Diastereoselective synthesis of highly substituted, amino- and pyrrolidino-tetrahydrofurans as lead-like molecular scaffolds

A series of highly substituted tetrahydrofurans (THFs), decorated with modifiable 2‐aryl, 3‐carboxy and 4‐amino substituents, has been prepared for biological evaluation within the European Lead Factory. Diastereoselective reductive amination of pre‐functionalised 4‐oxofurans, readily prepared from cinnamate esters via oxa Michael/Dieckmann annulation, provided the requisite THF cores on gram scale with three contiguous stereocentres, including full substitution at C‐3. In a second series, a pyrrolidine ring was fused to the same oxofuran scaffold via an intramolecular reductive amination, inverting the configuration at C‐4 relative to the other ring substituents. The resulting compounds, which displayed desirable physical properties as lead‐like scaffolds, were derivatised into a small library of 24 compounds, demonstrating their ability to serve as starting points for drug discovery. Ultimately, this chemistry enabled the preparation of 1948 THF‐containing compounds for inclusion in the Joint European Compound Library

Letztes kindliches Liebes Opfer wollten bey dem schmerzlichen Hintritt ihres im Leben herzlich geliebten Herrn Vaters, des weyland Hochedelgebohrnen und Hochgelahrten Herrn, Herrn Johann Christoph Appuns, Hochfürstl. Sachsen Coburg-Meiningischen wohlbestallten Raths und Amtmanns zu Schalkau, Als Derselbe den 8. April 1761. die Zeitlichkeit mit der frohen Ewigkeit verwechselte, und den 9ten darauf ... zu seiner Ruhestätte gebracht wurde, ... zu Tage legen Dessen ... Töchter Hedwig Eleonara Appunin, Amöna Wilhelmina Appunin

Gedächtnisgedicht auf Johann Christoph Appun, Fürstl Rat, +8. April 1761Autopsie nach Exemplar der ULB Sachsen-AnhaltVorlageform des Erscheinungsvermerks: Meiningen, gedruckt bey Friedemann Christoph Hartmann, F. S. Hofbuchdrucker

Feliciter! Feliciter! Admodum Reverendo, Clarissimo Pariter Atqve Eruditissimo Dn. M. Christiano Clajo, Ecclesiæ, qvæ Falckenhaynæ est, Pastori vigilantissimo, Cum ... Virgine Johanna Elisabetha Böttigern, ... Dn. Johannis Böttigers, In Civitate Torgensi Prætoris urbani pridentissimi ac meritissimi Filia Sponsa Nuptias iteranti Votis devotis Acclamat Die 4. April. M. DCCI. Henricus Georgius Appunius, apud Tammenhaynenses Pastor

Autopsie nach Exemplar der ULB Sachsen-AnhaltVorlageform des Erscheinungsvermerks: Torgae, Typis Johann. Zachar. Hempi[i]

Unter den tropen; wanderungen durch Venezuela, am Orinoco, durch Britisch Guyana und am Amazonenstrome in den jahren 1849-1868.

2.Bd (Britisch Guyana) (1871

Anion-Induced Intramolecular Cyclization of Urea-Based Receptors: Entrapment of Cyclic [SO₄(H₂O)₄^2–]_<i>n</i> Cluster and Encapsulation of Anions with Varied Dimensionality

Two unsymmetrical dipodal monourea anion receptors BPU-1 and BPU-2 with varying π-acidic terminal electron-withdrawing substituents (–NO2 and –CF3) can interact with anions of varied geometries (spherical, trigonal planar, and tetrahedral). Receptors are designed with an arm having a flexible urea unit, and the other arm contains a semirigid fluorophoric benzimidazole unit. BPU-1 could entrap cyclic sulfate water cluster, [SO4(H2O)42–]n, resulting in R44(8) and R44(12) arrangements in the solid state. Anion-sensing behavior of both receptors has been investigated in the aqueous medium, where BPU-1 could selectively sense SO42–/HSO4– among other biologically relevant anions. Anion-induced intramolecular cyclization of both receptors in the presence of F–/HO– to yield benzimidazo[1,2-c]quinazolin-6-ones has also been investigated in detail