2,4-diarylthiazoles directly under mild and transition-metal-free conditions.
Shibasaki, Kaho,Togo, Hideo
p. 2520 - 2527
(2019/04/04)

Synthesis and anti-inflammatory activity of 1,2-3-substituted 2a1,4,5-triazacyclopenta[cd]indene derivatives
The present study reports the synthesis of 1,2-3-substituted-2a1,4,5-triazacyclopenta[cd]indene derivatives. The synthetic methodology includes some of the prominent reaction steps as specified in sequence (i) Bromination of acetophenones (ii) Condensation of 2-bromo-1-(substituted phenyl) ethanone derivatives with 2-aminopyrimidine, and (iii) Coupling of imidazo[1,2-a]pyrimidine derivatives with 1,2-diaryl/diaklylethynes. The structures of the newly synthesized derivatives have been determined by 1H NMR, 13C NMR, LC-MS, and IR spectral analysis. Furthermore, these derivatives were screened for their preliminary anti-inflammatory activities using Carrageenan induced paw edema test method. These promising screening results suggested a huge potential for the molecular diversity from present compounds that can be inflated to better lead candidates.
Sanivarapu, Sumalatha,Vaddiraju, Namratha,Velide, Lakshmi
p. 1461 - 1470
(2019/07/05)

An efficient heterogeneous gold(I)-catalyzed hydration of haloalkynes leading to α-halomethyl ketones
A highly efficient heterogeneous gold(I)-catalyzed hydration of haloalkynes has been developed that proceeds smoothly under mild and neutral conditions and provides a general and practical route for the synthesis of a variety of α-halomethyl ketones with high atom-economy, excellent yield, and recyclability of the gold(I) catalyst. The presented method delivers an attractive alternative to classical α-halogenation of ketones.
Hu, Sifan,Liu, Dayi,Yan, Chenyu,Cai, Mingzhong
supporting information
p. 2983 - 2991
(2018/12/04)

Novel arylimino thiazole compound, preparation method and uses thereof
The present invention relates to a compound with antibacterial synergy activity, a preparation and uses thereof, particularly to a novel arylimino thiazole compound, a preparation method and uses thereof, and specifically discloses a class of compounds represented by a formula (I) or optical isomers, cis-trans isomers or pharmaceutically acceptable salts thereof, a preparation method and uses thereof. The invention further discloses a pharmaceutical composition containing the compound. The compound of the present invention can effectively enhance the antibacterial activity of antibiotics, andcan be used for treating antibiotic-resistant bacteria. The formula (I) is defined in the specification.
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Paragraph 0135; 0138; 0139; 0140

(2018/03/28)

Antibacterial synergist, preparation method and uses thereof
The present invention relates to an antibacterial synergist, a preparation method and uses thereof, and specifically discloses a compound represented by a formula (I) and having antibacterial synergyactivity, or an optical isomer, a cis-trans isomer or a pharmaceutically acceptable salt thereof, and a preparation method thereof. The present invention further discloses a medical composition containing the compound, and uses thereof. According to the present invention, the compound can effectively enhance the antibacterial activity of polymyxin B against Acinetobacter baumannii and Klebsiella pneumoniae, and can be used for the antibacterial treatment of pathogenic bacteria insensitive to polymyxin or having low bacterial inhibition activity. The formula (I) is defined in the specification.
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Paragraph 0212; 0213; 0214; 0215

(2018/03/28)

Nonenzymatic Dynamic Kinetic Resolution of in situ Generated Hemithioacetals: Access to 1,3-Disubstituted Phthalans
The first nonenzymatic DKR reaction of hemithioacetals is developed. Hemithioacetals were formed in situ via thiol addition and subsequently underwent an intramolecular oxa-Michael reaction. The scope of the reaction was quite broad ranging from aliphatic to aromatic substituents and 1,3-disubstituted-1,3-dihyroisobenzofuran products were obtained in good yields with moderate diastereoselectivities and high enantioselectivities. (Figure presented.).
Nath, Utpal,Chowdhury, Deepan,Pan, Subhas Chandra
supporting information
p. 1628 - 1633
(2018/03/21)

Synthesis of (Z)-nitroalkene derivatives through oxidative dehydrogenation coupling of α-aminocarbonyl compounds with nitromethane by copper catalysis
A novel copper-catalyzed cross-dehydrogenative coupling reaction of α-amino carbonyl compounds with nitromethane to synthesis of (Z)-nitroalkene derivatives has been established. (Z)-Nitroalkene derivatives are achieved through the cleavage of sp3 CsbndH bonds and formation of CsbndC double bond, with mild reaction conditions and excellent stereoselectivity.
Zhu, Menghua,Chen, De,Zeng, Sheng,Xing, Chenhu,Deng, Wei,Xiang, Jiannan,Wang, Rui-Jia
supporting information
p. 3214 - 3219
(2018/07/21)

Divergent synthesis of N-heterocycles by Pd-catalyzed controllable cyclization of vinylethylene carbonates
Here, we report a palladium-catalyzed controllable cyclization of vinyl ethylene carbonates that proceeds through formal migration [2+3] and [5+2] cycloadditions, respectively, under mild conditions. The transformation described here affords a series of synthetically versatile 5,7-membered N-heterocycles which are found in natural products and pharmaceuticals with biological and medicinal properties.
Yang, Yuwen,Yang, Weibo
supporting information
p. 12182 - 12185
(2018/11/21)

Efficient sulfonylation of ketones with sodium sulfinates for the synthesis of β-keto sulfones
The oxidative sulfonylation of ketones with sodium sulfinates as the sulfone source and DMSO as the oxidant is reported. A series of β-keto sulfones were obtained in good to excellent yields. The advantages of this efficient protocol include the low cost of DMSO and HBr, and a broad scope.
Deng, Siqi,Liang, En,Wu, Yinrong,Tang, Xiaodong
supporting information
p. 3955 - 3957
(2018/09/27)

Synthesis of 2-aminothiazoles from styrene derivatives mediated by 1,3-dibromo-5,5-dimethylhydrantoin (DBH)
An efficient procedure for the synthesis of 2-aminothiazoles via DBH-mediated oxidative cyclization of styrenes and thioureas is reported. Various alkenes were successfully transformed to the corresponding 2-aminothiazoles in yields of 10–81% via a two-step one-pot manner using DBH as both the bromine source and oxidant. The method can be readily carried out in gram-scale and successfully applied to the synthesis of anti-inflammatory drug fanetizole using styrene as starting material.
Ma, Chunhua,Miao, Yuqi,Zhao, Minghao,Wu, Ping,Zhou, Jianglu,Li, Zhi,Xie, Xilei,Zhang, Wei
p. 3602 - 3607
(2018/05/26)

Systematic Synthesis of Diphenyl-Substituted Carotenoids as Molecular Wires
A general method for the construction of diphenyl-substituted carotenoids has been developed through the stereoselective synthesis of dienyl sulfones with a phenyl substituent. Systematic synthetic pathways to the dienyl sulfones were delineated starting from readily available acetophenones with para-substituent X of various electronic natures, which provided the carotenoids with diverse physicochemical characteristics. The sulfone olefination method together with the Ramberg–B?cklund reaction produced a 9,9′-cis-10,10′-diphenylcarotene and all-trans-9,9′-diphenylcarotenes. Conductance measurements of the all-trans carotenoids by the scanning tunnelling microscopy break-junction method revealed a positional effect of the phenyl groups as well as a polar effect of the phenyl substituent X according to the electronic nature.
Lim, Boram,Oh, Eun-Taek,Im, JongOne,Lee, Kyu Sang,Jung, Hyunuk,Kim, Minsoo,Kim, Dahye,Oh, Jung Taek,Bae, Sung-Hee,Chung, Wook-Jin,Ahn, Kwang-Hyun,Koo, Sangho
p. 6390 - 6400
(2017/12/01)

Visible Light as a Sole Requirement for Intramolecular C(sp3)-H Imination
A novel, simple, and practical visible-light-mediated intramolecular α-C(sp3)-H imination of tertiary aliphatic amines containing β-O-aryl oximes leading to N-heterocycles has been developed. The reaction was performed well at rt with tolerance of some functional groups. Importantly, the selective C-H functionalization did not require added catalyst, oxidant, additive, acid, and base; visible light was the sole requirement.
Li, Jingjing,Zhang, Pengxiang,Jiang, Min,Yang, Haijun,Zhao, Yufen,Fu, Hua
supporting information
p. 1994 - 1997
(2017/04/28)

Synthesis of Novel 4-(Dimethylaminoalkyl)piperazine-1-carbodithioa t e Derivatives as Cholinesterase Inhibitors
Background: Carbamate compounds have attracted a great deal of interest in medicinal chemistry due to their inhibition potential against cholinesterase enzymes. Method: Hence, this study was undertaken to synthesize new piperazine derivatives including dithiocarbamate moiety, which is the bioisoster of carbamate. Twenty eight 4-(dimethylaminoalkyl) piperazine-1-carbodithioate derivatives (3a-3n, 4a-4n) were synthesized. Chemical structures of these compounds were confirmed by spectral data. Ellman's assay was applied in order to investigate inhibitory potency of the compounds against Acetylcholinesterase (AChE) and Butyrylcholinesterase (BChE) enzymes. Results and Conclusion: It was determined that some of the compounds have remarkable activity on AChE. ADME (Absorption, distribution, metabolism, elimination) predictions were theoretically performed for all compounds in the series. Enzyme kinetics and molecular docking studies were carried out for the most active compound (3n) and nature of inhibition and interactions between enzyme and ligand were described.
?evik, Ulviye Acar,Levent, Serkan,Saglik, Begüm Nurpelin,?zkay, Yusuf,Kaplancikli, Zafer Asim
p. 528 - 539
(2017/06/01)

Discovery of novel 2-(3-phenylpiperazin-1-yl)-pyrimidin-4-ones as glycogen synthase kinase-3β inhibitors
We herein describe the results of further evolution of glycogen synthase kinase (GSK)-3β inhibitors from our promising compounds containing a 2-phenylmorpholine moiety. Transformation of the morpholine moiety into a piperazine moiety resulted in potent GSK-3β inhibitors. SAR studies focused on the phenyl moiety revealed that a 4-fluoro-2-methoxy group afforded potent inhibitory activity toward GSK-3β. Based on docking studies, new hydrogen bonding between the nitrogen atom of the piperazine moiety and the oxygen atom of the main chain of Gln185 has been indicated, which may contribute to increased activity compared with that of the corresponding phenylmorpholine analogues. Effect of the stereochemistry of the phenylpiperazine moiety is also discussed.
Usui, Yoshihiro,Uehara, Fumiaki,Hiki, Shinsuke,Watanabe, Kazutoshi,Tanaka, Hiroshi,Shouda, Aya,Yokoshima, Satoshi,Aritomo, Keiichi,Adachi, Takashi,Fukunaga, Kenji,Sunada, Shinji,Nabeno, Mika,Saito, Ken-Ichi,Eguchi, Jun-ichi,Yamagami, Keiji,Asano, Shouichi,Tanaka, Shinji,Yuki, Satoshi,Yoshii, Narihiko,Fujimura, Masatake,Horikawa, Takashi
p. 3726 - 3732
(2017/07/27)

Copper-catalyzed oxidative cross-coupling of α-aminocarbonyl compounds with primary amines toward 2-oxo-acetamidines
A general and mild method for the construction of a carbon-nitrogen bond via copper-catalyzed oxidative cross-coupling of amines with α-aminocarbonyl compounds was achieved. Amines, either aliphatic primary amines, aromatic primary amines or secondary amines can be used as the starting materials. When R2 was different from R3, two isomers would be observed. Therefore, this reaction system has a broad substrate scope and provides a facile pathway for the synthesis of 2-oxo-acetamidines.
Chen, Chuang,Zhu, Menghua,Jiang, Lihui,Zeng, Zebing,Yi, Niannian,Xiang, Jiannan
p. 8134 - 8139
(2017/10/10)

1,3-Dibromo-5,5-dimethylhydantoin mediated oxidative amidation of terminal alkenes in water
A variety of terminal alkenes were converted to the corresponding amides in yields of 25 to 86% in water via treatment with 1,3-dibromo-5,5-dimethylhydantoin, followed by reaction with molecular iodine and aq. NH3 (or amine) in one pot. This metal- and organic solvent-free protocol is not only suitable for styrene derivatives, but also, for the first time, works well on terminal aliphatic alkenes.
Ma, Chunhua,Fan, Guojie,Wu, Ping,Li, Zhi,Zhou, Yang,Ding, Qingjie,Zhang, Wei
p. 9889 - 9894
(2017/12/12)

Organic light-emitting material in thiazole oxide derivative structure and organic light-emitting device prepared from organic light-emitting material
The invention discloses an organic light-emitting material in a thiazole oxide derivative structure and an organic light-emitting device prepared from the organic light-emitting material, belonging to the technical field of organic photoelectric materials. The organic light-emitting material provided by the invention utilizes thiazole oxide as a main body structure, and ligand groups with different polarities are linked, so that the molecular weight, pi conjugacy, eletrophilicity, cavity and load transmittability of the material can be adjusted, the organic light-emitting material in the thiazole oxide derivative structure with high light-emitting performance, electronic transmission performance, membrane stability, thermal stability and triplet energy level is obtained, and the problem of imbalanced current carriers of unipolar light-emitting materials can be effectively solved. The light-emitting efficiency of the organic light-emitting device prepared by virtue of the organic light-emitting material in the thiazole oxide derivative structure is improved, the light color is relatively stable, and the organic light-emitting device has the properties of excellent electron chemistry stability, heat stability and service life and further has high light-emitting efficiency under a low starting voltage.
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Paragraph 0041; 0042; 0043; 0044

(2017/09/01)

Catalytic dehydrogenative dual functionalization of ethers: Dealkylation-oxidation-bromination accompanied by C-O bond cleavage: Via aerobic oxidation of bromide
Catalytic dehydrogenative dual functionalization (DDF) of ethers via oxidation, dealkylation, and α-bromination by the aerobic oxidation of bromide was developed to obtain the corresponding α-bromo ketones in high yields. In particular, the reaction of substituted tetrahydrofurans as cyclic ethers provided 3,3-dibromo tetrahydrofuran-2-ols in high yields selectively through the double α-bromination.
Moriyama, Katsuhiko,Hamada, Tsukasa,Nakamura, Yu,Togo, Hideo
supporting information
p. 6565 - 6568
(2017/07/10)

Metal-free hydration of aromatic haloalkynes to α-halomethyl ketones
A highly regioselective and efficient metal-free hydration of aromatic haloalkynes to α-halomethyl ketones using cheap tetrafluoroboric acid as catalyst is described. The protocol is conducted under convenient conditions and affords products in good to excellent yields, with broad substrate scope, including a variety of aromatic alkynyl chlorides, alkynyl bromides, and alkynyl iodides.
Ye, Min,Wen, Yuelu,Li, Huifang,Fu, Yejuan,Wang, Qinghao
supporting information
p. 4983 - 4986
(2016/10/21)

Highly Efficient Synthesis of α-Halomethylketones via Ce(SO4)2/Acid Co-Catalyzed Hydration of Alkynes
A general atom-economical approach for the synthesis of α-halomethyl ketones is demonstrated through Ce(SO4)2/acid co-catalyzed hydration of a wide range of haloalkynes. The reactions are conducted under convenient conditions and provide products with excellent regioselectivity in good to excellent yields, with broad substrate scope. This protocol is an alternative to conventional α-halogenation of ketones.
Zou, Huaxu,Jiang, Jun,Yi, Niannian,Fu, Wenqiang,Deng, Wei,Xiang, Jiannan
supporting information
p. 1251 - 1254
(2016/12/27)

Direct Transformation of Ethylarenes into Primary Aromatic Amides with N -Bromosuccinimide and I2-Aqueous NH3
A variety of ethylarenes were converted into the corresponding primary aromatic amides in good yields via treatment with N-bromosuccinimide in the presence of a catalytic amount of 2,2′-azobis(isobutyronitrile) in a mixture of ethyl acetate and water, acetonitrile and water, or chloroform and water, followed by reaction with molecular iodine and aq NH3 in one pot. It was found that aryl α-bromomethyl ketones and/or aryl methyl ketones were formed at the first reaction step and their iodoform-type reaction occurred at the second reaction step to provide primary aromatic amides. The present reaction is a useful and practical transition-metal-free method for the preparation of primary aromatic amides from ethylarenes. (Chemical Equation Presented).
Shimokawa, Shohei,Kawagoe, Yuhsuke,Moriyama, Katsuhiko,Togo, Hideo
supporting information
p. 784 - 787
(2016/03/01)

AgF/TFA-promoted highly efficient synthesis of α-haloketones from haloalkynes
A AgF/TFA-promoted highly efficient synthesis of a wide range of α-haloketones from haloalkynes is described. The reactions are conducted under convenient conditions and provide products in moderate to excellent yields, with broad substrate scope, including a variety of aromatic chloroalkynes and bromoalkynes.
Chen, Zheng-Wang,Ye, Dong-Nai,Ye, Min,Zhou, Zhong-Gao,Li, Shen-Huan,Liu, Liang-Xian
supporting information
p. 1373 - 1375
(2014/03/21)

A one-pot hypoiodite catalysed oxidative cycloetherification approach to benzoxazoles
A practical one-pot hypoiodite catalysed oxidative cyclization approach to synthesize α-ketobenzoxazole derivatives was successfully developed. This operationally simple protocol utilizes easily-accessible starting materials and has a broad substrate scope with excellent yields. This journal is the Partner Organisations 2014.
Boominathan, Siva Senthil Kumar,Hu, Wan-Ping,Senadi, Gopal Chandru,Vandavasi, Jaya Kishore,Wang, Jeh-Jeng
supporting information
p. 6726 - 6728
(2014/06/23)

Silica gel catalyzed α-bromination of ketones using N-bromosuccinimide: An easy and rapid method
An easy and rapid method for the α-bromination of ketones using N-bromosuccinimide (NBS) catalyzed by silica gel in methanol under reflux conditions was developed. The expected products were formed in excellent isolated yields within a short period of time (5-20 min). Major advantages of the present procedure include use of inexpensive and readily available catalyst, exclusion of pre- and post-chemical treatment of catalyst and use of methanol as solvent instead of ethers and chlorinated solvents.
Mohan Reddy, Bodireddy,Venkata Ramana Kumar, Velpula,Chinna Gangi Reddy, Nallagondu,Mahender Rao, Siripragada
p. 179 - 182
(2014/02/14)

Synthesis and evaluation of non-dimeric HCV NS5A inhibitors
Based on the symmetrical bidentate structure of the NS5A inhibitor BMS-790052, a series of new monodentate molecules were designed. The synthesis of 36 new non-dimeric NS5A inhibitors is reported along with their ability to block HCV replication in an HCV 1b replicon system. Among them compound 5a showed picomolar range activity along with an excellent selectivity index (SI > 90,000).
Amblard, Franck,Zhang, Hongwang,Zhou, Longhu,Shi, Junxing,Bobeck, Drew R.,Nettles, James H.,Chavre, Satish,McBrayer, Tamara R.,Tharnish, Philip,Whitaker, Tony,Coats, Steven J.,Schinazi, Raymond F.
p. 2031 - 2034
(2013/05/09)

Silver(I)-Catalyzed conia-ene reaction: Synthesis of 3-pyrrolines via a 5-endo-dig cyclization
A novel method has been developed for the synthesis of 3-pyrrolines from β-ketopropargylamines via a 5-endo-dig carbocyclization. This transformation involves a silver-catalyzed Conia-ene type reaction tolerating broad substrate scope with good to excellent yields. Furthermore, this methodology has been extended for the construction of 2-substituted pyrroles under base-mediated conditions. Copyright
Boominathan, Siva Senthil Kumar,Hu, Wan-Ping,Senadi, Gopal Chandru,Wang, Jeh-Jeng
supporting information
p. 3570 - 3574
(2014/01/06)

Oxidative bromination of ketones using ammonium bromide and oxone
A highly efficient, environmentally safe and economic method for selective α-monobromination of aralkyl, cyclic, acyclic, 1,3-diketones and β-keto esters and α,α-dibromination of 1,3-diketones and β-keto esters without catalyst is reported using ammonium bromide as a bromine source and oxone as an oxidant. The reaction proceeds at ambient temperature and yields range from moderate to excellent. Bromination of unsymmetrical ketones takes place at the less substituted α-position predominantly. Aromatisation of tetralones is also carried out with this reagent system.
MacHarla, Arun Kumar,Chozhiyath Nappunni, Rohitha,Marri, Mahender Reddy,Peraka, Swamy,Nama, Narender
supporting information; experimental part
p. 191 - 195
(2012/01/17)

Synthesis, spectral characterization and biological evaluation of a novel series of 6-arylsubstituted-3-[2-(4-substitutedphenyl)propan-2-yl]-7H-[1,2,4] triazolo[3,4-b][1,3,4]thiadiazines
On account of the reported anticancer activity of triazolothiadiazines, we have synthesized a novel series of 6-arylsubstituted-3-[2-(4-substitutedphenyl) propan-2-yl]-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines and tested for in-vitro cytotoxicity by trypan blue exclusion and MTT assay. These compounds were also evaluated for their in-vivo anthelmintic activity, as well as in-vitro antimicrobial studies. Amongst the tested compounds, the compound 7j was the most promising cytotoxic agent with IC50 value of 10.54 μM in MCF-7 cells. The compounds 7l and 7q exhibited excellent anthelmintic activity. The compounds 7d, 7f, 7j, 7l, 7o, 7p and 7r showed good antibacterial activity, whereas compounds 7e and 7k exhibited excellent antifungal activity. The structures of newly synthesized compounds were characterized by IR, 1H NMR, 13C NMR and LCMS analysis.
Puthiyapurayil, Pushpan,Poojary, Boja,Chikkanna, Chandrashekhar,Buridipad, Sunil Kumar
p. 407 - 416
(2013/01/15)

Switching reversibility to irreversibility in glycogen synthase kinase 3 inhibitors: Clues for specific design of new compounds
Development of kinase-targeted therapies for central nervous system (CNS) diseases is a great challenge. Glycogen synthase kinase 3 (GSK-3) offers a great potential for severe CNS unmet diseases, being one of the inhibitors on clinical trials for different tauopathies. Following our hypothesis based on the enhanced reactivity of residue Cys199 in the binding site of GSK-3, we examine here the suitability of phenylhalomethylketones as irreversible inhibitors. Our data confirm that the halomethylketone unit is essential for the inhibitory activity. Moreover, addition of the halomethylketone moiety to reversible inhibitors turned them into irreversible inhibitors with IC50 values in the nanomolar range. Overall, the results point out that these compounds might be useful pharmacological tools to explore physiological and pathological processes related to signaling pathways regulated by GSK-3 opening new avenues for the discovery of novel GSK-3 inhibitors.
Perez, Daniel I.,Palomo, Valle,Pérez, Concepción,Gil, Carmen,Dans, Pablo D.,Luque, F. Javier,Conde, Santiago,Martínez, Ana
experimental part
p. 4042 - 4056
(2011/08/05)

Synthesis, semipreparative HPLC separation, biological evaluation, and 3D-QSAR of hydrazothiazole derivatives as human monoamine oxidase B inhibitors
The present study reports on synthesis in high yields (70-99%), HPLC enantioseparation, inhibitory activity against human monoamino oxidases, and molecular modeling including 3D-QSAR studies, of a large series of (4-aryl-thiazol-2-yl)hydrazones (1-45). Most of the synthesized compounds proved to be potent and selective inhibitors of hMAO-B isoform in the micromolar or nanomolar range, thus demonstrating that hydrazothiazole could be considered a good pharmacophore to design new hMAO-B inhibitors. Due to the presence in some derivatives of a chiral center, we also performed a semipreparative chromatographic enantioseparation of these compounds obtained by a stereoconservative pattern. The separated enantiomers were submitted to in vitro biological evaluation to point out the stereorecognition of the active site of the enzyme towards these structures. Finally, a 3D-QSAR study was carried out using Comparative Molecular Field Analysis (CoMFA), aiming to deduce rational guidelines for the further structural modification of these lead compounds.
Chimenti, Franco,Secci, Daniela,Bolasco, Adriana,Chimenti, Paola,Granese, Arianna,Carradori, Simone,MacCioni, Elias,Cardia, M. Cristina,Yanez, Matilde,Orallo, Francisco,Alcaro, Stefano,Ortuso, Francesco,Cirilli, Roberto,Ferretti, Rosella,Distinto, Simona,Kirchmair, Johannes,Langer, Thierry
experimental part
p. 5063 - 5070
(2010/09/08)

Direct synthesis of α-bromoketones from alkylarenes by aerobic visible light photooxidation
The direct synthesis of α-bromoketones from alkylarenes by aerobic photooxidation with hydrobromic acid is reported. The key success for this direct oxidative reaction is due to control of bromination with acetic acid and ethanol, which are generated in situ by solvolysis of ethyl acetate in the course of the reaction.
Tada, Norihiro,Ban, Kazunori,Hirashima, Shin-Ichi,Miura, Tsuyoshi,Itoh, Akichika
supporting information; experimental part
p. 4701 - 4704
(2010/11/17)

OXYGEN/NITROGEN HETEROCYCLE INHIBITORS OF TYROSINE PHOSPHATASES
Compounds, pharmaceutical compositions, and methods for treating, preventing, or ameliorating symptoms associated with diseases such as diabetes, cancer, neurodegenerative diseases, and obesity are provided. The compounds and compositions inhibit protein tyrosine phosphatase enzymes, e.g., PTP-1B.
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Page/Page column 83

(2008/06/13)

2, 3, 6-TRISUBSTITUTED-4-PYRIMIDONE DERIVATIVES
A pyrimidone derivative having tau protein kinase 1 inhibitory activity which is represented by formula (I) or a salt thereof, or a solvate thereof or a hydrate thereof; useful for prventive and/or therapeutic treatment of diseass such as neurodegenerative diseases (e.g. Alzheimer disease); wherein Q represents CH or nitrogen atom; R represents a C1-C12 alkyl group; the ring of Formula (I): represents piperazine ring or piperidine ring; each X independently represents a C1-C8 alkyl group, an optionally partially hydrogenated C6-C10 aryl ring, an indan ring or the like; m represents an integer of 1 to 3; each Y independently represents a halogen atom, a hydroxy group, a cyano group, a C1-C6 alkyl group or the like; n represents an integer of 0 to 8; when X and Y or two Y groups are attached on the same carbon atom, they may combine to each other to form a C2-C6 alkylene group.
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Page 285

(2008/06/13)

ANTIBACTERIAL BENZOIC ACID DERIVATIVES
The invention provides antimicrobial agents and methods of using the agents for sterilization, sanitation, antisepsis, disinfection, and treatment of infections in mammals.
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Page 355

(2010/02/06)

Azole antifungal agents, processes for the preparation thereof, and intermediates
A compound represented by the general formula: wherein R1 and R2 denote a halogen atom or hydrogen atoms; R3 means a hydrogen atoms or lower alkyl group; r and m stand for 0 or 1; A is N or CH; W denotes an aromatic ring or a condensed ring thereof; X means another aromatic rings, an alkanediyl group, an alkenediyl group, or an alkynediyl group; Y stand for -S-, etc.; Z denotes a hydrogen atom, etc., or a salt thereof, and intermediates thereof or a salt thereof as well as processes for the preparation thereof, and pharmacetical composition suitable for use as an antifungal agent.
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Page 73

(2010/01/31)