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  • 1
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 1-13 
    ISSN: 1434-193X
    Keywords: Dynemicin ; Enediynes ; Antitumor agents ; Antibiotics ; Cross-coupling ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Dynemicin A is a member of the family of enediyne natural products. It is unique in that it combines a ten-membered enediyne with an anthraquinone substructure. These features stimulated the development of synthetic approaches to the natural product itself and of analogs thereof. This review summarizes the total syntheses of dynemicin A. In addition, an overview of the known analogs is presented. The analogs can be classified according to the designed trigger mechanism. Most of the analogs contain a removable carbamate on the nitrogen atom. Others are quite similar to the natural lead in that they contain a quinone substructure, which upon reduction causes opening of the oxirane ring. In addition, there are analogs that contain an aromatic sector, the enediyne, and the oxirane ring but lack the nitrogen heterocycle. In these compounds the aryl ring assumes a different conformation from that in dynemicin A. Many of the simplified analogs proved to be quite active in vitro as well in vivo against murine tumor models. A highlight is compound 30 which is much more active than dynemicin A itself. However, looking at all analogs there is no clear-cut correlation between the DNA-cleaving ability at neutral pH and the in vitro results. From this one might conclude that there are possibly two mechanisms for antitumor activity. One involves diradical formation whereas the other might be due to a ligand-receptor interaction.
    Type of Medium: Electronic Resource
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  • 2
    ISSN: 1573-3297
    Keywords: Mice ; ultrasounds ; ultrasonic calls ; infants ; diallel cross ; individual differences
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Psychology
    Notes: Abstract Ultrasonic calls produced by young mice reliably elicit investigation and retrieval by adults. While there are large individual differences in the characteristics of these calls, little work has been done to partition that variation. We completed a 4 × 4 diallel cross and Hayman analyses on several characteristics of these cries. The major result was the detection of directional dominance toward a higher rate of calling, longer calls, and calls of lower overall frequency with a greater bandwidth. Within the context of biometrical genetic theory, we conclude that calls with such characteristics may have important fitness value. Extending this idea, we propose that within the population sampled for this study (the animals of the four inbred strains and 12 F1 hybrid groups), the calls most effectively eliciting investigation and retrieval would be calls with the average hybrid values of the diallel cross.
    Type of Medium: Electronic Resource
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  • 3
    Electronic Resource
    Electronic Resource
    Springer
    Behavior genetics 26 (1996), S. 463-470 
    ISSN: 1573-3297
    Keywords: Mice ; agonistic behavior ; aggression ; homogeneous set ; standard tester ; social behavior
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Psychology
    Notes: Abstract Though social behavior has not been overlooked by behavior geneticists, the number of studies is small when compared to those on individual traits. One reason for the neglect may be the difficulty of making connections between genes and social behaviors, which by definition involve the interaction of two or more organisms. Fuller and Hahn (1976) addressed this issue and described three means of establishing social groups that would facilitate genetic analysis. We survey the literature on agonistic behavior in mice from 1976 through 1994 and describe interesting uses of those three methods. One of those methods (the standard tester design) often employs a “noninteractive” social partner. We present data showing that the standard tester design may be more valuable when using an evocative and interactive standard tester.
    Type of Medium: Electronic Resource
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  • 4
    ISSN: 1573-3297
    Keywords: Mice ; ultrasonic calls ; infants ; individual differences ; signatures
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Psychology
    Notes: Abstract Infant house mice, Mus musculus, produce ultrasonic calls that reliably lead to retrieval by adult mice. While individual differences in calls have been demonstrated both among and within species, the influences of age and sex on call characteristics have not been systematically investigated in mice. This study examined the influences of age, sex, and genotype (inbred versus hybrid) on the rate, length, and frequency characteristics of the calls of 486 male and female mice from 2 to 12 days of age. Rate of calling followed a shallow inverted U-shaped function across days. Call lengths decreased and call frequency characteristics increased, in a linear manner, with age. Females emitted fewer calls, with a smaller bandwidth, at some ages than males. Hybrid pups produced more calls of greater length and a lower frequency than inbred pups. These results indicate the presence of cues that could allow adult mice to behave differentially toward pups as a function of their age and sex.
    Type of Medium: Electronic Resource
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  • 5
    ISSN: 0947-3440
    Keywords: Enediynes ; [2 + 2] Cycloaddition ; Bicyclo[3.2.0]heptanes ; Fragmentation ; Ring closing metathesis ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Two routes to 1,4-difunctionalized cycloheptenes are described. The first one is based on a fluoride-induced fragmentation reaction of the bicyclic [3.2.0]heptanesilyl monosulfate 10. This compound in turn was prepared by a ketene-cyclopentene cycloaddition route. An alternative strategy took advantage of a ring-closing metathesis (RCM) reaction of the diolefin 18 with the ruthenium catalyst 21. This reaction proved to be reliable even on a larger scale and allowed the isolation of the cycloheptene 19a in reasonably good yield.
    Type of Medium: Electronic Resource
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  • 6
    ISSN: 0170-2041
    Keywords: Enediynes ; 1,5 Diynes ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Bicyclo[7.3.1]diynes 19a and 19b were prepared by using dibromo olefin 11 and ketone 12 as building blocks. The key step of the synthetic sequence is an intramolecular Nicholas reaction of 17 to give the bicyclo[7.3.1]diyn-10-one dicobalthexacarbonyl adducts 18a and 18b (66% total yield). Oxidative decomplexation of 18a and 18b with cer(IV) ammonium nitrate gave the diynes 19a and 19b, respectively. Both diynes 19a and 19b could be oxidatively converted into the enediyne 20 by using DDQ. In contrast to the unsubstituted enediyne 4, compound 20 can be isolated at room temperature Quantitative kinetic measurements of the rate of the Bergman cyclization of 20 gave ΔG# (37°C) = 111 kJ mol-1. This value is 12.3 kJ mol-1 higher than that of 4. The difference in the free activation energy between 20 and 4 is attributed to electronic effects.
    Type of Medium: Electronic Resource
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  • 7
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1993 (1993), S. 1009-1016 
    ISSN: 0170-2041
    Keywords: Enediynes ; Nicholas reaction ; Macrocycles ; Eleven-membered rings ; Calculations, force-field ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: An efficient route to 11-membered enediyne ketones 13 and 22 was developed. This route is based on an intramolecular Nicholas reaction of 11 and 20, respectively. In the course of the preparation of the cyclization substrates 11 and 20, it was important to use the acetylenic alcohols 6 and 15 as building blocks for the construction of the cis-enediynes 8 and 17, respectively, instead of the corresponding ketones which were converted into unstable acyclic enediynes. Some transformations of enediyne ketone 22 were also studied. For example, 22 could be transformed into the 2-formyl compound 26 via the silyl enol ether 24. In addition, 24 was used for the preparation of the 2-amino ketone 29.
    Type of Medium: Electronic Resource
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