- Influence of liquid crystalline formation on the phase behavior of side-chain liquid crystalline block copolymers
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A series of narrowly distributed diblock copolymers composed of amorphous components and side-chain liquid crystalline (LC) polymer, poly (butyl acrylate)-block-poly [8-(4-cyano-4′-biphenyl)-1-octanoyl acrylate] (PBA-b-PCBOA), with side-chain LC block weight fraction (fw,PCBOA) ranging from 25% to 87%, were synthesized by atom transfer radical polymerization (ATRP). Their thermal property, LC behavior, bulk phase behavior and thin film morphology were studied by differential scanning calorimetry (DSC), polarizing optical microscope (POM), small-angle X-ray scattering (SAXS) techniques and atomic force microscopy (AFM), respectively. The results show the diblock copolymers with different composition could present sphere, lamellar and cylinder morphologies before the order-disorder transition. As the mesogen units self-organize to form smectic phase, the lamellar morphology dominates during the majority LC block weight fraction range (fw,PCBOA = 46%-77%) to minimized the surface energy. Interestingly, for spin-coated thin film, the lamella phase separation size decreased with increasing annealing time. For the copolymer with fw,PCBOA of 67%, a thermoreversible order-order transition (OOT) and lamella to lamella/modified layer (L/ML), were observed.
- Ji, Liangliang,Chen, Xiaofang,Wu, Yanhong,Yang, Xiaoming,Tu, Yingfeng
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Read Online
- Chemoenzymatic synthesis of (R)-(+)-2-methylbutan-1-ol, a chiral synthon for the preparation of optically active pheromones
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Optically active (R)-(+)-2-methylbutan-1-ol (which is not commercially available) was prepared by a chemoenzymatic synthesis, in which the key step involved a reduction catalyzed by baker's yeast. The synthon was used in the synthesis of (R)-10-methyldodecan-1-yl acetate, the chiral methyl-branched pheromone of Adoxophyes sp.
- Geresh, Shimona,Valiyaveettil, Thomas J.,Lavie, Yair,Shani, Arnon
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Read Online
- Identification and synthesis of the male produced volatiles of the carrion beetle, Oxelytrum erythrurum (Coleoptera: Silphidae)
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Necrophagous beetles belonging to the family Silphidae are recognized as potentially useful in forensic investigations (to estimate post mortem interval). Gas chromatography analyses of extracts of aerations of adult Oxelytrum erythrurum revealed the presence of two male-specific compounds. These compounds were identified as (Z)-1,10-nonadecadiene (major) and 1-nonadecene (minor) using microderivatizations of the natural male extract, such as hydrogenation, partial reduction and methylthiolation, mass spectrum comparisons, and co-injections with authentic standards. Both compounds might be components of a pheromone responsible for sexual communication in this species.
- Fockink, Douglas H.,Martins, Camila B.C.,Zarbin, Paulo H.G.
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Read Online
- Fluorinated analogs of ester components of red bollworm sex pheromone
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Fluorinated analogs of the two geometrical isomers of the red bollworm moth sex pheromone were synthetized by palladium-catalyzed cross coupling reactions.
- Tellier,Sauvetre
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Read Online
- Nucleophilic substitution reactions of unbranched alkyl amines using triazine reagents
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Since amines are present in many organic, biological, and drug molecules, a strategy of synthesizing desired compounds by nucleophilic substitution reactions of these amines is very attractive. By using triazine reagents, we have found that nucleophilic substitution reactions of unbranched alkyl amines via morpholine derivatives are feasible. This method can be performed under milder reaction conditions than those in previously reported methods.
- Kitamura, Masanori,Kitaoka, Yuki,Fujita, Hikaru,Kunishima, Munetaka
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supporting information
(2022/03/02)
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- Practical Synthesis and Field Application of the Synthetic Sex Pheromone of Rice Stem Borer, Chilo suppressalis (Lepidoptera: Pyralidae)
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Rice stem borer, Chilo suppressalis, is a common and major serious pest of rice, maize, and wheat crops across Asia, Europe, and Oceania countries. Its sex pheromone consists of three analogously compounds, i.e., (Z)-hexadec-11-enal (1), (Z)-octadec-13-enal (2), and (Z)-hexadec-9-enal (3), as long-chain aliphatic internal cis-alkenyl aldehydes. In order to perform an economic and widespread pest control management of rice stem borer, a versatile and efficient synthetic strategy is required. A versatile and efficient synthesis using a common synthetic route for cis-alkenals with high overall yields is described. Commercially available inexpensive aliphatic diols were chosen as starting materials. Two key steps were employed to synthesize the long-chain aliphatic internal cis-alkenes in excellent yields, including the alkylation of terminal alkynes without the utilization of a highly polar aprotic cosolvent and the versatile cis-selective semihydrogenation for the reduction of internal alkynes with excellent stereoselectivity. The results of field tests showed that the synthetic sex pheromone blend was highly effective for the capture of rice stem borer.
- Chien, Wei-Jynn,Gupta, Sachin,Liu, Bin,Lou, Da Wei,Shen, Yu-Jhe,Syu, Kun-Jie,Tseng, Jui-Chang,Zhang, Yuan-Xin
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- Synthesis method of (Z/E)-8-dodecen-1-alcohol acetate compound
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The invention provides a synthesis method of a (Z/E)-8-dodecane-1-alcohol acetate compound. Specifically, the method includes the following steps: preparing 8-bromooctanol from 1,8-octanediol, then performing esterification reaction to obtain 8-Bromooctanol acetate, and then preparing omega-acetoxyoctanyl triphenyl phosphine bromide salt, and finally performing reaction through Scholoer-wittig toobtain (Z/E)-8-dodecene-1-alcohol acetate. The synthesis method has the advantages of high availability of raw materials, high yield and good selectivity, and is suitable for industrial production.
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Paragraph 0060; 0061; 0062; 0069-0071; 0078-0080
(2019/05/21)
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- Simple synthesis method for sex pheromones of oriental fruit moths
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The invention belongs to the field of chemical synthesis, and particularly relates to a simple synthesis method for sex pheromones of oriental fruit moths. The method includes subjecting 1,8-octandiolas a raw material to unilateral bromination reaction to obtain 8-bromooctanol, reacting the 8-bromooctanol with triphenylphosphine to obtain 8-hydroxyoctyl triphenylphosphonium salt, subjecting the 8-hydroxyoctyl triphenylphosphonium salt and n-butanal to Wittig reaction under the action of an alkali to obtain (Z/E)-8-dodecene-1-alcohol, and performing acetylation under the action of pyridine andacetic anhydride to obtain a target product. The cis-trans ratio of enol obtained after the Wittig reaction ranges from 91.8:8.2 to 92.9:7.1; within the optimal attraction range, and by strictly controlling the amount of the acetic anhydride, the properly proportioned sex pheromones of the oriental fruit moths can be obtained according to a 'one-pot' method.
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Paragraph 0023-0025
(2019/06/27)
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- COMPOSITIONS AND METHODS FOR DELIVERY OF MACROMOLECULES
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The present disclosure provides endosomal disruptors, which are useful for facilitating delivery of a macromolecule to the cytoplasm of a cell. The present disclosure provides compositions comprising an endosomal disruptor and a macromolecule. The present disclosure provides methods of delivering a macromolecule to the cytoplasm of a cell.
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Paragraph 00432; 00437; 00438
(2019/06/23)
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- Reliably Regioselective Dialkyl Ether Cleavage with Mixed Boron Trihalides
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A protocol for the regioselective cleavage of unsymmetrical alkyl ethers to generate alkyl alcohol and alkyl bromide products is described. A mixture of trihaloboranes triggers this conversion and exhibits improved reactivity profiles (regioselectivity and yield) compared with BBr3 alone. Additionally, this procedure allows the efficient synthesis of (B-Cl) dialkyl boronate esters. There are limited methods to generate acyclic dialkoxyboryl chlorides, and these intermediates constitute important synthons in main-group chemistry.
- Atienza, Bren Jordan P.,Truong, Nam,Williams, Florence J.
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supporting information
p. 6332 - 6335
(2018/10/09)
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- DENTAL COMPOSITION
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The present invention relates to a dental composition comprising a specific polymerizable compound and a polymerization initiator system. Furthermore, the present invention relates to the specific polymerizable compound as such and its use in a dental composition. The specific polymerizable compound of the present invention has an N-allyl (meth)acrylamide group, which nitrogen atom is substituted with an alkyl or alkenyl group optionally substituted by a group selected from a hydroxyl group, a C1-4 alkoxy group, a tertiary amino group and a carboxyl group, wherein 1 to 8 carbon atoms in the main chain of the alkyl or alkenyl group may independently from each other be replaced by a heteroatom selected from an oxygen atom and a sulfur atom.
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Page/Page column 55
(2018/07/05)
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- DENTAL COMPOSITION
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The present invention relates to a dental composition comprising a specific radically polymerizable compound and a radical initiator system. Furthermore, the present invention relates to the specific radically polymerizable compound and its use in a dental composition. The specific radically polymerizable compound of the present invention has an allyl (meth)acrylamide group and a phosphoric acid ester group.
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Paragraph 60; 61
(2018/09/11)
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- Polyvalent Azasugar derivatives and its synthetic method
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The invention provides derivatives of multivalent azasugar of 3,4,5-trihydroxyl-1-octylpiperidine-2-ketone having a general formula (I), and a synthetic method of the derivatives. According to the derivatives and the preparation method thereof provided by the invention, multivalent azasugar is formed by connecting (3S,4R,5S)-3,4,5-trihydroxyl-1-(8-aminooctyl)piperidine-2-ketone as a monomer with a polyatomic acid or polyacyl chloride, or connecting (3S,4R,5S)-3,4,5-trihydroxyl-1-(8-azidooctyl)piperidine-2-ketone as a monomer with a derivative of a polyatomic acid, polyhydric alcohol or polyacyl chloride The multivalent azasugar synthesized by the method provided by the invention has the potential of serving as a pharmacological molecular chaperone in CMT (Pharmacological Chaperone Molecular therapy) for treating Gaucher disease, and thereby having a high application value.
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Paragraph 0075-0077
(2017/01/31)
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- A pheromone food heart insectthe pear is small (Z/E)-8-dodecene acetum acid ester synthetic method
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The invention provides a synthesis method of grapholitha molesta sex pheromone (Z/E)-8-dodecene acetate. The synthesis method comprises the following steps: (1) by taking methylbenzene or benzene as a solvent and 1,8-octanediol and hydrobromic acid as starting raw materials, performing unilateral bromination reaction to obtain 8-bromooctanol; (2) by taking ethanol as a solvent, adding 8-bromooctanol and triphenylphosphine into a reaction kettle, after the reaction, cooling and separating out 8-hydroxyl octyl triphenylphosphine crystals by taking methylbenzene as an eluent; (3) performing Witting reaction on the 8-hydroxyl octyl triphenylphosphine and n-butyraldehyde under the presence of a catalyst 18-crown ether-6 to obtain (Z/E)-8-dodeceneanol, wherein potassium carbonate is adopted as alkali; and (4) by taking pyridine as a solvent, reacting the (Z/E)-8-dodeceneanol with acetic anhydride or acetyl chloride to obtain (Z/E)-8-dodecene acetate. The method mild in conditions, fewer in steps, high in yield, and suitable for industrial production, and raw materials are easily available.
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Paragraph 0030-0032
(2017/02/28)
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- IMINOSUGARS USEFUL FOR THE TREATMENT OF VIRAL DISEASES
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Formula IA, ad their use for treating viral infections.
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Page/Page column 41; 42
(2016/06/01)
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- DEOXYNOJIRIMYCIN DERIVATIVES AND METHODS OF THEIR USING
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The present application provide novel iminosugars and their use in treatment of viral infections, such as Dengue infection and Influenza A infection. The present inventors discovered certain deoxynojirimycin derivatives may be effective against one or more viruses, which may be, for example, a Dengue virus and/or a virus belonging to the Orthomyxoviridae family, such as an Influenza A virus. In particular, such deoxynojirimycin derivatives may be useful for treating a disease or condition caused by or associated with one or more viruses. In certain embodiments, the deoxynojirimycin derivatives may increase a survival rate or probability for a subject infected with one or more viruses, which may be, for example, a Dengue virus and/or a virus belonging to the Orthomyxoviridae family, such as an Influenza A virus.
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Paragraph 0023
(2016/08/29)
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- Process intensification-assisted conversion of α,ω-alkanediols to dibromides
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The increasingly widespread applications of α,ω-dibromides motivated development of a scalable, inexpensive process to rapidly convert selected α,ω-alkanediols to the corresponding dibromides. Diols were heated with only 48% aq HBr and an organic solvent, using a Dean-Stark apparatus modified to fractionate the azeotropic distillate, thereby maintaining a higher HBr concentration and reaction rate in the pot. Intensified distillation also increased the reaction rate. Various other substrate, solvent, and parameter effects have been discovered and rationalized.
- Mekala, Shekar,Hahn, Roger C.
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supporting information
p. 630 - 632
(2015/03/03)
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- Synthesis of corn rootworm pheromones from commercial diols
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A mixture of stereoisomers of the corn rootworm pheromones was synthesised via the Grignard coupling of protected bromohydrins with alkylcuprate as a key step. The synthesis of 8-methyldec-2- yl propanoate (I), the northern corn rootworm Diabrotica longicornis Say pheromone, was achieved from pentane-1,5-diol in four steps with an overall yield of 35.1 % and 10-methyltridecan-2-one (II), the southern corn rootworm Diabrotica undecimpunctata howardi Barber pheromone, was synthesised from octane-1,8-diol as commercially available starting material in five steps with an overall yield of 28.7 %.
- Nguyen, Thanh-Danh,Nguyen, Cong-Hao,Im, Chan,Dang, Chi-Hien
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p. 380 - 384
(2015/02/19)
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- Monolayer to Interdigitated Partial Bilayer Smectic C Transition in Thiophene-Based Spacer Mesogens: X-ray Diffraction and 13C Nuclear Magnetic Resonance Studies
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Mesophase organization of molecules built with thiophene at the center and linked via flexible spacers to rigid side arm core units and terminal alkoxy chains has been investigated. Thirty homologues realized by varying the span of the spacers as well as the length of the terminal chains have been studied. In addition to the enantiotropic nematic phase observed for all the mesogens, the increase of the spacer as well as the terminal chain lengths resulted in the smectic C phase. The molecular organization in the smectic phase as investigated by temperature dependent X-ray diffraction measurements revealed an interesting behavior that depended on the length of the spacer vis-a-vis the length of the terminal chain. Thus, a tilted interdigitated partial bilayer organization was observed for molecules with a shorter spacer length, while a tilted monolayer arrangement was observed for those with a longer spacer length. High-resolution solid state 13C NMR studies carried out for representative mesogens indicated a U-shape for all the molecules, indicating that intermolecular interactions and molecular dynamics rather than molecular shape are responsible for the observed behavior. Models for the mesophase organization have been considered and the results understood in terms of segregation of incompatible parts of the mesogens combined with steric frustration leading to the observed lamellar order.
- Kesava Reddy,Varathan,Lobo, Nitin P.,Roy, Arun,Narasimhaswamy,Ramanathan
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p. 10831 - 10842
(2015/10/12)
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- First total synthesis of acetylenic alcohol 15-methyltricosa-2,4-diyne-1, 6-diol (strongylodiol-G) derived from marine sponge
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The first total and efficient synthesis of a naturally occurring acetylenic alcohol 15-methyltricosa-2,4-diyne-1,6-diol (strongylodiol-G) derived from marine sponge involving nine steps has been described. 1-Bromo-9- methyloctadecane (5) and hex-6-tetrahydropyranyloxyhex-2,4-diyn-1-al (9) which were initially synthesised separately starting from 1,8-octanediol (1) and propargyl alcohol (6), respectively, have been used as the final intermediates to obtain the title compound. The key steps in the synthesis involved ionic liquid-mediated bromination of 1,8-octanediol (1), tetrahydropyranylation of 8-bromooctan-1-ol (2) using acidic ionic liquid [bmim]HSO4 and monotetrahydropyranylation of hex-2,4-yn-1,6-diol (7) using ultrasonic energy.
- Gupta, Neeraj,Shallu,Kad, Goverdhan Lal,Singh, Jasvinder
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p. 424 - 430
(2014/04/17)
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- Synthesis of (3E)-dodecen-12-olide, a potential pheromone component of the emerald ash borer
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Emerald ash borer (EAB), Agrilus planipennis Fairmaire, is an invasive insect that has killed millions of ash trees in the USA and Canada. A concise synthesis of a potential EAB pheromone component, (3E)-dodecen-12-olide, using highly stereoselective Julia-Kocienski olefination as the key step, is reported. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.
- Magee,Mayo,Silk,Beattie
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p. 1368 - 1377
(2013/05/22)
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- Total synthesis of (-)-ecklonialactone B
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The total synthesis of (-)-ecklonialactone B as well as the 9,10-dihydro derivative by two different strategies is reported. The catalytic asymmetric Claisen rearrangement of Gosteli-type allyl vinyl ethers delivered elaborated α-keto ester building blocks. Ring-closing metatheses, including a notable diastereotopos-differentiating variant, a B-alkyl Suzuki-Miyaura cross-coupling reaction and a regio- and diastereoselective last-step epoxidation are key contributors.
- Becker, Julia,Butt, Lena,Von Kiedrowski, Valeska,Mischler, Elisabeth,Quentin, Florian,Hiersemann, Martin
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supporting information
p. 5982 - 5985
(2014/01/06)
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- Stabilization of the film morphology in polymer: Fullerene heterojunction solar cells with photocrosslinkable bromine-functionalized low-bandgap copolymers
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Novel bromine-functionalized photocrosslinkable low-bandgap copolymers, PBDTTT-Br25 and PBDTTT-Br50, are synthesized via Stille cross-coupling polymerization for the purpose of stabilizing the film morphology in polymer solar cells (PSCs). Photocrosslinking of PBDTTT-Br25 and PBDTTT-Br50 copolymers dramatically improves the solvent resistance of the active layer without disrupting the molecular ordering and charge transport, which is confirmed by the insolubility of the films washed by organic solvents and by their thermal behavior. As a result, the formation of large aggregations of fullerene is suppressed in polymer:fullerene blend films even after prolonged thermal annealing, and the stability of the device is enhanced when compared with cells based on noncrosslinkable PBDTTT. The power conversion efficiency of the PSCs based on PBDTTT-Br25 and PBDTTT-Br50 reaches 5.17% and 4.48%, respectively, which is improved obviously in comparison with that (4.26%) of the PSCs based on the control polymer PBDTTT.
- Qian, Deping,Xu, Qi,Hou, Xuliang,Wang, Fuzhi,Hou, Jianhui,Tan, Zhan'Ao
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p. 3123 - 3131
(2013/07/26)
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- Discotic liquid crystals of transition metal complexes 49:
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A homologous series of the phthalocyanine-fullerene dyads, C n-PcM(OFbaC60) (n = 6, 8, 10, 12; M = Cu, Ni, Co: 3a-3f) have been synthesized to obtain homeotropic alignment at rt and investigate the effects of spacer chain length (n = 6, 8, 10, 12) and central metal (M = Cu, Ni, Co) on the mesomorphism. Interestingly, the shorter-spacer-substituted (n = 6, 8; M = Cu) dyads 3a and 3b showed a hexagonal columnar mesophase (Col h), whereas the longer-spacer-substituted (n = 10, 12; M = Cu, Ni, Co) dyads 3c-3f showed a tetragonal columnar mesophase (Coltet). Moreover, each of the homologs 3a-3e shows perfect homeotropic alignment in both the Colh and Coltet mesophases at rt. More interestingly, these columnar mesophases gave a very unique XRD reflection peak denoted as Peak H in a very small angle region of 0.8 60 dyads 3a-3f between two glass plates. Hence, these novel Pc-C60 dyads 3a-3f may be very suitable to organic thin film solar cells. Copyright
- Tauchi, Lisa,Nakagaki, Takahiro,Shimizu, Masahiro,Itoh, Eiji,Yasutake, Mikio,Ohta, Kazuchika
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p. 1080 - 1093
(2014/01/06)
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- 1,2,3-Trimethoxypropane, a glycerol-based solvent with low toxicity: New utilization for the reduction of nitrile, nitro, ester, and acid functional groups with TMDS and a metal catalyst
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1,2,3-Trimethoxypropane (1,2,3-TMP) was prepared from glycerol in one step in good yield and selectivity by phase transfer catalysis. According to OECD guidelines, a toxicity study was realized for this compound. It revealed that 1,2,3-TMP has a low acute toxicity, no skin sensitization, no mutagenicity and no ecotoxicity in an aquatic environment. This compound was also used as a solvent for the reduction of organic functions using either aluminium hydride or 1,1,3,3-tetramethyldisiloxane (TMDS) as a benign hydride source. In particular, a new process for the reduction of nitriles to amines in 2-MeTHF and in 1,2,3-TMP was developed, using TMDS in combination with copper triflate (Cu(OTf)2).
- Sutter, Marc,Pehlivan, Leyla,Lafon, Romain,Dayoub, Wissam,Raoul, Yann,Metay, Estelle,Lemaire, Marc
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supporting information
p. 3020 - 3026
(2013/11/06)
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- Simple and efficient method for deprotection of tetrahydropyranyl ethers by using Silica supported sodium hydrogen sulphate
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Tetrahydropyranyl (THP) ethers have been efficiently and simply deprotected by using Silica supported sodium hydrogen sulphate (NaHSO4-SiO 2) in methanol at room temperature to regenerate the parent alcohols in high yields. Tetrahydropyranyl (THP) ethers have been efficiently and simply deprotected by using silica supported sodium hydrogen sulphate (NaHSO 4-SiO2) in methanol at room temperature to regenerate the parent alcohols in high yields.
- Kumar, K. Ravi,Satyanarayana,Reddy, B. Srinivasa
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experimental part
p. 1189 - 1191
(2012/07/27)
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- Hydroxylated Long-Chain Resveratrol Derivatives Useful as Neurotrophic Agents
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The present invention relates to a compound of general formula (I) below in which R1, R2 and R3 represent, independently of one another, a hydrogen atom or a C1-C6 alkyl group or a (C1-C6 alkyl)carbonyl group, R4, R5, R6 and R7 represent a hydrogen or a C1-C6 alkyl group, a C1-C6 alkoxy group or a (C1-C6 alkyl)carbonyloxy group, and n is an integer between 8 and 20, or its pharmaceutically acceptable addition salts, isomers, enantiomers and diastereoisomers, and also mixtures thereof. The invention also relates to a pharmaceutical composition comprising the compound and to the use thereof as a neurotrophic agent.
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Page/Page column 9
(2010/03/31)
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- A biomimetic approach to the synthesis of a mycolic acid motif
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A new method for the stereoselective synthesis of the (R,R)-β-hydroxy-α-alkyl fatty acid fragment of mycolic acids, via an asymmetric anti-aldol reaction is reported. The 'mycolic acid motif' fragment was prepared in three steps and >98% ee.
- Driver, Cathryn H.S.,Balogun, Mohammed O.,Toschi, Gianna,Verschoor, Jan A.,Baird, Mark S.,Pilcher, Lynne A.
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supporting information; scheme or table
p. 1185 - 1186
(2010/04/23)
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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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- First syntheses of model long-chain trichloro[ω-(trimethylsilyl)alkynyl]silanes suitable for self-assembled monolayers on silicon surfaces
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The preparation of the title compounds involves the introduction of the required Me3SiC{triple bond, long}C and trichlorosilyl groups at the termini of the alkyl chain via derivatization of easily accessible and inexpensive materials/reagents. Trichloro[ω-(trimethylsilyl)alkynyl]silanes are useful for the linkage to a hydroxylated silicon surface for multilayer formation and for further chemical modification of the tail group of the monolayer.
- Banaszak, Estelle,Xu, Li-Wen,Bardeau, Jean-Fran?ois,Castanet, Anne-Sophie,Mortier, Jacques
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body text
p. 3961 - 3966
(2009/09/30)
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- Anti-androgenic pyrrolidines with tumor-inhibiting action
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This invention relates to anti-androgenic N-[ω-[3-[4-cyano-3-(trifluoromethyl)-phenyl]-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]alkyl]-substituted pyrrolidines of general formula I, with a strongly pronounced antiproliferative profile of action; process for the production of the compounds of general formula I, pharmaceutical preparations and the use for the production of pharmaceutical agents.
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Page/Page column 21
(2009/10/18)
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- ALLYL SULFIDE COMPOUNDS, AND COMPOSITIONS AND METHODS USING SAID COMPOUNDS FOR REPELLING BLOOD-FEEDING ARTHROPODS
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This invention relates to compositions of one or more compounds that incorporate one or more allyl sulfide, allyl disulfide or allyl polysulfide moieties, or one or more allyl sulfide, allyl disulfide or allyl polysulfide moieties and one or more hydroxyl groups, used in effective amount in formulations, including emulsions, to repel blood-feeding ectoparasitic arthropods, including mosquitoes, and to deter them from landing and feeding when applied to the skin, clothing or environment of animals, including humans. Said compounds can include, but are not limited to, 8-allyl-sulfanyloctan-1-ol. This invention also relates to compositions comprising one or more of said compounds in further combination with other arthropod repellent and deterrent compounds, including vanillin. These compounds may be formulated with inert ingredients to form a liquid, gel, paste, soap, spray, aerosol or powder.
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Page/Page column 15
(2008/12/04)
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- Synthesis and biological properties of tensyuic acids B, C, and E, and investigation of the optical purity of natural tensyuic acid B
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The first, concise total synthesis of (±)-tensyuic acids B, C, and E, using chemoselective formal SN2′ type Grignard reactions and selective esterification, is described. In addition, the optical purity of natural (±)-tensyuic acid B was determined using Chirabite-AR. Synthetic tensyuic acids, together with their intermediate compounds, were found to possess useful bioactive properties, with some of them showing potent activity against Trypanosoma brucei brucei strain GUTat 3.1.
- Matsumaru, Takanori,Sunazuka, Toshiaki,Hirose, Tomoyasu,Ishiyama, Aki,Namatame, Miyuki,Fukuda, Takashi,Tomoda, Hiroshi,Otoguro, Kazuhiko,Omura, Satoshi
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p. 7369 - 7377
(2008/12/20)
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- A simple and cost effective synthesis of 3,11-dimethylnonacosan-2-one, a female sex pheromone of the German cockroach
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A convenient synthesis of 3,11-dimethylnonacosan-2-one (1) is described. Our strategy involves the use of well known C-alkylation and ethyl acetoacetate synthesis reactions as key steps. We expect that this method will prove to be useful for large scale preparation of 1 and modification of dimethylnonacosanones.
- Ahn, Kwang-Chan,Jung, Jae-Chul,Park, Oee-Sook
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p. 751 - 757
(2007/10/03)
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- Synthesis and characterization of 3,13- and 2,13-octadecadienyl compounds for identification of the sex pheromone secreted by a clearwing moth, Nokona pernix
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Several geometrical isomers of 3,13- and 2,13-octadecadien-1-ols and their acetates were synthesized starting from 1,8-octanediol or 1,9-nonanediol utilizing acetylene coupling reactions. In addition to commercially available compounds, all geometrical isomers of each dienyl compound were analyzed by NMR and GC-MS to accumulate chemical data for studies of sex pheromones secreted from clearwing moths classified into the family Sesiidae of Lepidoptera. Although acetoxy derivatives of the 3,13- and 2,13-dienes showed almost the same mass spectra, the alcohols were distinguished by comparing the relative intensities of [M - 18]+ at m/z 248, indicating direct differentiation of the two positional isomers without derivatization. Furthermore, each geometrical isomer eluted from a high-polar GC column with a different retention time. Base on these data, a pheromone gland extract of a sesiid moth, Nokona pernix, was analyzed by GC-EAD and GC-MS, and two EAG-active components were identified, viz., the (3E,13Z)- and (3Z,13Z)-isomers of 3,13-octadecadien-1-ol in a ratio of 9:1. In the field, the synthetic compounds mixed in 9:1 ratio attracted N. pernix males well, while a single component scarcely attracted the males. The number of attracted males peaked in the middle of June, and a small second peak was observed in August.
- Naka, Hideshi,Nakazawa, Tomotake,Sugie, Mieko,Yamamoto, Masanobu,Horie, Yoshiteru,Wakasugi, Ryohei,Arita, Yutaka,Sugie, Hajime,Tsuchida, Koji,Ando, Tetsu
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p. 508 - 516
(2008/02/10)
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- Method for the preparation of unsaturated hydroxy fatty acids and their esters, their use in pharmaceutical and/or cosmetic preparations
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A method of preparing unsaturated hydroxy fatty acids and esters thereof corresponding to general formula (Id): wherein n=1 to 4, m=2 to 16, R1═OH, Cl, Br, OR3 in which R3 is a straight or branched alkyl, alkenyl or alkynyl radical of 1 to 16 carbons or glycerol esters, optionally substituted by one or more atoms selected from the group consisting of carbon, nitrogen, sulfur and halogens, R2═H, SiR′1R′2R′3 in which R′1, R′2 and R′3 can be identical or different from each other and are a straight or branched alkyl, alkenyl or alkynyl radical of 1 to 16 carbons or glycerol esters, optionally substituted by one or more atoms selected from the group consisting of carbon, nitrogen, sulfur and halogens, or R2═C—Ar3 with Ar representing an aryl radical optionally substituted by one or more atoms selected from the group consisting of carbon, nitrogen, sulfur and halogens, or R2=the tetrahydropyranyl of formula: is disclosed.
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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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- ANTITUMORAL ANTIADROGENIC PYRROLIDINES
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The invention relates to substituted antiadrogenic pyrrolidines N-[ω-[3-[4-cyan-3-(trifluoromethyl)-phenyl]-5.5-dimethyl-4-oxo2-thioxoimidazoline-1-yle]alkyl] of formula (I) having a salient antiproliferative effect profile. Said invention also relates to a method for producing compounds of the formula (I), pharmaceutical preparations and to the use thereof for producing drugs.
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Page/Page column 29
(2008/06/13)
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- Total synthesis of cytotoxic sponge alkaloids hachijodines F and G
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The total synthesis of two cytotoxic sponge alkaloids hachijodines F and G has been achieved. The synthesis of both compounds utilises a common intermediate alkyne. By comparison of spectra the structure of the natural product has been confirmed.
- Goundry, William R. F.,Baldwin, Jack E.,Lee, Victor
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p. 1719 - 1729
(2007/10/03)
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- Functional group transformations of diols, cyclic ethers, and lactones using aqueous hydrobromic acid and phase transfer catalyst under microwave irradiation
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Synthesis of bromoalkanols has been achieved from diols, ethers, and lactones using aq HBr (48%) and tetrabutylammonium iodide/bromide as phase transfer catalyst under microwave irradiation. This environmentally benign route provides enhanced yields of products and does away with the use of benzene as compared to existing conventional methods.
- Kad, Goverdhan L.,Kaur, Irvinder,Bhandari, Monica,Singh, Jasvinder,Kaur, Jasamrit
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p. 339 - 340
(2013/09/06)
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- Synthesis of new C60 based phosphines
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Two series of new phosphine derivatives based on C60 protected by borane have been synthesized and characterized. These phosphines were used for two preliminary complexation trials with [RhCl(COD)]2 and [Re(S3CPh)2(S2CPh)] to afford, respectively, the corresponding complexes [RhCl(COD)(PRPh2)] and [Re(S 2CPh)3(PRPh2)].
- Ballot, Sandrine,Noiret, Nicolas
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p. 8811 - 8814
(2007/10/03)
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- Asymmetric synthesis of unnatural (Z,Z,E)-octadecatrienoid and eicosatrienoid by lipoxygenase-catalyzed oxygenation
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The asymmetric synthesis of unnatural 13-hydroxy-(6Z,9Z,11E,13S)-octadecatrienoid and 15-hydroxy-(8Z,11Z,13E,15S)-eicosatrienoid is described using a biomimetic oxidation route. The main highlights of this synthesis are the asymmetric hydroxylation of the substrate with soybean lipoxygenase and cis selective Wittig olefination.
- Nanda,Yadav
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p. 1799 - 1806
(2007/10/03)
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- Total synthesis of cytotoxic sponge alkaloids hachijodines F and G
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The total synthesis of two cytotoxic sponge alkaloids hachijodines F (1) and G (2) via a common intermediate 3 is described.
- Goundry, William R.F.,Lee, Victor,Baldwin, Jack E.
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p. 2745 - 2747
(2007/10/03)
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- Synthesis of dideuterated and enantiomers of monodeuterated tridecanoic acids at C-9 and C-10 positions
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We report a route for the preparation of mono and dideuterated tridecanoic acids: (R)-[9-2H1]-,(S)-[9-2H1]-,(R)-[10-2H1]-,(S)-[10-2H1]-,[9,9-2H2]-, and [10,10-2H2]-tridecanoic acids required as probes for biochemical studies on desaturases. The key intermediates in the synthesis of all these probes are ketones 9, which give rise to the corresponding alcohols 10 and 13 by reduction with LiAlD4 and LiAlH4, respectively. Derivatization of nondeuterated racemic alcohols 13 with (S)-(+)-9-anthranylmethoxyacetic acid ((S)-(+)-9-AMA) and chromatographic resolution of both diastereoisomers allowed us to determine the absolute configuration of the stereogenic centers by 1H NMR using an adaptation of the model proposed by Riguera and co-workers which was validated with alcohols of known absolute configuration. Both enantiomeric alcohols (R)- and (S)-13 were recovered by reduction of each diastereomeric ester with LiAlH4. Mesylation of alcohols 10 and 13 followed by nucleophilic substitution by LiAlD4 generated the saturated methoxymethyl derivatives 12 and 16, respectively. Final deprotection and Jones oxidation of the resulting alcohols afforded the above deuterated tridecanoic acids.
- Abad,Fabrias,Camps
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p. 8582 - 8588
(2007/10/03)
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- Asymmetric total synthesis of (-)-prosophylline
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The asymmetric total synthesis of (-)-prosophylline from D-glucal via (2S)-hydroxymethyl-dihydropyridone 6 by a 17-step synthesis and 12% overall yield is presented.
- Koulocheri, Sofia D.,Haroutounian, Serkos A.
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p. 6869 - 6870
(2007/10/03)
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- Scavenger assisted combinatorial process for preparing libraries of tertiary amine compounds
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This invention relates to a novel solution phase process for the preparation of tertiary amine combinatorial libraries. These libraries have utility for drug discovery and are used to form wellplate components of novel assay kits.
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- Restricting the flexibility of crosslinked, interfacial peptide inhibitors of HIV-1 protease
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Interfacial peptides of HIV-1 protease were crosslinked with varying length alkyl-chains containing either a single cis or trans double bond, or a triple bond to remove degrees of freedom within the tethers. The synthesis of these compounds and their effects on the activity of HIV-1 protease are described.
- Ulysse, Luckner G.,Chmielewski, Jean
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p. 3281 - 3286
(2007/10/03)
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- Pheromones of insects and their analogs. LII. Sythesis of dodec-9-en-1-yl and tetradec-11-en-1-yl acetates from the products of the partial ozonolysis of cycloocta-1z,5z-diene and cyclodeca-1e,5z-diene
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A new approach to the synthesis of octane-1,8-and decane-1,10-diols based on the partial ozonolysis of cyclic oligomers has been developed.
- Odinokov,Botsman,Gladysheva
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p. 381 - 383
(2007/10/03)
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- Homologous long-chain alkanediols from Papaver leaf cuticular waxes
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In cuticular waxes from leaves of Papaver alpinum sensu Markgr., P. dubium L., P. nudicaule L., P. orientale L., P. rhoeas L. and P. somniferum L., six new alkanediols carrying one primary and one secondary hydroxyl function were identified. Five of them, docosane-1,3-diol, hexacosane-1,7- diol, octacosane-1,9-diol, nonacosane-1,10-diol and triacontane-1,11-diol, form a homologous series. Their molecular geometries and relative proportions suggest a biosynthetic relationship to the corresponding primary alkanols.
- Jetter, Reinhard,Riederer, Markus,Seyer, Andre,Mioskowski, Charles
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p. 1617 - 1620
(2007/10/03)
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- Studies related to fatty acids desaturation. II. Preparation of iso-linoleic and iso-vernolic acids
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New iso-vernolic and iso-linoleic acids have been prepared in order to study their potential inhibition action during in vivo desaturation of oleic acid in vegetal sources. - Keywords: Δ12-desaturase / modified fatty acids / Z,ω-octenyl bromides / iso-linoleic acids / iso-vernolic acids
- Gruiec, Regine,Noiret, Nicolas,Patin, Henri
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p. 699 - 705
(2007/10/02)
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