Acetoxybenzhydrols as highly active and stable analogues of 1'S-1'-acetoxychavicol, a potent antiallergic principal from Alpinia galanga.
Through SAR studies on 1'S-1'-acetoxychavicol acetate (1) against Type I antiallergic activity by indexing release of beta-hexosaminidase, a marker of antigen-IgE-mediated degranulation in RBL-2H3 cells, more stable and potent analogue, 4-(methoxycarbonyloxyphenylmethyl)phenyl acetate (16), has been developed. The compound 16 also strongly inhibited the antigen-IgE-mediated TNF-alpha and IL-4 production.
School of Pharmacy, Kinki University, Higashiosaka, Osaka, Japan.
Tomohisa
T
Yasuhara
Yoshiaki
Y
Manse
Takayuki
T
Morimoto
Wang
W
Qilong
Hisashi
H
Matsuda
Masayuki
M
Yoshikawa
Osamu
O
Muraoka
D032429:Alpinia / Q000737:chemistry*; D000818:Animals; D018926:Anti-Allergic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001592:Benzyl Alcohols / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D045744:Cell Line, Tumor; D007073:Immunoglobulin E / Q000276:immunology / Q000378:metabolism; D015847:Interleukin-4 / Q000378:metabolism; D010648:Phenylacetates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D051381:Rats; D013329:Structure-Activity Relationship; D014409:Tumor Necrosis Factor-alpha / Q000378:metabolism; D001619:beta-N-Acetylhexosaminidases / Q000378:metabolism
C541969:4-(methoxycarbonyloxyphenylmethyl)phenyl acetate; D018926:Anti-Allergic Agents; D001592:Benzyl Alcohols; D010648:Phenylacetates; D014409:Tumor Necrosis Factor-alpha; D015847:Interleukin-4; D007073:Immunoglobulin E; D001619:beta-N-Acetylhexosaminidases; C047948:1'-acetoxychavicol acetate