- Synthesis and bioactivity of linear oligomers related to polymeric alkylpyridinium metabolites from the Mediterranean sponge Reniera sarai
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Dimers and tetramers of linear 3-alkylpyridinium salts have been synthesized by an efficient synthetic pathway, which is also applicable to the preparation of higher oligomers. Mono-, di- and tetrameric compounds have been tested for antibacterial and hem
- Mancini, Ines,Sicurelli, Adriana,Guella, Graziano,Turk, Tom,Macek, Peter,Sepcic, Kristina
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- Antibacterial Activity of Hexadecynoic Acid Isomers toward Clinical Isolates of Multidrug-Resistant Staphylococcus aureus
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In the present study, the structural characteristics that impart antibacterial activity to C16 alkynoic fatty acids (aFA) were further investigated. The syntheses of hexadecynoic acids (HDA) containing triple bonds at C-3, C-6, C-8, C-9, C-10, and C-12 were carried out in four steps and with an overall yield of 34–78%. In addition, HDA analogs containing a sulfur atom at either C-4 or C-5 were also prepared in 69–77% overall yields, respectively. Results from this study revealed that the triple bond at C-2 is pivotal for the antibacterial activity displayed by 2-HDA, while the farther the position of the triple bond from the carbonyl group, the lower its bactericidal activity against gram-positive bacteria, including clinical isolates of methicillin-resistant Staphylococcus aureus (CIMRSA) strains. The potential of 2-HDA as an antibacterial agent was also assessed in five CIMRSA strains that were resistant to Ciprofloxacin (Cipro) demonstrating that 2-HDA was the most effective treatment in inhibiting their growth when compared with either Cipro alone or equimolar combinations of Cipro and 2-HDA. Moreover, it was proved that the inhibition of S. aureus DNA gyrase can be linked to the antibacterial activity displayed by 2-HDA. Finally, it was determined that the ability of HDA analogs to form micelles can be linked to their decreased activity against gram-positive bacteria, since critical micellar concentrations (CMC) between 50 and 300 μg/mL were obtained.
- Carballeira, Néstor M.,Chorna, Nataliya,Díaz, Damarith,Medina, Solymar,Mooney, Joseph,Morales-Guzmán, Christian,Ocasio-Malavé, Carlimar,Pereles-De-León, Tomás,Rivera-Román, Ashley,Sanabria-Ríos, David J.
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- PYRIDINE COMPOUND SUBSTITUTED WITH AZOLE
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The present invention provides a compound represented by formula [I] shown below or a pharmaceutically acceptable salt thereof that has an inhibitory effect on 20-HETE producing enzyme. (in formula [I] above, the structure represented by formula [II] below: represents any of the structures represented by formula group [III] below: R1, R2, R3, and R4 independently represent a hydrogen atom, a fluorine atom, methyl, or the like, R5 represents any of the structures represented by formula group [IV]:
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Paragraph 0951
(2020/07/07)
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- Stereoselective synthesis of the Paulownia bagworm sex pheromone
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According to our retrosynthesis, the main chain of the target molecule could be constructed using a C5?+?C7?+?C5 strategy. The key induction reaction afforded chiral methyl group moieties using different Evans templates with different configurations. Li2CuCl4 was effectively employed in the Csp3[sbnd]Csp3 coupling protocol. The target molecular was obtained in a 12.6% overall yield with nine steps in the longest linear route.
- Sun, Zhi-Feng,Zhou, Lu-Nan,Zhang, Tao,Du, Zhen-Ting
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p. 558 - 562
(2017/06/19)
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- Method for synthesizing cis-7-tetradecenol acetate which is main component of sex pheromone of holcocerus vicarius walker
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The invention discloses a method for synthesizing cis-7- tetradecenol acetate which is a main component of sex pheromone of holcocerus vicarius walker. The method includes (1), preparing (7-bromo-heptyl-1-)-2-tetrahydropyran ether; (2), preparing (7-bromo
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Paragraph 0010
(2016/12/16)
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- A practical total synthesis of both e - And Z -isomers of optically pure (S)-14-methylhexadec-8-enal (Trogodermal)
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The total synthesis of both E- and Z-isomers of optically pure (S)-14-methylhexadec-8-enal (trogodermal) is described. Key steps involved Corey-Fuchs reaction, zipper isomerization, and different hydrogenation conditions for cis- and trans-isomers. Georg
- Yadav, Jhillu S.,Chandravathi,Thrimurtulu,Prasad,Ghamdi, Ahmad Alkhazim Al
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p. 1513 - 1518
(2013/07/05)
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- EPOXYEICOSATRIENOIC ACID ANALOGS AND METHODS OF MAKING AND USING THE SAME
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Compounds and compositions comprising epoxyeicosatrienoic acid (EET) analogs that act as EET agonists and are useful as medications in the treatment of drug-induced nephrotoxicity, hypertension and other related conditions. Methods of making and using the
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- 17(R),18(S)-Epoxyeicosatetraenoic acid, a potent eicosapentaenoic acid (EPA) derived regulator of cardiomyocyte contraction: Structure-activity relationships and stable analogues
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17(R),18(S)-Epoxyeicosatetraenoic acid [17(R),18(S)-EETeTr], a cytochrome P450 epoxygenase metabolite of eicosapentaenoic acid (EPA), exerts negative chronotropic effects and protects neonatal rat cardiomyocytes against Ca 2+-overload with EC50 ≈ 1-2 nM. Structure-activity studies revealed that a cis-Δ11,12- or Δ14,15- olefin and a 17(R),18(S)-epoxide are minimal structural elements for antiarrhythmic activity whereas antagonist activity was often associated with the combination of a Δ14,15-olefin and a 17(S),18(R)-epoxide. Compared with natural material, the agonist and antagonist analogues are chemically and metabolically more robust and several show promise as templates for future development of clinical candidates.
- Falck, John R.,Wallukat, Gerd,Puli, Narender,Goli, Mohan,Arnold, Cosima,Konkel, Anne,Rothe, Michael,Fischer, Robert,Müller, Dominik N.,Schunck, Wolf-Hagen
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supporting information; experimental part
p. 4109 - 4118
(2011/08/05)
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- Efficient synthesis of unsaturated 1-monoacyl glycerols for in meso crystallization of membrane proteins
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A highly efficient synthesis of unsaturated 1-monoacyl glycerols was established to fulfill the pressing need for materials that form lipidic mesophases utilized in membrane protein crystallization. Georg Thieme Verlag Stuttgart.
- Fu, Yu,Weng, Yue,Hong, Wen-Xu,Zhang, Qinghai
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experimental part
p. 809 - 812
(2011/06/21)
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- Novel eicosanoid derivatives
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The present invention provides compounds (n-3 PUFA derivatives) of formula (I): that modulate conditions associated with cardiac damage, especially cardiac arrhythmias.
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Page/Page column 22-23
(2010/08/07)
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- Total synthesis of three natural products: Decyl 8-hydroxyheptadecanoate, undecyl hexadecanoate and 2,3-dihydroxypropyl hexadecanoate
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First syntheses of decyl 8-hydroxyheptadecanoate 1 and undecyl hexadecanoate 2 via utilization of microwave energy and a new improved synthesis of 2,3-dihydroxypropyl hexadecanoate 3 have been accomplished from readily available starting compounds.
- Singh, Ashima,Sharma,Singh, Jasvinder
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experimental part
p. 1648 - 1652
(2011/03/17)
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- 4-DIMETHYLAMINOBUTYRIC ACID DERIVATIVES
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This invention relates to novel 4-dimethylaminobutyric acid derivatives of the formula wherein A1, A2, R1, m and n are as defined in the description and in the claims, as well as pharmaceutically acceptable salts thereof. These compounds inhibit carnitine palmitoyl transferase (CPT) activity, in particular CPT2 activity, and can be used as medicaments in methods for the treatment of diseases modulated by CPT2 inhibitors.
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Page/Page column 19
(2009/10/31)
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- SUBSTITUTED CYCLOPENTANES HAVING PROSTAGLANDIN ACTIVITY
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Disclosed herein are compounds having a formula: Therapeutic methods, medicaments, and compositions related thereto are also disclosed.
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Page/Page column 5
(2009/05/28)
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- New synthesis of nematocidal natural products dithiocynates thiocyanatin A and 1,8,16-trihydroxyhexadecane
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A new and short synthesis of nematocidal natural products, thiocyanatin A and 1,8,16-trihydroxyhexadecane, from readily available starting compounds 1,7-heptanediol and 1,9-nonanediol in six steps is described.
- Singh, Ashima,Sharma,Singh, Jasvinder
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experimental part
p. 1029 - 1034
(2010/08/19)
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- Light-driven rotary molecular motors on gold nanoparticles
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We report the synthesis of unidirectional light-driven rotary molecular motors based on chiral overcrowded alkenes and their immobilisation on the surface of gold nanoparticles through two anchors. Using a combination of 1H and 13C N
- Pollard, Michael M.,Ter Wiel, Matthijs K. J.,Van Delden, Richard A.,Vicario, Javier,Koumura, Nagatoshi,Van Den Brom, Coenraad R.,Meetsma, Auke,Feringa, Ben L.
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supporting information; experimental part
p. 11610 - 11622
(2009/12/09)
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- First total syntheses of (Z)-15-methyl-10-hexadecenoic acid and the (Z)-13-methyl-8-tetradecenoic acid
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The first total syntheses for the (Z)-15-methyl-10-hexadecenoic acid and the (Z)-13-methyl-8-tetradecenoic acid were accomplished in seven steps and in 31-32% overall yields. The (trimethylsilyl)acetylene was the key reagent in both syntheses. It is proposed that the best synthetic strategy towards monounsaturated iso methyl-branched fatty acids with double bonds close to the ω end of the acyl chain is first acetylide coupling of (trimethylsilyl)acetylene to a long-chain bifunctional bromoalkane followed by a second acetylide coupling to a short-chain iso bromoalkane, since higher yields are thus obtained. Spectral data is also presented for the first time for these two unusual fatty acids with potential as biomarkers and as topoisomerase I inhibitors.
- Carballeira, Nestor M.,Montano, Nashbly,Padilla, Luis F.
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- Concise synthesis of (8Z,11Z,14Z)-8,11,14-heptadecatrienal, (7Z,10Z,13Z)-7,10,13-hexadecatrienal, and (8Z,11Z)-8,11-heptadecadienal, components of the essential oil of marine green alga Ulva pertusa
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The long-chain aldehydes, (8Z,11Z,14Z)-8,11,14-heptadecatrienal, (7Z,10Z,13Z)-7,10,13-hexadecatrienal, and (8Z,11Z)-8,11-heptadecadienal, were concisely synthesized by using Grignard coupling, catalytic hydrogenation with the Lindlar catalyst, and oxidation with Dess-Martin periodinane as the key steps. Particularly, (8Z,11Z,14Z)-8,11,14-heptadecatrienal and (7Z,10Z, 13Z)-7,10,13-hexadecatrienal both possessed a seaweed-like odor.
- Akakabe, Yoshihiko,Washizu, Kensuke,Matsui, Kenji,Kajiwara, Tadahiko
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p. 1348 - 1352
(2008/02/01)
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- Ethynylation of the ether derivatives of ω-haloalkanols with lithium acetylide-ethylenediamide complex
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A new operationally simple and highly efficient procedure for the ethynylation of ether derivatives of ω-haloalkanols with lithium acetylide-ethylenediamine complex in N,N-dimethylacetamide is described.
- Karpinska,Lewandowska,Grodner
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p. 937 - 942
(2007/10/03)
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- Parthenogenesis, calling behavior, and insect-released volatiles of leafminer moth Phyllonorycter emberizaepenella.
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We proved that the leafminer moth Phyllonorycter emberizaepenella (Lepidoptera: Gracillariidae) reproduces by parthenogenesis of the thelytoky type. Despite a complete absence of males, parthenogenetically reproducing females diurnally demonstrated the calling posture normally used for releasing signaling compounds. Two compounds, which we collected from a calling female, were identified as potential sex pheromone components: (8E, 10E)-8,10-tetradecadienyl acetate and (8E,10E)-8,10-tetradecadienol, the latter occurring only in trace amounts. In field experiments, no males were attracted to traps baited with either the potential sex pheromone or with virgin females. Both the pattern of behavior and the chemical characteristics of the pheromone of Ph. emberizaepenella species were similar to those known for Lepidoptera with the usual amphimictic mode of reproduction. Theoretical speculations that in thelytoky, where there is no need to find a sexual partner, the individuals would obtain certain advantages due to reduction in their sexual behavior, were, thus, not confirmed for Ph. emberizaepenella.
- Mozuraitis, Raimondas,Buda, Vincas,Liblikas, Ilme,Unelius, Carl Rikard,Borg-Karlson, Anna-Karin
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p. 1191 - 1208
(2007/10/03)
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- Selective antiproliferative activity of caffeic acid phenethyl ester analogues on highly liver-Metastatic murine colon 26-L5 carcinoma cell line
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Caffeic acid phenethyl ester (CAPE, 2) and its 20 analogues (1, 3-21) were prepared. These esters were tested by MTT assay on growth of murine colon 26-L5 carcinoma, murine B16-BL6 malonoma, murine Lewis lung carcinoma, human HT-1080 fibrosarcoma, human lung A549 adenocarcinoma, and human cervix HeLa adenocarcinoma cell lines. It was found that CAPE analogues possessed selective antiproliferative activity toward highly liver-metastatic murine colon 26-L5 carcinoma cell line. Among them, 4-phenylbutyl caffeate (4), (Z)-8-phenyl-7-octenyl (10a) and (E)-8-phenyl-7-octenyl (10b) caffeate showed the most potent antiproliferative activity (EC50 value, 0.02μM). In addition, CAPE (2) induced DNA fragmentation at concentrations of 1 to 10μg/mL towards murine colon 26-L5 carcinoma cells. Copyright
- Nagaoka, Takema,Banskota, Arjun H,Tezuka, Yasuhiro,Saiki, Ikuo,Kadota, Shigetoshi
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p. 3351 - 3359
(2007/10/03)
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- Sequential substitution of 1,2-dichloro-ethene: A convenient stereoselective route to (9Z,11E)-, (10E,12Z)- and (10Z,12Z)-[1-14C] conjugated linoleic acid isomers
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Conjugated linoleic acid (CLA) isomers are present in human foods derived from milk or ruminant meat. To study their metabolism, (9Z,11E)-, (10E,12Z)- and (10Z,12Z)-[1-14C]-octadecadienoic acids with high radiochemical and isomeric purities (> 98%) were prepared by stereoselective multi-step syntheses involving sequential substitution of 1,2-dichloro-ethene. In the case of the (9Z,11E) isomer, a first metal-catalyzed cross-coupling reaction between (E)-1,2-dichloro-ethene and 2-non-8-ynyloxy-tetrahydro-pyran, obtained from 7-bromo-heptan-1-ol, gave a conjugated chloroenyne. A second coupling reaction with hexylmagnesium bromide provided a heptadecenynyl derivative. Stereoselective reduction of the triple bond and bromination afforded (7E,9Z)-17-bromo-heptadeca-7,9-diene. Formation of the Grignard reagent and carbonation with 14CO2 gave (9Z,11E)-[1-14C]-octadeca-9,11-dienoic acid (overall yield from 7-bromo-heptan-1-ol, 14.4%). (10E,12Z)- and (10Z,12Z)-[1-14C]-octadeca-10,12-dienoic acids were synthesized by the same methodology using 1-heptyne, 8-bromo-octan-1-ol and, respectively, (E)-1,2-dichloro-ethene and its (Z) isomer (overall yield from 8-bromo-octan-1-ol, 13.1% (10E,12Z); 17.2% (10Z,12Z)). Impurities ( 2% if present) were identified as being (E,E) CLA isomers and were removed by RP-HPLC. Metabolism studies in animal are in progress.
- Loreau,Maret,Chardigny,Sebedio,Noel
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- A mild and versatile method for the tetrahydropyranylation of alcohols and their detetrahydropyranylation
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An efficient and mild method for tetrahydropyranylation of alcohols and their detetrahydropranylation using NH4Cl is described. This protocol provides a useful alternative tetrahydropyranylation of alcohols and their deprotection at different pH.
- Yadav,Srinivas, Dale,Reddy, Gondi Sudershan
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p. 1399 - 1404
(2007/10/03)
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- Synthesis of anacardic acids utilizing an annelation reaction of isoxazoles with ethyl acetoacetate
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Anacardic acids, 6-pentadecylsalicylic acid (1) and 6-[8(Z)- pentadecenyl]salicylic acid (2) were synthesized from isoxazoles by annelation reactions with ethyl acetoacetate.
- Satoh, Mitsuru,Takeuchi, Naoki,Fujita, Takeshi,Yamazaki, Katsuya,Tobinaga, Seisho
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p. 1501 - 1505
(2007/10/03)
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- Functionalized aliphatic P2/P2' analogs of HIV-1 protease inhibitor DMP323
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A series of analogs of HIV protease inhibitor DMP323 containing functionalized aliphatic P2/P2' groups was prepared and evaluated for HIV protease inhibition and antiviral activity in a cell-based assay. Asymmetric compounds with a 5-hydroxypentyl substituent at P2 and a benzylic substituent at P2' showed increased potency over the corresponding symmetrically substituted analogs.
- Smallheer, Joanne M.,McHugh, Robert J.,Chang, Chong-Hwan,Kaltenbach III, Robert F.,Worley, Tabitha V.,Klabe, Ronald M.,Bacheler, Lee T.,Rayner, Marlene M.,Erickson-Viitanen, Susan,Seitz, Steven P.
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p. 1365 - 1370
(2007/10/03)
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- (Z)-Heptadec-8-enylboronic acid: a ppotential lipase inhibitor
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(Z)-Heptadec-8-enylboronic acid, a potential lipase inhibitor that is isosteric with oleic acid, and that is unexpectedly sensitive to aerial oxidation, has been prepared in 23percent overall yield from dec-1-yne and 7-bromoheptanol.Disappointingly, the target compound proved inactive under conditions where lipase inhibition would have been expected.
- Martichonok, Valeri,Jones, J. Bryan
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p. 2927 - 2930
(2007/10/02)
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- Syntesis, Conformational Analysis, and Stereoselective Reduction of 14-Membered Ring 3-Keto Lactones
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The synthesis of 3-oxo-13-tetradecanolide (5) and its 2-methyl and 2,2-dimethyl derivatives 7 and 8 have been carried out.The keto carbonyls in 5, 7, and 8 have been reduced with varying degrees of stereoselectivity.The stereoselectivity of the reduction depends on the counterion with the borohydride reducing agent, but selectivities approaching 100percent have been achieved for 5 and 7.The structure of the reduced products were determined by X-ray crystallography and chemical correlation.Heavy reliance on the stereoselectivity in the Frater dianion alkylation was used.The solution conformation of the β-keto lactones was found to be based on A both from NMR studies and molecular mechanics calculations.However, we are not able to predict the observed stereoselectivity in the hydride reduction of the ketones using this conformation.Thus we suggest the reduction proceeds through conformation B' in which the two carbonyls are chelated to the counterion.The conformations of the resulting alcohols are more complex and have both inter- and intramolecular hydrogen bonding which control the conformations.The use of polar maps to illustrate similarities and differences in conformations is demonstrated.These conformations are used to rationalize the physical and chemical properties of the β-keto and β-hydroxy 14-membered lactones.
- Neeland, Edward G.,Ounsworth, James P.,Sims, Russel J.,Weiler, Larry
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p. 7383 - 7394
(2007/10/02)
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- Synthesis and biological activity of new 3-hydroxy-3-methylglutaryl-CoA synthase inhibitors: 2-Oxetanones with a meta-substituent on the benzene ring in the side chain
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Isosteric side chain analogs of 3a were synthesized and tested for inhibitory activities towards 3-hydroxy-3-methylglutaryl coenzyme A (HMG- CoA) synthase and upon cholesterol production in Hep G2 cells and in mouse liver. It became clear that the lipophi
- Hashizume,Ito,Kanaya,Nagashima,Usui,Oshima,Kanao,Tomoda,Sunazuka,Kumagai,Omura
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p. 1272 - 1278
(2007/10/02)
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- Design, synthesis, and activity of membrane-disrupting bolaphiles
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Four new classes of bolaphiles ("double-headed" single-chain surfactants) have been prepared, via condensation of an homologous series of linear saturated, olefinic, and acetylenic α,ω-dicarboxylic acids with hexaethylene glycol, and evaluated for their ability to induce the release of 5(6)-carboxyfluorescein (CF) entrapped within large unilamellar vesicles derived from 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC). Operationally, the membrane-disrupting activity of the bolaphiles has been found to vary by a factor of ca. 100, when the total number of carbon atoms which separate the carboxylate moieties range from 12 to 24; the most active bolaphile is approximately three times more active than Triton X-100. When the affinity of the bolaphiles toward POPC membranes is considered, the intrinsic membrane-disrupting activity varies by a factor of ca. 230. A "loop" model is proposed to account for the general trends in bolaphile activity that are observed, where the depth of loop penetration and loop width are presumed to be the key factors involved in determining membrane-disrupting activity. The potential utility of these surfactants as antimicrobial agents, and as anti-HIV agents in particular, is briefly discussed.
- Jayasuriya, Nimal,Bosak, Stanislav,Regen, Steven L.
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p. 5844 - 5850
(2007/10/02)
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- Synthesis of Large Macrocyclic Tetraaza Compounds with A Methylene Backbone: Cyclo4, (n = 6,7,8,9 and 10). The Formation of 28-, 32-, 36-, 40- and 44-Membered Rings.
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A series of macrocyclic tetraamines with 28-, 32-, 36-, 40- and 44-membered rings have been efficiently prepared from the corresponding ditosylamide and monobromoalcohol derivatives in 6 steps via a double condensation reaction.Overall yields were: 41, 41, 46, 29, and 33 percent, respectively, for 1,8,15,22-tetraazacyclooctacontane (11a), 1,9,17,25-tetraazacyclodotriacontane (11b), 1,10,19,28, tetraazacyclohexatriacontane (11c), 1,11,21,31-tetraazacyclotetracontane (11d) and 1,12,23,34-tetraazacyclotetratetracontane (11e).
- Tomohiro, Takenori,Uoto, Kouichi,Okuno, Hiroaki (Yohmei)
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p. 1233 - 1239
(2007/10/02)
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- Systematic Syntheses and Charactarization of Dodecadien-1-ols with Conjugated Double Bond, Lepidopterous Sex Pheromones
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Four geometrical isomers of 5,7-, 6,8-, 7,9- and 8,10-dodecadein-1-ols were systematically synthesized by two routes.One involved the Wittig reaction between (E)-2-alkenal and a phosphorane with an appropriate carbon chain, and yielded a mixture of (E,Z)- and (E,E)-isomers in a ratio of ca. 3:2.The other route comprised of the Wittig reaction of a 2-alkynal and the stereoselective reduction of the triple bond to a (Z)-double bond via hydroboration with dicyclohexylborane to give a mixture of (Z,Z)- and (Z,E)-isomers in a ratio of 6:1 10:1.Both the mixtures were separately chromatographed on a silica gel column impregnated with silver nitrate to give four geometrically pure isomers.With 9,11-diene they were analysed by GC on a capillary column, HPLC, silver nitrate impregnated TLC, and 13C NMR.
- Ando, Tetsu,Kurotsu, Yuichi,Kaiva, Mieko,Uchiyama, Masaaki
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p. 141 - 148
(2007/10/02)
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- 245. Studies on Monoterpene Glucosides and Related Natural Products. Part 51. Absolute Structures of Hydrangenosides A, B, C, D, E, F, and G. Novel Type Secoiridoid Glucosides from Two Hydrangea Plants
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From Hydrangea macrophylla var. macrophylla, four new secoiridoid glucosides, hydrangenosides A, B, C and D, were isolated, along with the known iridoid glucosides loganin, secologanin, secologanic acid and sweroside.Moreover, hydrangenosides E, F, and G,
- Uesato, Shinici,Takeda, Yoshio,Hashimoto, Toshihiro,Uobe, Kenichi,Inouye, Hiroyuki,et al.
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p. 2111 - 2127
(2007/10/02)
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