Fifteen pyrrole alkaloids were isolated from the Red Sea marine sponge Stylissa carteri and investigated for their biological activities. Four of them were dibrominated [(+) dibromophakelline, Z -3-bromohymenialdisine, (±) ageliferin and 3,4-dibromo-1 H -pyrrole-2-carbamide], nine compounds were monobrominated [(−) clathramide C, agelongine, (+) manzacidin A, (−) 3-bromomanzacidin D, Z -spongiacidin D, Z -hymenialdisine, 2-debromostevensine, 2-bromoaldisine and 4-bromo-1 H -pyrrole-2-carbamide)] and finally, two compounds were non-brominated derivatives viz., E -debromohymenialdisine and aldisine. The structure elucidations of isolated compounds were based on 1D & 2D NMR spectroscopic and MS studies, as well as by comparison with literature. In-vitro, Z -spongiacidin D exhibited a moderate activity on (ARK5, CDK2-CycA, CDK4/CycD1, VEGF-R2, SAK and PDGFR-beta) protein kinases. Moreover, Z -3-bromohymenialdisine showed nearly similar pattern. Furthermore, Z -hymenialdisine displayed a moderate effect on (ARK5 & VEGF-R2) and (−) clathramide C showed a moderate activity on AURORA-A protein kinases. While, agelongine, (+) manzacidin A, E -debromohymenialdisine and 3,4-dibromo-1 H -pyrrole-2-carbamide demonstrated only marginal inhibitory activities. The cytotoxicity study was evaluated in two different cell lines. The most effective secondary metabolites were (+) dibromophakelline and Z -3-bromohymenialdisine on L5178Y. Finally, Z -hymenialdisine, Z -3-bromohymenialdisine and (±) ageliferin exhibited the highest cytotoxic activity on HCT116. No report about inhibition of AURORA-A and B by hymenialdisine/hymenialdisine analogs existed and no reported toxicity of ageliferin existed in literature.