Preparation of novel (Z)-4-ylidenebenzo[b]furo[3,2-d][1,3]oxazines and their biological activity.
A reaction of 2-acetyl-3-acylaminobenzo[b]furans (9d-o) with Vilsmeier (VM) reagent afforded a mixture of (E)- and (Z)-{(E)-2-aralkenylbenzo[b]furo[3,2-d][1,3]oxazin-4-ylidene}acetaldehydes (5) with a characteristic exo-formylmethylene group on the oxazine ring. The Z-isomer was more stable than the E-isomer. The Z-isomers ((Z)-5) were reacted with phosphonate reagents under two different conditions to obtain various butadiene derivatives (12) containing benzo[b]furo[3,2-d][1,3]oxazine skeleton. Typical compounds (5 and 12) were evaluated for their anti-osteoclastic bone resorption activity, antagonistic activity for the cysLT1 receptor and growth inhibitory activity for MIA PaCa-2 and MCF-7. Compounds 12f and 12j showed potent anti-osteoclastic bone resorption activity comparable to E(2) (17beta-estradiol).
Tabuchi
Yukako
Y
School of Pharmaceutical Sciences, Mukogawa Women's University, 11-68 Koshien Kyubancho, Nishinomiya, Hyogo 663-8179, Japan.
Ando
Yuko
Y
Kanemura
Hidemi
H
Kawasaki
Ikuo
I
Ohishi
Takahiro
T
Koida
Masao
M
Fukuyama
Ryo
R
Nakamuta
Hiromichi
H
Ohta
Shunsaku
S
Nishide
Kiyoharu
K
Ohishi
Yoshitaka
Y
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001862:Bone Resorption; D001943:Breast Neoplasms / Q000188:drug therapy; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D005260:Female; D006801:Humans; D008297:Male; D051379:Mice; D015394:Molecular Structure; D010006:Osteoblasts / Q000187:drug effects*; D010078:Oxazines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D010190:Pancreatic Neoplasms / Q000188:drug therapy
D000970:Antineoplastic Agents; D010078:Oxazines