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Palladium assisted substitution of 3-benzo[b]furan triflates
Triflates of 3-coumaranones were prepared, and experimented as coupling partners in palladium catalyzed Stille, Heck, Suzuki, and Sonogashira coupling reactions. The corresponding 3-substituted benzo[b]furans were obtained in excellent yields.
Morice, Christophe,Garrido, Fabrice,Mann, André,Suffert, Jean
p. 501 - 503
(2002)
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Synthesis of 8-aryltetrahydroisoquinolines as dopamine antagonists and evaluation for potential neuroleptic activity
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Ellefson,Prodan,Brougham,Miller
p. 977 - 980
(1980)
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Photostability of 4,4′-dihydroxythioindigo, a mimetic of indigo
The photochemical properties of indigo, a widely used industrial dye, has attracted both experimentalists and theoreticians from the beginning. Especially the high photostability of indigo has been the subject of intensive research. Recently, it was propo
Dittmann, Marc,Graupner, Franziska F.,Maerz, Benjamin,Oesterling, Sven,Devivie-Riedle, Regina,Zinth, Wolfgang,Engelhard, Martin,Luettke, Wolfgang
p. 591 - 594
(2014)
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Synthesis and antioxidant activities of berberine 9-: O -benzoic acid derivatives
Although berberine (BBR) shows antioxidant activity, its activity is limited. We synthesized 9-O-benzoic acid berberine derivatives, and their antioxidant activities were screened via ABTS, DPPH, HOSC and FRAP assays. The para-position was modified with halogen elements on the benzoic acid ring, which led to an enhanced antioxidant activity and the substituent on the ortho-position was found to be better than the meta-position. Compounds 8p, 8c, 8d, 8i, 8j, 8l, and especially 8p showed significantly higher antioxidant activities, which could be attributed to the electronic donating groups. All the berberine derivatives possessed proper lipophilicities. In conclusion, compound 8p is a promising antioxidant candidate with remarkable elevated antioxidant activity and moderate lipophilicity.
Liu, Yanfei,Long, Shuo,Zhang, Shanshan,Tan, Yifu,Wang, Ting,Wu, Yuwei,Jiang, Ting,Liu, Xiaoqin,Peng, Dongming,Liu, Zhenbao
p. 17611 - 17621
(2021/05/29)

Remarkably Efficient Iridium Catalysts for Directed C(sp2)-H and C(sp3)-H Borylation of Diverse Classes of Substrates
Here we describe the discovery of a new class of C-H borylation catalysts and their use for regioselective C-H borylation of aromatic, heteroaromatic, and aliphatic systems. The new catalysts have Ir-C(thienyl) or Ir-C(furyl) anionic ligands instead of the diamine-type neutral chelating ligands used in the standard C-H borylation conditions. It is reported that the employment of these newly discovered catalysts show excellent reactivity and ortho-selectivity for diverse classes of aromatic substrates with high isolated yields. Moreover, the catalysts proved to be efficient for a wide number of aliphatic substrates for selective C(sp3)-H bond borylations. Heterocyclic molecules are selectively borylated using the inherently elevated reactivity of the C-H bonds. A number of late-stage C-H functionalization have been described using the same catalysts. Furthermore, we show that one of the catalysts could be used even in open air for the C(sp2)-H and C(sp3)-H borylations enabling the method more general. Preliminary mechanistic studies suggest that the active catalytic intermediate is the Ir(bis)boryl complex, and the attached ligand acts as bidentate ligand. Collectively, this study underlines the discovery of new class of C-H borylation catalysts that should find wide application in the context of C-H functionalization chemistry.
Chattopadhyay, Buddhadeb,Hassan, Mirja Md Mahamudul,Hoque, Md Emdadul
supporting information
p. 5022 - 5037
(2021/05/04)

Oxygen Reduction by Iron Porphyrins with Covalently Attached Pendent Phenol and Quinol
Phenols and quinols participate in both proton transfer and electron transfer processes in nature either in distinct elementary steps or in a concerted fashion. Recent investigations using synthetic heme/Cu models and iron porphyrins have indicated that p
Singha, Asmita,Mondal, Arnab,Nayek, Abhijit,Dey, Somdatta Ghosh,Dey, Abhishek
p. 21810 - 21828
(2021/01/11)

Metal-free Synthesis of Spiro-2,2′-benzo[b]furan-3,3′-ones via PhI(OAc)2-Mediated Cascade Spirocyclization
Treating the benzyl protected 3-hydroxy-1,3-bis(2-hydroxyphenyl)prop-2-en-1-ones solely with PhI(OAc)2 (PIDA) in DCE at room temperature readily furnished the seldom studied spiro-2,2′-benzo[b]furan-3,3′-ones in satisfactory to excellent yields. The hypervalent iodine reagent enables the metal-free cascade spirocyclization resulting in the dual oxidative C?O bond formation. (Figure presented.).
Xing, Qingyu,Liang, Huiyuan,Bao, Mingmai,Li, Xuemin,Zhang, Jingran,Bi, Tianhao,Zhang, Yilin,Xu, Jun,Du, Yunfei,Zhao, Kang
p. 4669 - 4673
(2019/09/17)

Design, synthesis, and preliminary biological evaluation of 3′,4′,5′-trimethoxy flavonoid salicylate derivatives as potential anti-tumor agents
According to the pharmacophore combination principle, a set of new 3′,4′,5′-trimethoxy flavonoid salicylate derivatives were designed, synthesized, and evaluated for biological activity. The cytotoxicity evaluation revealed that compound 10v exhibited higher potency than 5-Fu against HCT-116 cells. Preliminary biological activity studies showed that compound 10v could inhibit the colony formation and migration of HCT-116 cells. Besides, the Hoechst 33258 staining assay and flow cytometry revealed that treatment with compound 10v induced the apoptosis of HCT-116 cells in a concentration-dependent manner, while it had no effect on their cell cycle. The WB analysis suggested that HIF-1α, tubulin, HK-2, and PFK might be the potential pharmacophore targets of compound 10v. Tubulin was a potential drug target for compound 10v, which was explained by analyzing the crystal structure of compound 10v complexed with tubulin. These results indicated that compound 10v might be a promising anti-tumor agent candidate, deserving further optimization and evaluation.
Deng, Xiangping,Liu, Renbo,Li, Junjian,Li, Zhongli,Liu, Juan,Xiong, Runde,Lei, Xiaoyong,Zheng, Xing,Xie, Zhizhong,Tang, Guotao
p. 1874 - 1884
(2019/01/28)

Preparation method of 2-methoxybenzoyl chloride
The present invention discloses a preparation method of 2-methoxybenzoyl chloride and belongs to the technical field of medical technology. A technical problem to be solved relates to the more advanced preparation method of the 2-methoxybenzoyl chloride. The main point of the technical scheme of the technical problem to be solved is the new preparation method of the compound.
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Paragraph 0008; 009; 0010

(2019/01/07)

A General Cp*CoIII-Catalyzed Intramolecular C?H Activation Approach for the Efficient Total Syntheses of Aromathecin, Protoberberine, and Tylophora Alkaloids
Herein, we report a Cp*CoIII-catalyzed C?H activation approach as the key step to create highly valuable isoquinolones and pyridones as building blocks that can readily be applied in the total syntheses of a variety of aromathecin, protoberberine, and tylophora alkaloids. This particular C?H activation/annulation reaction was achieved with several terminal as well as internal alkyne coupling partners delivering a broad scope with excellent functional group tolerance. The synthetic applicability of this protocol reported herein was demonstrated in the total syntheses of two Topo-I-Inhibitors and two 8-oxyprotoberberine cores that can be further elaborated into the tetrahydroprotoberberine and the protoberberine alkaloid core. Moreover these building blocks were also transformed to six different tylophora alkaloids in expedient fashion.
Lerchen, Andreas,Knecht, Tobias,Koy, Maximilian,Daniliuc, Constantin G.,Glorius, Frank
supporting information
p. 12149 - 12152
(2017/09/13)

A cyclotrimethoxone-substituted salicylate compound and anti-tumor effect thereof
The invention relates to the technical field of medicines, and designs and synthesizes a novel A cyclotrimethoxy 4'-hydroxyflavone compound and an A cyclotrimethoxone-substituted salicylate compound. The figure 1 is a general formula of the A cyclotrimethoxone-substituted salicylate compound, wherein in the formula, R1, R2 and R3 are equal to OCH3 or R2, R3 and R4 are equal to OCH3; R5- is equal to OCH3, CH3, F, Cl, Br, I or the like. The novel A cyclotrimethoxy 4'-hydroxyflavone compound and the A cyclotrimethoxone-substituted salicylate compound can have an obvious inhibiting effect on MGC-803 (human gastric carcinoma cells), HepG2 (human hepatoma carcinoma cells), MCF-7 (human breast cancer cells) and hopefully become anti-tumor drugs. The invention discloses a preparation method of the novel A cyclotrimethoxy 4'-hydroxyflavone compound and the A cyclotrimethoxone-substituted salicylate compound.
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(2017/07/19)

Conformations, equilibrium thermodynamics and rotational barriers of secondary thiobenzanilides
The article deals with conformational behaviour of 2-methoxy-2′-hydroxythiobenzanilides. The CS-NH group of these compounds preferentially adopts the Z-conformation. Entropy favours the Z-conformer over the E-conformer, whereas enthalpy slightly favours the E-conformer over the Z-conformer. The rotational barrier about the CS-NH bond was determined to be (81.5±0.4) kJ/mol. No significant rotational barrier was found on the Ar-CS and Ar-NH bonds. All experimental outcomes are compared with the results of quantum-chemical calculations.
Kozic, Ján,Novák, Zdeněk,?ímal, Václav,Profant, Václav,Kune?, Ji?í,Vin?ová, Jarmila
p. 2072 - 2083
(2016/04/09)

* One derivative containing nitrogen and its preparation method and application (by machine translation)
The invention discloses a formula (I) of formula (II) containing nitrogen mouth Shan Tong derivative and its preparation method and application, A new synthesis of this invention containing nitrogen mouth Shan Tong derivatives of the salt and its acid salt, increased solubility, active research indicates part of the compound at the same time with treating and/or preventing diabetes and complications from diabetes mellitus the role of the, can further carry out development research as a model for treating and/or preventing diabetes caused by the complications of diabetes medicine. (by machine translation)
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(2017/01/31)

Preparing method for o-methoxybenzoyl chloride
The invention provides a preparing method for o-methoxybenzoyl chloride and belongs to the technical field of carbon compounds. According to the method, o-methoxybenzoic acid serves as a raw material, triphosgene-C2H4C12 serves as a sulfonyl chlorination reagent, an initiator is added, and the mixture reacts at backflow temperature to prepare o-methoxybenzoyl chloride; the amount-of-substance concentration of a triphosgene-C2H4C12 solution is 2 mol/L, the feeding molar ratio of o-methoxybenzoic acid to the initiator to triphosgene is 1:(0.04-0.06):0.31, and the mass ratio of solvent dichloroethane to o-methoxybenzoic acid is (2-4):1. According to the preparing method, the reaction condition is mild, the technology is simple, operation is easy, the obtained product is high in purity and yield, and the method is suitable for industrial production.
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Paragraph 0023; 0024

(2016/10/31)

Synthesis and bio-evaluation of novel salicylic acid-oriented thiourea derivatives with potential applications in agriculture
A series of salicylic acid-oriented thiourea derivatives was conveniently synthesized via multi-steps mainly including alkylation, chlorination, nucleophilic substitution and addition reaction. The structure of all these newly synthesized derivatives was confirmed and characterized by IR, 1H NMR and MS. The preliminary bioassay indicated that these new compounds have some herbicidal activity or plant growth regulating activity against tested plants.
Li, Shaowei,Li, Huangyong,Cao, Xiufang,Chen, Changshui
p. 98 - 103
(2014/01/06)

Detection of synthetic cannabinoids
The invention describes methods and kits for detecting and determining current and future synthetic cannabinoids from the JWH and RCS families. Unique antibodies derived from immunogens enable said methods and kits.
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(2014/03/22)

Synthesis and evaluation of novel azoles as potent antifungal agents
Using a rational approach to the design of antifungal agents, a series of azole agents with 1,3,4-oxadiazole side chains were designed and synthesized. The results of preliminary in vitro antifungal tests with eight human pathogenic compounds showed that all of the title compounds exhibited excellent activities against all of the tested fungi except Aspergillus fumigatus. Compounds 11e and 11f were found to be the most effective, with a minimum inhibitory concentration of 0.0039 μg/mL, followed by voriconazole, which has a MIC of 0.0625 μg/mL. The 1,3,4-oxadiazole side chain is not the major contributor but plays a role in eliciting the observed antifungal activity.
Li, Liangjing,Ding, Hao,Wang, Baogang,Yu, Shichong,Zou, Yan,Chai, Xiaoyun,Wu, Qiuye
supporting information
p. 192 - 194
(2014/01/17)

Syntheses, third-order optical nonlinearity and DFT studies on benzoylferrocene derivatives
A series of benzoylferrocene derivatives were synthesized and their third-order nonlinear optical (NLO) properties were evaluated in N,N-dimethyl-formamide at 800 nm using femtosecond degenerate four-wave mixing. The third-order NLO susceptibilities of synthesized compounds were 3.065-7.859 × 10-13 esu, with the response times in 49-70 fs. The second-order hyperpolarizabilities of the molecules of the compounds were 1.018-2.611 × 10-31 esu. The Density Functional Theory was used to calculate these benzoylferrocene derivatives. The theoretical study showed that the third-order NLO properties were increased with the increasing electron-withdrawing ability, which is accordance with the decreasing energy gap between the highest occupied and the lowest unoccupied molecular orbital. With the increasing of electron-withdrawing ability, the transferred charge to the substituent was increased and the affection on the electronic reallocate was increased. The experiment and theoretical results showed that the benzoylferrocene derivatives had potential nonlinear optical applications.
Jia, Jianhong,Cui, Yanhong,Han, Liang,Sheng, Weijian,Li, Yujin,Gao, Jianrong
p. 137 - 145
(2014/02/14)

A palladium-catalyzed carbonylation approach to acid chloride synthesis
We describe a new approach to acid chloride synthesis via the palladium-catalyzed carbonylation of aryl iodides. The combination of sterically encumbered phosphines (PtBu3) and CO coordination has been found to facilitate the rapid carbonylation of aryl iodides into acid chlorides via reductive elimination from (tBu3P)(CO) Pd(COAr)Cl. The formation of acid chlorides can also be exploited to perform traditional aminocarbonylation reactions under exceptionally mild conditions (ambient temperature and pressure), and with a range of weakly nucleophilic substrates.
Quesnel, Jeffrey S.,Arndtsen, Bruce A.
supporting information
p. 16841 - 16844
(2013/12/04)

Efficient synthesis of anacardic acid analogues and their antibacterial activities
Anacardic acid derivatives exhibit a broad range of biological activities. In this report, an efficient method for the synthesis of anacardic acid derivatives was explored, and a small set of salicylic acid variants synthesised retaining a constant hydrophobic element (a naphthyl tail). The naphthyl side chain was introduced via Wittig reaction and the aldehyde installed using directed ortho-metalation reaction of the substituted o-anisic acids. The failure of ortho-metalation using unprotected carboxylic acid group compelled us to use directed ortho-metalation in which a tertiary amide was used as a strong ortho-directing group. In the initial route, tertiary amide cleavage during final step was challenging, but cleaving the tertiary amide before Wittig reaction was beneficial. The Wittig reaction with protected carboxylic group (methyl ester) resulted in side-products whereas using sodium salt resulted in higher yields. The novel compounds were screened for antibacterial activity and cytotoxicity. Although substitution on the salicylic head group enhanced antibacterial activities they also enhanced cytotoxicity.
Mamidyala, Sreeman K.,Ramu, Soumya,Huang, Johnny X.,Robertson, Avril A.B.,Cooper, Matthew A.
supporting information
p. 1667 - 1670
(2013/04/10)

An efficient method for the preparation of hydroxamic acids
Reactions of acyl chlorides with hydroxylamine hydrochloride and NaHCO 3 generate the corresponding hydroxamic acid products in ethyl acetate and water at room temperature for 5 min. This is a simple and efficient method to synthesize a wide range of hydroxamic acids from carboxylic acids in excellent yield and high purity after simple post-treatment without chromatographic purification. In this process, the highlights are the simple separation of products and cheaply available reagents.
Gao, Xi-Ai,Wang, Xian-Xue,Yan, Hao,Li, Jian,Yan, Ru-Long,Huang, Guo-Sheng
p. 381 - 385
(2013/05/22)

Synthesis and antibacterial evaluation of novel pleuromutilin derivatives
A series of novel pleuromutilin derivatives possessing thioether moiety has been synthesized via acylation reaction under mild conditions. Their in vitro antibacterial activity against methicillin-resistant Staphylococcus aureus, methicillin-resistant Staphylococcus epidermidis, Escherichia coli, and Streptococcus agalactiae were tested by agar dilution method and Oxford cup assay. Among the 17 compounds screened, 14-O-[(4-methoxybenzamide-2- methylpropane-2-yl) thioacetate] mutilin 4i, 14-O-[(2-aminobenzamide-2- methylpropane-2-yl) thioacetate] mutilin 5a and 14-O-[(4-aminobenzamide-2- methylpropane-2-yl) thioacetate] mutilin 5c were resulted as most active antibacterial agents.
Shang, Ruofeng,Liu, Yu,Xin, Zhijun,Guo, Wenzhu,Guo, Zhiting,Hao, Baocheng,Jianping, Liang
p. 231 - 238
(2013/07/27)

MCL-1 MODULATING COMPOSITIONS
The present invention relates to marinopyrrole A derivatives and pyoluteorin derivatives and methods of treatment of disorders associated with misregulation of Mcl-l, e.g., leukemia, lymphoma, multiple myeloma, melanoma, or pancreatic cancer. We describe exemplary compounds, which may be contained in pharmaceutical compositions, and their use as therapeutic agents either alone or in combination with other anti-cancer treatments, e.g., anti-Bcl- 2 agents.
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Page/Page column 48; 49

(2013/08/15)

Gram-scale ketone synthesis by direct reductive coupling of alkyl iodides with acid chlorides
Alkyl aryl ketones were prepared on a gram scale by the nickel-catalyzed reductive coupling of alkyl iodides with aroyl chlorides. When scaled up 30-fold, this reaction shows a comparable coupling efficiency to the previously reported reaction performed under small-scale conditions. The mild and convenient reaction conditions show excellent tolerance to a range of functional groups and provide the ketones in good to excellent yields. Georg Thieme Verlag Stuttgart. New York.
Lu, Wenbin,Liang, Zhuye,Zhang, Yuwei,Wu, Fan,Qian, Qun,Gong, Hegui
p. 2234 - 2240
(2013/09/02)

Probing the reactivity of o-phthalaldehydic acid/methyl ester: Synthesis of N-isoindolinones and 3-arylaminophthalides
A new method for the synthesis of N-substituted isoindolinones and 3-arylaminophthalides was developed through aza-Wittig/cyclisation. The reaction of o-phthalaldehydic acid methyl ester with benzylic, aromatic and aliphatic azides gave N-isoindolinones w
Mamidyala, Sreeman K.,Cooper, Matthew A.
supporting information
p. 8407 - 8409
(2013/09/23)

Novel TypeII Fatty Acid Biosynthesis (FAS II) Inhibitors as Multistage Antimalarial Agents
Malaria is a potentially fatal disease caused by Plasmodium parasites and poses a major medical risk in large parts of the world. The development of new, affordable antimalarial drugs is of vital importance as there are increasing reports of resistance to the currently available therapeutics. In addition, most of the current drugs used for chemoprophylaxis merely act on parasites already replicating in the blood. At this point, a patient might already be suffering from the symptoms associated with the disease and could additionally be infectious to an Anopheles mosquito. These insects act as a vector, subsequently spreading the disease to other humans. In order to cure not only malaria but prevent transmission as well, a drug must target both the blood- and pre-erythrocytic liver stages of the parasite. P.falciparum (Pf) enoyl acyl carrier protein (ACP) reductase (ENR) is a key enzyme of plasmodial typeII fatty acid biosynthesis (FASII). It has been shown to be essential for liver-stage development of Plasmodium berghei and is therefore qualified as a target for true causal chemoprophylaxis. Using virtual screening based on two crystal structures of PfENR, we identified a structurally novel class of FAS inhibitors. Subsequent chemical optimization yielded two compounds that are effective against multiple stages of the malaria parasite. These two most promising derivatives were found to inhibit blood-stage parasite growth with IC50 values of 1.7 and 3.0μM and lead to a more prominent developmental attenuation of liver-stage parasites than the gold-standard drug, primaquine.
Schrader, Florian C.,Glinca, Serghei,Sattler, Julia M.,Dahse, Hans-Martin,Afanador, Gustavo A.,Prigge, Sean T.,Lanzer, Michael,Mueller, Ann-Kristin,Klebe, Gerhard,Schlitzer, Martin
p. 442 - 461
(2013/08/25)

Synthesis of biaryl imino/keto carboxylic acids via aryl amide directed C-H activation reaction
A novel Pd-catalysed C-H activation reaction for the synthesis of biaryl imino/keto carboxylic acids is developed. This reaction underwent aryl amide directed C-H activation ortho-acylation followed by ring closing and ring opening processes to give a range of biaryl imino/keto carboxylic acids. Our methodology features the utilization of a cheap and green oxidant (TBHP) as well as readily available aldehydes.
Zhang, Nana,Yu, Qingzhen,Chen, Ruixue,Huang, Jianhui,Xia, Yeqing,Zhao, Kang
supporting information
p. 9464 - 9466
(2013/10/01)

Total synthesis of the natural product benzo[j]fluoranthene-4,9-diol: An approach to the synthesis of oxygenated benzo[j]fluoranthenes
A synthetic sequence to the benzo[j]fluoranthene nucleus is described. Crucial steps of the procedure include a Suzuki coupling between appropriately substituted 2-bromo-acenaphthylene-1-carbaldehydes and 2-formylbenzeneboronates followed by McMurry ring closure. The synthesis represents a new approach to the benzo[j]fluoranthene ring system and specifically provides a method for the rapid preparation of differently substituted derivatives. Following this strategy, the first total synthesis of the recently isolated natural product benzo[j]fluoranthene-4,9-diol was carried out.
Lahore, Santosh,Narkhede, Umesh,Merlini, Lucio,Dallavalle, Sabrina
p. 10860 - 10866
(2013/11/19)

Novel salicylic acid-oriented thiourea-type receptors as colorimetric chemosensor: Synthesis, characterizations and selective naked-eye recognition properties
Based on the salicylic acid backbone, three highly sensitive and selective colorimetric chemosensors with an acylthiourea binding unit have been designed, synthesized and characterized. These chemosensors have been utilized for selective recognition of fluoride anions in dry DMSO solution by typical spectroscopic titration techniques. Furthermore, the obtained chemosensors AR1-3 have shown naked-eye sensitivity for detection of biologically important fluoride ion over other anions in solution.
Li, Shaowei,Cao, Xiufang,Chen, Changshui,Ke, Shaoyong
p. 18 - 23
(2012/10/30)

Photochemically induced synthesis of the topoisomerase i inhibitors indeno [1,2-c]isoquinoline-5,11-diones
A convenient synthesis of indeno[1,2-c]isoquinoline-5,11-diones has been achieved using combinational photochemical and carbocationic cyclization tactics. The synthetic route involved first the construction of adequately functionalized N-styryl benzamides via Suzuki-Miyaura cross-coupling reaction with enol phosphate combined with a six - electron photocyclization process. The assembling of the title compounds was readily ensured through sequential carbocationic annulation reaction and ultimate oxidation of a latent hydroxy functionality. Georg Thieme Verlag Stuttgart · New York.
Dubois, Mélanie,Deniau, Eric,Couture, Axel,Grandclaudon, Pierre
scheme or table
p. 1047 - 1051
(2012/06/17)

Enantioselective synthesis of anti-β-hydroxy-α-amido esters by asymmetric transfer hydrogenation in emulsions
Herein, we present two methods for an asymmetric transfer hydrogenation through the dynamic kinetic resolution of α-amido-β-ketoesters. These procedures yield the corresponding anti-β-hydroxy-α-amido esters in good yields and with good diastereo- and enantioselectivities. First, the scope of the reduction of α-amido-β-ketoesters by using triethylammonium formate azeotrope is examined. Then, an emulsion technology with sodium formate is explored, which allows for broader substrate scope, faster reaction times, and lower catalyst loading. Furthermore, these reactions are operationally simple and can be set up in air.
Seashore-Ludlow, Brinton,Villo, Piret,Somfai, Peter
supporting information; experimental part
p. 7219 - 7223
(2012/07/13)

Synthesis and Preliminary Biologic Evaluation of 5-Substituted-2-(4-substituted phenyl)-1,3-Benzoxazoles as A Novel Class of Influenza Virus A Inhibitors
The diversity-oriented chemistry synthesis together with the random screening approach has permitted the discovery and optimization of novel antiviral lead compounds. In this paper, a series of novel 5-substituted-2-(4-substituted phenyl)-1,3-benzoxazoles was synthesized and evaluated for their in vitro anti-influenza A virus and anti-influenza B virus activity. The activity was monitored by the MTS assay in the Madin-Darby canine kidney cells. Compound 7h showed excellent inhibitory activity and selective index against A/H3N2 (EC50=37.03μm, SI>5), which were all higher than that of the reference drug oseltamivir (EC50>59.00μm, SI>1). However, no compound displays inhibitory activity against influenza B virus.
Li, Zhenyu,Zhan, Peng,Naesens, Lieve,Vanderlinden, Evelien,Liu, Ailin,Du, Guanhua,De Clercq, Erik,Liu, Xinyong
experimental part
p. 1018 - 1024
(2012/07/30)

Synthesis, antimicrobial evaluation, and QSAR analysis of 2-isopropyl-5-methylcyclohexanol derivatives
A series of 2-isopropyl-5-methylcyclohexanol derivatives were synthesized and evaluated for their antibacterial activity against Gram-positive Staphylococcus aureus and Bacillus subtilis and Gram-negative Escherichia coli and in vitro antifungal activity against Candida albicans and Aspergillus niger. The results of antimicrobial activity demonstrated that the compounds 10, 20, and 21 were the most active ones among the synthesized compounds. The QSAR studies revealed the importance of dipole moment (μ), total energy (Te), and topological parameters (κ1 and κ3) in describing the antimicrobial activity of 2-isopropyl-5-methylcyclohexanol derivatives. Springer Science+Business Media, LLC 2011.
Singh, Manjeet,Kumar, Sunil,Kumar, Ashwani,Kumar, Pradeep,Narasimhan, Balasubramanian
experimental part
p. 511 - 522
(2012/08/07)

Ketone formation via mild Nickel-catalyzed reductive coupling of alkyl halides with aryl acid chlorides
The present work highlights unprecedented Ni-catalyzed reductive coupling of unactivated alkyl iodides with aryl acid chlorides to efficiently generate alkyl aryl ketones under mild conditions.
Wu, Fan,Lu, Wenbin,Qian, Qun,Ren, Qinghua,Gong, Hegui
supporting information; scheme or table
p. 3044 - 3047
(2012/08/07)

Phosphine/palladium-catalyzed syntheses of alkylidene phthalans, 3-deoxyisoochracinic acid, isoochracinic acid, and isoochracinol
In this study we used sequential catalysis-PPh3-catalyzed nucleophilic addition followed by Pd(0)-catalyzed Heck cyclization-to construct complex functionalized alkylidene phthalans rapidly, in high yields, and with good stereoselectivities (E/Z ratios of up to 1:22). The scope of this Michael-Heck reaction includes substrates bearing various substituents around the alkylidene phthalan backbone. Applying this efficient sequential catalysis, we accomplished concise total syntheses of 3-deoxyisoochacinic acid, isoochracinic acid, and isoochracinol.
Fan, Yi Chiao,Kwon, Ohyun
supporting information; scheme or table
p. 3264 - 3267
(2012/08/28)

Synthesis and evaluation of boronic acids as inhibitors of Penicillin Binding Proteins of classes A, B and C
In response to the widespread use of β-lactam antibiotics bacteria have evolved drug resistance mechanisms that include the production of resistant Penicillin Binding Proteins (PBPs). Boronic acids are potent β-lactamase inhibitors and have been shown to display some specificity for soluble transpeptidases and PBPs, but their potential as inhibitors of the latter enzymes is yet to be widely explored. Recently, a (2,6-dimethoxybenzamido) methylboronic acid was identified as being a potent inhibitor of Actinomadura sp. R39 transpeptidase (IC50: 1.3 μM). In this work, we synthesized and studied the potential of a number of acylaminomethylboronic acids as inhibitors of PBPs from different classes. Several derivatives inhibited PBPs of classes A, B and C from penicillin sensitive strains. The (2-nitrobenzamido)methylboronic acid was identified as a good inhibitor of a class A PBP (PBP1b from Streptococcus pneumoniae, IC50 = 26 μM), a class B PBP (PBP2xR6 from Streptococcus pneumoniae, IC50 = 138 μM) and a class C PBP (R39 from Actinomadura sp., IC50 = 0.6 μM). This work opens new avenues towards the development of molecules that inhibit PBPs, and eventually display bactericidal effects, on distinct bacterial species.
Zervosen, Astrid,Bouillez, Andre,Herman, Alexandre,Amoroso, Ana,Joris, Bernard,Sauvage, Eric,Charlier, Paulette,Luxen, Andre
experimental part
p. 3915 - 3924
(2012/08/28)

Antioxidant xanthone derivatives induce cell cycle arrest and apoptosis and enhance cell death induced by cisplatin in NTUB1 cells associated with ROS
In an effort to develop novel antioxidant as anticancer agents, a series of xanthones were prepared. In vitro screening, the synthetic xanthones revealed significant inhibitory effects on xanthine oxidase and ABTS radical-cation scavenging activity. The selective compounds 2 and 8 induced an accumulation of NTUB1 cells in the G1 phase arrest and cellular apoptosis by the increase of ROS level. The combination of cisplatin and 2 significantly enhanced the cell death in NTUB1 cells. Compounds 2 and 8 did not show cytotoxic activity in selected concentrations against SV-HUC1 cells. The present results suggested that antioxidants 2 and 8 may be used as anticancer agent for enhancing the therapeutic efficacy of anticancer agents and to reduce their side effect.
Cheng, Jen-Hao,Huang, A-Mei,Hour, Tzyh-Chyuan,Yang, Shyh-Chyun,Pu, Yeong-Shiau,Lin, Chun-Nan
experimental part
p. 1222 - 1231
(2011/04/22)

Total synthesis and biological evaluation of marinopyrrole A and analogs
A five-step total synthesis of the antibiotic marinopyrrole A (1) is described. The developed synthetic technology enabled the synthesis of several marinopyrrole A analogs whose antibacterial properties against methicillin-resistant Staphylococcus aureus TCH1516 were evaluated.
Nicolaou,Simmons, Nicholas L.,Chen, Jason S.,Haste, Nina M.,Nizet, Victor
supporting information; experimental part
p. 2041 - 2043
(2011/05/09)

Regiocontrolled rearrangement of isobenzofurans
Regioselective alkylation and oxidative rearrangement of isobenzofurans has been achieved to generate substituted 4,8- ihydroxyisochromanones in good yields and with complete regiocontrol.
Egan, Ben A.,Paradowski, Michael,Thomas, Lynne H.,Marquez, Rodolfo
supporting information; experimental part
p. 2086 - 2089
(2011/06/25)

Synthesis, spectroscopic characterisation and X-ray analysis of regioisomeric 1,3,5-trisubstituted pyrazoles
A new series of regioisomeric 1,3,5-trisubstituted pyrazoles 7-9(a,b) have been synthesized by the reaction of β-diketones (4-6) with methyl hydrazine in ethanol. All the compounds are characterised by the FT-IR, 1H, 13C NMR and mass spectrometry. The crystal structure of compounds 7a, 7b and minor isomer 8b have been determined by X-ray single crystal analysis which showed either of the substituted groups attached to pyrazole ring are essentially non-planar to the central pyrazole ring. Addition of trace amounts of acetic acid during the synthesis of compound 8 resulted in an unexpected compound 10 which is characterised by the X-ray single crystal analysis and is essentially planar. However, crystal structure of 10 is already reported. All structures are further stabilized by the classic and non-classic inter- and intramolecular hydrogen bonding.
Yunus, Uzma,Kauser, Rukhsana,Bhatti, Moazzam H.,Zia-Ul-Haq, Muhammad,Wong, Wai-Yeung
scheme or table
p. 173 - 180
(2011/07/31)

Design, synthesis and anti-tubercular evaluation of new 2-acylated and 2-alkylated amino-5-(4-(benzyloxy)phenyl)thiophene-3-carboxylic acid derivatives. Part 1
A series of 2-acylated and 2-alkylated amino-5-(4-(benzyloxy)phenyl) thiophene-3-carboxylic acid derivatives were synthesized and evaluated for anti-tubercular activity. Among these compounds, 10d, 15, 12h and 12k inhibited Mycobacterium tuberculosis (Mtb
Lu, Xiaoyun,Wan, Baojie,Franzblau, Scott G.,You, Qidong
experimental part
p. 3551 - 3563
(2011/10/19)

Self-complementary quadruply hydrogen-bonded duplexes based on imide and urea units
The quadruply hydrogen-bonded duplexes based on an imide-urea structure preorganized by three-center hydrogen bonds were found to associate via bifurcated hydrogen bonds. 1H NMR dilution experiments revealed the high stability of the homodimer in apolar solvent (Kdim > 10 5 M-1 in CDCl3) and enhancement of association ability due to electron-withdrawing substituent effects. The ready synthetic availability and adjustable association affinity via electronic effects may render these association units potentially applicable in constructing supramolecular architectures.
Li, Xianghui,Fang, Yuyu,Deng, Pengchi,Hu, Jinchuan,Li, Tian,Feng, Wen,Yuan, Lihua
supporting information; experimental part
p. 4628 - 4631
(2011/11/06)

Ruthenium-catalyzed isoquinolone synthesis through C-H activation using an oxidizing directing group
The oxidant directs: A mild, practical, efficient, and regioselective Ru-catalyzed isoquinolone synthesis with a broad substrate scope was reported (see scheme). In this redox neutral process, the aromatic CiH bond functionalization can be performed at room temperature without using any external oxidant. The mechanism of the reaction was probed, and it was found that CiH activation is the turnover-limiting step.
Li, Bin,Feng, Huiliang,Xu, Shansheng,Wang, Baiquan
supporting information; experimental part
p. 12573 - 12577
(2011/12/03)

Cyclization of N-(2-cyclopent-1-en-1-ylphenyl)benzamides in solution and under mass-spectrometric conditions
The cyclization has been studied of N-(2-cyclopent-1-en-1-ylphenyl) benzamides into the corresponding 3,1-benzoxazines by the action of gaseous hydrogen chloride, trifluoroacetic acid, or bromine, and also under conditions of electron impact in the gas ph
Kazaryants,Erastov,Galkin,Vyrypaev,Salikhov, Sh. M.,Abdrakhmanov
experimental part
p. 355 - 362
(2011/12/15)

On the synthesis and optical properties of sulfur-bridged analogues of triangulenium cations and their precursors
Several sulfur-bridged heterocyclic carbocations of the acridinium and triangulenium family were prepared using 9-(2,6-dimethoxyphenyl)-1,8-dimethoxy- thioxanthenium tetrafluoroborate [7][BF4] as key synthetic intermediate. Thanks to simple yet
Nicolas, Cyril,Bernardinelli, Gerald,Lacour, Jerome
scheme or table
p. 1049 - 1056
(2011/07/08)

Intramolecular hydrogen bonding in medicinal chemistry
The formation of intramolecular hydrogen bonds has a very pronounced effect on molecular structure and properties. We study both aspects in detail with the aim of enabling a more rational use of this class of interactions in medicinal chemistry. On the basis of exhaustive searches in crystal structure databases, we derive propensities for intramolecular hydrogen bond formation of five- to eight-membered ring systems of relevance in drug discovery. A number of motifs, several of which are clearly underutilized in drug discovery, are analyzed in more detail by comparing small molecule and protein-ligand X-ray structures. To investigate effects on physicochemical properties, sets of closely related structures with and without the ability to form intramolecular hydrogen bonds were designed, synthesized, and characterized with respect to membrane permeability, water solubility, and lipophilicity. We find that changes in these properties depend on a subtle balance between the strength of the hydrogen bond interaction, geometry of the newly formed ring system, and the relative energies of the open and closed conformations in polar and unpolar environments. A number of general guidelines for medicinal chemists emerge from this study
Kuhn, Bernd,Mohr, Peter,Stahl, Martin
experimental part
p. 2601 - 2611
(2010/08/05)

Synthesis and biological activity of halophenols as potent antioxidant and cytoprotective agents
A series of new bromophenols and chlorophenols were prepared by a practical route. The in vitro antioxidative activity of the halophenols was evaluated by the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging assay, and their cytoprotective activity was also tested on hydrogen peroxide (H2O2)-induced injury in human umbilical vein endothelial cells (HUVEC). All halophenols tested displayed moderate to good DPPH radical-scavenging activity, and two bromophenols, 2,3′-dibromo-4,5,6′-trihydroxydiphenylmethanone (16c) and 2,3-dibromo-4,5-dihydroxydiphenylmethanone (17c) exhibited high protective activity against H2O2-induced injury in HUVEC with EC50 values of 0.4 and 0.8 μM, respectively. The preliminary structure-activity relationships of these compounds were also investigated in order to determine the essential structures required for their bioactivities.
Zhao, Wanyi,Feng, Xiue,Ban, Shurong,Lin, Wenhan,Li, Qingshan
scheme or table
p. 4132 - 4134
(2010/08/20)

Design and synthesis of 1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazoles and pyrazolo[3,4-b]pyridines for Aurora-A kinase inhibitors
Two series of 3-aminopyrazole compounds including 24 1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazoles and 16 pyrazolo[3,4-b]pyridines were synthesized and evaluated against HCT116, A549, and A2780 tumor cell lines. Among them, three compounds were found to have the ideal anti-proliferative activities in vitro. Docking experiments showed that the novel pyrazolo[3,4-b]pyridines share the similar interaction mode with Aurora-A kinase as PHA739358.
Shi, Jianyou,Xu, Guobin,Zhu, Wei,Ye, Haoyu,Yang, Shengyong,Luo, Youfu,Han, Jing,Yang, Jincheng,Li, Rui,Wei, Yuquan,Chen, Lijuan
supporting information; experimental part
p. 4273 - 4278
(2010/09/04)

Synthesis and bioactivity of N-benzoyl-N'-[5-(2'-substituted phenyl)-2-furoyl] semicarbazide derivatives
In order to find novel chitin synthesis inhibitors (CSIs) with good activity, benzoylphenylurea, a typical kind of CSIs, was chosen as the lead compound and 15 novel derivatives containing furan moieties were designed by converting the urea linkage of benzoylphenylureas into a semicarbazide and changing the aniline part into furoyl groups. The title compounds were synthesized by the reaction of substituted benzoyl isocyanates with 5-(substituted phenyl)-2-furoyl hydrazine, and the structures were confirmed by IR, 1H-NMR, elemental analysis and single crystal X-ray diffraction analyses (compound E2). The bioassay results indicated that the title compounds exhibit good insecticidal activity, especially towards Plutella xylostella L., but had lower fungicidal activity. Inspiringly, the title compounds possessed obvious anticancer activity against human promyelocytic leukemic cell line (HL-60), and some of the title compounds also had activity against human hepatocellular carcinoma cell line (Bel-7402), human gastric carcinoma cell line (BGC-823), and human nasopharyngeal carcinoma cell line (KB). The results indicated that the linkage in the lead compounds was important to the bioactivity and spectra. The modification on the urea linkage is an effective strategy to discover new pesticide and drug candidates.
Cui, Zining,Ling, Yun,Li, Baoju,Li, Yongqiang,Rui, Changhui,Cui, Jingrong,Shi, Yanxia,Yang, Xinling
scheme or table
p. 4267 - 4282
(2010/10/03)

Novel 4- and 7-sulfonylated 2-substituted benzoxazoles
The efficient synthesis of sulfonylated benzoxazoles at positions C 4 or C7 is reported. The condensation reactions involve original anilide acetal reagents which, upon acid catalysis, allow an easy cyclization reaction with the sulfonylated o-aminophenol partners. This method circumvents the classical use of orthoesters which drawback is the limited access to aromatic reagents. Georg Thieme Verlag Stuttgart.
Bruyneel, Frédéric,Marchand-Brynaert, Jacqueline
supporting information; experimental part
p. 1974 - 1978
(2010/10/03)

Enantioselective synthesis of anti -β-hydroxy-α-amido esters via transfer hydrogenation
The asymmetric transfer hydrogenation of α-amido-β-keto esters to provide the corresponding anti-β-hydroxy-α-amido esters in good to excellent yields, diastereoselectivity, and enantioselectivity is reported. The procedure is operationally simple, and delicate handling of the catalyst is not necessary.
Seashore-Ludlow, Brinton,Villo, Piret,Haecker, Christine,Somfai, Peter
supporting information; experimental part
p. 5274 - 5277
(2011/01/12)

N-aroylated isatins: Antiglycation activity
A series of N-aroylated isatins 1-15 was synthesized and evaluated for their antiglycation activity. All compounds showed a varying degree of glycation inhibitory activity with IC50 values between 18.01 ± 0.05-693.7 ± 3.0 μM, when compared with the standard (aminoguanidine) having an IC50 = 268.7 ± 12.4 μM. Compound 1 was found to be the most active member of this series with an IC50 = 18.01 ± 0.05 μM. Compound 10 showed an IC50 = 72.5 ± 0.09 μM, whereas compound 7 has an IC50 = 80.18 ± 0.07 μM. Compounds 3, 9, and 13 showed IC50 values 170.2 ± 0.62, 117.91 ± 2.9, 171.3 ± 0.79 μM, respectively. Rest of the compounds along with parent isatin were found to be inactive. The structures of all the synthetic compounds were deduced by spectroscopic analysis.
Khan, Khalid Mohammed,Mughal, Uzma Rasool,Khan, Ambreen,Naz, Farzana,Perveen, Shahnaz,Choudhary, M. Iqbal
scheme or table
p. 188 - 193
(2011/02/21)