<p>Kinases are important targets for the development of novel cancer therapeutics. In this thesis ligand-based methods are used to design novel pyrrole-annelated N-heterocycles as kinase inhibitor templates. On one hand, the research focuses on "privileged motifs" based on an <i>ortho</i>-diaryl substituted 5-membered heterocycle as underlying structure. In this context, novel 2,3-diaryl-substituted azaindoles are projected. As known synthetic routes fail to deliver the particularly interesting and unprecedented 4- and 7-azaindoles bearing an electron withdrawing cyano-group in the 5-position, two highly flexible synthesis routes are developed offering a variable late-stage derivatization regarding the aryl-substituents in 2- or 3-position. One method is based on Larock's indole synthesis: the reaction of <i>ortho</i>-iodo-anilines or -pyridines, respectively, with internal alkynes for the construction of the annelated pyrrole moiety. For this purpose the presence of an electron donating protecting group is ascertained to be necessary and the removable THP-protection identified as such. Employing the THP-group within the Larock reaction a successful pyrrole annelation process with internal, sterically demanding, aryl or trialkylsilyl-substituted alkynes can be consequently performed. The second synthesis route employs an optimized one-pot base-induced 5-<i>endo</i>-dig cycli¬zation/halo-genation/pro¬tection sequence to deliver novel templates for the final arylation via Suzuki coupling in 3-position of the 4- and 7-azaindoles. To demonstrate the synthesis methodology a structure-activity-relation and selectivity study is conducted with several compounds regarding their activity against the p38 mitogen-activated protein kinase and c-Met-kinase. The study leads to unprecedented highly active and partially highly selective inhibitors with two-digit nanomolar IC<sub >50</sub>-values. The chemistry was also applied for several other projects in the field of kinase and metallo¬protease inhibitors, delivering several structurally novel and potent inhibitors. On the other hand the thesis' research focuses on the development of a feasible synthesis route to the rarely known and synthetically insufficiently accessible pyrrolo[2,3-<i>d</i>]thiazoles. This ligand-based approach opens access to the "preferred structure" of an adjacent acceptor-donor-motif for kinase inhibitors as hinge-binding element, on basis of a pyrrole-annelated heterocycle. For their flexible synthesis the previously explored base-induced 5-<i>endo</i>-dig cyclization is used. With a highly effective protocol employing an enhanced microwave synthesis procedure the desired 5-substituted pyrrolo[2,3-<i>d</i>]thiazoles are conveniently derived from the corresponding <i>o</i>-aminoalkynylthiazoles. Methylene-bridged substituents in the 6-position are directly obtained from intramolecular 5-<i>exo</i>-Heck cyclization based on the same iodoaminothiazole precursor. Further structural variety is accessible via Suzuki reaction of 2-chloroaminothiazoles. These unprecedented fragment-like compounds show high activity within low-concentration kinase inhibition assays and very promising selectivity pattern in broad selectivity screenings. A first co-crystal structure of focal adhesion kinase (FAK) with a pyrrolo[2,3-<i>d</i>]thiazole is disclosed.</p>