AIM To screen optimal drugs against postmenopausal osteoporosis with cardiovascular protective activities. METHODS A series of benzodihydropyran derivatives were designed and synthesized in view of comprehensive observations of raloxifene and ipriflavone. The antiosteoporosis activities of compounds a-e (10 -7 mol·L -1 ) on the proliferation of human osteoblast cell HOS TE85 were studied. The cardiovascular protective activities were evaluated by observing their effects on proliferation of human vascular endothelium cell ECV 304 and their protective effects on ECV 304 damaged by H 2O 2. RESULTS Their structures were determined by spectrums. Compounds a, b and c (10 -7 mol·L -1 ) were shown to significantly help proliferation of HOS TE85. In addition, b, d and e (10 -8 mol·L -1 ) helped proliferation of ECV 304 significantly. Compounds b and c (10 -6 mol·L -1 ) showed strong protective activity on ECV 304 damaged by H 2O 2. Compounds b and c shifted the KCl dose response curves to the right and decreased the maximal response. CONCLUSION Compounds b and c showed some bone and vascular protective activities which benefit postmenopausal osteoporosis and cardiovascular diseases.