- The reaction of prop-2-ynylsulfonium salts and sulfonyl-protected β-amino ketones to epoxide-fused 2-methylenepyrrolidines and S-containing pyrroles
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A novel divergent domino annulation reaction of prop-2-ynylsulfonium salts with sulfonyl-protected β-amino ketones has been developed, affording various epoxide-fused 2-methylenepyrrolidines and S-containing pyrroles in moderate to excellent yields. Prop-2-ynylsulfonium salts act as C2synthons in the reactions providing a promising epoxide-fused skeleton in a single operation with readily accessible starting materials.
- Jia, Tingting,Zeng, Gongruixue,Zhang, Chong,Zeng, Linghui,Zheng, Wenya,Li, Siyao,Wu, Keyi,Shao, Jiaan,Zhang, Jiankang,Zhu, Huajian
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supporting information
p. 2657 - 2660
(2021/03/16)
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- Design, synthesis and evaluation of novel 5-phenylthiophene derivatives as potent fungicidal of Candida albicans and antifungal reagents of fluconazole-resistant fungi
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A series of 5-phenylthiophene derivatives with novel structures were designed and synthesized to combat the increasing incidence of susceptible and drug-resistant fungal infections. The antifungal activity of the synthesized compounds was assessed against seven susceptible strains and six fluconazole-resistant strains. It is especially encouraging that compounds 17b and 17f displayed significant antifungal activities against all tested strains. Furthermore, the potent compounds 17b and 17f could prevent the formation of fungi biofilms and 17f displayed satisfactory fungicidal activity. Preliminary mechanistic studies showed that the potent antifungal activity of compound 17f stemmed from inhibition of C. albicans CYP51. In addition, Compounds 17b and 17f were almost nontoxic to mammalian A549, MCF-7, and THLE-2 cells. These results strongly suggested that compounds 17b and 17f are promising as novel antifungal drugs.
- Cheng, Maosheng,Cui, Hengxian,Jiang, Hong,Li, Song,Liu, Lei,Su, Xin,Sun, Yin,Wu, Tianxiao,Yin, Wenbo,Zhang, Yuxin,Zhao, Dongmei,Zhao, Liyu,Zheng, Yang
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- 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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- Synthesis, characterization, COX1/2 inhibition and molecular modeling studies on novel 2-thio-diarylimidazoles
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Heterocyclic compounds with diaryl substituents have been a milestone approach for selective cyclooxygenase 2 (COX 2) inhibition by bioisosteric replacements and modifications. It is also known that thiazole derivatives have different pharmacological acti
- ?ahin, Zafer,Bender, Ceysu,Berk, Bark?n,Biltekin Kaleli, Sevde Nur,Demirayak, ?eref,Ko?o?lu Kalkan, Melike,Yurtta?, Leyla
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p. 1841 - 1853
(2022/01/08)
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- Synthesis of 2-Amino Substituted Oxazoles from α-Amino Ketones and Isothiocyanates via Sequential Addition and I2-Mediated Desulfurative Cyclization
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Oxazol-2-amines were synthesized by annulation of α-amino ketones and isothiocyanates. This sequential synthetic process involves addition of α-amino ketones to isothiocyanates and I2-promoted desulfurative cyclization omitting isolation of the less stable thiourea intermediates. It is transition metal-free and operationally simple, providing access to a variety of 2-amino substituted oxazole derivatives under mild reaction conditions. (Figure presented.).
- Chang, Junbiao,Yu, Wenquan,Zhang, Shuangshuang,Zhao, Qiongli,Zhao, Yifei
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supporting information
(2020/04/29)
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- Toward a treatment of diabesity: In vitro and in vivo evaluation of uncharged bromophenol derivatives as a new series of PTP1B inhibitors
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Protein tyrosine phosphatase 1B (PTP1B) has been considered as a validated biological target for type 2 diabetes treatment, but past endeavors to develop inhibitors of PTP1B into drugs have been unsuccessful. Two challenging aspects are selective inhibition and cell permeability. A structure-based strategy was employed to develop uncharged bromophenols as a new series of PTP1B inhibitors. The most potent compound 22 (LXQ46) inhibited PTP1B with an IC50 value of 0.190 μM, and showed remarkable selectivity over other protein tyrosine phosphatases (PTPs, 20–200 folds). In the SPR study, increasing concentrations of compound 22 led to concentration-dependent increases in binding responses, indicating that compound 22 could bind to the surface of PTP1B via noncovalent means. By treating insulin-resistant C2C12 myotubes with compound 22, enhanced insulin and leptin signaling pathways were observed. Long-term oral administration of compound 22 reduced the blood glucose level of diabetic BKS db mice. The glucose tolerance tests (OGTT) and insulin tolerance tests (ITT) in BKS db mice showed that oral administration of compound 22 could increase insulin sensitivity. In addition, long-term oral administration of compound 22 could protect mice from obesity, which was not the result of toxicity. Our pharmacokinetics results from the rat-based assays showed that orally administered compound 22 was absorbed rapidly from the gastrointestinal tract, extensively distributed to the tissues, and rapidly eliminated from the body. All these results indicate that compound 22 could serve as a qualified agent to treat type II diabetes.
- Li, Xiangqian,Xu, Qi,Li, Chao,Luo, Jiao,Li, Xiuxue,Wang, Lijun,Jiang, Bo,Shi, Dayong
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supporting information
p. 178 - 185
(2019/02/05)
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- Structure-Activity Relationships of New Natural Product-Based Diaryloxazoles with Selective Activity against Androgen Receptor-Positive Breast Cancer Cells
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Targeted therapies for ER+/PR+ and HER2-amplified breast cancers have improved patient survival, but there are no therapies for triple negative breast cancers (TNBC) that lack expression of estrogen and progesterone receptors (ER/PR), or amplification or
- Robles, Andrew J.,McCowen, Shelby,Cai, Shengxin,Glassman, Michaels,Ruiz, Francisco,Cichewicz, Robert H.,McHardy, Stanton F.,Mooberry, Susan L.
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p. 9275 - 9289
(2017/11/30)
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- 3. 4 - diaryl maleic imide derivative and its preparation method and application
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The invention discloses a 3,4-diarylmaleimide derivative and a preparation method as well as application thereof. The general formula of the 3,4-diarylmaleimide derivative is shown in the specification. The 3,4-diarylmaleimide derivative can be applied to
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Paragraph 0081; 0082
(2017/07/07)
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- Discovery of 2-azetidinone and 1H-pyrrole-2,5-dione derivatives containing sulfonamide group at the side chain as potential cholesterol absorption inhibitors
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Cholesterol absorption inhibitor (CAI) targeting Niemann-Pick C1-like1 protein was developed for the treatment of hyperlipidaemia and only ezetimibe was approved so far. For developing novel CAIs, we synthesized sixteen 2-azetidinone derivatives and thirt
- Yuan, Xinrui,Lu, Peng,Xue, Xiaojian,Qin, Hui,Fan, Chen,Wang, Yubin,Zhang, Qi
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p. 849 - 853
(2016/05/24)
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- Investigation of the mechanism of racemization of litronesib in aqueous solution: Unexpected base-catalyzed inversion of a fully substituted carbon chiral center
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Mitosis inhibitor (R)-litronesib (LY2523355) is a 1,3,4-thiadiazoline- bearing phenyl and N-(2-ethylamino)ethanesulfonamido-methyl substituents on tetrahedral C5. Chiral instability has been observed at pH 6 and above with the rate of racemization increas
- Baertschi, Steven W.,Jansen, Patrick J.,Montgomery, Robert M.,Smith, William K.,Draper, Jerry R.,Myers, David P.,Houghton, Peter G.,Sharp, V. Scott,Guisbert, Andrea L.,Zhuang, Hong,Watkins, Michael A.,Stephenson, Gregory A.,Harris, Thomas M.
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p. 2797 - 2808
(2014/11/07)
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- Compositions and Methods for Affecting Mental State and Body Composition
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The invention discloses compositions, including nutritional products and dietary supplements, comprising aegeline, which is a compound that occurs naturally in the Bael plant. The invention also describes methods comprising the administration of aegeline to mammals. The methods result in increased mental stamina, focus, and energy level, improved mood, increased thermogenesis, increased libido, and anabolic effects and increased strength output and/or muscle mass. These effects can improve cognition, influence body composition, promote weight loss, and/or promote fitness and well-being. A novel method for the synthesis of aegeline is also provided.
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Paragraph 0088-0089
(2014/05/20)
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- Rearrangement of N-tert-butanesulfinyl α-halo imines with alkoxides to N-tert-butanesulfinyl 2-amino acetals as precursors of N-protected and N-unprotected α-amino carbonyl compounds
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Reaction of N-tert-butanesulfinyl α-halo imines with alkoxides afforded new N-tert-butanesulfinyl 2-amino acetals in good to excellent yield. These N-tert-butanesulfinyl 2-amino acetals are convenient precursors for the TMSOTf-promoted synthesis of the co
- Colpaert, Filip,Mangelinckx, Sven,Denolf, Bram,De Kimpe, Norbert
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p. 6023 - 6032
(2012/10/08)
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- CHEMICAL COMPOUNDS
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The invention is directed to 6-(4-pyι?midinyl)-1 H-indazole derivatives. Specifically, the invention is directed to compounds according to Formula (I) wherein R1 - R4 are defined herein. The compounds of the invention are inhibitors of PDK1 and can be useful in the treatment of immune and metabolic diseases and disorders characterized by constitutively activated ACG kinases such as cancer and more specifically cancers of the breast, colon, and lung. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting PDK1 activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.
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Page/Page column 238
(2010/07/10)
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- Synthesis and biological evaluation of imidazol-2-one derivatives as potential antitumor agents
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A new series of aryl substituted imidazol-2-one derivatives structurally related to combretastatin A-4 (CA-4) were synthesized and evaluated for their cytotoxic activities in vitro against various human cancer cell lines including MDR cell line. The cytotoxic effects of compounds 7b and 7i proved to be similar to or greater than that of docetaxel. The highly active compound 7b also exhibited excellent inhibitory activity on tumor growth in vivo.
- Xue, Na,Yang, Xiaochun,Wu, Rui,Chen, Jing,He, Qiaojun,Yang, Bo,Lu, Xiuyang,Hu, Yongzhou
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p. 2550 - 2557
(2008/09/21)
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- 2,5-SUBSTITUTED OXAZOLE DERIVATIVES AS PROTEIN KINASE INHIBITORS FOR THE TREATMENT OF CANCER
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Certain oxazole-based compounds exhibiting ATP-utilizing enzyme inhibitory activity, methods of using compounds exhibiting ATP-utilizing enzyme inhibitory activity, and compositions comprising compounds exhibiting ATP-utilizing enzyme inhibitory activity, are disclosed.
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Page/Page column 57
(2010/11/29)
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- Design of emission ratiometric metal-ion sensors with enhanced two-photon cross section and brightness
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To develop metal-responsive fluorescence probes with optimized nonlinear optical properties for two-photon excitation fluorescence microscopy (TPEM), we investigated the utility of donor-acceptor architectures where the metal-ion coordinates to the acceptor rather than donor site of the fluorophore. Zn(II) binding to such a probe consisting of a tris(picolyl)amine-substituted acceptor site connected with an anisole donor moiety and an oxazole central core resulted in a significant increase of the two-photon absorption cross section (δ) and fluorescence brightness (ηδ). The fluorophore showed also a strong shift of the emission peak upon saturation with Zn(II), rendering the proposed approach suitable for two-photon excited emission ratiometric sensing. Copyright
- Sumalekshmy,Henary, Maged M.,Siegel, Nisan,Lawson, PaDreyia V.,Wu, Yonggang,Schmidt, Karin,Bredas, Jean-Luc,Perry, Joseph W.,Fahrni, Christoph J.
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p. 11888 - 11889
(2008/03/27)
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- Asymmetric hydrogenation of α-primary and secondary amino ketones: Efficient asymmetric syntheses of (-)-arbutamine and (-)-denopamine
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Two ss-receptor agonists (-)-denopamine and (-)-arbutamine were prepared in good yields and enantioselectivities by asymmetric hydrogenation of unprotected amino ketones for the first time by using Rh catalysts bearing electron-donating phosphine ligands. A series of α-primary and secondary amino ketones were synthesized and hydrogenated to produce various 1,2-amino alcohols in good yields and with good enantioselectivies. This Rh electron-donating phosphine-catalyzed asymmetric hyderogenation repI resents one of the most promising and convenient approaches towards the asymmetric synthesis of chiral amino alcohols.
- Shang, Gao,Liu, Duan,Allen, Scott E.,Yang, Qin,Zhang, Xumu
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p. 7780 - 7784
(2008/04/03)
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- THROMBOPOETIN RECEPTOR ACTIVATOR AND PROCESS FOR PRODUCING THE SAME
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A preventive, therapeutic or improving agent for diseases against which activation of the thrombopoietin receptor is effective or a platelet increasing agent, which contains a thrombopoietin receptor activator represented by the formula (1): [wherein each
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Page/Page column 15-16
(2008/06/13)
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- ANTIBACTERIAL BENZOIC ACID DERIVATIVES
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The invention provides antimicrobial agents and methods of using the agents for sterilization, sanitation, antisepsis, disinfection, and treatment of infections in mammals.
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- New heteroarylbenzenesulphonamides as matrix metalloproteinase inhibitors
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A series of derivatives of 2,4- and 2,5-thiazolyl- or oxazolylbenzenesulphonamides has been prepared and evaluated as potential MMP inhibitors. The thiazole 15b have been found to exhibit MMP-2 and MMP-9 inhibitions higher than reference compounds GI 129471 and CGS 27023A.
- Delbecq, Frederic,Cordonnier, Guy,Pommery, Nicole,Barbry, Didier,Henichart, Jean-Pierre
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p. 1119 - 1121
(2007/10/03)
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- Mesomorphic compound, liquid crystal composition, liquid crystal device, display apparatus and display method
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A mesomorphic compound represented by the following formula (I): STR1 wherein R1 denotes a linear or branched alkyl group having 2-16 carbon atoms capable of including one or non-neighboring two methylene groups which can be replaced with --O--
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- Syntheses and Photophysical Properties of Some 5(2)-Aryl-2(5)-(4-pyridyl)oxazoles and Related Oxadiazoles and Furans
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A number of 5-aryl-2-(4-pyridyl)oxazoles, a 2-aryl-5-(4-pyridyl)oxazole, the related oxadiazole and furan, several 2-(4-pyridyl)cycloalkanooxazoles, and many of their quaternary salts were prepared.No single standard synthesis was effective for preparation of more than a few of the 25 free bases described; methods often unique to a base were employed.Minor variations in structure sometimes produced large differences in absorption and emission wavelengths, as well as in the magnitude of the extinction coefficient.The salts are of interest as laser dyes, scintillation fluors, biological stains, and shifters for luminescent solar concentrators.
- Hall, J. Herbert,Chien, Joseph Yuming,Kauffman, Joel M.,Litak, Peter T.,Adams, Jeffrey K.,et al.
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p. 1245 - 1273
(2007/10/02)
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- A Convenient Synthesis of Aminomethyl Ketones (α-Amino Ketones)
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Several N,N-diformylaminomethyl ketones 3 were prepared by treating the respective bromomethylketone 1 with sodium diformylamide in acetonitrile at room temperature.This reaction produced from N-formylaminomethyl ketones 4 when ethanol was used as the solvent.One of the formyl groups of N,N-difomylaminomethyl ketones was selectively removed by using a catalytic amount of sodium or potassium hydroxide in alcohol to the corresponding N-formylaminomethyl ketones 4.The formyl groups of both N,N-diformyl- and N-formylaminomethyl ketones could be easily removed by either5percent hydrochloric acid in ethanol or 6N hydrochloric acid to give the corresponding aminomethyl ketone hydrochlorides 5.These reactions are general and give high yield of the products.
- Yinglin, Han,Hongwen, Hu
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p. 615 - 618
(2007/10/02)
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- 1,2,4-triazinone derivatives, their preparation and use
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Compounds of formula (I): STR1 (in which: R1 is hydrogen or alkl; R2 is a variety of groups or atoms; R3 is optionally substituted hydroxy or --(NH)n --NR5 R6, wherein R5 and R6 are a variety of groups or atoms, preferably alkyl substituted by heterocyclic, and n is 0 or 1; Q is oxygen or sulfur; and A is a C1 -C6 alkylene group) have valuable cardiotionic activity and may be used for the treatment of cardiac disorders. They may be prepared from corresponding compounds containing a benzene ring with a group --QH at the 1-position and a group --CO--CHR1 --NH--COOR7 at the 4-position by ring closure and introduction of the group of formula --A--CO--R3 in any order.
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- SYNTHESIS OF α-AMINO KETONE HYDROCHLORIDES VIA CHEMOSELECTIVE HYDROGENATION OF α-NITRO KETONES
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Chemoselective hydrogenation of various α-nitro ketones was accomplished with 5percent Pt sulfide on carbon as a catalyst to afford α-amino ketone hydrochlorides in good yields.
- Tamura, Rui,Oda, Daihei,Kurokawa, Hiroshi
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p. 5759 - 5762
(2007/10/02)
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- Dye lasers using 2-(4-pyridyl)-5-aryloxazoles and quaternary salts of these compounds
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2-(4-pyridyl)-5-aryloxazoles and certain quaternary salts of these compounds are useful as visible-wavelength lasing dyes. These dyes are used in solution with non-interferring polar solvents, such as low molecular weight alcohols, H2 O, and D2 O, to form lasing media useful in dye lasers. Such lasers generally include a reservoir for containing the laser dye solution and a pumping energy source operably coupled therewith for producing stimulated emission of the dye solution.
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- New Anticancer Agents: Synthesis of 1,2-Dihydropyridopyrizines (1-Deaza-7,8-dihydropteridines)
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Reaction of α-aminoacetophenone oximes (2) with ethyl 6-amino-4-chloro-5-nitropyridine-2-carbamate (1) gave ethyl 6-amino-5-nitro-4-pyridine-2-carbamate oximes (3), which were hydrolyzed under acidic conditions to give the corresponding ketones (4).Related pyridines substituted with keto side chain were prepared from 1 and 1,3-diaminopropanone oximes and by oxidation of the side-chain hydroxy group of ethyl 6-amino-4-amino>-5-nitropyridine-7-carbamates (6).Catalytic hydrogenation of the nitro group of 4 over Raney nickel in a large volume of ethanol gave the 1-deaza-7,8-dihydropteridines (7).Several of the oximes 3 were successfully hydrogenated to give 7 directly.The resulting 1-deaza-7,8-dihydropteridines showed potent cytotoxicity against cultured L1210 cells and significant anticancer activity against lymphocytic leukemia P-388 in mice.THese biological activities are attributed to the accumulation of cells at mitosis.
- Temple, Carroll,Wheeler, Glynn P.,Elliott, Robert D.,Rose, Jerry D.,Kussner, Conrad L.,et al.
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p. 1045 - 1050
(2007/10/02)
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