- Synthesis of a New Phorbazole and Its Derivatives
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Phorbazoles are chlorinated marine alkaloids containing pyrrole, oxazole and phenol ring units, and differ in the number and positions of chlorine atoms. They are isolated from sea sponges and nudibranchs. In this work, a convenient synthetic method leading to a new phorbazole and its derivatives is developed. This synthesis of synthetic phorbazole G and its derivatives is achieved in seven steps in good overall yields of 26-52%. It involves formation of the pyrrole-oxazole skeleton followed by chlorination. The pyrrole-oxazole skeleton is synthesized from pyrrole and substituted acetophenones, and the key step involves cyclodehydration of amide intermediates to give protected oxazoles, followed by hydrolysis.
- Louglin, Wendy A.,Muderawan, I Wayan,Young, David J.
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- Facile Synthesis of α-Haloketones by Aerobic Oxidation of Olefins Using KX as Nonhazardous Halogen Source
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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
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supporting information
p. 173 - 177
(2020/01/02)
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- Reaction of ketone hydrazones with TeCl4: Isolation and reactions of novel divinyl telluride
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The reaction of acetophenone hydrazones with TeCl4 in the presence of DBU gave a mixture of divinyl ditellurides and divinyl tellurides, which easily reacted with Cu powder in refluxing toluene to afford divinyl tellurides in good yields. The reaction of divinyl tellurides with bromine (1.2 eq.) gave the corresponding tellurium dibromide rather than the addition of the double bond whereas 3 molar amount of bromine gave excess brominated and oxidized products. The reaction of divinyl tellurides with 2-(trimethylsilyl)phenyl triflate in the presence of CsF gave (E)-2-alkenyldiaryl tellurides in good yields.
- Nagahora, Noriyoshi,Okuma, Kentaro,Qu, Yuxuan,Suetome, Aoi
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p. 4583 - 4589
(2020/07/04)
-
- Microwave-assisted synthesis and luminescent activity of imidazo[1,2-a]pyridine derivatives
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In this work, a series of phenacyl bromide derivatives was synthesized and employed as key intermediate for the synthesis of substituted imidazo[1,2-a]pyridines. First, phenacyl bromide molecules were obtained from the bromination reaction of acetophenones assisted by microwave irradiation, obtaining the products 4a-v in a 15 minutes reaction with yields in the range of 50% to 99%. Subsequently, the conjugation of these molecules with 2-aminopyridine conduced to the production of imidazo[1,2-a]pyridine derivatives (7a-v) in a 60-second reaction with yields of 24% to 99%. Improved yields were determined with respect to those obtained with more tedious methodologies like thermally and mechanically assisted routes. Intense luminescence emissions in the purple and blue regions of the electromagnetic spectra were observed under UV excitation according to the nature of the substituents. This environmentally friendly methodology is expected to constitute an important class of organic compounds for the development of biomarkers, photochemical sensors, and medicinal applications.
- Rodríguez, Juan C.,Maldonado, Rony A.,Ramírez-García, Gonzalo,Díaz Cervantes, Erik,de la Cruz, Fabiola N.
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p. 2279 - 2287
(2020/03/16)
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- Synthesis of Novel Heterocycles by Amide Activation and Umpolung Cyclization
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Herein, we report a metal-free synthesis of cyclic amidines, oxazines, and an oxazinone under mild conditions by electrophilic amide activation. This strategy features an unusual Umpolung cyclization mode and enables the smooth union of α-aryl amides and diverse alkylazides, effectively rerouting our previously reported α-amination transform.
- Maulide, Nuno,Riomet, Margaux,Roller, Alexander,Zhang, Haoqi
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supporting information
(2020/03/24)
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- 2-Amino-4-arylthiazoles through One-Pot Transformation of Alkylarenes with NBS and Thioureas
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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
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p. 2520 - 2527
(2019/04/04)
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- Application of poly(vinylphenyltrimethylammonium tribromide) resin as an efficient polymeric brominating agent in the α-bromination and α-bromoacetalization of acetophenones
-
The applications of a new supported tribromide reagent based on poly(vinylbenzyltrimethylammonium hydroxide) resin (Amberlite 717) were reported. This supported tribromide resin was used directly in α-bromination and α-bromoacetalization of acetophenones without any other catalyst under mild conditions. The effects of solvents and the amount of the supported tribromide resin on the reactions were investigated. Under the optimal conditions, most of α-bromo and α-bromoacetal of acetophenones were selectively obtained in excellent yields.
- Han, Bingbing,Zheng, Zubiao,Zheng, Dongcheng,Zhang, Lei,Cui, Peng,Shi, Jianjun,Li, Changjiang
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supporting information
p. 2512 - 2520
(2019/07/04)
-
- Synthesis of 2-aminothiazoles from styrene derivatives mediated by 1,3-dibromo-5,5-dimethylhydrantoin (DBH)
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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
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p. 3602 - 3607
(2018/05/26)
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- Facile and efficient preparation of α-halomethyl ketones from α-diazo ketones catalyzed by iron(III) halides and silica gel
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An efficient and mild method for the synthesis of α-halomethyl ketones from α-diazo ketones was developed using ferric chloride or bromide as the halogen source and silica gel as the hydrogen source, with good to excellent yields.
- Shi, Xinxia,Zhang, Lingqiong,Yang, Pengfei,Sun, Han,Zhang, Yilan,Xie, Chunsong,Ou-yang, Zhen,Wang, Min
-
supporting information
p. 1200 - 1203
(2018/03/08)
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- High-bromine-atom-utilization-rate method for preparing alpha-monobrominated aromatic ketones
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The invention belongs to the technical field of chemical engineering, and particularly relates to a high-bromine-atom-utilization-rate method for preparing alpha-monobrominated aromatic ketones. The method comprises the following steps: taking an aromatic
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-
Paragraph 0026-0027
(2018/07/30)
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- Novel arylimino thiazole compound, preparation method and uses thereof
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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.
- -
-
Paragraph 0181; 0184; 0185; 0186
(2018/03/28)
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- 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 0297; 0298; 0299; 0300
(2018/03/28)
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- A novel 18F labelled imidazo-oxazolopyridine derivative as β-amyloid imaging agent: Synthesis and preliminary evaluation
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Visualization of β-amyloid plaques in brain is pivotal for the diagnosis of Alzheimer’s disease. In the present study, we have designed, synthesized and evaluated an imidazo-oxazolopyridine derivative, 2-[2-(4-fluorophenyl)imidazo[1,2-a]pyridine-6- yl]oxa
- Singh, Shivani,Singh, Sweta,Tiwari, Anjani Kumar,Sharma, Rakesh Kumar,Mathur, Rashi,Kaul, Ankur
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p. 183 - 190
(2017/12/26)
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- A new and versatile one-pot strategy to synthesize alpha-bromoketones from secondary alcohols using ammonium bromide and oxone
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A new, efficient and green protocol for the one-pot synthesis of α-bromoketones from secondary alcohols using cheap, air stable and non-toxic reagents such as NH4Br and oxone has been developed. This reaction proceeds via two consecutive steps such as oxidation of secondary alcohols and oxidative bromination of in situ generated ketones.
- Rammurthy, Banothu,Swamy, Peraka,Naresh, Mameda,Srujana, Kodumuri,Durgaiah, Chevella,Krishna Sai, Gajula,Narender, Nama
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p. 3710 - 3714
(2017/07/12)
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- One-pot synthesis of α-bromo- and α-azidoketones from olefins by catalytic oxidation with in situ-generated modified IBX as the key reaction
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Simple one-pot protocols for the syntheses of α-bromoketones and α-azidoketones starting from olefins have been developed by employing catalytic oxidation of the intermediary bromohydrins with in situ-generated modified IBX as the key reaction. The improved procedure involves initial formation of bromohydrin by the reaction of olefin with NBS in acetonitrile-water mixture (1:1) at rt followed by oxidation with in situ-generated 3,4,5,6-tetramethyl-2-iodoxybenzoic acid (TetMe-IBX), produced in catalytic amounts from 3,4,5,6-tetramethyl-2-iodobenzoic and Oxone. α-Bromoketones are further converted in the same pot to the corresponding α-azidoketones using NaN3/NaHCO3. The one-pot conversions are versatile for a variety of olefins that include cyclic as well as acyclic aliphatic olefins and electron-rich and electron-deficient styrenes. Chemoselective bromohydroxylation of electron-rich double bond and subsequent oxidation to the α-bromoketone is demonstrated for a substrate that contains both electron-rich and deficient double bonds.
- Chandra, Ajeet,Parida, Keshaba Nanda,Moorthy, Jarugu Narasimha
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p. 5827 - 5832
(2017/09/09)
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- 1,3-Dibromo-5,5-dimethylhydantoin mediated oxidative amidation of terminal alkenes in water
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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
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p. 9889 - 9894
(2017/12/12)
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- Method for selective bromination of phenyl alkyl ketone derivatives or phenyl alkyl alcohol derivatives
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The present invention refers to phenyl alkyl ketone derivatives or phenyl alkyl alcohol for the preparation of bromide to method are disclosed. Bromination reaction which is an expensive raw material without said number [...] cap, a photocuring liquid bromine (Br) toxic substances toxic to all the remaining wastewater has been exhausted not environment-friendly method are disclosed. In addition, regioselective bromination reaction so as to control, high yield can be undesired compounds. (by machine translation)
- -
-
Paragraph 0069; 0087; 0088; 0090
(2018/02/27)
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- Synthesis and antifungal activity of novel oxazolidin-2-one-linked 1,2,3-triazole derivatives
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Novel oxazolidin-2-one-linked 1,2,3-triazole derivatives (4a-k) were synthesized by straightforward and versatile azide-enolate (3 + 2) cycloaddition. The series of compounds was screened for antifungal activity against four filamentous fungi as well as six yeast species of Candida spp. According to their efficiency and breadth of scope, they can be ordered as 4k > 4d > 4h > 4a, especially in relation to the activity displayed against Candida glabrata ATCC-34138, Trichosporon cutaneum ATCC-28592 and Mucor hiemalis ATCC-8690, i.e. compounds 4d, 4h and 4k showed excellent activity against C. glabrata (MIC 0.12, 0.25 and 0.12 μg mL-1, respectively), better than that of itraconazole (MIC 1 μg ml-1). The activity of compound 4d (MIC = 2 μg mL-1) was higher than that observed for the standard antifungal drug (MIC = 8 μg mL-1) against Trichosporon cutaneum, while compound 4k displayed an excellent antimycotic activity against Mucor hiemalis (MIC = 2 μg mL-1vs. 4 μg mL-1 for itraconazole). In addition, we describe herein a novel mild and eco-friendly synthetic protocol for obtaining β-ketosulfones (adducts to afford compounds 4a-k) from α-brominated carbonyls in an aqueous nanomicellar medium at room temperature.
- Ramírez-Villalva, Alejandra,González-Calderón, Davir,Rojas-García, Roxana I.,González-Romero, Carlos,Tamaríz-Mascarúa, Joaquín,Morales-Rodríguez, Macario,Zavala-Segovia, Nieves,Fuentes-Benítes, Aydeé
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p. 2258 - 2262
(2017/12/26)
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- Synthesis and antimicrobial evaluation of some new thiazolo imidazole analogs
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Thiazole and imidazole derivatives have attracted medicinal chemists owing to their extensive biological activities. Present paper describes the synthesis of some new thiazolo imidazole derivatives. 4-Substituted phenacyl bromides were prepared from subst
- Ramamurthy,Jayachandran
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p. 2639 - 2642
(2017/11/10)
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- Systematic Synthesis of Diphenyl-Substituted Carotenoids as Molecular Wires
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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
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p. 6390 - 6400
(2017/12/01)
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- 1,3-Dibromo-5,5-dimethylhydantoin (DBH) mediated one-pot syntheses of α-bromo/amino ketones from alkenes in water
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α-Bromo ketones are versatile intermediates of high practical utility. Traditional approaches to these compounds are restricted to a relatively hazardous/complex reagent combination, a long reaction time, the use of non-environmentally friendly solvents, or a limited substrate scope. Herein, we describe the development of a new methodology for the preparation of α-bromo ketones from alkenes using 1,3-dibromo-5,5-dimethylhydantoin (DBH) as a bromine source and an oxidant simultaneously. This easy to carry out two-step one-pot protocol proceeds in water and provides high yield of a great variety of α-bromo ketones. Addition of an amine to the intermediate α-bromo ketone further enables the preparation of α-amino ketones in a one-pot sequence.
- Xu, Senhan,Wu, Ping,Zhang, Wei
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p. 11389 - 11395
(2016/12/18)
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- One pot synthesis of substituted imidazopyridines and thiazoles from styrenes in water assisted by NBS
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Heating of commercially available styrenes with NBS in water followed by reaction with 2-aminopyridines or thioamides afforded important heterocyclic scaffolds in a one pot procedure. The reaction proceeds via co-oxidant free, in situ formation of α-bromoketone using NBS as a bromine source as well as an oxidant followed by trapping with suitable nucleophiles to provide imidazopyridines and thiazoles.
- Shinde, Mahesh H.,Kshirsagar, Umesh A.
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supporting information
p. 1455 - 1458
(2016/04/04)
-
- Synthesis, activity, and docking study of phenylthiazole acids as potential agonists of PPARγ
-
Peroxisome proliferator-activated receptor gamma (PPARγ) is a ligand-mediated transcription factor playing key roles in glucose and lipid homeostasis, and PPARγ ligands possess therapeutic potential in these as well as other areas. In this study, a series of phenylthiazole acids have been synthesized and evaluated for agonistic activity by a convenient fluorescence polarization-based PPARγ ligand screening assay. Compound 4t, as a potential PPARγ agonist with half maximal effective concentration (EC50) 0.75±0.20 μM, exhibited in vitro potency comparable with a 0.83±0.14 μM of the positive control rosiglitazone. Molecular docking and molecular dynamics simulations indicated that phenylthiazole acid 4t interacted with the amino acid residues of the active site of the PPARγ complex in a stable manner, consistent with the result of the in vitro ligand assay.
- Ma, Liang,Wang, Taijin,Shi, Min,Ye, Haoyu
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p. 1807 - 1815
(2016/06/09)
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- Direct Transformation of Ethylarenes into Primary Aromatic Amides with N -Bromosuccinimide and I2-Aqueous NH3
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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)
-
- Highly Efficient Synthesis of α-Halomethylketones via Ce(SO4)2/Acid Co-Catalyzed Hydration of Alkynes
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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
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supporting information
p. 1251 - 1254
(2016/12/27)
-
- Metal-free hydration of aromatic haloalkynes to α-halomethyl ketones
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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
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supporting information
p. 4983 - 4986
(2016/10/21)
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- Ammonium hydrotribromide salts as convenient and selective brominating agents of aryl methyl ketones
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A simple and improved protocol for the α-monobromination of acetophenone and acetyl carbazole derivatives using different ammonium hydrotribromide salts under mild reaction condition was described.
- Badali, Mohammad,Khalafy, Jabbar,Alidoost, Elnaz,Aghazadeh, Masomeh
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p. 859 - 863
(2016/11/21)
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- A process for preparing 4-amino-3 - (4-aminophenyl) furo [2,3-d] pyrimidine method
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The invention discloses a method for preparing 4-amino-3-(4-aminobenzene)furo[2,3-d] pyrimidine. The method comprises the following steps: using nitroacetophenone as a raw material, reacting the nitroacetophenone and N-bromo-succinimide to generate 2-brom
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-
Paragraph 0035-0037
(2016/10/10)
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- Copper nitrate-catalyzed α -bromination of aryl ketones with hydrobromic acid
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An efficient method for α-bromination of aryl ketones, using the combination of molecular oxygen and aqueous hydrobromic acid as a brominating agent in the presence of the copper nitrate, has been developed. This catalytic system, which uses cheap and readily available reactants, shows good atom economy with water as the only by-product.
- Wang, Jianqiang,Wang, Xiaolei,Niu, Zong-Qiang,Wang, Jian,Zhang, Man,Li, Jing-Hua
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p. 165 - 168
(2016/02/23)
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- Design, synthesis, antibacterial activity and docking study of some new trimethoprim derivatives
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In present study, nineteen novel trimethoprim (TMP) derivatives were designed, synthesized and evaluated for their antibacterial potential. Hydroxy trimethoprim 2 (HTMP) was synthesized by following the demethylation of 4-methoxy group at trimethoxy benzy
- Rashid, Umer,Ahmad, Waqas,Hassan, Syed Fahad,Qureshi, Naveeda Akhtar,Niaz, Basit,Muhammad, Bakhtiar,Imdad, Sameera,Sajid, Muhammad
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supporting information
p. 5749 - 5753
(2016/11/28)
-
- Dehydrozingerone Inspired Styryl Hydrazine Thiazole Hybrids as Promising Class of Antimycobacterial Agents
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Series of styryl hydrazine thiazole hybrids inspired from dehydrozingerone (DZG) scaffold were designed and synthesized by molecular hybridization approach. In vitro antimycobacterial activity of synthesized compounds was evaluated against Mycobacterium tuberculosis H37Rv strain. Among the series, compound 6o exhibited significant activity (MIC = 1.5 μM; IC50 = 0.48 μM) along with bactericidal (MBC = 12 μM) and intracellular antimycobacterial activities (IC50 = 0.098 μM). Furthermore, 6o displayed prominent antimycobacterial activity under hypoxic (MIC = 46 μM) and normal oxygen (MIC = 0.28 μM) conditions along with antimycobacterial efficiency against isoniazid (MIC = 3.2 μM for INH-R1; 1.5 μM for INH-R2) and rifampicin (MIC = 2.2 μM for RIF-R1; 6.3 μM for RIF-R2) resistant strains of Mtb. Presence of electron donating groups on the phenyl ring of thiazole moiety had positive correlation for biological activity, suggesting the importance of molecular hybridization approach for the development of newer DZG clubbed hydrazine thiazole hybrids as potential antimycobacterial agents.
- Hampannavar, Girish A.,Karpoormath, Rajshekhar,Palkar, Mahesh B.,Shaikh, Mahamadhanif S.,Chandrasekaran, Balakumar
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supporting information
p. 686 - 691
(2016/07/26)
-
- Synthesis and free radical scavenging activity of 2-alkyl/arylchalcogenyl-N-(4-aryl-1,3-thiazol-2-yl)acetamide compounds
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The synthesis of a new series of organochalcogen-derivatives, 2-alkyl/arylchalcogenyl-N-(4-aryl-1,3-thiazol-2-yl)acetamides 5a-r, provided products in satisfactory yields, which varied from 42% to 95%. All these novel compounds were screened for their in vitro free radical scavenging activity against 2,2-diphenyl-2-picrylhydrazyl (DPPH) and 2,2′-azino-bis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radicals. Compounds 5 (m, h, i, f, q, g, l, c, n) were effective scavengers against the ABTS radical species but less effective on scavenging the DPPH radical, indicating that the antioxidant effect of these compounds were related to protonated radical scavenger activity.
- Wolf, Lucas,Quoos, Natália,Mayer, Jo?o C.P.,De Souza, Diego,Sauer, André C.,Meichtry, Luana,Bortolotto, Vandreza,Prigol, Marina,Rodrigues, Oscar E.D.,Dornelles, Luciano
-
supporting information
p. 1031 - 1034
(2016/02/16)
-
- HEPARAN SULFATE BIOSYNTHESIS INHIBITORS FOR THE TREATMENT OF DISEASES
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Described herein are compounds of Formula I, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or conditions in need of inhibition of heparan sulfate biosynthesis.
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Paragraph 000341
(2016/05/02)
-
- 2-((Benzimidazol-2-yl)thio)-1-arylethan-1-ones: Synthesis, crystal study and cancer stem cells CD133 targeting potential
-
In order to develop a potent anti-tumor agent that can target both cancer stem cells and the bulk of tumor cells, a series of 2-((benzimidazol-2-yl)thio)-1-arylethan-1-ones 5a-o was synthesized. All compounds were evaluated for their anti-proliferative activity towards colon HT-29 cancer cell line. In addition, their inhibitory effect against cell surface expression of CD133, a potent cancer stem cells (CSCs) marker, in the same cells was evaluated by flow cytometry at 10 μM. Compound 5l emerged as the most active anti-proliferative analog against HT-29 (IC50 Combining double low line 18.83 ± 1.37 μM), that almost equipotent as 5-fluorouracil (IC50 Combining double low line 15.83 ± 1.63 μM) with 50.11 ± 4.05% inhibition effect on CD133 expression, suggested dual targeted effect. Also, compounds 5h, 5j, 5k and 5m-o inhibited the expression of CD133 with more than 50%. The SAR study pointed out the significance of substitution of the pendent phenyl group with lipophilic electron-donating groups or replacing it by 2-thienyl or 2-furyl groups.
- Abdel-Aziz, Hatem A.,Ghabbour, Hazem A.,Eldehna, Wagdy M.,Al-Rashood, Sara T.A.,Al-Rashood, Khalid A.,Fun, Hoong-Kun,Al-Tahhan, Mays,Al-Dhfyan, Abdullah
-
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- Synthesis, in vitro and in Silico studies of some novel 5-nitrofuran-2-yl hydrazones as antimicrobial and antitubercular agents
-
In this study, we synthesized two series of novel 5-nitrofuran-2-carbohydrazides 21a-h and 22a-e in addition to a third series of thiophene-2-carbohydrazides 23a-g to develop potent antimicrobial and/or antitubercular agents. The newly synthesized compounds were evaluated in vitro for their antimicrobial and antimycobacterial activities. Most of the 5-nitrofuran-2-carbohydrazides 21a-h and 22a-e displayed variable activity against Aspergillus fumigates, Staphylococcus aureus, Streptococcus pneumonia, Bacillis subtilis, Salmonella typhimurium, Klebsiella pneumonia, Escherichia coli and Mycobacterium tuberculosis. The sulfonamide derivative 21f exhibited superior potency and broad-spectrum antimicrobial activity with minimum inhibitory concentration (MIC)=0.06-0.98 μg/mL and antimycobacterial activity with MIC=3.9 μg/mL. The 5-nitrofuran-2-carbohydrazides 21a, b, g, h and 22a-c exhibited significant antibacterial activity with MIC values in the range of 0.12-7.81 μg/mL. The significances of the 5-nitrofuran moiety and sulfonamide function were explored via the structure-activity relationship (SAR) study. In addition, docking studies revealed that the p-amino benzoic acid (PABA) and binding pockets of the dihydropteroate synthase (DHPS) were successfully occupied by compound 21f. Furthermore, two quantitative structure-activity relationship (QSAR) models were built to explore the structural requirements which controlled the activity.
- Abdel-Aziz, Hatem Abdel-Kader,Eldehna, Wagdy Mohamed,Fares, Mohamed,Elsaman, Tilal,Abdel-Aziz, Marwa Mostafa,Soliman, Dalia Hussein
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p. 1617 - 1630
(2015/11/24)
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- AgF/TFA-promoted highly efficient synthesis of α-haloketones from haloalkynes
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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
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supporting information
p. 1373 - 1375
(2014/03/21)
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- Silica gel catalyzed α-bromination of ketones using N-bromosuccinimide: An easy and rapid method
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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
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p. 179 - 182
(2014/02/14)
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- Design and synthesis of novel carbazolo-thiazoles as potential anti-mycobacterial agents using a molecular hybridization approach
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Various substituted carbazolo-thiazoles (compounds 6a-6o) were synthesized in good yields using a molecular hybridization approach. The synthesized compounds were evaluated for their in vitro anti-tubercular activity against Mycobacterium tuberculosis H37Rv strain at the National Institute of Allergy and Infectious Diseases (Bethesda, MD, USA). Among the tested series, compound 6c (minimum inhibitory concentration 21 μM) showed the most promising anti-mycobacterial activity. Brief structure-activity relationship studies showed that the electron-donating groups (OCH3 and OH), particularly on the phenyl ring of the thiazole motif, had a positive correlation with the anti-mycobacterial activity. In addition, they displayed low cytotoxicity against a mammalian Vero cell line using the MTT assay, thereby having a high therapeutic index. This study shows the importance of molecular hybridization and the scope for the development of carbazole-thiazole compounds as potential anti-mycobacterial agents.
- Shaikh, Mahamadhanif S.,Palkar, Mahesh B.,Patel, Harun M.,Rane, Rajesh A.,Alwan, Wesam S.,Shaikh, Mahidansha M.,Shaikh, Iqbal M.,Hampannavar, Girish A.,Karpoormath, Rajshekhar
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p. 62308 - 62320
(2015/02/19)
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- Synthesis and antifungal activity of phenacyl azoles
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A new N-(4-methoxyphenacyl)imidazole and three new substituted N-(phenacyl)triazoles were prepared by reaction of the heterocycle with a phenacyl halide. The former ketone and one example of the latter were reduced to the corresponding alcohols. All six compounds were screened in vitro for antifungal activity against two pathogenic fungal strains, Candida albicans (fluconazole-resistant) and Aspergillus fumigatus. The results revealed that most of the compounds showed activity against both strains at 100 μg mL-1and 80 μg mL-1, some comparable with control compound fluconazole. The alcohols were less active than the corresponding ketones.
- Nelson, Ronald,Kesternich, Vctor,Perz-Fehrmann, Marcia,Salazar, Fernanda,Marcourt, Laurence,Christen, Philippe,Godoy, Patricio
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p. 549 - 552
(2014/12/11)
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- Synthesis and evaluation of cyclohexane carboxylic acid head group containing isoxazole and thiazole analogs as DGAT1 inhibitors
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Diacylglycerol acyltransferase 1 (DGAT1) is known to play an important catalytic role in the final step of triglyceride biosynthesis. High fat diet fed DGAT1 knockout mice were resistant to weight gain and exhibited increased insulin and leptin sensitivity thereby indicating a plausible role for DGAT1 inhibitors in the treatment of obesity. 4-Phenylpiperidine-1-carbonyl cyclohexanecarboxylic acid (compound 6, DGAT1 IC50 = 57 nM) has been lately reported as a potent DGAT1 inhibitor. In our search for newer scaffolds possessing potent DGAT1 activity we undertook a systematic diversification of compound 6 to identify a 4-(5-phenylthiazole-2-carboxamido)cyclohexanecarboxylic acid scaffold. Further linker optimization of this scaffold identified compound 9e (DGAT1 IC50 = 14.8 nM) as a potent DGAT1 inhibitor. Coupled with its in vitro potency, compound 9e also exhibited 112 percent plasma triglyceride reduction at a 3 mpk dose in an oral fat tolerance test (FTT) when studied in Swiss mice.
- Kandre, Shivaji,Bhagat, Pundlik Rambhau,Kumar Reddy, M. Mahesh,Dalal, Roda,Dixit, Amol,Deshmukh, Nitin J.,Anthony, Jessy,Bose, Julie,Anupindi, Raghuram,Sharma, Rajiv,Gupte, Amol
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p. 203 - 215
(2014/05/06)
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- Multi-dimensional target profiling of N,4-diaryl-1,3-thiazole-2-amines as potent inhibitors of eicosanoid metabolism
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Eicosanoids like leukotrienes and prostaglandins play a considerable role in inflammation. Produced within the arachidonic acid (AA) cascade, these lipid mediators are involved in the pathogenesis of pain as well as acute and chronic inflammatory diseases like rheumatoid arthritis and asthma. With regard to the lipid cross-talk within the AA pathway, a promising approach for an effective anti-inflammatory therapy is the development of inhibitors targeting more than one enzyme of this cascade. Within this study, thirty N-4-diaryl-1,3-thiazole-2- amine based compounds with different substitution patterns were synthesized and tested in various cell-based assays to investigate their activity and selectivity profile concerning five key enzymes involved in eicosanoid metabolism (5-, 12-, 15-lipoxygenase (LO), cyclooxygenase-1 and -2 (COX-1/-2)). With compound 7, 2-(4-phenyl)thiazol-2-ylamino)phenol (ST-1355), a multi-target ligand targeting all tested enzymes is presented, whereas compound 9, 2-(4-(4-chlorophenyl)thiazol-2-ylamino)phenol (ST-1705), represents a potent and selective 5-LO and COX-2 inhibitor with an IC50 value of 0.9 ± 0.2 μM (5-LO) and a residual activity of 9.1 ± 1.1% at 10 μM (COX-2 product formation). The promising characteristics and the additional non-cytotoxic profile of both compounds reveal new lead structures for the treatment of eicosanoid-mediated diseases.
- R?dl, Carmen B.,Vogt, Dominik,Kretschmer, Simon B.M.,Ihlefeld, Katja,Barzen, Sebastian,Brüggerhoff, Astrid,Achenbach, Janosch,Proschak, Ewgenij,Steinhilber, Dieter,Stark, Holger,Hofmann, Bettina
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supporting information
p. 302 - 311
(2014/08/05)
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- Diarylthiazole: An antimycobacterial scaffold potentially targeting PrrB-PrrA two-component system
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Diarylthiazole (DAT), a hit from diversity screening, was found to have potent antimycobacterial activity against Mycobacterium tuberculosis (Mtb). In a systematic medicinal chemistry exploration, we demonstrated chemical opportunities to optimize the potency and physicochemical properties. The effort led to more than 10 compounds with submicromolar MICs and desirable physicochemical properties. The potent antimycobacterial activity, in conjunction with low molecular weight, made the series an attractive lead (antibacterial ligand efficiency (ALE) >0.4). The series exhibited excellent bactericidal activity and was active against drug-sensitive and resistant Mtb. Mutational analysis showed that mutations in prrB impart resistance to DAT compounds but not to reference drugs tested. The sensor kinase PrrB belongs to the PrrBA two component system and is potentially the target for DAT. PrrBA is a conserved, essential regulatory mechanism in Mtb and has been shown to have a role in virulence and metabolic adaptation to stress. Hence, DATs provide an opportunity to understand a completely new target system for antimycobacterial drug discovery.
- Bellale, Eknath,Naik, Maruti,Vb, Varun,Ambady, Anisha,Narayan, Ashwini,Ravishankar, Sudha,Ramachandran, Vasanthi,Kaur, Parvinder,McLaughlin, Robert,Whiteaker, James,Morayya, Sapna,Guptha, Supreeth,Sharma, Sreevalli,Raichurkar, Anandkumar,Awasthy, Disha,Achar, Vijayshree,Vachaspati, Prakash,Bandodkar, Balachandra,Panda, Manoranjan,Chatterji, Monalisa
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supporting information
p. 6572 - 6582
(2014/10/15)
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- Design and synthesis of 3-trifluoromethyl-3h-pyrazoles and further investigations of their transformation to 1h-pyrazoles
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An efficient intramolecular cycloaddition strategy for the synthesis of trifluoromethyl-substituted 3H-pyrazoles was developed. Subsequently, their wide applications were demonstrated: they (1) react with dioxane by a radical process and (2) undergo [1,5] sigmatropic rearrangements. These applications are useful as the products were obtained in high yields and with excellent regioselectivity.
- Sha, Qiang,Liu, Haixuan,Wei, Yunyang
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supporting information
p. 7707 - 7715
(2015/04/22)
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- Design, synthesis and biological evaluation of bivalent ligands against A 1-D 1 receptor heteromers
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Aim:To design and synthesize bivalent ligands for adenosine A 1-dopamine D 1 receptor heteromers (A 1-D 1 R), and evaluate their pharmacological activities.Methods:Bivalent ligands and their corresponding A 1 R monovalent ligands were designed and synthesized. The affinities of the bivalent ligands for A 1 R and D 1 R in rat brain membrane preparation were examined using radiolabeled binding assays. To demonstrate the formation of A 1-D 1 R, fluorescence resonance energy transfer (FRET) was conducted in HEK293 cells transfected with D 1-CFP and A 1-YFP. Molecular modeling was used to analyze the possible mode of protein-protein and protein-ligand interactions.Results:Two bivalent ligands for A 1 R and D 1 R (20a, 20b), as well as the corresponding A 1 R monovalent ligands (21a, 21b) were synthesized. In radiolabeled binding assays, the bivalent ligands showed affinities for A 1 R 10-100 times higher than those of the corresponding monovalent ligands. In FRET experiments, the bivalent ligands significantly increased the heterodimerization of A1R and D 1 R compared with the corresponding monovalent ligands. A heterodimer model with the interface of helixes 3, 4, 5 of A1R and helixes 1, 6, 7 from D 1 R was established with molecular modeling. The distance between the two ligand binding sites in the heterodimer model was approximately 48.4 ?, which was shorter than the length of the bivalent ligands.Conclusion:This study demonstrates the existence of A 1-D 1 R in situ and a simultaneous interaction of bivalent ligands with both the receptors.
- Shen, Jian,Zhang, Lei,Song, Wan-Ling,Meng, Tao,Wang, Xin,Chen, Lin,Feng, Lin-Yin,Xu, Ye-Chun,Shen, Jing-Kang
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p. 441 - 452
(2013/08/25)
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- Evaluation of thiazole containing biaryl analogs as diacylglycerol acyltransferase 1 (DGAT1) inhibitors
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Biphenyl carboxylic acids, exemplified by compound 5, are known potent inhibitors of diacylglycerol acyltransferase, DGAT1, an enzyme involved in the final committed step of triglyceride biosynthesis. We have synthesized and evaluated 2-phenylthiazole, 4-
- Kadam, Kishorkumar S.,Jadhav, Ravindra D.,Kandre, Shivaji,Guha, Tandra,Reddy, M. Mahesh Kumar,Brahma, Manoja K.,Deshmukh, Nitin J.,Dixit, Amol,Doshi, Lalit,Srinivasan, Shaila,Devle, Jayendra,Damre, Anagha,Nemmani, Kumar V. S.,Gupte, Amol,Sharma, Rajiv
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p. 337 - 347
(2013/10/01)
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- Regioselective α-bromination of aralkyl ketones using n-bromosuccinimide in the presence of montmorillonite K-10 clay: A simple and efficient method
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A simple and more convenient method has been developed for regioselective α-bromination of various aralkyl ketones with N-bromosuccinimide (NBS) in the presence of Montmorillonite K-10 catalyst in methanol at 60-65 °C. The present procedure offers advantages of short reaction time, simple workup, good yields of products and reusability of the catalyst for four times without loss of activity. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.
- Mohan, Reddy Bodireddy,Reddy, N. C. Gangi
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p. 2603 - 2614
(2013/07/26)
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- Comparative material study and synthesis of 4-(4-nitrophenyl)oxazol-2-amine via sonochemical and thermal method
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The present paper deals with the synthesis of aminooxazole derivatives via thermal and ultrasonic methods using deep eutectic solvent as medium. It was observed that ultrasound-assisted method gave 90% yield in just 8 min as against 3.5 h required to get
- Singh, Balvant S.,Lobo, Hyacintha R.,Pinjari, Dipak V.,Jarag, Krishna J.,Pandit, Aniruddha B.,Shankarling, Ganapati S.
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p. 633 - 639
(2013/02/22)
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- Potent and selective tariquidar bioisosters as potential PET radiotracers for imaging P-gp
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Compounds 8a-d have been designed as bioisosters of tariquidar for imaging P-gp expression and density by PET. The results displayed that compounds 8b and 8d could be considered potential P-gp/BCRP ligands suitable as 11C and 18F radiotracers, respectively.
- Contino, Marialessandra,Zinzi, Laura,Perrone, Maria Grazia,Leopoldo, Marcello,Berardi, Francesco,Perrone, Roberto,Colabufo, Nicola Antonio
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supporting information
p. 1370 - 1374
(2013/03/14)
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- Synthesis and antibacterial, antimycobacterial and docking studies of novel N-piperazinyl fluoroquinolones
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The present study deals with the synthesis of some novel fluoroquinolone derivatives as antibacterial and antitubercular agents. The titled compounds 7a-g and 8a-g were found to possess comparable or more potent activity than the reference compounds ciprofloxacin, norfloxacin, isoniazid and rifampicin. The synthesized compounds showed activity against S. aureus and C. bacterium, whereas poor activity was observed against P. aeruginosa and E. coli. These compounds were subjected to in vitro cytotoxicity study by MTT assay, and their selectivity index was calculated. Compound 7d was found to be the most efficient antimycobacterial agent amongst the series. Molecular docking revealed that synthesized derivatives and target proteins were actively involved in a binding pattern and had significant correlation with biological activity. Graphical abstract: Novel N-piperazinyl fluoroquinolone derivatives were synthesized and evaluated for their in vitro antibacterial, antimycobacterial and cytotoxic properties. Activity results were compared with the docking results. [Figure not available: see fulltext.]
- Agrawal, Kapil M.,Talele, Gokul S.
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p. 818 - 831
(2013/04/24)
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- Synthesis and evaluation of non-dimeric HCV NS5A inhibitors
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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.
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p. 2031 - 2034
(2013/05/09)
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