- COMPOUNDS AND COMPOSITIONS FOR INTRACELLULAR DELIVERY OF AGENTS
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The disclosure features amino lipids and compositions involving the same. Nanoparticle compositions include an amino lipid as well as additional lipids such as phospholipids, structural lipids, PEG lipids, or a combination thereof. Nanoparticle compositions further including therapeutic and/or prophylactic agents such as RNA are useful in the delivery of therapeutic and/or prophylactic agents to mammalian cells or organs to, for example, regulate polypeptide, protein, or gene expression.
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Paragraph 001000
(2019/01/08)
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- AuBr3- and Cu(OTf)2-catalyzed intramolecular [4 + 2] cycloaddition of tethered alkynyl and alkenyl enynones and enynals: A new synthetic method for functionalized polycyclic hydrocarbons
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(Chemical Equation Presented) Treatment of tethered alkynyl enynones 8, in which a carbon chain is attached to the carbonyl group, with a catalytic amount of AuBr3in (ClCH2)2 gave the naphthyl ketones 9 in good to high yields (top-down approach). Analogously, the AuBr 3-catalyzed benzannulations of 10, in which a carbon tether is extended from the alkynyl terminus, also proceeded smoothly, and the cyclized naphthyl ketones 11 were obtained in high yields (bottom-up approach). Similarly, when two kinds of tethered alkenyl enynones 12 and 14 were treated with Cu(OTf)2 catalyst, the corresponding dihydronaphthyl ketone products 13 and 15 were obtained in high yields, respectively. The present formal [4 + 2] intramolecular cycloaddition proceeds most probably through the coordination of the triple bond at the ortho position of substrates to Lewis acids, the formation of benzopyrylium ate complex 16 via the nucleophilic addition of the carbonyl oxygen atom, the reverse electron demand type Diels-Alder addition of the tethered alkynes or alkenes to the ate complex, and subsequent bond rearrangement.
- Asao, Naoki,Sato, Kenichiro,Menggenbateer,Yamamoto, Yoshinori
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p. 3682 - 3685
(2007/10/03)
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- (E4,Z9)-Tetradecadienal, a sex pheromone for three North American moth species in the genus Saturnia
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The lepidopteran genus Saturnia has three representatives in North America, S. walterorum, S. mendocino, and S. albofasciata. (E4,Z9)-Tetradecadienal (E4,Z9-14:Aid) was identified as a sex pheromone component for all three species by combinations of coupled gas chromatography-electroantennogram detection (GC-EAD), GC-mass spectrometry (MS), and field trials. In field trials, all three species were strongly attracted to (E4,Z9-14:Ald) as a single component, Small amounts of (Z)-9-tetradecenal (Z9-14:Ald) also were found in extracts of all three species, but blends of this compound with E4,Z9-14:Aid were no more attractive to male moths than E4,Z9-14:Ald alone. Extracts of pheromone glands of female S. walterorum occasionally contained a third, trace compound eliciting responses from male antennae in GC-EAD experiments, but this compound was not identified. It is suggested that the three species can use the same, single component as a sex attractant because the flight period of S. albofasciata (fall) is different than that of the other two species (spring), whereas the geographic distributions of S. mendocino and S. walterorum overlap over only small portions of their ranges. Furthermore, the latter two species readily hybridize, so there may be minimal fitness cost to cross-attraction.
- Mcelfresh, J. Steven,Millar, Jocelyn G.,Rubinoff, Daniel
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p. 791 - 806
(2007/10/03)
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- A convergent and highly efficient synthesis of (E,Z)-2,13-octadecadienyl acetate and (E,Z)-3,13-octadecadienyl acetate, components of the sex pheromone of the Leopard Moth Zeuzera pyrina, through sulfones
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(equation presented) A new, convergent synthesis of (E,Z)-2,13-octadecadienyl acetate (1) and (E,Z)-3,13-octadecadienyl acetate (2), the two key components of the leopard moth Zeuzera pyrina, from 2-chloromethyltetrahydrofuran in good overall yields and stereomeric purity is reported. The synthesis of both components utilizes the common intermediate sulfone 12 as a convenient building block to be coupled with iodoacetylenic derivatives 9 or 17 in the key step.
- Capdevila, Anna,Prasad, Attaluri R.,Quero, Carmen,Petschen, Ine?s,Bosch, Maria P.,Guerrero, Angel
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p. 845 - 848
(2008/02/09)
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- Bioisosteric approach to elucidation of binding of the acetate group of a moth sex pheromone component to its receptor
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A number of analogs of (Z)-5-decenyl acetate, a pheromone component of the turnip moth, Agrotis segetum, in which the acetate group has been replaced by functional groups that may function as bioisosters, have been synthesized and tested using single-cell electrophysiology. The activities have been interpreted in terms of the molecular electrostatic potentials of the polar functional group as calculated by ab initio quantum mechanical calculations. It is concluded that both oxygens of the acetate group in (Z)-5-decenyl acetate contribute to the interactions between the pheromone component and its receptor. Furthermore, the results indicate that the crucial interaction between the carbonyl group and the receptor, which is most probably a hydrogen bonding interaction, takes place in a direction pointing away from the hydrocarbon chain of the pheromone component.
- Gustavsson, Anna-Lena,Tuvesson, Malena,Larsson, Mattias C.,Wenqi, Wu,Hansson, Bill S.,Liljefors, Tommy
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p. 2755 - 2776
(2007/10/03)
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- Preparation of Geometrical Isomers of 2,7-Dodecadienal, 2,7-Dodecadienyl Formate, and Other 1,6-Diene System-containing Compounds and Their Electroantennography Activities toward Male Eri-Silk Moths
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We measured the electroantennography (EAG) activities of the geometrical isomers of several pheromone-related compounds towards male eri-silk moths (Samia cynthia richini) using EAG-gas chromatography (GC).C16-aldehyde and formyl ester, with the same chain length as C16-aldehyde, were found to be much more active than other compounds with a shorter chain.For the compounds with (1Z,6Z)- or (1E,6E)-configuration, the activity in decreasing order was C14-formyl ester > C16-aldehyde > C14-aldehyde > C12-formyl ester, while that for the compounds with (1Z,6E)- or (1E,6Z)-configuration is C16-aldehyde > C14-formyl ester > other compounds with a shorter C14 chain.
- Hatanaka, Akihiko,Ishii, Yasushige,Tomida, Ichiro
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p. 2036 - 2038
(2007/10/02)
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- STEREOSPECIFIC SYNTHESIS OF COMPONENTS OF THE NATURAL SEX PHEROMONE OF Pectinophora gossypiella
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A multistage stereospecific synthesis of components of the natural pheromone was realized.Conditions were found for stereospecific trans-reduction of the triple bonds.A procedure was developed for regiospecific dehydrohalogenation of 1,2-dibromoalkanes.Conditions giving the Z and E isomers in ratio of 96 : 4 were found for the Wittig reaction.
- Matveeva, E. D.,Kvasha, M. P.,Kurts, A.L.
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p. 1017 - 1021
(2007/10/02)
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- Pheromones: 87. An efficient synthesis of (6E,11Z)-6,11-hexadecadienyl acetate and (6E,11Z)-6,11-hexadecadienal: Female sex pheromone components of Antheraea pernyi and A. polyphemus (Lepidoptera: Saturniidae)
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(6E,11Z)-Hexadecadienyl acetate (15) and the corresponding aldehyde 16, the female sex pheromone components of Antheraea pernyi and A. polyphemus (Lepidoptera; Saturniidae) have been synthesized in 32% and 27% overall yields, respectively, and in 99% isomeric purity. Tetrahydropyran (1) was used as the starting material to obtain 5-bromopentanol (3) which was subsequently chain elongated to 7-(tetrahydropyran-2-yloxy)-1-heptyne (5) by the standard procedures. The organolithium compound from 5 was coupled with (Z)-1-bromo-4-nonene (11), obtained from the Wittig reaction between pentyltriphenylphosphonium bromide (9) and 4-(tetrahydropyran-2-yloxy)butanal (8) followed by bromination. The product, (Z)-1-(tetrahydropyran-2-yloxy)-11-hexadecen-6-yne (12) which resulted, was reduced with sodium/liquid ammonia to give 13 with the E-6 bond. Removal of the protecting group resulted in the desired alcohol 14 which on acetylation and oxidation gave the desired acetate 15 and the aldehyde 16, respectively.
- Bestmann,Gunawardena
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p. 1239 - 1241
(2007/10/02)
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- An efficient and stereoselective synthesis of insect pheromones by way of nickel-catalyzed Grignard reactions. Syntheses of gossyplure and pheromones of Eudia pavonia and Droxophila melanogaster
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Three pheromones, (6Z,11Z)-hexadeca-6,11-dien-1-yl acetate (from Eudia pavonia), (5Z,9Z)-heptacosa-5,9-diene (from Drosophila melanogaster) and gossyplure, have been synthesized each by two consecutive consequences of nickel-assisted Grignard reactions with cyclic enol ethers and preparation of Grignard reagents from the resultant alcohols.
- Ducoux, Jean-Philippe,Le Menez, Patrick,Kunesch, Nicole,Kunesch, Gerhard,Wenkert, Ernest
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p. 6403 - 6412
(2007/10/02)
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- OZONOLYSIS OF ALKENES AND REACTIONS OF POLYFUNCTIONAL COMPOUNDS. XLII. SYNTHESIS OF (9Z)-TETRADECENYL ACETATE AND (9Z)-HEXADECENAL FROM (Z,Z)-1,5-CYCLOOCTADIENE
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A stereocontrolled synthesis of (9Z)-tetradecenyl acetate and (9Z)-hexadecenal, which are components of the sex pheromones of the pine (Panolis flammea) and cotton (Heliothis armigera) moths respectively, was realized on the basis of the partial ozonolysis of (Z,Z)-1,5-cyclooctadiene.
- Odinokov, V. N.,Galeeva, R. I.,Ishmuratov, G. Yu.,Kargapol'tseva, T. A.,Sokol'skaya, O. V.,et al.
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p. 1986 - 1989
(2007/10/02)
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- SHORT, REGIO- AND STEREO-SELECTIVE PREPARATION OF 1,5- AND 1,6-DIENES. SYNTHESES OF EUDIA PAVONIA PHEROMONE AND GOSSYPLURE.
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Two pheromones, (Z)-6,(Z)-11-hexadecadien-1-yl acetate (from Eudia pavonia) and gossyplure, have been synthesized each by two consecutive sequences of nickel-assisted Grignard reactions with cyclic enol ethers and the preparation of Grignard reagents from the resultant alcohols, followed each by copper-promoted Grignard reaction with a small-ring ether and subsequent acetylation.
- Ducoux, Jean-Philippe,Menez, Patrick Le,Kunesch, Nicole,Kunesch, Gerhard,Wenkert, Ernest
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p. 2595 - 2598
(2007/10/02)
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- A New Synthesis of (Z)-9-Tetradecen-1-yl Acetate
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Alkylation of propargyl alcohol dianion with n-butyl bromide provides hept-2-yn-1-ol (II) which is converted into its bromide (III) and subsequently alkylated with monosodio ethyl malonate to furnish the diester (IV).The latter on decarbethoxylation with NaCl/DMSO affords the ester (V).Catalytic hydrogenation of V in the presence of Lindlar's catalyst produces ethyl non-4Z-en-1-oate (VI) which on LAH reduction gives the carbinol (VII) whose corresponding bromide (VIII) on coupling reaction with 1-bromo-5-tetrahydropyranyloxypentane gives IX.Removal of the protective pyranyl moiety from IX followed by treatment with acetic acid-acetyl chloride yields the title compound (I).
- Vig, O. P.,Sharma, M. L.,Kumari, Sarla,Vohra, Neelam
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p. 962 - 964
(2007/10/02)
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- STEREOSELECTIVE AND VERSATILE APPROACH FOR THE SYNTHESIS OF GOSSYPLURE AND ITS COMPONENTS
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Efficient synthetic routes to gossyplure and its components (1a and 1b) were formulated.The three key units viz the alkynol 3, the bromide 5, and the alkanal 13 were derived from easily accessible starting materials.Alkylation of 3 with 5, and subsequent semihydrogenation followed by oxidation, provided the C11-alkenal 8 which was subjected to a stereocontrolled Wittig reaction with a C5-phosphonium salt, to yield directly the disired pheromone (1a + 1b).The synthesis of its individual components involved the manipulation via an acetylenic intermediate, viz the alkynol 14 which was obtained through alkylation of 3.A sequence of well-established reactions on 14, then provided the corresponding (E)- and (Z)-alkenylphosphonium salts which upon a (Z)-specific Wittig olefination with the C7-aldehyde (13), led to the stereoselective synthesis of 1a and 1b.
- Joshi, N. N.,Mamdapur, V. R.,Chadha, M. S.
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p. 3285 - 3290
(2007/10/02)
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- PHEROMONES OF INSECTS AND THEIR ANALOGS. V. A NEW APPROACH TO THE SYNTHESIS OF THE SEX PHEROMONES OF INSECTS OF THE ORDER Lepidoptera WHICH IS BASED ON THE SELECTIVE OZONOLYSIS OF 1-METHYLCYCLOOCTA-1Z,5Z-DIENE
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A new synthesis of 1-acetoxyalk-Z-enes (sex pheromones of insects of the order Lepidoptera) has been developed which is based on the selective ozonolysis of 1-methylcycloocta-1Z-5Z-diene - a cooligomer of isoprene and butadiene.
- Tolstikov, G. A.,Odinokov, V. N.,Galeeva, R. I.,Bakeeva, R. S.,Akhunova, V. R.
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p. 219 - 224
(2007/10/02)
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