Synthesis and biological evaluation of polymethoxylated 4-heteroarylcoumarins as tubulin assembly inhibitor

Catalytic methods of creation and functionalization of the coumarin skeleton

“…Thus, the Suzuki-Miyaura [36][37][38][39][40][41][42][43][44][45], Stille [37], Negishi [46], Sonogashira [47][48][49], Heck [50,51], and Buchwald-Hartwig [52][53][54] reactions are used to obtain various aryl-, hetaryl-, alkenyl-, alkynyl-, and also N-hetaryl-and amino-containing coumarins in high yield. [Pd]-cat.…”

Synthesis and Evaluation of Azetidinone Analogues of Combretastatin A-4 as Tubulin Targeting Agents

“…The majority of these compounds replace the cis-double bond in 2a with a heterocyclic rigid ring scaffold structures which prevents isomerisation of the cis-double bond. These analogues include the heteroarylcoumarin 29 ,…”

Lead identification of conformationally restricted benzoxepin type combretastatin analogs: synthesis, antiproliferative activity, and tubulin effects

“…Many cis-restricted analogs of CA-4 have been synthesized to improve the solubility, stability, and therapeutic index 4 of these drugs. A number of examples where the olefinic group is replaced by a conformationally restricted ring structure have demonstrated significant antiproliferative activity 13 , including those based on coumarin (1) 14,15 , 2(5H)-furanone (2) 16 , imidazole 17 , 1,3-oxazole (3) 17 , furazan (4) 4 and furan (5) 18 , diarylindole 17,19 , and arylthioindole 20 , illustrated in Figure 1. We have previously reported the application of the benzoxepin 21 and benzothiepin scaffolds 22 for the design of antiproliferative agents as estrogen receptor (ER) antagonists.…”