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  • Atropisomeric 8,8'-biquinolyl derivatives : synthesis, properties and applications

    Creator:
    Milicevic, Selena D.
    Abstract:
    7,7'-Dihydroxy-8,8'-biquinolyl (azaBINOL) was prepared from 7-hydroxyquinoline via N,N-dimethyl O-quinol-7-yl carbamate by directed ortho-metallation followed by FeCl₃-mediated oxidative coupling of the 8-lithioquinoline intermediate. Saponification of the resulting dicarbamate provided crystalline (±)-azaBINOL in 56% overall yield. 6,6'-Bis(dimethylaminocarbonyl)-7,7'-dihydroxy-8,8´-biquinolyl was prepared from the same dicarbamate by a double anionic-Fries rearrangement in 43% yield. 7,7'-Bis(diethylamino-carbonyloxy)-6,6'-diiodo-8,8´-biquinolyl...
    Resource Type:
    Dissertation
    Full Text:
    discussed in Chapter 4. Of interest here is the synthesis of benzo[1,2-h:4,3-h´]biquinolyl (42) via

  • New Treatments for HIV and Cancer: Uncovering Bioactive Compounds from Small Molecule Sources

    Creator:
    Overacker, Ross D.
    Abstract:
    Small molecule drugs have been instrumental in our fight against diseases, beginning when some of the earliest ancient cultures used plant remedies to treat illnesses. More recently, the skill of isolating and characterizing the active ingredients within bioactive plants and microbial extracts has led to the isolation and design of...
    Resource Type:
    Dissertation
    Full Text:
    level inhibition (∼7 µM) of HIV-1 by acting on the RNase H activity of the viral reverse transcriptase

  • Part I: Synthesis and evaluation of synosutine as an inhibitor of serotonin, norepinephrine, and dopamine transporters Part II: Asymmetric approach to the tetracyclic core of neomangicol A

    Creator:
    Juniku, Rajan B.
    Abstract:
    Part I: Racemic and asymmetric syntheses of a new substance with prospective antidepressant properties were achieved. In vitro assays with synthetic racemates (±)-25 and (±)-26 suggested that the former is a relatively selective inhibitor of serotonin transporter whereas the latter is a more balanced inhibitor of both serotonin and norepinephrine...
    Resource Type:
    Dissertation
    Full Text:
    (Fig 4).2 Me3N O O Acetylcholine (1) HO HO NH2 HO HO (R) NH2 OH HO N H NH2 Dopamine (5

  • Studies towards the total syntheses of (+)-phomactins A, D and G

    Creator:
    Schwartz, Keith D.
    Abstract:
    Studies towards the total synthesis of (+)-Phomactin A (1), D (6), and G (9), fungal metabolites with unique molecular architecture and pronounced biological activity, are described. These studies resulted in the synthesis of advanced intermediates 354 and 356, which contain all of the carbon atoms of 1, 6 and 9....
    Resource Type:
    Dissertation
    Full Text:
    phomactin B2 4 O O OH H α -OH; phomactin B 2 β- OH; phomactin B1 3 O O OH H HO H O O H CHO

  • Studies toward the total synthesis of sanglifehrin A

    Creator:
    Suttisintong, Khomson
    Abstract:
    Studies toward synthesis of subunits of sanglifehrin A, an immunosuppressant featuring a highly substituted [5,5]-spirolactam moiety as well as a 22-membered macrocycle are described. The macrolactone contains a peptidic backbone characterized by an unusual [beta]-substituted (S)-piperazic acid and (S)-m-hydroxyphenylalanine units. These studies resulted in the synthesis of advanced intermediate 358...
    Resource Type:
    Dissertation
    Full Text:
    steps 12: R = Bn 13: R = H H2, Pd/C, EtOH 25 ºC 100% TPAP, NMO, 4 A MS DCM, 25 ºC O O O PivO O P